Entire home
PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!
Cottage with kitchen, steps from Ernest Hemingway Home and Museum
Photo gallery for PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!





Reviews
9.6 out of 10
Exceptional
1 bedroom 1 bathroom Sleeps 4 50.5 sq m
Popular amenities
Explore the area

Key West, FL
- Place, Duval Street1 min walk
- Place, Ernest Hemingway Home and Museum2 min walk
- Place, Southernmost Point11 min walk
- Airport, Key West, FL (EYW-Key West Intl.)9 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...
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...
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

A Stones Throw Away from Duval - Downtown -Caroline's Cottage KW
A Stones Throw Away from Duval - Downtown -Caroline's Cottage KW
- Kitchen
- Washer
- Dryer
- Free WiFi
9.6 out of 10, (11 reviews)
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 deadlock
Property Registration Number 25230-112332
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 Fort Zachary Taylor Historic State Park and South Beach. MLK Community Pool & Community Center and Florida Keys Eco - Discovery Center are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with cycling and ecotours.

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
- South Beach - 9 min walk - 0.8 km
- Southernmost Point - 11 min walk - 0.9 km
- Mallory Square - 15 min walk - 1.3 km
Getting around
Restaurants
- Blue Heaven - 2 min walk
- Moondog Cafe & Bakery - 2 min walk
- Bourbon Street Pub - 3 min walk
- 801 Bourbon Bar - 3 min walk
- Rams Head Southernmost - 1 min walk
Frequently asked questions
About the host
Hosted by Wendy Zintsmaster & Team

Languages:
English
Premier Host
They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback