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

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Entire home

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!

Overview
Amenities
Policies
Location
Host

Exceptional

2 bedrooms2 bathroomsSleeps 4

Popular amenities

Parking available
Dryer
Washer
Barbecue grill
Kitchen

Explore the area

Key West, Florida

Duval Street
‪1 min walk‬
Ernest Hemingway Home and Museum
‪8 min walk‬
Mallory Square
‪13 min walk‬
Key West, FL (EYW-Key West Intl.)
‪12 min drive‬

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

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.

**Pool heat is optional at $25 a day.**

Property manager

The Team at Preferred Properties

Premier Host

Languages

English

Add dates for prices

Amenities

Pool

Kitchen

Washer

Dryer

Free WiFi

Air conditioning

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Pool
Kitchen
Washer
Dryer

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, Florida

What's nearby

Duval Street - 1 min walk - 0.2 km
Ernest Hemingway Home and Museum - 8 min walk - 0.7 km
Mallory Square - 13 min walk - 1.1 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

‪Margaritaville - ‬3 min walk
‪Green Parrot Bar - ‬5 min walk
‪Willie T's - ‬2 min walk
‪Mangoes Restaurant & Island Cuisine - ‬3 min walk
‪Pinchers - ‬4 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.

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.

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

9.8/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

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

10/10 Excellent

Beverly C.

25 February 2025

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.

20 January 2025

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

10/10 Excellent

nick c.

13 January 2025

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

Great Time

Wonderful and clean house

Stayed 6 nights in Dec 2024

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

10/10 Excellent

eberts j.

24 December 2024

Wonderful Stay!

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

10/10 Excellent

Kevin F.

16 December 2024

Pineapple House 2024

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

10/10 Excellent

Erik K.

6 December 2024

Great location and excellent home

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: This place is awesome. Nice pool and tropical garden. Very private. House had everything we needed and more. Super clean and communication with the host was quick and simple.

Stayed 3 nights in Dec 2024

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

10/10 Excellent

William T.

5 November 2024

Perfect for Two Couples!

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 wonderful time at this oasis. Off of Duval St so you are in your own little world. Quiet and comfortable it is perfect for two couples. Upstairs has a great main suite with a big sitting room. Clean and ready for your use. Property management company is wonderful with communication. Property very well maintained. Great location. You can walk everywhere from here. Coffee shop right next door, plenty of foodie spots in every direction.

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

10/10 Excellent

Peter S.

10 October 2024

Excellent 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: The Pineapple Cottage is a great place to stay if you are heading to key west. Location is prime with loads of space for outdoor relaxation. Quiet at night even though the location is in the heart of town. Management company was great with communication and made our stay a breeze.

Stayed 4 nights in Oct 2024

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

10/10 Excellent

Mason L.

7 October 2024

Third times a charm

10/10 Excellent

Peter M.

22 September 2024

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

Hidden Paradise

Pineapple cottage is just yards from Duval street, a hidden paradise but close enough to walk everywhere

Stayed 5 nights in Sep 2024

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

10/10 Excellent

Carole G.

30 August 2024

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

10/10 Excellent

Jack B.

24 July 2024

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

Love it

Great location. Surprising tranquil. Excellent accommodations. Very helpful and responsive caretaker

Stayed 7 nights in Jul 2024

10/10 Excellent

James U.

20 July 2024

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

Love the keys

Great place very convenient

Stayed 7 nights in Jul 2024

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

10/10 Excellent

Phillip R.

12 July 2024

Great place with privacy.

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: Had a great time in Key West while staying at the pineapple cottage. The home was clean are ready early. Management kept us I formed throughout the booking process and leading up to our arrival. AC worked great and private pool was the main event. Spent evenings cooling off after a day waking around town or relaxing on the beach. Thank you.

Stayed 5 nights in Jun 2024

10/10 Excellent

Matt S.

30 June 2024

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

Perfect private getaway near Duval

This place is great. It feels very private and secluded even though it’s close to Duval. It was a great location. The property managers were awesome. The pool is very nice. Ours was a group of 5 adults in their 20s and 30s and it was a perfect fit. The showers were big and nice the lower level shower had dual shower heads and tons of hot water, perfect for a couple. The AC worked well. Everything was just great I can’t recommend this property enough.

Stayed 2 nights in Jun 2024

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

10/10 Excellent

Gary D.

18 June 2024

Wonderful Place

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

10/10 Excellent

Phillip T.

15 June 2024

Amazing

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

10/10 Excellent

Mason L.

29 April 2024

Another great trip....

10/10 Excellent

Nelson S.

17 April 2024

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

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

10/10 Excellent

David M.

10 April 2024

5 Days 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 more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Pineapple Cottage is perfectly located just a half block from Duval. The cottage was exceptionally clean. Only negative was the beds, new mattresses would make the cottage perfect. Out door area was also very nice, with a grill and plenty of seating. We would definitely recommend this cottage to friends and family.

Stayed 5 nights in Apr 2024

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

10/10 Excellent

Michele C.

3 April 2024

Pineapple Cottage

Stayed 11 nights in Mar 2024

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

6/10 Okay

Jill Q.

15 March 2024

Key West Rental

Rating Details: The property manager was very helpful. The vacation rental was clean. I was very happy with the location. I was somewhat dissatisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The location of the cottage is perfect, close to everything but a bit away from the noise. The pool and yard is an adorable oasis. For the nightly price it would be reasonable to expect nicer beds, paint touch ups, repair of cracked stairs, repaired decking, replacement of torn patio furniture, etc.

Stayed 5 nights in Mar 2024

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

10/10 Excellent

Jerry T.

13 March 2024

Another wonderful stay at Pineapple Cottage, 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: Staying at the Pineapple Cottage allows you to have an effortless enjoyable vacation in Key West! It's central location allows you to walk wherever you want to go. No need to rent any type of transportation. The private pool retreat allows you to just relax when you choose to. This is our 3rd stay and we will be back for our 4th!

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

10/10 Excellent

Cindy F., Grosse Pointe Park, MI

13 February 2024

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