Labors' End

Nestled in Key West's premier neighborhood, Casa Marina, Labors' End is a charming Southern Craftsman style pool home.

Location

1101 Flagler Avenue
33040 Key West , FL
United States
24° 33' 0.45" N, 81° 47' 17.3832" W
Florida US

Labors' End

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Historic Casa Marina Location-Only 2 blocks from the Atlantic Ocean!

Unit Code: 1101F

Labors' End

Nestled in Key West's premier neighborhood, Casa Marina, Labors' End is a charming Southern Craftsman style pool home.
Escape to paradise in this charming 2-bedroom, 2-bathroom pool home located just 2 blocks from the serene Higgs Beach and iconic White Street Pier. Perfectly situated on a corner lot, this home offers ample off-street parking and a tranquil environment for your stay. As you step inside, you'll be greeted by an open and inviting living area to the left, with a formal dining space for six on your right. The large windows throughout the home invite in the warm Florida sunshine and refreshing Key West evening breezes, creating the perfect atmosphere for relaxation. The spacious kitchen is equipped with updated appliances, ideal for preparing your meals or hosting a dinner party. French doors open directly onto the outdoor deck, providing seamless indoor-outdoor living for al fresco dining and lounging by the pool. Down the hallway, you'll find the primary bedroom with an en suite bathroom, along with a guest bedroom and a guest bathroom. The primary bedroom offers its own private access to the outdoor deck, perfect for a quiet moment of relaxation. For added convenience, the home also features a laundry area as a part of the primary bedroom closet area, as well as a dedicated desk for any work you may need to do while enjoying your getaway. Whether you're looking to explore Key West or unwind by the pool, this home is the perfect retreat for your monthly vacation rental. Book now and make this tropical paradise your home away from home! Monthly rental only Linens included Free Wi-Fi
April 2025
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Age 24 and under.
DatesPrice
04/20/2025 - 04/24/2025$346 /nt
04/20/2025 - 04/24/2025$324 /nt
04/27/2025 - 04/30/2025$324 /nt
04/27/2025 - 04/30/2025$346 /nt
04/01/2025 - 04/30/2025$324 /nt
04/01/2025 - 04/30/2025$411 /nt
05/01/2025 - 05/01/2025$545 /nt
05/01/2025 - 05/01/2025$378 /nt
05/04/2025 - 05/08/2025$378 /nt
05/04/2025 - 05/08/2025$545 /nt
05/11/2025 - 05/15/2025$545 /nt
05/11/2025 - 05/15/2025$378 /nt
05/18/2025 - 05/22/2025$378 /nt
05/18/2025 - 05/22/2025$545 /nt
05/25/2025 - 05/29/2025$378 /nt
05/25/2025 - 05/29/2025$545 /nt
05/01/2025 - 05/31/2025$378 /nt
05/01/2025 - 05/31/2025$709 /nt
05/01/2025 - 05/31/2025$1,822 /wk
05/01/2025 - 05/31/2025$2,729 /wk
05/01/2025 - 05/31/2025$8,289 /month
05/01/2025 - 05/31/2025$8,292 /month
06/01/2025 - 06/05/2025$510 /nt
06/01/2025 - 06/05/2025$445 /nt
06/08/2025 - 06/12/2025$445 /nt
06/08/2025 - 06/12/2025$510 /nt
06/15/2025 - 06/19/2025$445 /nt
06/15/2025 - 06/19/2025$510 /nt
06/22/2025 - 06/26/2025$445 /nt
06/22/2025 - 06/26/2025$510 /nt
06/29/2025 - 06/30/2025$445 /nt
06/29/2025 - 06/30/2025$510 /nt
06/01/2025 - 06/30/2025$445 /nt
06/01/2025 - 06/30/2025$644 /nt
06/01/2025 - 06/30/2025$2,381 /wk
06/01/2025 - 06/30/2025$2,820 /wk
06/01/2025 - 06/30/2025$10,316 /month
07/01/2025 - 07/03/2025$648 /nt
07/01/2025 - 07/03/2025$462 /nt
07/06/2025 - 07/10/2025$462 /nt
07/06/2025 - 07/10/2025$648 /nt
07/13/2025 - 07/17/2025$462 /nt
07/13/2025 - 07/17/2025$648 /nt
07/20/2025 - 07/24/2025$462 /nt
07/20/2025 - 07/24/2025$648 /nt
07/27/2025 - 07/31/2025$462 /nt
07/27/2025 - 07/31/2025$648 /nt
07/01/2025 - 07/31/2025$462 /nt
07/01/2025 - 07/31/2025$771 /nt
07/01/2025 - 07/31/2025$2,555 /wk
07/01/2025 - 07/31/2025$3,611 /wk
07/01/2025 - 07/31/2025$11,875 /month
07/01/2025 - 07/31/2025$12,176 /month
08/03/2025 - 08/07/2025$415 /nt
08/03/2025 - 08/07/2025$551 /nt
08/10/2025 - 08/14/2025$415 /nt
08/10/2025 - 08/14/2025$551 /nt
08/17/2025 - 08/21/2025$415 /nt
08/17/2025 - 08/21/2025$551 /nt
08/24/2025 - 08/28/2025$415 /nt
08/24/2025 - 08/28/2025$551 /nt
08/31/2025 - 08/31/2025$551 /nt
08/31/2025 - 08/31/2025$415 /nt
08/01/2025 - 08/31/2025$691 /nt
08/01/2025 - 08/31/2025$415 /nt
08/01/2025 - 08/31/2025$2,319 /wk
08/01/2025 - 08/31/2025$3,123 /wk
08/01/2025 - 08/31/2025$11,571 /month
08/01/2025 - 08/31/2025$11,670 /month
09/01/2025 - 09/04/2025$514 /nt
09/01/2025 - 09/04/2025$415 /nt
09/07/2025 - 09/11/2025$514 /nt
09/07/2025 - 09/11/2025$415 /nt
09/14/2025 - 09/18/2025$415 /nt
09/14/2025 - 09/18/2025$514 /nt
09/21/2025 - 09/25/2025$415 /nt
09/21/2025 - 09/25/2025$514 /nt
09/28/2025 - 09/30/2025$415 /nt
09/28/2025 - 09/30/2025$514 /nt
09/01/2025 - 09/30/2025$415 /nt
09/01/2025 - 09/30/2025$574 /nt
09/01/2025 - 09/30/2025$2,007 /wk
09/01/2025 - 09/30/2025$2,451 /wk
09/01/2025 - 09/30/2025$8,529 /month
10/01/2025 - 10/02/2025$427 /nt
10/01/2025 - 10/02/2025$789 /nt
10/05/2025 - 10/09/2025$427 /nt
10/05/2025 - 10/09/2025$789 /nt
10/12/2025 - 10/16/2025$427 /nt
10/12/2025 - 10/16/2025$789 /nt
10/19/2025 - 10/23/2025$427 /nt
10/19/2025 - 10/23/2025$789 /nt
10/26/2025 - 10/30/2025$427 /nt
10/26/2025 - 10/30/2025$789 /nt
10/01/2025 - 10/31/2025$427 /nt
10/01/2025 - 10/31/2025$1,050 /nt
10/01/2025 - 10/31/2025$2,160 /wk
10/01/2025 - 10/31/2025$5,089 /wk
10/01/2025 - 10/31/2025$13,052 /month
10/01/2025 - 10/31/2025$13,290 /month
11/02/2025 - 11/06/2025$788 /nt
11/02/2025 - 11/06/2025$518 /nt
11/09/2025 - 11/13/2025$518 /nt
11/09/2025 - 11/13/2025$788 /nt
11/16/2025 - 11/20/2025$518 /nt
11/16/2025 - 11/20/2025$788 /nt
11/23/2025 - 11/27/2025$518 /nt
11/23/2025 - 11/27/2025$788 /nt
11/30/2025 - 11/30/2025$518 /nt
11/30/2025 - 11/30/2025$788 /nt
11/01/2025 - 11/30/2025$514 /nt
11/01/2025 - 11/30/2025$957 /nt
11/01/2025 - 11/30/2025$3,121 /wk
11/01/2025 - 11/30/2025$4,947 /wk
11/01/2025 - 11/30/2025$16,189 /month
12/01/2025 - 12/04/2025$479 /nt
12/01/2025 - 12/04/2025$1,233 /nt
12/07/2025 - 12/11/2025$479 /nt
12/07/2025 - 12/11/2025$1,233 /nt
12/14/2025 - 12/18/2025$479 /nt
12/14/2025 - 12/18/2025$1,233 /nt
12/21/2025 - 12/25/2025$479 /nt
12/21/2025 - 12/25/2025$1,233 /nt
12/28/2025 - 12/31/2025$479 /nt
12/28/2025 - 12/31/2025$1,233 /nt
12/01/2025 - 12/31/2025$479 /nt
12/01/2025 - 12/31/2025$1,263 /nt
12/01/2025 - 12/31/2025$3,342 /wk
12/01/2025 - 12/31/2025$6,921 /wk
12/01/2025 - 12/31/2025$17,681 /month
12/01/2025 - 12/31/2025$18,465 /month
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2 Bed
2 Baths
Sleeps 4

