Pineapple Cottage

We had a wonderful time at this oasis. Off of Duval St so you are in your own little world. Quiet and comfortable it is perfect for two couples. Upstairs has a great main suite with a big sitting room. Clean and ready for your use. Property management company is wonderful with communication. Property very well maintained. Great location. You can walk everywhere from here. Coffee shop right next door, plenty of foodie spots in every direction.

The Pineapple Cottage is a great place to stay if you are heading to key west. Location is prime with loads of space for outdoor relaxation. Quiet at night even though the location is in the heart of town. Management company was great with communication and made our stay a breeze.

This was our third visit to Pineapple Cottage, we love this place and will continue to come back. The location can not be beat, everything walking distance. Thank again Preferred Properties for another great stay.

We had the most perfect stay at pineapple cottage. It was absolutely brilliant- the pool was perfect, the house was immaculate but above all the location was incredible. It was just a 2 minute walk from Duval Street and all the exciting bars and shops, but once in the property all the hustle disappeared and it was serene. Highly recommend

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Stayed with Family of Five during July.

Manager's Response

Had a great time in Key West while staying at the pineapple cottage. The home was clean are ready early. Management kept us I formed throughout the booking process and leading up to our arrival. AC worked great and private pool was the main event. Spent evenings cooling off after a day waking around town or relaxing on the beach. Thank you.

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Amazing!

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Great location. Lots of privacy and quiet time when you need it. Will be back..

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This is our second time staying at Pineapple Cottage. We absolutely love this rental. It is in the heart of everything, yet so private at the same time. Everything you need is here. We will be back.

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Pineapple Cottage is perfectly located just a half block from Duval. The cottage was exceptionally clean. Only negative was the beds, new mattresses would make the cottage perfect. Out door area was also very nice, with a grill and plenty of seating. We would definitely recommend this cottage to friends and family.

Manager's Response

We had a wonderful time at Pineapple cottage.
Great location, great pool, comfortable home and easy to reach property manager. Thank you.

Manager's Response

Staying at the Pineapple Cottage allows you to have an effortless enjoyable vacation in Key West! It's central location allows you to walk wherever you want to go. No need to rent any type of transportation. The private pool retreat allows you to just relax when you choose to. This is our 3rd stay and we will be back for our 4th!

Manager's Response

Preferred Properties was the best management company I have ever worked with in Key West. Thank you so much for the great communication, kind and friendly service.
The downstairs bed had seen better days, but okay for one person. otherwise the property was absolutely beautiful, quiet and so private. All the comforts of home were provided.

Manager's Response

If we ever go back to Key West, we are absolutely going to stay here. The house is private and in a perfect location. Thank you!

This cottage is just adorable! Very spacious with bedrooms up and down. We loved the outdoor patio as we had coffee every morning out there. We would relax in the pool in the afternoon. Everything was within walking distance.

We enjoyed our stay so much! It is close to the busy Duval street, but at the same time feels very private. Great experience overall, although I would have proffered a heads up about a pool guy showing up and just walking though in the middle of the day - was very much unexpected :)

good

Perfect location. Management was great. Pool was relaxing.

This place is amazing. You can’t beat the location, walk to everything in minutes. The house and pool area were great. Definitely will be my go to place to rent.

Awesome!

Great location Clean and well appointed. Enjoyed our stay. Group of 4, easily accommodated.

Great location, perfect layout for two couples, very private pool

Great Property! Had everything you could possibly need. Enjoyed Family time in the pool and the location was perfect!

Always LOVE staying at Pineapple Cottage. The place itself is awesome, and you can’t beat the location. The staff, especially this most recent time, was beyond friendly; really great.

We’ve stayed at this home several times. The location is great with several restaurants and shops in close walking distance. The layout is perfect for two couples. The outdoor space is exactly what we were looking for with a large pool and plenty of deck/seating space. Preferred Properties and Angela specifically are easy to work with and very responsive. We look forward to booking this place again.

Pineapple Cottage is a great place! So close to Duval St. but you wouldn’t know it from the house. Love the pool and the grounds. We’ve stayed there 3 years in a row and would stay there again and again.

Great place and so easily accessible to everything. Definitely enjoyed the heated pool!

Very private oasis in a busy town. Nicely appointed, clean VRBO with beautiful patio space and awesome heated pool. Great location for popular tourist destinations. Has it's own dedicated off-street parking space. Excellent communication with Preferred properties folks. Would highly recommend.

