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PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!

Photo gallery for PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!

A light blue house with a white porch and a white picket fence.
A kitchen with a stainless steel refrigerator, a microwave, and a stove. There is a granite countertop and a sink.
A rectangular pool with a tiled edge, surrounded by a stone patio, white fencing, and various potted plants.
A bedroom with a wooden bed, a nightstand with a lamp, a dresser, a ceiling fan, and a window with blinds.
A spacious kitchen with a central island, wooden cabinets, and a stainless steel refrigerator.

Reviews

9.8 out of 10
Exceptional
This 1-bedroom cottage in the heart of the city accommodates 4 guests. It features a patio for outdoor relaxation. Enjoy nearby activities like sailing, snorkeling, and scuba diving, along with attractions such as Duval Street and the Ernest Hemingway Home and Museum.

Highlights

  • Top-rated for value
    Guests love how much they get for what they pay.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Duval Street
1 bedroom1 bathroomSleeps 4

Popular amenities

  • Heated pool
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue
  • Deck or patio

Explore the area

View map
Key West, FL
  • Place, Duval Street
    ‪1 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪2 min walk‬
  • Place, Key West Lighthouse and Keeper's Quarters Museum
    ‪2 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪11 min drive‬

Rooms & beds

1 bedroom (sleeps 4)

Bedroom 1

1 Queen Bed

Other Space 1

1 Double Sofa Bed

1 bathroom

Bathroom 1

Bathtub or shower

Spaces

Deck or patio
Porch or lanai
Kitchen

About this property

PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!

RELAXED DOWNTOWN LIVING...
Envelop yourself in true island living in this cute cottage just for the two of you. One of six homes in this exclusive compound located in the heart of Old Town. Located one block from Duval with charming porch and shared heated pool. Walk or stroll to dining, night life, galleries, shopping, and be at fabulous Ft. Zachary beach beach in minutes.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

FURNISHINGS...
Cozy one queen bedroom and one bath.  Great open floor plan with hardwood floors, plenty of Key West sunshine and blue skies through the large windows. Flat screens in the living and bedroom.  Well stocked kitchen to use your culinary skills.  Washer and dryer.  Sofa sleeper in the living room is also available.

OUTSIDE LIVING...
Beautiful heated pool and waterfall.  The pool and courtyard area is shared with five other homes, but it will feel like your own quiet piece of paradise with little to no traffic.

NEIGHBORHOOD ATTRACTIONS...
Stroll through Bahama Village located in downtown Key West; aptly named because of it's many inhabitants that are of Bahamian decent. This lively neighborhood offers many popular restaurants such as Blue Heaven, Santiago's Bodega and La Creppiere. You can also find many small boutiques filled with treasures made by local artisans, some specialty wares and even antiques.  Directly across from Hemingway's Home, Moon Dog restaurant and steps from the Southernmost Point.

PARKING...
This home does not have designated parking but there is on street parking in the surrounding neighborhood.  Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates.

PETS...
No pets allowed.

MULTI MONTH RESERVATIONS...
For monthly reservations, the following fees will be added PER MONTH:
Mid-stay clean
Pool/hot tub heating fee (if applicable)
Pet fee (if applicable)

BOOKING DATES...
This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.

CONCIERGE SERVICES...
Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!

CANCELLATION...
Bookings canceled at least 90 days before the start of stay will receive a 100% refund.

Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).

INDULGE IN DOWNTOWN LIVING...

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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

No 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

Property Registration Number 25230-112332
Property # 990915
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 deadlock

About the area

Key West

Located by the sea, this cottage is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with cycling and ecotours.
Map
Key West, FL

What's nearby

  • Duval Street - 1 min walk - 0.2 km
  • Ernest Hemingway Home and Museum - 2 min walk - 0.2 km
  • Key West Lighthouse and Keeper's Quarters Museum - 2 min walk - 0.2 km
  • South Beach - 9 min walk - 0.8 km
  • Southernmost Point - 11 min walk - 0.9 km

Getting around

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

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Blue Heaven - ‬3 min walk
  • ‪Moondog Cafe & Bakery - ‬2 min walk
  • ‪Circle K - ‬6 min walk
  • ‪Old Town Tavern - ‬4 min walk

Frequently asked questions

Does PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! have a pool?

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

How much does it cost to stay at PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!?

As of 27 August 2026, prices found for a 1-night stay for 2 adults at PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! on 30 November 2026 start from NZ$13,563, 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 ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!?

Check-in begins at 4:00 PM.

What time is check-out at PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!?

Checkout is at 10:00 AM.

Where is PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! located?

Located in Old Town Key West, this cottage is within a 5-minute walk of Ernest Hemingway Home and Museum and Duval Street. Florida Keys Beaches and Southernmost Point are also within 15 minutes.

About the host

Hosted by Wendy Zintsmaster & Team

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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