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Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath

Photo gallery for Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath

An outdoor patio with a table, chairs, and a large striped umbrella.
A poolside area with a pool, lounge chairs, a table, and a striped umbrella.
A modern kitchen with white cabinetry, a central island, and a dining area with a blue and white patterned rug.
A narrow wooden pathway leading to a white building with a covered entrance.
A living room with a sofa, armchairs, a coffee table, and a staircase leading to an outdoor area.

Reviews

10 out of 10
Exceptional

Highlights

  • Dive into relaxation
    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

Popular amenities

  • Patio
  • Private pool
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Washing machine

Explore the area

View map
Key West, FL
  • Place, Duval Street
    ‪1 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪9 min walk‬
  • Place, Mallory Square
    ‪11 min walk‬
  • 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

Add dates for prices

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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.
View more Cottages in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Duval Street - 1 min walk - 0.0 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
  • Mallory Square - 11 min walk - 0.9 km
  • South Beach - 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
  • ‪Green Parrot Bar - ‬3 min walk
  • ‪Mangoes Restaurant - ‬3 min walk
  • ‪Bourbon Street Pub - ‬4 min walk
  • ‪Jack Flats - ‬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 28 Oct 2026, prices found for a 1-night stay for 2 adults at Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath on 27 Nov 2026 start from AU$4,970, 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 242 out of 249 reviews
Rating 8 - Good. 4 out of 249 reviews
Rating 6 - Okay. 2 out of 249 reviews
Rating 4 - Poor. 0 out of 249 reviews
Rating 2 - Terrible. 1 out of 249 reviews

9.8/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location and easy walking to Duvall street. We loved our stay and will definitely be back.
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We couldn’t have stayed in a more perfect spot to celebrate my boyfriend turning 50! Walkable to everything & a perfect oasis back yard & pool that was so peaceful every night. We would definitely stay here again!
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Outstanding location, one block from Duval Street. Truly appreciated the pool/backyard privacy and the staff was awesome.
Stayed 3 nights in Aug 2026
From a partner site

10/10 Excellent

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: Fantastic
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful home tucked away off the street. You feel like you are in an oasis with the pool and landscape. House was very well equipped with everything we needed in the kitchen. Management company was very responsive and accommodating of our requests. Would definitely stay in the Pineapple cottage again!
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location with a pool & parking!
Stayed 4 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fun house in an excellent location. Quiet. Friendly, helpful host.
Stayed 5 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay! Will book again!
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Family Vacation

Location is perfect, property and pool are awesome!
Stayed 7 nights in Apr 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was perfect from the property management to the decor of cottage and the location. We will be returning!
Stayed 3 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location for fun times on Duval Street! Staff at Preferred Properties were helpful and kind!
Stayed 5 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This place is truly a hidden gem. Great location. Right near Duval but yet secluded. Highly recommend the Pineapple Cottage.
Stayed 4 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was awesome, very clean and the host was very accommodating and stayed in touch. Quiet neighborhood and great location!!
Stayed 5 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
I was a great location. Cozy private place next to everything. Little slice of heaven
Stayed 3 nights in Nov 2025
From a partner site

10/10 Excellent

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.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing stay right off of Duval

The property was incredible - clean, roomy and exactly as listed. We loved the central location and used the private pool a ton.
Stayed 4 nights in Feb 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Pineapple cottage stay

Amazing property and perfect location just a block from the middle of Duval! Would love to stay here again!
Stayed 5 nights in Oct 2019
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Pineapple Cottage

Lovely place Great location. Would definitely go again
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

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.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Location Location Location

Great place to stay, around everything but the courtyard is your private escape!
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!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic spot for two couples perfectly located.

We stayed here for New Year. It was the perfect spot. Close to everything, but quiet and a wonderful little refuge with a pool.
Stayed 2 nights in Dec 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Love the keys

Great place very convenient
Stayed 7 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paradise out the front doorz

Perfect location with everything in walking distance. Loved the place.
Stayed 6 nights in Mar 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key West Stay

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
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!
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