Pineapple cottage is amazing in every way.....clean, well appointed kitchen, great outdoor space and great location. The grocery store just a block away. close to duval for all the restaurants and bars but far enough away to have peace and guiet. We’ve stayed her 2 years in a row and hope to be back next year....love it !

Pineapple Cottage has everything needed for a great getaway close to the Old Town hotspots yet quiet enough to relax by the pool and chill. We will definitely seek to stay again. Working the the staff from Preferred Properties was easy, open and concise communication!

Pineapple Cottage was a great location just off Duval. Enjoyed the pool in the evenings. Management was great. Highly recommend!

Everything about this property was great. The location was perfect. The backyard is very secluded and the pool was wonderful for relaxing after a few hours of action on Duval street. The pool was clean and warm and totally private. The Preferred Properties office is very close and the people there were very helpful and professional. We will definitely stay here again.

Great location, close to everything! The staff at the rental agency was very communicative and helpful. The house was perfect for two couples and room for more. We enjoyed the pool too.

This place was amazing from location to bedding to NO noise and ALL the privacy a person and family could need!. Everything was amazing! The staff at the office welcomed us when we were there early and Kevin was able to get us what we needed. Angela was a HUGE help as well- even keeping us posted after the Hurricane came through before we came down. Clean, TONS of space and convenient. Will definitely be coming back!!!!!

Adorable cottage centrally located. very spacious. the outdoor area was spectacular, the concierge service was incredible. can’t wait to come back.

My husband and I along with my sister and her husband stayed at the cottage for a second time this summer and it was everything we hoped for! The property was very clean and very private. We loved hanging out in the pool and the location to Duval street can't be beat! The Preferred Properties team was also so helpful. kind and accommodating to our needs. We will definitely be back again!

We absolutely LOVED our time at this property. The location was perfect. Everything about the property was exceptional. The outdoor space was a relaxing retreat. Indoor space was clean, updated and had everything we needed for our stay. We can’t wait to come back and have already recommended this property to friends. Thank you for making our time in Key West special!

This Key West house was even better in person! So clean, so private, and best location to everything!!!! Will absolutely stay here again in the future.

I dont know how many houses like this are hid away in Key West, but we are very fortunate to have found the Pineapple Cottage. Located so close to everything. Go walking along Duval, get a little sweaty, just come right back and jump in the pool! With your very own parking spot, located right behind the house, we never had to worry.

Seriously I am concerned if I say just how much my girls and I enjoyed our stay the price will go up and availability will go down! Just a spectacular home in a perfect location! Old town Key West is so much fun for everyone! We can’t wait to return and hopefully stay at pineapple cottage...

Pineapple Cottage is a hidden gem. From the cozy comfortable cottage to the beautiful lush pool area. This is a great place to relax!

Great property ,Great location ,Awesome management team, we will definitely be back !

As always Great stay at The Pineapple Cottage. Great location , clean. Can't wait for next year!!

We had a wonderful experience staying at Pineapple Cottage. As nice as the interior was, the outside living space was magnificent. Except for sleeping inside, we were outside enjoying the pool. Definitely a place we would stay again and suggest to other people.

This is one of our favorite houses to stay in. The location is fantastic, walkable to everything, 1/2 block from Duval, but very private. Highly recommend. The team at Preferred Properties is top notch.

We had a lovely vacation at Pineapple Cottage. Everything lived up to the pictures and descriptions - which does not always occur. We loved the location, close to everything we wanted to do, yet quiet and private. The pool and deck were perfect for late afternoon relaxation. The only negative was the parking spot (which isn't always available at other properties). The bad thing was, it was next to trees, and evidently the local birds did not approve of our car, and showed their feelings by decorating it with their droppings. (Not sure how to fix that, but it was a negative...) We'd return in a heartbeat for our next visit to Key West!

Location...fabulous. Grocery store one block
Outdoor space...fabulous......grill...fabulous
Pool...fabulous
Kitchen ...fabulous....everything you could possibly need
Best place in Key West.....we stayed other places but none compare
No need to look further this place has it all...fabulous
Great customer service...Angela was also fabulous

Most enjoyable. Great location, Nothing like a Key West Christmas!

Everything you need!! Location is perfect 1/2 block off Duval yet no noise. Block from coffee and store, both convenient. Nothing negative about this property. Already planning next year!!

The property was very nice and well maintained. The area is also quiet and in a great location.

We really enjoyed the Pineapple Cottage. It is located for easy access to bars, grocery, restaurants, and other attractions. We loved it!!

