Unwind in the top-rated pool, your perfect spot for relaxation.
Games
A rare find - enjoy a variety of games available on-site.
Centrally-located
You're never far from where you need to be with this convenient location.
Discover nearby landmarks
Near Duval Street
Sleeps 5•2 bedrooms•3 beds
Popular amenities
Private pool
Onsite parking available
Kitchen
Washing machine
Air-conditioning
Barbecue grill
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
11 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. 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 Smathers 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 ecotours and cycling nearby.
Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
Mallory Square - 11 min walk - 0.9 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
Green Parrot Bar - 3 min walk
Margaritaville - 3 min walk
Wendy's - 5 min walk
Mangoes Restaurant - 3 min walk
801 Bourbon Bar - 5 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 20 Aug, 2026, prices found for a 1-night stay for 2 adults at Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath on 12 Jul, 2027 start from S$4,902, 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.
About the host
Hosted by The Team at Preferred Properties
Languages:
English
Premier Host
They consistently provide great experiences for their guests