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The Emma House

This charming 1923 home in Bahama Village is just steps from Key West’s top attractions, making it the perfect base for your island adventure.

Location

827 ½ Emma Street
33040 Key West , FL
United States
24° 33' 2.4336" N, 81° 48' 13.5756" W
Florida US

The Emma House

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Charming 1923 2 Bedroom, 1 Bath home with bonus loft.

Unit Code: 827E

The Emma House

This charming 1923 home in Bahama Village is just steps from Key West’s top attractions, making it the perfect base for your island adventure.
Welcome to The Emma House! A delightful 1923 Key West retreat located in the heart of historic and vibrant Bahama Village. Immerse yourself in the unique charm of Key West, where colorful streets, lively culture, and iconic attractions await. The Emma House is ideally situated just a short stroll from Duval Street’s famous nightlife, the literary allure of Hemingway House, and the serene sunsets at Truman Waterfront Park. Whether you’re visiting for adventure or relaxation, this cozy retreat offers the perfect home base. About the Home Bedrooms: - Two Queen Bedrooms: Located on the first floor, these serene and inviting bedrooms are designed for ultimate comfort. A full bathroom conveniently sits between the two rooms, offering privacy and ease. - Bonus Loft Space: Accessible via a sturdy wall-mounted ladder, the loft features a Queen mattress, creating a fun and unique sleeping or lounging space. While not considered a formal bedroom, this nook is ideal for adventurous guests seeking something a little different. Living & Dining: - The open-concept living room and kitchen are bright and welcoming, perfect for unwinding after a day of island adventures. The kitchen is equipped with modern appliances, ample counter space, and seating for four at the breakfast bar—making it a great spot for morning coffee or evening cocktails. Outdoor Space: - Step outside to your private back porch, where you can relax with a book, share a meal at the patio dining table, or fire up the propane grill for a barbecue. This outdoor area offers a peaceful escape after exploring the bustling streets of Key West. Additional Amenities - High-Speed Wi-Fi: Stay connected, whether you’re working remotely or streaming your favorite shows. - Washer and Dryer: Enjoy the convenience of in-home laundry during your stay. - Bedding and Linens Provided: Arrive ready to relax—everything you need is already here. - 1 Off-Street Parking Space: A true luxury in Key West! **What to Expect in the Neighborhood** Bahama Village is one of Key West’s most historic neighborhoods, known for its vibrant culture, unique charm, and walkable proximity to the island’s best attractions. Community Center Nearby: Directly outside the front door is a large brick community center offering local amenities, including a basketball gym and kids' art classes. While the building reflects its age, a brand-new community center is under construction next door, slated for completion by mid-2025. Please note that the construction and the original building may impact the view from the front porch but should not disrupt your stay. Why Choose The Emma House? Located just two blocks from Hemingway House and moments from Duval Street, this home offers unmatched convenience for exploring Key West. Sleeps up to 4 comfortably: While the loft provides extra sleeping options, this home is best enjoyed as a cozy 2-bedroom retreat. Monthly rentals only! Whether you’re soaking in the sun, enjoying the vibrant local scene, or retreating to your peaceful hideaway, The Emma House invites you to experience the best of Key West with charm and comfort. Book your stay at The Emma House today and get ready for your island adventure!
April 2025
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DatesPrice
05/01/2025 - 05/31/2025$213 /nt
05/01/2025 - 05/31/2025$226 /nt
06/01/2025 - 06/30/2025$236 /nt
07/01/2025 - 07/31/2025$209 /nt
08/01/2025 - 08/31/2025$226 /nt
09/01/2025 - 09/30/2025$206 /nt
10/01/2025 - 10/31/2025$256 /nt
11/01/2025 - 11/30/2025$234 /nt
12/01/2025 - 12/31/2025$366 /nt
Leave a Review
2 Bed
1 Bath
Sleeps 5

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On the Rocks

On the Rocks is the perfect choice for those looking for a luxurious oceanfront getaway with all the comforts of home.

Location

1800 Atlantic Blvd Unit C341
33040 Key West , FL
United States
24° 33' 5.22" N, 81° 46' 40.6308" W
Florida US

On the Rocks

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Sunshine Sweet ��

Reviewed by Unknown on 2025-03-15
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
This is absolutely my favorite property that I’ve stay at in Key West. It’s SAFE, well maintained, quiet and directly on the water.

On the Rocks, 3 Bedroom, 2 Bath Condo right on the beach!

