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Pineapple Conch House Vacation Rental With Heated Pool

Home Rental in Key West Florida

Contemporary conch house in Key West with 2 bedrooms, 2 baths, and a heated saltwater pool plus lanai and deck, set in the Historic District.

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Historic Hideaways
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Rates from
$183 / night
Additional fees may apply
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Rental overview

Why You'll Love This Rental

Pineapple Conch House is a 2-bedroom, 2-bath home in Key West, Florida (Florida Keys) that sleeps 4 and offers 1,616 square feet of living space. Set in a town/village setting near a beach, it combines historic character with updated comforts and a private outdoor area centered on a pool and deck. The home is listed on the National Register of Historic Places and features classic Key West architectural details, including hand-carved trim and Dade County Pine.

Inside, the layout includes a living room with a TV and a sleeper sofa, plus internet access and split A/C units. Sleeping is arranged with a queen bedroom downstairs with an ensuite bath and an open master suite upstairs with a king bed and a private bath; the washer/dryer is located upstairs. The kitchen includes a dishwasher and a pass-through window to the outdoor lanai. Outside, the covered lanai is set up for relaxing and dining and looks onto the pool area; a grill is also provided. Please note there is no on-site car/truck parking, and the homeowner has exterior surveillance equipment.

Good fit for
Honeymoon
Private pool area Outdoor space includes a pool with deck and a covered lanai.
Sleeps up to 4 Two bedrooms plus a sleeper sofa provide accommodations for 4 guests.
King and queen beds Sleeping setup includes a king bed upstairs and a queen bed downstairs.
Washer and dryer Washer/dryer is located upstairs in the closet area.
No on-site car parking No car/truck parking on the rear lanes; on-street parking is on White and/or Frances.
At a glance

Property Highlights

Town / VillageLocation Setting
Near a BeachBeach Access
2 BedroomsBedrooms
2 Full BathroomsBathrooms
Sleeps 4Guest Capacity
1616 sq. ft.Living Space
PoolPool
Internet AccessInternet
TelevisionTelevision
YesWasher / Dryer
Key West Florida
Location & nearby Explore the Area

This home is in Key West, Florida, within the Key West Historic District, and is listed as near a beach. The setting is described as town/village, placing the residence in an in-town environment rather than a remote area. Parking is limited: there is no car or truck parking on the rear lane or the lane behind the home, and the closest on-street car parking is on White and/or Frances.

Plan your stay

Rates & Availability (USD)

Rates from
$183 per night
29-day minimum stay
Check current rates & availability

Live booking details are maintained by Historic Hideaways.

Check Availability

Availability Calendar

Use the calendar as a guide, then confirm current availability directly with the manager.

Available Booked
Season Nightly Weekly Monthly
PMS Rate
Nov 10, 2026 - Nov 30, 2026
Minimum Stay: 30 Days
$216 $1,512 $6,480
PMS Rate
Dec 01, 2026 - Dec 31, 2026
Minimum Stay: 30 Days
$280 $1,960 $8,400
PMS Rate
Jan 01, 2027 - Jan 30, 2027
Minimum Stay: 30 Days
$400 $2,800 $12,000
PMS Rate
Jan 31, 2027 - Mar 02, 2027
Minimum Stay: 29 Days
$666 $4,662 $19,980
PMS Rate
Mar 03, 2027 - Mar 31, 2027
Minimum Stay: 30 Days
$500 $3,500 $14,800
PMS Rate
Apr 01, 2027 - Apr 30, 2027
Minimum Stay: 30 Days
$300 $2,100 $9,000
PMS Rate
May 01, 2027 - Jul 31, 2027
Minimum Stay: 30 Days
$200 $1,400 $6,000
PMS Rate
Aug 01, 2027 - Sep 30, 2027
Minimum Stay: 30 Days
$183 $1,281 $5,490
PMS Rate
Oct 01, 2027 - Oct 31, 2027
Minimum Stay: 30 Days
$216 $1,512 $6,480
About this rental

About This Rental

Pineapple Conch House is a 1,616-square-foot Key West home with 2 bedrooms and 2 full bathrooms, accommodating up to 4 guests. Located in the Key West Historic District and listed on the National Register of Historic Places, the residence retains hallmark architectural elements such as hand-carved wooden trim and Dade County Pine, while incorporating modern essentials for day-to-day comfort. The setting is town/village, and the home is noted as near a beach.

The main level includes the living room with television and seating, plus a sleeper sofa for flexible sleeping. Internet access is provided, and the home is air conditioned with split units; ceiling fans are also listed. The downstairs bedroom is furnished with a queen bed and has an ensuite bathroom.

Upstairs, the open master suite spans the second floor and includes a king bed and a private bath. The washer/dryer is located upstairs within the closet area. In the upstairs bath, the shower opens into the room (as noted by the owner).

Outdoor living is a central part of the stay, with a covered lanai and deck area oriented to the pool. The kitchen connects to the lanai via a pass-through window, and the kitchen is equipped with a dishwasher and microwave. A grill is available outside. Parking notes: there is no car/truck parking on the rear lane or the lane behind the home; the closest on-street car parking is on White and/or Frances. The homeowner has exterior surveillance equipment. The property is for residential accommodations only; no special events, parties, or functions are permitted.

NOW OPEN - MARCH 2027!

Welcome to a vacationer’s contemporary conch house with 2-bedrooms, 2-baths, and a secluded pool and deck oasis. Room by room the residence reflects its past and its present. This vacation home located in the Key West Historic District with its intricate, hand carved wooden trim and abundance of Dade County Pine (both hallmarks of classic Key West architecture) reflects the past as recognized by its listing on the National Register of Historic Places. Inside, this home has been updated so that its historic roots blend seamlessly with modern amenities to meet the needs of today’s savvy vacationer while offering easy access to everything Key West has to offer.

