Relax in this charming Key West cottage, just one block from Duval Street and steps from fabulous Ft. Zachary beach. Enjoy the shared heated pool with a waterfall, perfect for unwinding after exploring downtown's dining, nightlife, galleries and shopping.
Reviews
9.69.6 out of 10
Exceptional
Entire home
1 bedroom1 bathroom544 sq ft
Popular amenities
Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Add dates for prices
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...
Property amenities
Pool/Spa
Communal pool
Heated pool
Internet
Available in the cottage: Free WiFi
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Microwave
Oven
Refrigerator
Stovetop
Toaster
Bedrooms
Bedroom
Bedsheets provided
Bathroom
1 bathroom
Bathtub or shower
Hair dryer
Towels provided
Living spaces
Living room
Entertainment
TV with cable/satellite channels
Outdoor areas
Barbecue grill
Patio
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Pets
No pets allowed
Suitability/Accessibility
Hardwood flooring in public areas
Smoking not allowed
Services and conveniences
Concierge services
Housekeeping (on request)
Iron/ironing board
Location highlights
In the city center
Near a hospital
Near the marina
Near the sea
Things to do
Heated pool
Basketball nearby
Birdwatching nearby
Cycling nearby
Ecotours nearby
Fishing nearby
Jet skiing nearby
Sailing nearby
Scuba diving nearby
Snorkeling nearby
Swimming nearby
Water skiing nearby
Windsurfing nearby
Safety features
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
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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
Pets not 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
Onsite 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
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
Property Registration Number 25230-112332
About the area
Located by the sea, this cottage is in Old Town Key West, a neighborhood 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. MLK Community Pool & Community Center and Florida Keys Eco - Discovery Center are also worth visiting. Visit our Key West travel guide
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.
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!?
Check-out 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.
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PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! Reviews
Reviews
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 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:
This cottage has everything you need and the location is perfect. We have rented it many times and each and every time we only had one problem.....TODD! He does his best to try and make our stay miserable.
Robin H.
From a partner site
10/10 Excellent
Stephanie J.
Jul 13, 2024
Location, Location, Location.
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:
Absolutely cannot beat the location ... on the less busy end of Duval only a few blocks from the Southernmost Point. The cottage was just the right size for 2 people, was clean and well appointed. Walking distance to so many restaurants and lots of people watching from the front porch. A bonus was we got to meet several of the neighbors (Paul/Emily/Todd/David/Less) around us and they were all great - happy hour to celebrate Paul's birthday month was one of our best nights). Todd was super helpful and answered any question we had about the house and neighborhood. Communication with Whitney at Best of Key West Rentals was always prompt and helpful. Highly recommend.
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
From a partner site
10/10 Excellent
Dina T.
Oct 25, 2021
Great place / attentive management / unhinged neighbor
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very unhappy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I do not recommend this vacation rental.
Reviewer Comments:
The cottage is exactly as described. Super cute and practical. Brian, the property manager, was excellent. Above and beyond service. Sadly, you will be living next door to a very unwell man named Todd. He’s the only downfall to the property.
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.
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.
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
From a partner site
8/10 Good
Robin H.
Feb 2, 2021
Pineapple Cottage
Rating Details:
The property manager was very helpful.
The vacation rental was very clean.
I was very happy with the location.
I was satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Great location to sit on porch and people watch!
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.
Verified traveller
Stayed 29 nights in Oct 2020
From a partner site
10/10 Excellent
Chloe I.
Aug 6, 2020
Wonderful
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:
Loved this little cottage and pool. Walking distance to everything. Clean, neat, just the right size with washer/dryer.
Chloe I.
From a partner site
10/10 Excellent
Mark G.
Apr 19, 2020
Great Location
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:
Outstanding
Mark G.
From a partner site
10/10 Excellent
Robin H.
Feb 6, 2020
Pineapple Cottage 2020
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:
Our stay at Pineapple Cottage has always been great and the rental people we have dealt with have been wonderful. We only have one complaint regarding this years stay. The couple that occupied the cottage next to us were heavy smokers. Even though they never smoked on the property, their car was parked out front and they sat in it with the doors open and smoked or stood on the sidewalk in front of their cottage and smoked constantly. It was unpleasant for us to sit on the porch (which we love to do) because there was constant cigar and cigarette smoke. They also enjoyed their alcohol to the point of falling down on the sidewalk and having a stranger assist them back on the porch. We enjoy this property so much, but this year was less pleasant because of them.
Robin H.
Archival
10/10 Excellent
Karen P.
Dec 19, 2016
Exceeded our expectations. Very well presented.
Arrival and departure was extremely easy, we were given the door code and did a self check in and when we left, we basically left the cottage the way we found it and closed the door. A few days after we arrived the garburator started to leak, and also the BBQ grill ran out of propane. We contacted Truman properties and both were fixed immediately. When we walked into the cottage it was exactly as it appeared on the website which was very satisfying. The location of the property was basically in the middle between the harbor and the beaches, each being about a 10 minute walk in either direction and it was just one block from Duval so that we didn’t hear or see all the action, but were close enough to wander over. We did not rent a car for our month’s stay and really did not need one to get around. We rented bicycles for a few days which was nice to give our feet a rest and to see just a little bit more of the island. There were many great restaurants and happy hours to take in. The weather was amazing every day, and there were also many events happening each week while we were there. I would recommend this cottage to experience all that Key West has to offer.
Karen P.
Archival
10/10 Excellent
nancy j.
Apr 22, 2015
Heart of Everything? You bet!
818-2 Whitehead really is in the heart of it all. 1/2 block from Hemingway House, 1 block from Blue Heaven, and 2 blocks from Green Parrot. We were there for two months and couldn't have been happier with it all. Particularly the staff at the rental office -- always helpful and friendly. Parking can be a bit tough some times, but with the location, and our bicycles, we would sometimes go a week or more with just walking wherever we wanted to go. A great place to relax on the front porch and let the world (or at lease the tourists) go by.