Unit Code: 1800C341

On the Rocks

On the Rocks is the perfect choice for those looking for a luxurious oceanfront getaway with all the comforts of home.
Welcome to On the Rocks – Your Oceanfront Escape Experience coastal living at its finest in On the Rocks, a spacious and beautifully designed 3-bedroom, 2-bathroom condo with breathtaking views of the Atlantic Ocean. Located just steps from the shore, this open-concept vacation home offers the perfect retreat for relaxation, entertaining, and soaking in the natural beauty of Key West. Key Features: Stunning Ocean Views: As soon as you step inside, you’ll be greeted by floor-to-ceiling sliding glass doors that offer an uninterrupted, panoramic view of the Atlantic Ocean. The wrap-around balcony is perfect for dining al fresco, morning coffee, or simply taking in the fresh ocean air and stunning Key West sunsets. Open-Concept Living & Dining: The expansive living area is filled with natural light and is perfect for both relaxation and entertainment. With ample seating, you and your guests can enjoy the sea breeze while lounging or hosting a gathering. The sliding glass doors can be opened in the winter to let in the refreshing ocean breeze. Gourmet Kitchen: The large, fully equipped kitchen is ideal for whipping up anything from a quick breakfast to a full dinner party. With counter seating for four and a dining table that also seats four, there’s plenty of space for everyone to enjoy meals together. Guest Bedrooms: Down the hall, you’ll find two beautifully appointed guest bedrooms. One features a queen bed, while the other has a king-size bed. Both rooms are equipped with their own TVs and share a spacious bathroom with dual sinks and a large shower. Master Suite: The master bedroom is your personal sanctuary, complete with a luxurious en suite bathroom featuring a jetted tub, separate shower, and a walk-in closet for all your belongings. Like the guest rooms, the master bedroom also has its own private entrance to the balcony, where you can enjoy your morning coffee or relax with a good book. Outdoor Living: The wrap-around balcony is the highlight of the condo, offering breathtaking views of the ocean and providing the perfect setting for outdoor dining or lounging. Each bedroom has direct access to the balcony, allowing you to step outside and take in the beauty of Key West at any time. Additional Amenities: TVs in every bedroom for your entertainment High-speed Wi-Fi Ample closet and storage space Proximity to local dining, shopping, and attractions On the Rocks is the perfect choice for those looking for a luxurious oceanfront getaway with all the comforts of home. Whether you're traveling with family or friends, this condo has everything you need to make your Key West vacation unforgettable. Book your stay today and enjoy the beauty and tranquility of On the Rocks!
April 2025
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DatesPrice
05/01/2025 - 05/31/2025$230 /nt
05/01/2025 - 05/31/2025$244 /nt
06/01/2025 - 06/30/2025$278 /nt
07/01/2025 - 07/31/2025$286 /nt
08/01/2025 - 08/31/2025$256 /nt
09/01/2025 - 09/30/2025$256 /nt
10/01/2025 - 10/31/2025$381 /nt
11/01/2025 - 11/30/2025$381 /nt
12/01/2025 - 12/31/2025$531 /nt
5.0000
(1 Review)

Sunshine Sweet ��

February 2025
, Bloomington, IN Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This is absolutely my favorite property that I’ve stay at in Key West. It’s SAFE, well maintained, quiet and directly on the water.

Leave a Review
3 Bed
2 Baths
Sleeps 6

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Blue Gem

Blue Gem is a 4BR/3BA waterfront home with a pool, Tiki bar, and boat dock. Located on a deep-water canal, it's just 10 miles from Key West. Perfect for island-style relaxation.

Location

5 Sapphire Dr
33040 Key West , FL
United States
24° 36' 0.3888" N, 81° 39' 14.9112" W
Florida US

Blue Gem

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Perfect for my family

Reviewed by Alexandria H. on 2025-03-25
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
We enjoyed this house & everything it offered. it’s on a quiet street, perfect for your morning walk & not far from the heart of key west. We were never bored. Friendly neighbors and welcoming neighborhood.
Manager response on 2025-04-04 - Response from Preferred Properties Management LLC
Thank you so much for the kind words — we’re grinning ear to ear! We're thrilled you enjoyed your stay at Blue Gem. It’s tucked away just enough to give you that peaceful, laid-back escape, but still close enough to the energy of Key West when you're in the mood for it. Kind of the best of both worlds, right? And as our very first guest, you’ll always hold a special place in the story of this home. From peaceful mornings to neighborhood strolls (and maybe even a first step or two ), your visit helped bring the Gem to life in the most meaningful way. We also really appreciate you letting us know that the 4-star on property condition was an error, the property owner was ready to make things better — these things happen! While we can’t make changes to the rating, your message means a lot and adds helpful context for future guests. We’d love to welcome you back anytime — the Blue Gem will be here, polished and ready, whenever the next adventure calls!

4BR/3BA Waterfront Home w/ Pool, Tiki Bar, Dock, close to Key West, Sleeps 10

Unit Code: 5Sap

Blue Gem

Blue Gem is a 4BR/3BA waterfront home with a pool, Tiki bar, and boat dock. Located on a deep-water canal, it's just 10 miles from Key West. Perfect for island-style relaxation.
Welcome to Blue Gem! We’re so glad you’re considering Blue Gem for your next getaway! This beautiful 4-bedroom, 3-bathroom home is nestled on a serene deep-water canal that leads right to the Atlantic Ocean, making it the perfect escape for you and your loved ones. Imagine waking up just minutes from stunning sandbars like Jewfish Channel and Snipes, where you can spend your days soaking up the sun and splashing in the waves. And the sunrises and sunsets? Simply breathtaking. Located in the charming Porpoise Point Subdivision, you’re just 10.5 miles from vibrant Duval Street and only 5 miles from Key West International Airport and local beaches. You’ll have the best of both worlds—peaceful island living and easy access to the area's excitement! Step inside and let the spirit of island life embrace you. Our cozy family room is the perfect spot to unwind with a movie or enjoy some friendly competition with video games. The kitchen is fully equipped, whether you’re whipping up a family feast or just savoring your morning coffee. Gather in the spacious dining and main living area, where wood-beam cathedral ceilings and travertine tile floors create an inviting atmosphere. French doors open to let in the breeze, and a coral rock fireplace adds a touch of charm—perfect for lazy days spent relaxing with a good book. Now, let’s talk about the outdoor paradise that awaits you! The beautifully landscaped backyard features a heated pool, Tiki bar, fire pits, and a pergola for shaded relaxation. The Tiki bar includes a margarita machine, mini freezer/refrigerator, sink and even a popcorn popper for those movie nights under the stars. Plus, a large grill, outdoor TV and outdoor screen with a projector to enhance your island experience! Beyond the pergola, the clear canal invites you to fish, swim, paddleboard, or kayak. With evening lighting, it transforms into a mesmerizing live aquarium filled with tarpons and colorful fish. Have a boat? You’re in luck! Our property includes convenient docking at the 80-foot seawall with lots of cleats, giving you easy access to the ocean. (Note: The owner’s boat, as shown in the photos, will be out of the water during your stay and unavailable.) Upstairs, you’ll find all the bedrooms, ensuring a peaceful retreat for everyone: Bedroom 1: A spacious primary suite with a king-size bed and master bath. Bedroom 2: A cozy queen-size bedroom with an adjacent bathroom. Bedroom 3: Another queen bed, complete with a dedicated office space for those who need to stay connected. Bedroom 4: Bunk beds (full on bottom, twin on top) located off the primary bedroom, perfect for kids. The property also offers off-street parking with space for your trailer in the large front yard. Blue Gem is the perfect spot for a month-long vacation or a quick getaway. We can’t wait to welcome you—book your stay today and dive into the ultimate waterfront living experience!
April 2025
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DatesPrice
05/01/2025 - 05/31/2025$212 /nt
05/01/2025 - 05/31/2025$229 /nt
06/01/2025 - 06/30/2025$343 /nt
06/01/2025 - 06/30/2025$345 /nt
07/01/2025 - 07/31/2025$486 /nt
07/01/2025 - 07/31/2025$515 /nt
08/01/2025 - 08/31/2025$417 /nt
08/01/2025 - 08/31/2025$425 /nt
09/01/2025 - 09/30/2025$302 /nt
09/01/2025 - 09/30/2025$305 /nt
10/01/2025 - 10/31/2025$302 /nt
10/01/2025 - 10/31/2025$306 /nt
11/01/2025 - 11/30/2025$430 /nt
11/01/2025 - 11/30/2025$434 /nt
12/01/2025 - 12/31/2025$487 /nt
12/01/2025 - 12/31/2025$533 /nt
5.0000
(1 Review)

Perfect for my family

February 2025
, wolverine , MI United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

We enjoyed this house & everything it offered. it’s on a quiet street, perfect for your morning walk & not far from the heart of key west. We were never bored. Friendly neighbors and welcoming neighborhood.

