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

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Welcome to Pineapple Cottage!
Residential feel!
Front porch lounging for 2
Open space with hardwood floors
Flat screen TV

Reviews

9.6 out of 10
Exceptional
1 bedroom1 bathroomSleeps 4544 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View in a 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.)
    ‪14 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...

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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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

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 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. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with cycling and ecotours.
View more Cottages in Key WestOpens in a new window
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

  • ‪Bourbon Street Pub - ‬3 min walk
  • ‪801 Bourbon Bar - ‬3 min walk
  • ‪Mangoes Restaurant - ‬4 min walk
  • ‪Blue Heaven - ‬3 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 18 Apr, 2026, prices found for a 1-night stay for 2 adults at PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! on 31 May, 2026 start from S$151, 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.

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 11 out of 14 reviews
Rating 8 - Good. 3 out of 14 reviews
Rating 6 - Okay. 0 out of 14 reviews
Rating 4 - Poor. 0 out of 14 reviews
Rating 2 - Terrible. 0 out of 14 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

9.6/10

Location

8.4/10

Listing accuracy

Reviews

Verified

8/10 Good

david p.

Liked: Cleanliness, check-in, communication, location

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
Stayed 30 nights in Nov 2024
From a partner site

10/10 Excellent

Robin H.

We love this place/

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.
Response from VrboOwner on 6 Feb, 2024
Thank you for your wonderful review Robin. It was a pleasure hosting you again! You are fantastic guests and our entire team looks forward to welcoming you again next time you are in paradise!
From a partner site

10/10 Excellent

Dina T.

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.
Response from VrboOwner on 10 Nov, 2021
Thank you for your review Dina, we are so glad you enjoyed your stay at Pineapple Cottage. It is unfortunate some locals don't appreciate the diversity rental properties offer to the neighborhood. I can assure you the rest of us really enjoyed having you on the island!
From a partner site

10/10 Excellent

Stephanie J.

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.
Response from VrboOwner on 14 Jul, 2024
Thank you for your fantastic review Chris. We are thrilled you enjoyed the house so much and made new friends during your stay. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!
Verified

10/10 Excellent

Sharon W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 30 nights in Nov 2022
Response from VrboOwner on 10 Jan, 2023
Thank you for your feedback on your recent stay Sharon. We are so glad that you enjoyed your time spent at this home. We appreciate your feedback that we will relay back to our team. Thank you again and please reach out to us for your next Key West vacation!
Verified

8/10 Good

Jan S.

Liked: Cleanliness, check-in, communication, location

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.
Stayed 31 nights in Dec 2021
Response from VrboOwner on 20 Jan, 2022
Thank you for your review Jan, we are glad you enjoyed the property so much. We would love to find you a home with a private pool next time you plan a trip to the Keys. We hope to welcome you in paradise again soon!
Verified

10/10 Excellent

Earl S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 28 nights in Nov 2021
Response from VrboOwner on 16 Dec, 2021
Thank you for your review Earl, we are glad you enjoyed your stay and hope to host you again next time you visit the island!
From a partner site

8/10 Good

Robin H.

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!
Response from VrboOwner on 9 Feb, 2021
Thank you for this incredible review. We loved hosting you in Paradise and hope to see you again soon!
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 29 nights in Oct 2020
Response from VrboOwner on 17 Nov, 2020
Thank you for your incredible review. We enjoyed hosting you and hope to see you again!
From a partner site

10/10 Excellent

Chloe I.

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.
Response from VrboOwner on 6 Aug, 2020
Thank you for your wonderful review. We are so thrilled to hear how much you loved this adorable home and hope to see you back soon.
From a partner site

10/10 Excellent

Mark G.

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
Response from VrboOwner on 26 May, 2022
Dear Mark, Thank you for your wonderful review. We are so happy to hear how much you loved these accommodations and hope to see you back soon. Best Regards, Wendy Zintsmaster and Team
From a partner site

10/10 Excellent

Robin H.

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.
Response from VrboOwner on 27 May, 2022
Dear Robin, Thank you for your recent review. We enjoyed hosting you in Paradise. We are so sorry if the neighbors's smoking disturbed your stay and will speak with the association immediately on this matter as they have very strict rules regarding smoking near the homes. Next time please notify us immediately and we will contact the HOA to remedy the situation. We hope your vacation was otherwise very enjoyable and hope to see you back soon. Best Regards, Wendy Zintsmaster and Team
Archival

10/10 Excellent

Karen P.

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.
Response from VrboOwner on 29 Mar, 2020
Thank you so much for your kind review. We hope to have to back soon!! Best of Key West Rentals
Archival

10/10 Excellent

nancy j.

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.

About the host

Hosted by Wendy Zintsmaster & Team

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Languages:

English

Premier Host

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