Behind a white picket fence and up a few stairs is the front porch that runs the width of the house. Comfy chairs and a double swing make a great place for coffee or cocktails on the quiet lane, while green palms and bright yellow hibiscus add color and tranquility to the scene. A tall metal chicken with crazy eyes stands guard by the wooden screen door. Once inside and to the left is the living room with hard wood floors, Dade County Pine walls, and a decorative ceiling fan above. The ceiling itself is a light wood that bounces light from the four louvered windows back into the room to create an airy feeling. End tables with lamps, a handsome couch with pullout bed, cushioned armchairs, and an ottoman that can also function as a coffee table make this the right spot for conversation. Across the room is a cabinet and a large flat screen TV perfectly positioned for viewing from the couch. And of course there’s A/C, high speed internet, and cable.

The downstairs bedroom features a queen bed with ensuite bath. A dresser, chairs, bookcase, and corner desk area make this a relaxing space for the quieter pursuits like reading and sleeping. A ceiling fan with light above and louvered windows guarantee plenty of daytime light in the room or closed for quiet solitude at night. The ensuite bath enhances convenience and privacy. Its emerald glass vessel sink is a one-of-a-kind statement piece and the visual centerpiece of the room while a closet for fluffy towels and other amenities provide convenience and space for storage.

The U-shaped kitchen follows with a striking glass ceiling light shade made by local Key West artisans, illustrating colorful forms of sea life like fish, turtles, shells, and coral. The second striking aspect is the large pass-through window to the pool oasis beyond. The kitchen itself offers a modern blend of expected appliances and accoutrements for preparing food in a comfortable and attractive layout. Multiple white cupboards above and below store dishes and more for the convenience of cooking in for a break from Key West social life, with a small table and three chairs that can function as a mini breakfast nook just steps from the covered lanai.

Upstairs the open master suite spans the second floor. A full-length window lights the length, with side windows adding a treehouse feel to the room. There is a large desk for computer work or play, an upholstered chaise lounge for stretching out and reading, and a wonderfully comfortable king bed with an intricate filigree headboard beautifully backlit by a window behind. Upstairs also includes a generous closet complex for hanging clothes, for folded accessories, and for the washer/dryer. In the shower, an oblong porthole window provides function and interest, with a view of the bougainvillea over the patio. (Note the shower opens into the room (see pic.)) The adjoining private bath area includes a toilet with bidet, sink cabinet, another set of shelves, and a counter for storage and workspace for daily wash-up activities.

Back downstairs is what many name the most compelling aspect of this amazing cottage: the covered lanai; the deck; the heated, saltwater pool; the small, covered patio; the back-lit tropical landscaping. The covered lanai is serviced from the large and handsome pass-thru window connecting food and drink from the kitchen ever so easily to the outside table and chairs. A TV, carved ceiling fan, small refrigerator, and decorative flourishes make the area irresistible. Not to mention the view of the pool/deck oasis. On one side is a row of colorful Adirondack chairs and on the other a deep blue tile back drop with water feature. In between is a magical saltwater pool that could easily be where you spend most of your home time swimming or floating. Above is an incredible Key West sky with puffy white clouds and an occasional water bird flying over. The whole back area is ringed in a white fence and palms that create beauty and privacy. Behind the gleaming tile wall is a small, covered pavilion to park a golf cart, scooters, or bikes (access is through a lane at the rear of the property but it is too small of an egress/ingress for anything larger than a golf cart – NO cars, etc.) or as an extended social area or work area or most anything you want. A grill area and hammock invite you to savor lazy afternoons or festive gatherings. There is no car/truck parking on this lane nor the one behind the home. The closest on-street car parking is on the main side streets - White and/or Frances.

This homeowner has exterior surveillance equipment. Historic Hideaways is not in the care, custody, or control of their placement, use, or what they may or may not record.

The Property may only be used for residential accommodations. No special events, parties, or functions of any kind are permitted on the Property. To know what's going on from day to day, check out Historic Hideaways' informative Events website page. Other information on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section) or in the print publication Paradise, available at various locations around town every Thursday.
Things to enjoy

Activities and Special Interests

This property provides access to the following activities and special interests:

Beach
Biking
Boating
Catamaran
Fishing
Deep Sea Fishing
Golfing
State National Parks
Ocean
Sailing
Scuba Diving
Theatre
Wind Surfing
Kayaking
Honeymoon
Canoeing
Fly Fishing
Surfing
What's included

Property Amenities

Featured Amenities

Dishwasher
Grill
Internet Access
Pool
Television
Washer/Dryer

Property Features

Ceiling Fan(s)
Microwave

Other Property Amenities

Bed Size 1st/Master: King
Bed Size 2nd Rm: Queen
Beds Pull-out: Sleep Sofa
Number of Baths: 2 Full
Square Footage, Est.: 1,616
Patio
Air Conditioned: Split Units
Beach Distance: Biking
Helpful details

Frequently Asked Questions

Pineapple Conch House is located in Key West, Florida.

Pineapple Conch House accommodates up to 4 guests.

2 Bedrooms and 2 Full Bathrooms.

The listed beach access for Pineapple Conch House is Near a Beach.

Yes. The property lists Pool.

The property lists a 29-night minimum stay.
Local management

Professionally Managed By

Historic Hideaways
In business since 1996
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Property reference
#186953 · Pineapple Conch House
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