This cottage places you in the centre of Key West, steps from Ernest Hemingway Home and Museum and within a short 5-minute stroll of Duval Street. .Accommodation features a washing machine, free WiFi and a patio. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A living room, a TV and a coffee/tea maker are also available. Housekeeping is available on request.
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
Blue Heaven - 3 min walk
Bourbon Street Pub - 3 min walk
801 Bourbon Bar - 3 min walk
Mangoes Restaurant - 4 min walk
Old Town Tavern - 4 min walk
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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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Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Smoke detector (host has indicated there is a smoke detector on the property)
Fire extinguisher
Deadbolt lock
General
Housekeeping (on request)
Unit size: 544 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
No pets allowed
Children and extra beds
Children are welcome.
Events
No events 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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector and a deadbolt lock in all accommodation.
Property Registration Number 25230-112332
Property is also known as
2450-154416
Frequently asked questions
Are there any beaches close to PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!?
Yep, PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! is a short 11-minute walk from Florida Keys Beaches.
Fun beach activities include jet skiing, snorkelling and scuba diving.
Does PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! have a pool?
Take your pick from a heated pool, a pool and a communal pool.
Is there a free airport shuttle available at PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!?
No, PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! does not offer an airport shuttle service.
What time are check-in & check-out at PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!?
Check-in begins at 4:00 PM. Check-out time is 10:00 AM.
Are pets allowed at PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool!?
No, pets are not allowed.
PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! Reviews
Reviews
9.6
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 12 out of 15 reviews
10 - Excellent
12
Rating 8 - Good. 3 out of 15 reviews
8 - Good
3
Rating 6 - Okay. 0 out of 15 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 15 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 15 reviews
2 - Terrible
0
9.8/10
Cleanliness
Reviews
10/10 Excellent
Paula A.
26 Apr 2026
Liked: Cleanliness
The house was immaculate and what I expected from the listing The surrounding neighbors were extremely friendly and helpful The only negative was the pool was over chlorinated. It was clean and warm but chlorine smell was very strong. I would definitely recommend or rent this house again. It was a short walk to the beaches and to Mallory Square and just far enough from Duval Street I loved every minute of my stay in Key West
Paula A.
Stayed 28 nights in Mar 2026
8/10 Good
david p.
1 Dec 2024
Liked: Cleanliness
Review
Great location good layout but outdated and for the price paid should be more up to date. The bed was very uncomfortable and the pillows were subpar but the interaction with the management was amazing
david p.
Stayed 30 nights in Nov 2024
10/10 Excellent
Sharon W., Avon USA
12 Dec 2022
Liked: Cleanliness
818 Whitehead, Key West
Overall great. Loved location. Friendly locals enhanced experience.
Only complaint was with mid stay clean that was required.
Suggestions for mid clean-
Should be different in some ways than final clean - - - -
I’d set time on coffee pot so could
set up night before and have coffee
ready in am.
Was unplugged during clean. Making me have to reset time again.
Blender/toaster set out on counter to use without having to get down on floor to retrieve them from small cabinet between stove and wall.
Were put away. So had to get out again.
I’d brought a kitchen sponge from home to use for hand washing a few of the dishes. I’d put it in dishwasher flatware holder to cleanse with the
dishes like I do at home. Dishwasher emptied and my sponge gone.
No reason to get rid of it mid clean.
Also think if a mid visit cleaning
is required a small safe should be provided for valuables- passport, jewelry, cash, credit cards etc.
Sharon W.
Stayed 30 nights in Nov 2022
8/10 Good
Jan S.
2 Jan 2022
Liked: Cleanliness
Location was just what I wanted. The cottage itself was wonderful.
My issue was the location of the pool I had been so looking forward to. It is right outside and in the walking pathway of the other cottages. All cottages are located almost on top of each other.
Jan S.
Stayed 31 nights in Dec 2021
10/10 Excellent
Earl S.
1 Dec 2021
Liked: Cleanliness
Recommended
The location was perfect. The cottage was clean, well maintained and very comfortable. when we had a small thing that needed seeing to, the manager responded the same day.
Earl S.
Stayed 28 nights in Nov 2021
10/10 Excellent
Verified traveller
14 Nov 2020
Liked: Cleanliness
Pineapple Cottage, Key West
Great location and property making walking around and exploring Key West very easy!
Brain, property manager, and team were very helpful, responsive and accessible.
Thank you.