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

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

Reviews

9.8 out of 10
Exceptional

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

Popular amenities

  • Patio
  • Swimming pool
  • Barbecue grill
  • Air-conditioning
  • Refrigerator
  • Washing machine

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.)
    ‪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

Add dates for prices

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  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
9.6 out of 10, Exceptional, (13 reviews)
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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.
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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

  • ‪Blue Heaven - ‬3 min walk
  • ‪Moondog Cafe & Bakery - ‬2 min walk
  • ‪801 Bourbon Bar - ‬3 min walk
  • ‪Bourbon Street Pub - ‬3 min walk
  • ‪Mangoes Restaurant - ‬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.

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 Mallory Square are also within 15 minutes.

Reviews

9.8

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. 13 out of 16 reviews
Rating 8 - Good. 3 out of 16 reviews
Rating 6 - Okay. 0 out of 16 reviews
Rating 4 - Poor. 0 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

9.6/10

Location

8.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
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
Stayed 28 nights in Mar 2026
Response from VrboOwner on 11 May 2026
We’re grateful for your glowing review Paula! It was such a pleasure to host you, and we’re already looking forward to your return to the island.
Verified review

8/10 Good

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

Perfect Retreat for 2 people

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: The rental was clean and with all the required amenities. There are only 2 issues - the tv was quite small with distorted sound and whilst we dont holiday to watch tv we were there for a month. The other was the outdoor space around the pool was very small. Other than those issues it was a perfect place to stay in an excellent location. We have rebooked for next year!
Response from VrboOwner on 4 Jun 2026
Your kind words mean the world to us Frank! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.
From a partner site

10/10 Excellent

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

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

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 review

10/10 Excellent

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 review

8/10 Good

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 review

10/10 Excellent

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

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 review

10/10 Excellent

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

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

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

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

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

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.
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