Our experience was such an smooth one from renting, arriving, our stay and our departure. The place is amazing! The location was just perfect. We were able to keep our vehicle parked off the street (which is a big thing considering the public parking situation). We walked just about anywhere we needed to go which was a blessing. We could walk to sunset each day!
For four adults, the accommodations were awesome and exactly what we hoped for. The pictures and the property matched well. Beds were comfortable, all appliances were in good working order, a/c was good and the full size washer and dryer was a great bonus!
We would rent this property again if it is available when we return to Key West. The management company is very professional and keeps you up to date as you get near to your stay.

Our experience was such an smooth one from renting, arriving, our stay and our departure. The place is amazing! The location was just perfect. We were able to keep our vehicle parked off the street (which is a big thing considering the public parking situation). We walked just about anywhere we needed to go which was a blessing. We could walk to sunset each day!
For four adults, the accommodations were awesome and exactly what we hoped for. The pictures and the property matched well. Beds were comfortable, all appliances were in good working order, a/c was good and the full size washer and dryer was a great bonus!
We would rent this property again if it is available when we return to Key West. The management company is very professional and keeps you up to date as you get near to your stay.

Great place to relax and enjoy all Key West has to offer. Location is perfect within a short walk to either end of Duval. We have stayed there many times and its always perfect. The pool and deck area seems like there is nothing around.

Pineapple cottage is a great place to stay in Key West. It is totally private, Very clean and well appointed and in a great location! Preferred Properties Staff were very helpful and accommodating.

This house was perfect! We went in August so it was super hot outside..... the pool was a godsend.
The house was neat and had everything we needed.
I am going to miss waking up and walking a few doors down to get my Cuban con leche coffee
We all loved are daily iguana visits!!!

Pineapple Cottage is perfect for a stay in Key West! So conveniently located but with loads of privacy and equipped with everything you need.

Loved everything about the house. It was very comfortable and exactly as described. Very conveniently located and the pool was the perfect escape from the heat. We would definitely stay here again if we are in Key West.

Loved everything about the house. It was very comfortable and exactly as described. Very conveniently located and the pool was the perfect escape from the heat. We would definitely stay here again if we are in Key West.

We stayed here for five nights in late June. The house was very clean and the pool was amazing. It was a short walk to everything so we didn’t even rent bikes or a golf cart. We had a wonderful time here and hope to visit again in the future.

We had a fantastic stay in this little oasis in the heart of Key West. The pool and landscaping were amazing and provided ample privacy and relaxation. The staff at Preferred Properties were top notch and attentive. Of all the vacation properties we have stayed at, this was by far the cleanest and most well-cared for property we have experienced. We will be back!

We loved our stay at the Pineapple Cottage in Key West! We are a family of two adults and two daughters 18 & 25 years old. The entire experience from the booking, arrival, the stay, and departure was handled in the best possible way by Preferred Properties on behalf of the owners. Such great communication and accessibility (even after hours). The location of the property is ideal; 1/2 block from Duval Street but completely secluded and private with a large (by Key West standards) private swimming pool surrounded by decks. You don't even know you are that close to the craziness of Duval Street when you are sitting by the pool in the back yard. There are breakfast places, coffee houses, restaurants, a small grocery store, and a liquor store all within 2 blocks of the property. The house itself is perfectly laid out and contained absolutely everything we needed during our 1 week stay. The property owners thought of everything! We rented bikes for the week to see the island and Preferred Properties even arranged that for us prior our visit. The property was clean when we arrived and is in good condition considering the amount of rentals they must have at this property all year long. I honestly can't come up with a complaint or downside to staying at this wonderful property. I will recommend that you bring bug spray because it was very buggy (mosquitos and gnats) at the property; however, that is probably just a function of the weather in Key West in June most likely. If there is ever any availability here in the near future, we will definitely come back to the Pineapple Cottage. Once you stay here, it will be your "go to" for lodging in Key West.

We took a 41st wedding anniversary trip with another couple who were celebrating their 50th birthdays. We spent a week in the Keys with our last 3 days at Pineapple Cottage. We definitely saved the best for last, although each of our 3 VRBO properties were wonderful in their own unique way. The location of Pineapple Cottage was awesome! Right in the middle of everything, yet it felt like a private hidden oasis! Well equipped and very comfortable property with its own pool!

The Pineapple Cottage was absolutely perfect!! It was centrally located, fully stocked, clean, spacious and the pool was an oasis. The owner was extremely accommodating and checked in frequently. We had the best time and we will be back! Thanks!!