Manager's Response

Thank you so much for the kind words — we’re grinning ear to ear! We're thrilled you enjoyed your stay at Blue Gem. It’s tucked away just enough to give you that peaceful, laid-back escape, but still close enough to the energy of Key West when you're in the mood for it. Kind of the best of both worlds, right?


And as our very first guest, you’ll always hold a special place in the story of this home. From peaceful mornings to neighborhood strolls (and maybe even a first step or two ), your visit helped bring the Gem to life in the most meaningful way.


We also really appreciate you letting us know that the 4-star on property condition was an error, the property owner was ready to make things better — these things happen! While we can’t make changes to the rating, your message means a lot and adds helpful context for future guests.


We’d love to welcome you back anytime — the Blue Gem will be here, polished and ready, whenever the next adventure calls!

Leave a Review
4 Bed
3.5 Baths
Sleeps 10

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Island Pearls

Brand New luxury listing at Island Pearls, a premier Key West, chic two-bedroom condo near Duval. Enjoy upscale amenities and elegant decor in this exquisite vacation escape.

Location

527 Fleming Street Back Unit
33040 Key West , FL
United States
24° 33' 24.3216" N, 81° 48' 7.29" W
Florida US

Island Pearls

Request More Information

1st but not last trip to the Keys!

Reviewed by Unknown on 2025-04-11
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Loved our stay at Island Pearls! Great location and very clean!

Florida National Park Trip

Reviewed by Unknown on 2024-11-02
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
This Home is Beautiful inside & out! Incredible Family Room, Kitchen and two bedrooms all decorated beautifully! In a great area, walkable to everything including a grocery store across the street! Would definitely stay here again!

Beautiful oasis near everything

Reviewed by Charlie L. on 2024-07-23
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
The 2 bed/2 bath home is in impeccable condition and perfectly decorated with high-end appliances and furnishings. Three, count them, three coffee makers to cover all your early morning needs (espresso, drip, or Keurig). Great places to eat within 50 yrds, and a quick walk to Duval or Historic Seaport. Do not hesitate to book a stay at Island Pearls!

Excellent Rental

Reviewed by Nichole V. on 2024-09-04
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
We had an absolutely wonderful stay at Island Pearls. The location could not have been better to enjoy the nightlife of Key West. The home was absolutely immaculate with very comfortable and top-of-the-line amenities. We didn't have a chance to use the pool but that and the driveway are a major bonus! The grocery store across the street came in quite handy as well. Note to the owner: This appears to be a newer rental and clearly a lot of thought went into the comfort of your guests. A few things to make their stay easier would be beach/pool towels. There was only one in the house. An iron/steamer combo would be great as most traveling are dressing out of a suitcase. And also some baking sheets for the oven would be a nice addition to the kitchen. This truly was the best home we've rented and we travel ALOT! We will definitely seek out this home again when we visit Key West. Thank you for the great accomodations!

Beautiful property!

Reviewed by Angie G. on 2024-09-15
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
This is a beautiful newly renovated property. It was perfectly located within walking distance of Duvall Street. It has a great front porch for people watching. Is directly across the street from a great little grocery store, which is super convenient. The kitchen is great if you like to cook and it has an awesome set up for coffee. The backyard is perfect for relaxing, but you should know there is also a small cottage behind the house that is a separate rental property. Apparently, if it is rented at the same time as this property, you would be sharing the swimming With strangers. That did not happen to us, but we also did not know it was a possibility until we were already there. The listing should be very clear about this, but it’s not. The property management company was very helpful with any questions we had and super responsive. I would definitely stay here again.
Manager response on 2024-09-20 - Response from Preferred Properties Management LLC
Thank you for the suggestion! The pool is now exclusive to the unit you rented, though there is a long-term rental apartment upstairs. However, the pool remains solely for the main unit’s guests.

NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

Unit Code: 527F-R#2

Island Pearls

Brand New luxury listing at Island Pearls, a premier Key West, chic two-bedroom condo near Duval. Enjoy upscale amenities and elegant decor in this exquisite vacation escape.
Looking for the perfect spot to soak up some sunshine and unwind in Key West? You’ve found it. Island Pearls is a stylish and comfy 2-bedroom, 2-bath vacation rental located right on charming Fleming Street—just one block from all the action on Duval and directly across from the local favorite, Fausto's grocery store. You’ll be close to everything, so no need for a car (though there’s a driveway if you have one). Step inside and you’ll feel instantly at home. The kitchen is modern and fully equipped, with sleek white finishes and custom cabinets that keep everything looking clean and polished. Whether you’re whipping up breakfast or sharing cocktails at the island, it’s a space that makes cooking and gathering easy and fun. The living area is cozy yet modern, with hardwood floors, comfy seating, and just the right amount of Key West charm. Throw open the plantation shutters and let in that sweet Florida sunshine—it’s the perfect spot to kick back after a day of exploring. Both bedrooms are en-suites, thoughtfully designed with comfy beds, soft linens, and fun, tropical wallpaper that’ll remind you you’re on island time. Each has its own private bathroom, making it great for couples, friends, or a small family traveling together. Outside, the private pool and deck are where you’ll probably spend most of your time. Whether you’re sunbathing, taking a dip, or just enjoying the breeze with a drink in hand, it’s a peaceful spot that feels like your own slice of paradise. Island Pearls is all about comfort, convenience, and that laid-back Key West vibe. It’s not just a place to stay—it’s a place to relax, recharge, and make some great memories. P.S. The pool is all yours—no sharing here!
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DatesPrice
04/20/2025 - 04/24/2025$629 /nt
04/20/2025 - 04/24/2025$596 /nt
04/27/2025 - 04/30/2025$596 /nt
04/27/2025 - 04/30/2025$629 /nt
04/01/2025 - 04/30/2025$596 /nt
04/01/2025 - 04/30/2025$673 /nt
05/01/2025 - 05/01/2025$750 /nt
05/01/2025 - 05/01/2025$445 /nt
05/04/2025 - 05/08/2025$445 /nt
05/04/2025 - 05/08/2025$750 /nt
05/11/2025 - 05/15/2025$750 /nt
05/11/2025 - 05/15/2025$445 /nt
05/18/2025 - 05/22/2025$445 /nt
05/18/2025 - 05/22/2025$750 /nt
05/25/2025 - 05/29/2025$750 /nt
05/25/2025 - 05/29/2025$445 /nt
05/01/2025 - 05/31/2025$445 /nt
05/01/2025 - 05/31/2025$808 /nt
05/01/2025 - 05/31/2025$3,258 /wk
05/01/2025 - 05/31/2025$4,274 /wk
05/01/2025 - 05/31/2025$15,726 /month
05/01/2025 - 05/31/2025$15,747 /month
06/01/2025 - 06/05/2025$597 /nt
06/01/2025 - 06/05/2025$532 /nt
06/08/2025 - 06/12/2025$532 /nt
06/08/2025 - 06/12/2025$597 /nt
06/15/2025 - 06/19/2025$532 /nt
06/15/2025 - 06/19/2025$597 /nt
06/22/2025 - 06/26/2025$597 /nt
06/22/2025 - 06/26/2025$532 /nt
06/29/2025 - 06/30/2025$532 /nt
06/29/2025 - 06/30/2025$597 /nt
06/01/2025 - 06/30/2025$532 /nt
06/01/2025 - 06/30/2025$792 /nt
06/01/2025 - 06/30/2025$3,802 /wk
06/01/2025 - 06/30/2025$4,283 /wk
06/01/2025 - 06/30/2025$16,397 /month
07/01/2025 - 07/03/2025$1,011 /nt
07/01/2025 - 07/03/2025$585 /nt
07/06/2025 - 07/10/2025$585 /nt
07/06/2025 - 07/10/2025$1,011 /nt
07/13/2025 - 07/17/2025$585 /nt
07/13/2025 - 07/17/2025$1,011 /nt
07/20/2025 - 07/24/2025$585 /nt
07/20/2025 - 07/24/2025$1,011 /nt
07/27/2025 - 07/31/2025$585 /nt
07/27/2025 - 07/31/2025$1,011 /nt
07/01/2025 - 07/31/2025$585 /nt
07/01/2025 - 07/31/2025$1,122 /nt
07/01/2025 - 07/31/2025$4,382 /wk
07/01/2025 - 07/31/2025$6,389 /wk
07/01/2025 - 07/31/2025$21,457 /month
07/01/2025 - 07/31/2025$20,852 /month
08/03/2025 - 08/07/2025$487 /nt
08/03/2025 - 08/07/2025$748 /nt
08/10/2025 - 08/14/2025$487 /nt
08/10/2025 - 08/14/2025$748 /nt
08/17/2025 - 08/21/2025$487 /nt
08/17/2025 - 08/21/2025$748 /nt
08/24/2025 - 08/28/2025$487 /nt
08/24/2025 - 08/28/2025$748 /nt
08/31/2025 - 08/31/2025$487 /nt
08/31/2025 - 08/31/2025$748 /nt
08/01/2025 - 08/31/2025$487 /nt
08/01/2025 - 08/31/2025$1,022 /nt
08/01/2025 - 08/31/2025$5,438 /wk
08/01/2025 - 08/31/2025$3,989 /wk
08/01/2025 - 08/31/2025$20,572 /month
08/01/2025 - 08/31/2025$20,970 /month
09/01/2025 - 09/04/2025$427 /nt
09/01/2025 - 09/04/2025$608 /nt
09/07/2025 - 09/11/2025$427 /nt
09/07/2025 - 09/11/2025$608 /nt
09/14/2025 - 09/18/2025$427 /nt
09/14/2025 - 09/18/2025$608 /nt
09/21/2025 - 09/25/2025$427 /nt
09/21/2025 - 09/25/2025$608 /nt
09/28/2025 - 09/30/2025$427 /nt
09/28/2025 - 09/30/2025$608 /nt
09/01/2025 - 09/30/2025$427 /nt
09/01/2025 - 09/30/2025$897 /nt
09/01/2025 - 09/30/2025$3,427 /wk
09/01/2025 - 09/30/2025$4,476 /wk
09/01/2025 - 09/30/2025$15,196 /month
10/01/2025 - 10/02/2025$504 /nt
10/01/2025 - 10/02/2025$633 /nt
10/05/2025 - 10/09/2025$504 /nt
10/05/2025 - 10/09/2025$633 /nt
10/12/2025 - 10/16/2025$504 /nt
10/12/2025 - 10/16/2025$633 /nt
10/19/2025 - 10/23/2025$504 /nt
10/19/2025 - 10/23/2025$633 /nt
10/26/2025 - 10/30/2025$504 /nt
10/26/2025 - 10/30/2025$633 /nt
10/01/2025 - 10/31/2025$504 /nt
10/01/2025 - 10/31/2025$954 /nt
10/01/2025 - 10/31/2025$3,926 /wk
10/01/2025 - 10/31/2025$10,165 /wk
10/01/2025 - 10/31/2025$26,013 /month
10/01/2025 - 10/31/2025$26,589 /month
11/01/2025 - 11/30/2025$800 /nt
11/01/2025 - 11/30/2025$1,546 /nt
11/01/2025 - 11/30/2025$6,166 /wk
11/01/2025 - 11/30/2025$9,872 /wk
11/01/2025 - 11/30/2025$32,783 /month
12/01/2025 - 12/31/2025$808 /nt
12/01/2025 - 12/31/2025$1,916 /nt
12/01/2025 - 12/31/2025$6,611 /wk
12/01/2025 - 12/31/2025$10,315 /wk
12/01/2025 - 12/31/2025$35,758 /month
12/01/2025 - 12/31/2025$37,353 /month
5.0000
(5 Review)

1st but not last trip to the Keys!

March 2025
, Rutledge, TN US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Loved our stay at Island Pearls! Great location and very clean!

Florida National Park Trip

October 2024
, Sanford, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This Home is Beautiful inside & out! Incredible Family Room, Kitchen and two bedrooms all decorated beautifully! In a great area, walkable to everything including a grocery store across the street! Would definitely stay here again!

Beautiful property!

September 2024
, Lexington, SC United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
4

This is a beautiful newly renovated property. It was perfectly located within walking distance of Duvall Street. It has a great front porch for people watching. Is directly across the street from a great little grocery store, which is super convenient. The kitchen is great if you like to cook and it has an awesome set up for coffee. The backyard is perfect for relaxing, but you should know there is also a small cottage behind the house that is a separate rental property. Apparently, if it is rented at the same time as this property, you would be sharing the swimming With strangers. That did not happen to us, but we also did not know it was a possibility until we were already there. The listing should be very clear about this, but it’s not. The property management company was very helpful with any questions we had and super responsive. I would definitely stay here again.

Manager's Response

Thank you for the suggestion! The pool is now exclusive to the unit you rented, though there is a long-term rental apartment upstairs. However, the pool remains solely for the main unit’s guests.

Excellent Rental

August 2024
, Naples, Fl United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We had an absolutely wonderful stay at Island Pearls. The location could not have been better to enjoy the nightlife of Key West. The home was absolutely immaculate with very comfortable and top-of-the-line amenities. We didn't have a chance to use the pool but that and the driveway are a major bonus! The grocery store across the street came in quite handy as well. Note to the owner: This appears to be a newer rental and clearly a lot of thought went into the comfort of your guests. A few things to make their stay easier would be beach/pool towels. There was only one in the house. An iron/steamer combo would be great as most traveling are dressing out of a suitcase. And also some baking sheets for the oven would be a nice addition to the kitchen. This truly was the best home we've rented and we travel ALOT! We will definitely seek out this home again when we visit Key West. Thank you for the great accomodations!

Beautiful oasis near everything

July 2024
, TAMPA, FL US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

The 2 bed/2 bath home is in impeccable condition and perfectly decorated with high-end appliances and furnishings. Three, count them, three coffee makers to cover all your early morning needs (espresso, drip, or Keurig). Great places to eat within 50 yrds, and a quick walk to Duval or Historic Seaport. Do not hesitate to book a stay at Island Pearls!

Leave a Review
2 Bed
2 Baths
Sleeps 4

Search Availability

Sweet Tee

Your ultimate escape awaits, where outdoor charm and indoor comfort harmonize seamlessly.

Location

48 Merganser Lane
33040 Key West , FL
United States
24° 34' 39.4716" N, 81° 44' 21.2388" W
Florida US

Sweet Tee

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New Listing-Golf Course Charmer!

