Cottage in Key West, FL
5 guests · 2 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this cottage rental
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
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
Amenities at Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath
Non-smoking
No pets allowed
Family friendly
Map of Key West, FL
Ratings and reviews
Summary of reviewsPerfect location, spotless rental, comfortable beds, and private pool. Highly recommended!
10 / 10Outstanding·May 2026
Cottage was in a great location and everything was in great shape. It was very clean and the property is private, but close to everything.
10 / 10Outstanding·May 2026
Fun house in an excellent location. Quiet. Friendly, helpful host.
10 / 10Outstanding·May 2026
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.
10 / 10Outstanding·Apr 2026
Plus: Very private location. Clean. In the heart of heart of historic Key West a half block from Duval, yet away from the mayhem. Quiet at night. Private pool. Two bathrooms. A block from Fausto's, CVS, Walgreens, and great restaurants. Four blocks from Duffy's Steak and Seafood supper club. Basically walkable to tourist places like Mallory Sq., Southern Most Point. Airport is 3 miles (we've walked back rom it).Negative: Very lush. Might have to scoop out falling leaves from pool.
$$$$
Top rated by guests
9.8Outstanding
(237 Ratings)
Perfect location, spotless rental, comfortable beds, and private pool. Highly recommended!
From real guest reviews summarized by AIDon't miss out! Price and availability may change
