Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath
WELCOME TO PINEAPPLE COTTAGE!
The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town Key West. It offers a private pool and is just half a block away from Duval Street, making it an ideal tropical oasis for your vacation.
As you enter the cottage, you'll step onto a deck overlooking the backyard, where you'll find the inviting private pool, a charcoal grill, and various seating and lounging areas surrounded by lush tropical landscaping, ensuring your privacy and creating a serene atmosphere.
Inside, the cottage features an open living area and kitchen space, perfect for easy flow and entertaining. The living area is equipped with a fully loaded entertainment system, including cable TV, a sound system, CD player, and DVD player. You'll also find board games for some indoor fun, whether in the living room or at the outdoor table. The kitchen is fully equipped and includes a breakfast bar with bar chairs, providing a convenient division from the couch and comfortable viewing chairs in the living room.
On the first level of the cottage, there is a full bathroom and a hidden bedroom tucked away to the right of the kitchen. This bedroom features a queen-size bed and all the amenities necessary to ensure a comfortable stay. You can choose to keep the curtains and blinds closed for a peaceful sleep-in or open them up to let the tropical sun awaken you for an adventurous day.
The second floor of the cottage offers another spacious living area with cable TV, a large comfortable sofa, and chairs for relaxation. The master bedroom on this level boasts a king-size bed and an en-suite full bathroom. Additionally, the washer and dryer are conveniently located in this bathroom for the guests' use.
The backyard of the Pineapple Cottage is a true haven. With its sparkling pool, grill, and dining areas, you have everything you need to enjoy meals at home while entertaining and making the most of your vacation. The cottage location in the Old Town district allows you to easily walk to Duval Street, where you'll find a variety of shopping, beaches, and restaurants in close proximity.
Overall, Pineapple Cottage offers top-of-the-line amenities and comfort, ensuring a delightful and enjoyable stay in Key West.
Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know.
Guests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check.
**Pool heat is optional at $25 a day.** Virtual Tour Url: https://my.matterport.com/show/?m=khS5nBShNSP
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
About the area
Key West
Located near the beach, this cottage is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. USCGC Ingham Maritime Museum and Mel Fisher Maritime Museum are also worth visiting. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and ecotours nearby.
Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
Florida Keys National Marine Sanctuary - 11 min walk - 0.9 km
Mallory Square - 12 min walk - 1.0 km
Southernmost Point - 15 min walk - 1.3 km
Getting around
Key West, FL (EYW-Key West Intl.) - 12 min drive
Restaurants
Margaritaville - 3 min walk
Mangoes Restaurant - 3 min walk
Jack Flats - 3 min walk
Kaya Island Eats - 3 min walk
DJ's Clam Shack - 3 min walk
Frequently asked questions
Does Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath?
As of 16 May 2026, prices found for a 1-night stay for 2 adults at Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath on 26 June 2026 start from AU$992, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath pet-friendly?
No, pets are not allowed at this property.
How much is parking at Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath?
On-site parking is available at the property.
What time is check-in at Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath?
Check-in begins at 4:00 PM.
What time is check-out at Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath?
Checkout is at 10:00 AM.
Where is Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath located?
Located in Old Town Key West, this cottage is within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum. Florida Keys Beaches and Mallory Square are also within 15 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
The Preferred Properties staff were very friendly and wonderful to work with.
This place is truly a hidden gem. Great location. Right near Duval but yet secluded. Highly recommend the Pineapple Cottage.
Bryan B.
Stayed 4 nights in Oct 2025
From a partner site
10/10 Excellent
Judith L.
13 Jan 2026
A Peaceful Retreat
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was more than satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
A lovely place with the courtyard and pool providing a relaxing environment. We ate most of our meals on the deck.
Location is perfect, property and pool are awesome!
Marianne M.
Stayed 7 nights in Apr 2023
From a partner site
10/10 Excellent
Stacie D.
14 Mar 2026
Pineapple Cottage
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
We’ve stayed in this home several times. The location is close to everything you want/need and still provides a lot of privacy. Angela and Kevin at Preferred are outstanding to work with and the reason we hope to continue to rent properties from this company. Angela makes the process smooth from start to finish and Kevin is there for any of our maintenance questions. Thank you to another wonderful stay you two!
Stacie D.
From a partner site
10/10 Excellent
JIM W.
2 Sept 2025
Labor Day Stay
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
We had a great time in your fantastic home
The location was amazing. We could walk to all kinds of things but it still felt like you were in your own private oasis in the pool/yard. Couldn’t have asked for a better spot.
We loved staying there! The whole house was amazing. The bedrooms were just the right size. And the showers in both bathrooms were amazing.The pool was just the right size and great for evening relaxation. And ot was so close to Duval Street was awesome!.
Lovely place Great location. Would definitely go again
Garry J.
Stayed 4 nights in Jan 2024
Response from VrboOwner on 24 Jan 2024
Thanks so much for staying with us at Pineapple Cottage. We are happy that you enjoyed your time here. Please let us know if we can be of any help with future vacation rental plans We hope to see you again soon in Key West!
From a partner site
10/10 Excellent
12 Oct 2025
Little piece of paradise
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Great experience. Excellent support staff, cozy comfortable home, beautiful location steps off duval street, could not have asked for better.
Great place to stay, around everything but the courtyard is your private escape!
Mark K.
Stayed 5 nights in Nov 2023
Response from VrboOwner on 24 Jan 2024
Thanks so much for staying with us at Pineapple Cottage. Please let us know if we can be of help with any future vacation rental needs. We look forward to hopefully seeing you back soon in Key West!
Very nice property, well maintained, great pool and backyard. Perfect location practically in the middle of all the activities and right off of Duval Street. Easy walking to excursions and restaurants. Would stay again
Paul G.
Stayed 3 nights in Jun 2023
Response from VrboOwner on 26 July 2023
Thanks for your review! We totally agree that Pineapple Cottage location is perfect and we are glad you enjoyed the property! We do hope you stay with us again when you come back to Key West!