Unit Code: 48M

Sweet Tee

Your ultimate escape awaits, where outdoor charm and indoor comfort harmonize seamlessly.
As you make your way into The Sweet Tee, an immediate sense of relaxation and vacation mode envelops you. The carefully chosen soft muted colors and decor create an inviting ambiance that sets the stage for a tranquil getaway. The fully functional kitchen is equipped with all the amenities you would expect to find in your own home. From morning breakfasts to elaborate evening meals, you'll have everything you need at your fingertips. The dining area with seating for four, provides a cozy spot to enjoy your meals, fostering a sense of togetherness and shared experiences. Unwind in the living room which has a 79 inch Smart TV, offering endless entertainment options. For your convenience, a half bathroom is thoughtfully situated on the first floor without having to ascend to the second floor. Additionally, the washer and dryer are conveniently located on the same level enabling you to keep up with your laundry needs. When it's time to retire upstairs, you'll find the retreats two bedrooms. These cozy sanctuaries provide the perfect spaces to rest and rejuvenate after your day's adventures. Positioned between the bedrooms in the hallway is a full bathroom. Each bedroom is equipped with its own television to unwind in your own personal space. This beautiful unit offers a variety of outdoor spaces to suit your preferences. Start your day by sipping your morning coffee on the lovely screened in porch, where you can take in the tranquil environment while staying shielded from the elements. In your inclined to bask in the sunlight, an inviting lower deck awaits your outside, ensconced in lush Florida landscaping that creates a natural oasis. As you unwind on the deck, you have the added pleasure of a view of the 8th hole on the golf course. All in all, The Green Door Retreat is a carefully curated space where comfort, functionality, and relaxation seamlessly blend. It's a place where you can truly unwind, recharge, and make lasting memories during your stay.
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DatesPrice
05/01/2025 - 05/31/2025$154 /nt
05/01/2025 - 05/31/2025$163 /nt
06/01/2025 - 06/30/2025$176 /nt
07/01/2025 - 07/31/2025$181 /nt
08/01/2025 - 08/31/2025$170 /nt
08/01/2025 - 08/31/2025$171 /nt
09/01/2025 - 09/30/2025$166 /nt
10/01/2025 - 10/31/2025$196 /nt
11/01/2025 - 11/30/2025$196 /nt
12/01/2025 - 12/31/2025$281 /nt
Leave a Review
2 Bed
1.5 Baths
Sleeps 4

Search Availability

Sea La Vie

**Sea La Vie** is a 3-bedroom, 3-bath oceanfront home in Cudjoe Key, FL, offering breathtaking views and a perfect blend of relaxation and fun. In-water docking, a screened veranda for dining, WiFi & parking, Sea La Vie is ideal for a month-long escape.

Location

22936 Teach Lane
33042 Cudjoe Key , FL
United States
24° 39' 11.8476" N, 81° 28' 33.8988" W
Florida US

Sea La Vie

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Sea La Vie: Your Oceanfront Escape in Cudjoe Key, Florida 3BD/3BA

Unit Code: 22936T

Sea La Vie

**Sea La Vie** is a 3-bedroom, 3-bath oceanfront home in Cudjoe Key, FL, offering breathtaking views and a perfect blend of relaxation and fun. In-water docking, a screened veranda for dining, WiFi & parking, Sea La Vie is ideal for a month-long escape.
Sea La Vie: Oceanfront Vacation Rental in Cudjoe Key, Florida Looking for the perfect oceanfront getaway in the Florida Keys? Welcome to Sea La Vie, a 3-bedroom, 3-bathroom elevated home in Cudjoe Key, offering stunning Atlantic Ocean views, modern amenities, and a relaxing atmosphere. Please note: A 30-day minimum stay is required due to local ordinances. Why Choose Sea La Vie? * Prime Location: Nestled in the serene Cudjoe Bay, steps from crystal-clear waters and endless ocean adventures. * Spacious Layout: Features 3 bedrooms and 3 bathrooms, including a master suite with a king-size bed and en suite bathroom. * Open-Concept Design: Bright, airy living space with ocean views and a fully equipped kitchen for easy meal prep. Outdoor Highlights * Screened Veranda: Perfect for morning coffee, sunset dinners, or simply enjoying the sea breeze. * Dock Access: Swim, fish, or dock your boat (up to 40 feet with in-water docking). * Relaxation Spaces: Lounge in the hammock, grill your fresh catch, or stargaze after a day of adventure. Key Amenities * High-speed WiFi to stay connected. * Linens and essentials provided for a hassle-free stay. * Dedicated parking space with additional trailer parking in the large front yard. * Fully equipped kitchen with counter seating and a cozy dining area. Perfect for Extended Stays Sea La Vie is designed for month-long rentals, making it ideal for extended vacations in the Florida Keys. Whether you’re boating, fishing, or simply unwinding, this home offers the perfect blend of comfort and adventure. Book Your Stay Today! Escape to Sea La Vie and experience oceanfront living at its finest. Secure your dates now and start planning your dream vacation!
April 2025
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DatesPrice
05/01/2025 - 05/31/2025$106 /nt
05/01/2025 - 05/31/2025$117 /nt
06/01/2025 - 06/30/2025$226 /nt
06/01/2025 - 06/30/2025$228 /nt
07/01/2025 - 07/31/2025$325 /nt
07/01/2025 - 07/31/2025$341 /nt
08/01/2025 - 08/31/2025$261 /nt
08/01/2025 - 08/31/2025$268 /nt
09/01/2025 - 09/30/2025$170 /nt
09/01/2025 - 09/30/2025$173 /nt
10/01/2025 - 10/31/2025$166 /nt
10/01/2025 - 10/31/2025$168 /nt
11/01/2025 - 11/30/2025$254 /nt
11/01/2025 - 11/30/2025$256 /nt
12/01/2025 - 12/31/2025$293 /nt
12/01/2025 - 12/31/2025$321 /nt
Leave a Review
3 Bed
3 Baths
Sleeps 6

Search Availability

Gumbo Limbo Cottage

Escape to The Gumbo Limbo Cottage, a charming 2BR, 2.5BA vacation rental with indoor-outdoor living and lush backyard oasis in laid-back Key West

Location

1112 Margaret Street
33040 Key West , FL
United States
24° 33' 9.072" N, 81° 47' 38.184" W
Florida US

Gumbo Limbo Cottage

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Tropical escape

Reviewed by Emily R. on 2025-04-22
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
We have stayed at the cottage twice and have just reserved it for a third visit. Aside from the numerous supplies and comforts, the cottage is art-filled and charming. We couldn’t get enough of the backyard deck and will dream of it until we return.

A Home Away From Home

Reviewed by Unknown on 2025-02-15
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
This was our second January stay. It was nice to return to a comfortable place. The house has everything you need, and then some. The location is perfect —near the buzz of Duval Street, yet apart, and a turn in the other direction has you at the gulf waters for scenic running or walking. The house has a comfortable seating area for reading or watching tv; outside is a private deck with green space. The kitchen had all we needed.

Charming cottage

Reviewed by Emily R. on 2024-04-16
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Lovely conch cottage filled with local art and situated in a private tropical garden. We immediately reserved the cottage for next year!
Manager response on 2024-04-19 - Response from Preferred Properties Management LLC
Thank you for your review and we are thrilled to have you back next year!

