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PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest

Cottage with private pool, steps from Duval Street

Photo gallery for PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest

Pool, Table, Lounge Chairs, everything you need for a day by the
Pool, Table, Lounge Chairs, everything you need for a day by the - Your own private pool!
Pool, Table, Lounge Chairs, everything you need for a day by the - Outdoor dining too!
Living Room/Kitchen/Dining
Entrance into Living Room

Reviews

10 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 4

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Barbecue grill
  • Kitchen

Explore the area

View map
  • Place, Duval Street
  • Place, Ernest Hemingway Home and Museum
  • Place, Mallory Square
  • Airport, Key West, FL (EYW-Key West Intl.)

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- RealKeyWest

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.**

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

Events allowed
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Pets

No pets allowed
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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
Parties and events are allowed on site
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.
Map
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
  • Key West Lighthouse and Keeper's Quarters 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

Getting around

  • Key West, FL (EYW-Key West Intl.) - 12 min drive

Restaurants

  • ‪Willie T's - ‬2 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: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest pet-friendly?

No, pets are not allowed at this property.

How much is parking at PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest?

On-site parking is available at the property.

What time is check-in at PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest?

Check-in begins at 4:00 PM.

What time is check-out at PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest?

Checkout is at 10:00 AM.

Where is PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest 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. 219 out of 226 reviews
Rating 8 - Good. 4 out of 226 reviews
Rating 6 - Okay. 2 out of 226 reviews
Rating 4 - Poor. 0 out of 226 reviews
Rating 2 - Terrible. 1 out of 226 reviews

9.8/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Little piece of paradise

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: Great experience. Excellent support staff, cozy comfortable home, beautiful location steps off duval street, could not have asked for better.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

DAVID F.

Hidden Gems in paradise

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 only thing that I found to be an issue was the musty smell thru out the house. But I guess that is to be expected due to the high heat and humidity in the area otherwise it was a very good time

10/10 Excellent

Emily W.

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

10/10 Excellent

Kimberly s.

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

outstanding location and house

stayed for 4 nights. Absolutely love this house and location. The house was cute, well maintained and tactfully decorated. The best part was 1-2 blocks from all the activity but very quiet at the property. Kind of hidden. The outdoor pool was so great. loved floating around everyday after exploring the town. communications were quick and efficient. had a great experience and would highly recommend.
Stayed 4 nights in May 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

eberts j.

Wonderful 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: Excellent in every way! No complaints whatsoever.

10/10 Excellent

JIM W.

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

Overall

NIce place
Stayed 4 nights in Aug 2023

10/10 Excellent

Tom S.

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

Great location and outdoor area

Great location ... literally feet to nearest bar/coffee/Walgreens. Right off Duval. But felt secluded with vegetation and trees in back. Great surround sound systems inside and on back patio. Nice little living room and kitchen. Would stay again in a heartbeat.
Stayed 4 nights in Jun 2020
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Carole G.

An oasis in downtown 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: We had the most perfect stay at pineapple cottage. It was absolutely brilliant- the pool was perfect, the house was immaculate but above all the location was incredible. It was just a 2 minute walk from Duval Street and all the exciting bars and shops, but once in the property all the hustle disappeared and it was serene. Highly recommend
Stayed 4 nights in Aug 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Roger A.

Gem in the Heart of it All

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 spent the first half of our vacation at the Pier House and actually preferred this property with its private pool, iguanas, beautiful floral landscape, dedicated parking space, well-appointed kitchen and great location to all in midtown Duval.
Stayed 4 nights in Jul 2020

10/10 Excellent

Nelson S.

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

KW '24

This property was as described...and more!! Awesome place...just 1/2 block from Duval, but you would never know it - -quite and beautiful. Perfect place for two couples! Property manager/team were great to deal with you, catering to your needs! We will be back and use again - except next time, little longer!! Thanks,
Stayed 5 nights in Apr 2024

10/10 Excellent

Kaye R., Paducah

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

Excellent

Everything was perfect. Not a single negative comment could be made. Couple of small issues were addressed immediately. Property was 1/2 block from Duval. Mr Zs Pizza a few doors down would rate 4-5 stars. Coffee shop was near, through the alley. Convenient to all sides of the island. Will definitely stay here again.
Stayed 4 nights in Jan 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Cindy F., Grosse Pointe Park, MI

A wonderful tranquil week 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: Preferred Properties was the best management company I have ever worked with in Key West. Thank you so much for the great communication, kind and friendly service. The downstairs bed had seen better days, but okay for one person. otherwise the property was absolutely beautiful, quiet and so private. All the comforts of home were provided.
Stayed 7 nights in Feb 2024

2/10 Terrible

richard p.

Disliked: Cleanliness, check-in

Extremely disappointed

We were unable to travel to Florida due to hurricane Ian. Property manager was unwilling to work with us on a reschedule. I was just coming off a deployment (USN) and this was to be an opportunity to spend some time with just my family. Very dissatisfied a great deal of money waisted.
Stayed 2 nights in Oct 2022

10/10 Excellent

Bryan B.

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

10/10 Excellent

chris g.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderfuf but the key west change its beautiful fresh painted like post card but lost it homy warm character bit too expensive and food is medicore
Stayed 5 nights in Sep 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

JIM W.

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

10/10 Excellent

Heather V.

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

August 2025

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!.
Stayed 4 nights in Aug 2025

10/10 Excellent

Wayne G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay! Will book again!
Stayed 3 nights in Aug 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Tom M.

Better then I could imagine

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: What a great experience at Pineapple Cottage. We have been coming to Key West for over 25 years and this is the first time staying here. Great quiet location, very roomy, the pool is awesome and the iguana is an added bonus. We will definitely return to stay here.

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Feb 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kirsten M.

Perfect!

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: Pineapple Cottage was perfection! The private pool and back patio were amazing, beds were comfortable, home was cute and clean. Preferred Properties was excellent, they really went out of their way to make sure we were comfortable and we wanted for nothing. 10/10, we'll be back!

10/10 Excellent

John S.

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

No Title

Excellent.
Stayed 7 nights in Apr 2025

10/10 Excellent

Sherri G.

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

Great Rental in a GREAT Location

This house is everything it says it is. There were no surprises and no disappointments. It's a beautiful property in the heart of downtown Key West. We took an Uber from the airport and never once wished we had a car. We walked to everything. We will be back next year.
Stayed 5 nights in Apr 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Beverly C.

Our Oasis

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 location of Pineapple Cottage couldn't be better, close to all the action but you'd never know it. The pool was wonderful. We chose to have it heated and it was prefect for floating after getting in from the beach. The cottage itself was exactly as described. Angela from Preferred Properties was the there to answer all of our questions from check-in to check out. We will be returning!

10/10 Excellent

Daniel C.

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

Excellent Service

Exceeded all expectations. Even the bathroom tissue was top notch.
Stayed 4 nights in Dec 2024

About the host

Hosted by The Team at Preferred Properties

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Languages:

English

Premier Host

They consistently provide great experiences for their guests