Our group waited an extra year to visit Key West and we were not disappointed in our choice to stay at the Pineapple Cottage. The house was immaculate! The floor plan was ideal for traveling with another couple as it made it feel like two separate spaces. Every necessary utensil was provided in the kitchen. The pool and outdoor space were amazing and relaxing. We were just steps from Duval but in our own little oasis. We will definitely return!

Location, Location, Great place , clean , Can't wait to return next year

We had a great time in Key West (this was our first time). The Pineapple Cottage was great! The pool was a savior. We were in it every day prior to going out and hitting the town mid-afternoon. Made several iguana friends each day in the backyard...

The home was exactly as advertised. Well appointed and comfortable. The location is perfect - steps away from Duval but hidden away and very private. We will definitely return!

This was our second time renting the Pineapple Cottage and once again it was perfect. The location, the pool, the quiet seclusion, and the cleanliness are excellent. If we come back to KW, we will definitely rent this cottage!

House location could not have been better. The home had everything that you would need. Pool was clean and quite. Privacy was not an issue. I would rent this home again without a 2nd thought.

We had a great time and were extremely impressed by the Pineapple Cottage. On any future visits to Key West, we would only consider staying there again!

Our 2nd stay at Pineapple Cottage was better than our 1st visit back in 2017. The centralized location in Old Town is perfect! No need to rent a vehicle since everything is within a mile! The home and the private pool is truly a wonderful piece of paradise! Can't wait for our 3rd visit!!!

Our 2nd stay at Pineapple Cottage was better than our 1st visit back in 2017. The centralized location in Old Town is perfect! No need to rent a vehicle since everything is within a mile! The home and the private pool is truly a wonderful piece of paradise! Can't wait for our 3rd visit!!!

This was a reschedule due to early 2020 COVID restrictions. The team at PPM assisted us in finding a new date and accomodating our new needs. The property was properly prepared and was well-equipped. This lead to a very enjoyable stay.

We had such a great Thanksgiving in 2019 at Pineapple Cottage we said we’d be back and we made it happen! The house was perfect for our family. Quiet, private and a beautiful backyard and pool. Here’s to our new tradition. We’ll be back in 2021!

My husband and I have stayed at Pineapple Cottage many times. We love the privacy, the pool and we simply feel very comfortable in the cottage! We loved the upgrades! Preferred Properties have always been very good to us, they are indeed number one when it comes to vacation rentals!

Manager's Response

I cannot say enough great things about the staff at Pineapple...they are all amazing!! The house, the pool, and the location was perfect in every way! We rented a vehicle and only used it once to drive to Marathon to look at some properties. If you have no plans to drive anywhere save the money on the rental....the location is within walking distance to everything! We will be back very soon!!

We spent the first half of our vacation at the Pier House and actually preferred this property with its private pool, iguanas, beautiful floral landscape, dedicated parking space, well-appointed kitchen and great location to all in midtown Duval.

Manager's Response

Wonderful property, great location, and superior customer service from Preferred Properties

Manager's Response

We've been coming to Key West for the last 8 seasons. We normally rent from a different company, but they didn't have a home that would work. We couldn't have been happier with Preferred Properties, and Angela specifically. She was great to work with, and the house was one of the best we've stayed in. The location is awesome, and the pool was extremely private, which is what we wanted. We will for sure try to stay here again, if it's available on our next trip.

This rental experience was top-notch from the initial booking to the final departure. Staff was helpful and communication was excellent. Property was immaculate, and exactly as described in the summary. Best experience I've had renting a vacation property - I plan to return to the area every year, and wouldn't dream of using any other agency to help plan my stay.

The property was exactly what we had hoped for and the location was even better than expected. We really enjoyed the pool and the proximity to Duval. The parking spot was an added bonus!

We enjoyed our stay at Pineapple Cottage! It was very neat and clean, exactly as the pictures show. We loved the pool and the fact that you could request to heat it. The cottage is close to shopping and restaurants. In a walks distance to everything we wanted to see. Excellent customer service from the property management. We felt very comfortable and valued as guests. We would love to stay here again in the future.

every aspect of our stay was great, from the booking process to the regular updates to the property itself. Already considering booking for next year. House and pool were amazing and the location could not be beat. Quiet but so close to everything

every aspect of our stay was great, from the booking process to the regular updates to the property itself. Already considering booking for next year. House and pool were amazing and the location could not be beat. Quiet but so close to everything