Convenient, comfortable and charming

Reviewed by Unknown on 2024-02-02
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Property managers are responsive and helpful. Owners have paid attention to detail and it is well-equipped. It is nicely-decorated, just a comfortable place to be. The green space and deck are attractive and useful.
Manager response on 2024-02-09 - Response from Preferred Properties Management LLC
Elizabeth, Thank you so much for your kind review and for staying with us at Gumbo Limbo. We greatly appreciate your comments and always strive to maintain high standards and meet our guests expectations. Please let us know if we can be of further help with your future vacation plans We look forward to seeing you back in Key West very soon! All the best! The Preferred Properties Team

Delight in Paradise!

Reviewed by Maura F. on 2024-03-02
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Gumbo Limbo exceeded expectations! The layout worked perfectly for my parents and I during our month long stay, and the front room was perfect for remote work. The house felt clean and well maintained, and all of the bed linens and towels were fresh/new (it’s the small things!). My only recommendation would be one or two more comfortable chairs for the deck, to be able to take more full advantage of the gorgeous backyard.
Manager response on 2024-03-21 - Response from Preferred Properties Management LLC
Thank you for the wonderful review. We will certainly pass along the suggestion for some extra lounge chairs.

Escape to The Gumbo Limbo Cottage, a charming 2BR, 2.5BA vacation rental

Unit Code: 1112M

Gumbo Limbo Cottage

Escape to The Gumbo Limbo Cottage, a charming 2BR, 2.5BA vacation rental with indoor-outdoor living and lush backyard oasis in laid-back Key West
Escape to the laid-back charm of Key West with The Gumbo Limbo Cottage, a beautiful and beachy vacation rental. Nestled in the heart of the island, this charming 1933 shotgun house has been impeccably restored and uniquely decorated, creating a tranquil and inviting atmosphere for your month-long getaway. As soon as you step inside, you'll be greeted by hardwood floors and vaulted ceilings that flow throughout the home. The front reading room, complete with a small refrigerator and desk, is the perfect spot for an early morning coffee or an afternoon nap, while the foyer doubles as a dining room with seating for four. The master bedroom is just inside French doors that lead to a king-size bed and a separate bathroom, including a private outdoor shower that can be accessed via a side door off of the bathroom. The guest room features a comfortable queen size bed, and both rooms are located off the main dining area, along with a guest bathroom with a large soaker tub and shower combo. The open living room and kitchen provide the perfect space for entertaining and cooking for your family and guests. The kitchen is complete with dishware and cookware, ready for you to create your own delicious items. There is countertop seating for two and a gas grill on the lower deck for BBQs. When the living room becomes too warm, you can lower the solar screens to let in natural light without the heat. The sliding glass doors open to the sundeck, complete with a table for six and lounging furniture, making it easy to enjoy indoor-outdoor living. The backyard is a true oasis, with lush Florida foliage and a large Florida almond tree, and Gumbo Limbo, which are native to Key West. Spend your days lounging on the sundeck or exploring all that this vibrant island has to offer. And, when it's time to wind down, retire to the comfort of your cozy home-away-from-home, complete with linens included and free WiFi. Please inquire about our pet policy. Don't miss out on the opportunity to experience the laid-back charm of Key West this winter - book your stay at this beautiful vacation rental today! ------------- Free WiFi Cookware, Dishware, linens, & towels are provided. Monthly Rental Only: Due to a local city ordinance, the property is not licensed to be rented for less than 29 days
April 2025
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DatesPrice
05/01/2025 - 05/31/2025$230 /nt
05/01/2025 - 05/31/2025$244 /nt
06/01/2025 - 06/30/2025$219 /nt
07/01/2025 - 07/31/2025$226 /nt
08/01/2025 - 08/31/2025$186 /nt
09/01/2025 - 09/30/2025$186 /nt
10/01/2025 - 10/31/2025$231 /nt
11/01/2025 - 11/30/2025$231 /nt
12/01/2025 - 12/31/2025$281 /nt
5.0000
(7 Review)

Peace in the Tropics

February 2023

Overall
5

Extremely quiet and private backyard. Very clean, tastefully decorated and within walking distance to beaches, shops, bars, restaurants, museums, and art galleries. I highly recommend this property.

Tropical escape

February 2025
, Washington, DC US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

We have stayed at the cottage twice and have just reserved it for a third visit. Aside from the numerous supplies and comforts, the cottage is art-filled and charming. We couldn’t get enough of the backyard deck and will dream of it until we return.

A Home Away From Home

January 2025
, Lexington, KY Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This was our second January stay. It was nice to return to a comfortable place. The house has everything you need, and then some. The location is perfect —near the buzz of Duval Street, yet apart, and a turn in the other direction has you at the gulf waters for scenic running or walking. The house has a comfortable seating area for reading or watching tv; outside is a private deck with green space. The kitchen had all we needed.

Charming cottage

March 2024
, Washington, DC US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Lovely conch cottage filled with local art and situated in a private tropical garden. We immediately reserved the cottage for next year!

Manager's Response

Thank you for your review and we are thrilled to have you back next year!

Delight in Paradise!

February 2024
, Jamaica Plain, MA United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Gumbo Limbo exceeded expectations! The layout worked perfectly for my parents and I during our month long stay, and the front room was perfect for remote work. The house felt clean and well maintained, and all of the bed linens and towels were fresh/new (it’s the small things!). My only recommendation would be one or two more comfortable chairs for the deck, to be able to take more full advantage of the gorgeous backyard.

Manager's Response

Thank you for the wonderful review. We will certainly pass along the suggestion for some extra lounge chairs.

Convenient, comfortable and charming

January 2024
, Lexington, KY US

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Property managers are responsive and helpful. Owners have paid attention to detail and it is well-equipped. It is nicely-decorated, just a comfortable place to be. The green space and deck are attractive and useful.

Manager's Response

Elizabeth, Thank you so much for your kind review and for staying with us at Gumbo Limbo. We greatly appreciate your comments and always strive to maintain high standards and meet our guests expectations. Please let us know if we can be of further help with your future vacation plans We look forward to seeing you back in Key West very soon! All the best! The Preferred Properties Team

Convenient, comfortable and charming

January 2024
, Lexington, KY Unknown

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Property managers are responsive and helpful. Owners have paid attention to detail and it is well-equipped. It is nicely-decorated, just a comfortable place to be. The green space and deck are attractive and useful.

Manager's Response

Elizabeth, Thank you so much for your kind review and for staying with us at Gumbo Limbo. We greatly appreciate your comments and always strive to maintain high standards and meet our guests expectations. Please let us know if we can be of further help with your future vacation plans We look forward to seeing you back in Key West very soon! All the best! The Preferred Properties Team

Leave a Review
2 Bed
2.5 Baths
Sleeps 4

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Caroline On My Mind

Beautiful Key West Retreat 1 Block from Duval Street

Location

616 Caroline St #4
33040 Key West , FL
United States
24° 33' 32.256" N, 81° 48' 9.216" W
Florida US

Caroline On My Mind

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Caroline On My Mind-New Listing-Light, Bright and Airy!

