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PINEAPPLE COTTAGE, 2BR/2BA-Pvt Pool, 1/2 block to Duval
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Reviews
10 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 4
Popular amenities
Rooms & beds
2 bedrooms (sleeps 4)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen 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, 2BR/2BA-Pvt Pool, 1/2 block to Duval
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.
**Pool heat is optional at $25 a day.**
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.
**Pool heat is optional at $25 a day.**
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
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10.0 out of 10, Exceptional, (5 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
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 ecotours and cycling nearby.

Key West, FL
What's nearby
- Duval Street - 1 min walk - 0.0 km
- Ernest Hemingway Home and Museum - 6 min walk - 0.6 km
- Harry S. Truman Little White House - 7 min walk - 0.7 km
- Mallory Square - 12 min walk - 1.0 km
- Southernmost Point - 15 min walk - 1.3 km
Getting around
Restaurants
- Margaritaville - 3 min walk
- Willie T's - 2 min walk
- Mangoes Restaurant - 3 min walk
- Jack Flats - 3 min walk
- Kaya Island Eats - 3 min walk
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.8/10
Cleanliness
9.8/10
Check-in
10/10
Communication
10/10
Location
9.8/10
Listing accuracy
Reviews
Verified
15 Jan 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Dec 2025
From a partner site
10/10 Excellent
James H.
4 Mar 2026
Great Vacation in Key West
James H.
Verified
10/10 Excellent
Amy K.
29 Nov 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amy K.
Stayed 5 nights in Nov 2025
Verified
10/10 Excellent
Rebecca S.
11 Nov 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Rebecca S.
Stayed 5 nights in Nov 2025
Verified
10/10 Excellent
Jonathan P.
22 Nov 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Jonathan P.
Stayed 3 nights in Nov 2025
Verified
10/10 Excellent
Wayne G.
18 Aug 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wayne G.
Stayed 3 nights in Aug 2025
Verified
10/10 Excellent
Bryan B.
17 Oct 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Bryan B.
Stayed 4 nights in Oct 2025
From a partner site
10/10 Excellent
Judith L.
13 Jan 2026
A Peaceful Retreat
Judith L.
Verified
10/10 Excellent
Marianne M.
10 Apr 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Family Vacation
Marianne M.
Stayed 7 nights in Apr 2023
From a partner site
10/10 Excellent
JIM W.
2 Sept 2025
Labor Day Stay
JIM W.
From a partner site
10/10 Excellent
12 Oct 2025
Little piece of paradise
Verified
10/10 Excellent
Heather V.
23 Aug 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
August 2025
Heather V.
Stayed 4 nights in Aug 2025
Verified
10/10 Excellent
Verified traveller
13 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Verified traveller
Stayed 3 nights in Feb 2025
Verified
10/10 Excellent
Emily W.
15 Feb 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing stay right off of Duval
Emily W.
Stayed 4 nights in Feb 2023
Verified
10/10 Excellent
Katie C.
23 Oct 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Pineapple cottage stay
Katie C.
Stayed 5 nights in Oct 2019
Verified
10/10 Excellent
Garry J.
18 Jan 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Pineapple Cottage
Garry J.
Stayed 4 nights in Jan 2024
Verified
10/10 Excellent
Mark K.
7 Dec 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Location Location Location
Mark K.
Stayed 5 nights in Nov 2023
Verified
10/10 Excellent
Peter M.
22 Sept 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Hidden Paradise
Peter M.
Stayed 5 nights in Sep 2024
Verified
10/10 Excellent
nick c.
13 Jan 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Time
nick c.
Stayed 6 nights in Dec 2024
Verified
10/10 Excellent
James U.
20 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Love the keys
James U.
Stayed 7 nights in Jul 2024
From a partner site
10/10 Excellent
DAVID F.
25 Sept 2025
Hidden Gems in paradise
DAVID F.
Verified
10/10 Excellent
Kevin M.
3 Jan 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic spot for two couples perfectly located.
Kevin M.
Stayed 2 nights in Dec 2022
Verified
10/10 Excellent
Paul G.
25 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Key West Stay
Paul G.
Stayed 3 nights in Jun 2023
Verified
10/10 Excellent
William S.
3 Apr 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise out the front doorz
William S.
Stayed 6 nights in Mar 2023
Verified
10/10 Excellent
Verified traveller
8 Dec 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Getaway
Verified traveller
Stayed 3 nights in Dec 2022
About the host
Hosted by The Team at Preferred Properties
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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