Unwind in the top-rated pool, your perfect spot for relaxation.
Games
A rare find - enjoy a variety of games available on-site.
Discover nearby landmarks
Near Duval Street
2 bedrooms2 bathroomsSleeps 5
Popular amenities
Private pool
Onsite parking available
Kitchen
Washing machine
Air-conditioning
Barbecue
Explore the area
Key West, FL
Duval Street
Place, Duval Street
1 min walk
Ernest Hemingway Home and Museum
Place, Ernest Hemingway Home and Museum
9 min walk
Mallory Square
Place, Mallory Square
12 min walk
Key West, FL (EYW-Key West Intl.)
Airport, Key West, FL (EYW-Key West Intl.)
11 min drive
Rooms & beds
2 bedrooms (sleeps 5)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
Other Space 1
1 Double Sofa Bed
2 bathrooms
Bathroom 1
Toilet · Shower only
Bathroom 2
Toilet · Shower only
Spaces
Deck or patio
Kitchen
Dining area
About this property
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. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. 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
Mallory Square - 12 min walk - 1.0 km
Fort Zachary Taylor Historic State Park - 14 min walk - 1.2 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
Kaya Island Eats - 3 min walk
Jack Flats - 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 30 June 2026, prices found for a 1-night stay for 2 adults at Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath on 23 Aug 2026 start from AU$1,078, 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.
Everything was perfect from the property management to the decor of cottage and the location. We will be returning!
Gigi A.
Stayed 3 nights in Jan 2026
From a partner site
10/10 Excellent
Lori B.
19 May 2026
Complete Relaxation
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:
We had a wonderful week of relaxation at Pineapple Cottage celebrating Mother's Day. The pool was perfect, private, and the deck area was great to chill out on, have meals at the huge table, read, and relax. The cottage has a great layout with tons of privacy for two couples. The location can't be beat and there is very little noise to interrupt your vacation.
Lori B.
From a partner site
10/10 Excellent
James H.
4 Mar 2026
Great Vacation in Key West
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.
Perfect property! Communication was top notch! The house had all the extras! Blankets, so many towels, fans, sunscreen, beach towels, pool floats. We have been vacationing in keywest for years and this is by far the nicest place we have ever stayed. Location was perfect. Half block from Duval and surprisingly quiet. Love love love!! We will be back!
Location is perfect, property and pool are awesome!
Marianne M.
Stayed 7 nights in Apr 2023
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.
Amazing property and perfect location just a block from the middle of Duval! Would love to stay here again!
Katie C.
Stayed 5 nights in Oct 2019
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!
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!
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.
Verified traveller
Stayed 3 nights in Feb 2025
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
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!.
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!