Unit Code: 616C

Caroline On My Mind

Beautiful Key West Retreat 1 Block from Duval Street
This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting experience. The location is highlighted as a key factor, emphasizing the significance of its surroundings. As you enter "Caroline on My Mind," you'll notice a stairway adorned with wainscoting, leading you to the entry. The home boasts an open and comfortable living area, allowing ample natural light to fill the space. The living room features high-vaulted ceilings and cathedral windows, creating an instant vacation-like ambiance. There is a flat-top electric stove, two-door refrigerator, and dishwasher available to facilitate your cooking needs. The countertop seating for three also provides a convenient space for dining or socializing while in the kitchen. Overall, the kitchen offers functionality and amenities that will allow you to enjoy preparing meals during your stay. The guest room is located on the same floor, accompanied by a full shower bathroom and a washer/dryer for added convenience. One of the standout features of this home is the large balcony that overlooks Caroline Street below. Equipped with fans, the balcony serves as a perfect spot for savoring morning coffee or enjoying cocktails. A four-person table allows for al fresco dining, while you can also engage in people-watching and relish the refreshing evening breezes of Key West. To access the floor above, a spiral staircase takes you to the treetops, providing a unique vantage point. The primary bedroom on this floor features a queen-sized bed that can be converted into two twins upon request. Additionally, for those who need to work while in paradise, there is a functional desk with great views, enabling mental breaks amidst the scenic surroundings. Lastly, there's a skylight in the primary bedroom, offering the opportunity for star gazing while lying in bed at night, adding to the enchanting atmosphere of this Key West home. Monthly Rental Only Shared Pool/6 units Pets Not Allowed
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05/01/2025 - 05/31/2025$170 /nt
05/01/2025 - 05/31/2025$180 /nt
06/01/2025 - 06/30/2025$205 /nt
07/01/2025 - 07/31/2025$211 /nt
08/01/2025 - 08/31/2025$181 /nt
09/01/2025 - 09/30/2025$181 /nt
10/01/2025 - 10/31/2025$256 /nt
11/01/2025 - 11/30/2025$256 /nt
12/01/2025 - 12/31/2025$451 /nt
Leave a Review
2 Bed
2 Baths
Sleeps 4

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Ashe Street Serenade

Discover luxury in this 3-bed, 3.5-bath Old Town oasis. Revel in the gourmet kitchen, private pool, and elegant decor, while exploring Key West's vibrant attractions. Embrace serenity and adventure in paradise.

Location

613 Ashe Street
33040 Key West , FL
United States
24° 33' 33.1128" N, 81° 47' 38.7384" W
Florida US

Ashe Street Serenade

Request More Information

Serenaded by Ashe Street

Reviewed by Unknown on 2025-04-15
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
This is a very special house on a very special street. Spacious & extremely well-appointed it was the perfect property for us for a three-month stay. We are returning again next year. Having lived in Key West for 24+ years, this was our first time renting and it lived up to our expectations.

Our Preferred choice for Key West rentals

Reviewed by Christine B. on 2024-01-16
Overall satisfaction
Services from rental manager
Cleanliness
Location
Property condition
Recommend to Others
Preferred is a good company with attentive service. We were very pleased.
Manager response on 2024-02-10 - Response from Preferred Properties Management LLC
Good afternoon. We want to thank you and say how much we appreciate you staying with us at Ashe St Serenade. We trust your time here was enjoyable and that we were able to address any concerns during your stay. Please let us know if we can be of help with any future vacation plans. We hope you will return to Key West and paradise very soon. The Preferred Properties Team

Ashe St Serenade: 3BD/3.5BA Luxury Retreat, Private Pool in an Island Oasis.

Unit Code: 613A

Ashe Street Serenade

Discover luxury in this 3-bed, 3.5-bath Old Town oasis. Revel in the gourmet kitchen, private pool, and elegant decor, while exploring Key West's vibrant attractions. Embrace serenity and adventure in paradise.
Welcome to your dream getaway in the charming Old Town Key West, where the tranquility of island living meets the excitement of tropical adventures. This enchanting 3 bedroom, 3.5 bathroom monthly vacation rental offers a serene retreat amidst the vibrant atmosphere of the island, ensuring an unforgettable experience for you and your loved ones. As you enter this magnificent residence, you'll be captivated by the dramatic ceiling heights, elegant wood flooring, and designer accents that exude sophistication and coastal elegance. The open-concept gourmet kitchen invites you to indulge in Key West's culinary delights, featuring a 48" gas range, an expansive island with seating, quartz countertops, stainless steel appliances, and a wine chiller. The telescoping door wall connects the indoor dining area to the outdoor seating, creating the perfect ambiance for memorable meals and tropical libations. For entertaining purposes, the residence offers comfortable seating arrangements that cater to socializing and dining. In addition to the living room, there is a separate dining room that accommodates up to six people. Furthermore, the kitchen is equipped with an island that offers additional seating for up to four people. The primary suite, situated on the first level, provides a tranquil retreat for relaxation and rest. It features a spacious king-size bed, ensuring a comfortable and luxurious sleeping experience. Within the master suite, you'll find the ensuite, a private bathroom attached exclusively to the primary bedroom. The ensuite is designed to enhance your indulgence and rejuvenation. It boasts a large soaker tub, inviting you to immerse yourself in a soothing bath or enjoy a sizable walk-in shower. On the second floor of the residence, you will find two additional guest bedrooms, each equipped with a king-size bed and ensuite bathrooms with showers. These guest bedrooms are designed to provide a comfortable and private space for your family and friends during their stay. Moreover, the second floor also features a bonus space, dedicated to providing a comfortable area for family and friends to relax and unwind. Step outside to your private oasis, where the lush landscaping and gentle sounds of the waterfall create a soothing backdrop for leisurely afternoons by the heated pool. The composite decking offers an inviting space for sunbathing, lounging poolside, or enjoying the island breeze. Nestled on a peaceful street just a short stroll from Duval Street and the Historic Seaport, you'll be ideally positioned to explore Key West's famous attractions, delightful shops, world-class dining, and vibrant nightlife. With its walkable and bike-friendly location, your island adventures are just steps away from your luxurious retreat. Immerse yourself in the enchanting atmosphere of Key West and create lasting memories with your loved ones at this stunning vacation rental. From its exquisite design and modern amenities to its unbeatable location, your unforgettable island getaway awaits. Book your stay at this luxurious Key West oasis today.
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DatesPrice
05/01/2025 - 05/31/2025$374 /nt
05/01/2025 - 05/31/2025$397 /nt
06/01/2025 - 06/30/2025$404 /nt
07/01/2025 - 07/31/2025$366 /nt
08/01/2025 - 08/31/2025$322 /nt
09/01/2025 - 09/30/2025$316 /nt
10/01/2025 - 10/31/2025$456 /nt
11/01/2025 - 11/30/2025$366 /nt
12/01/2025 - 12/31/2025$566 /nt
5.0000
(2 Review)

Serenaded by Ashe Street

January 2025
, New York, NY United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

This is a very special house on a very special street. Spacious & extremely well-appointed it was the perfect property for us for a three-month stay. We are returning again next year. Having lived in Key West for 24+ years, this was our first time renting and it lived up to our expectations.

Our Preferred choice for Key West rentals

November 2023
, Key West, Fl United States

Overall
5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5

Preferred is a good company with attentive service. We were very pleased.

Manager's Response

Good afternoon. We want to thank you and say how much we appreciate you staying with us at Ashe St Serenade. We trust your time here was enjoyable and that we were able to address any concerns during your stay. Please let us know if we can be of help with any future vacation plans. We hope you will return to Key West and paradise very soon. The Preferred Properties Team

Leave a Review
3 Bed
3.5 Baths
Sleeps 6

Search Availability

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