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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. - PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! (Key West)
A rectangular pool with a tiled edge, surrounded by a stone patio, white fencing, and various potted plants. - PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! (Key West)
A kitchen with a stainless steel refrigerator, a microwave, and a stove. There is a granite countertop and a sink. - PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! (Key West)
A spacious kitchen with a central island, wooden cabinets, and a stainless steel refrigerator. - PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! (Key West)
A bedroom with a wooden bed, a nightstand with a lamp, a dresser, a ceiling fan, and a window with blinds. - PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! (Key West)
A short walk from Duval Street and Southernmost Point, PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! provides laundry facilities and more. Stay connected with free in-room WiFi.

Reviews

9.8 out of 10
Exceptional

Entire home

1 bedroom1 bathroom51 sq m

Popular amenities

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

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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...

Property amenities

Pool/Spa

  • Communal pool
  • Heated pool

Internet

  • Available in the cottage: Free WiFi

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • 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
  • Smoke-free property

Services and conveniences

  • Concierge services
  • Housekeeping on request
  • Iron/ironing board

Location highlights

  • In the city centre
  • 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
  • Snorkelling 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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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

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
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
Property Registration Number 25230-112332

About the area

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. Visit our Key West travel guide
View more Cottages in Key West
Map
Key West, FL

What's nearby

  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    1 min walk - 0.2 km
  • A vintage typewriter on a wooden table with a notebook and pen beside it.
    Ernest Hemingway Home and Museum
    2 min walk - 0.2 km
  • A white lighthouse with a black top, surrounded by lush greenery and residential buildings.
    Key West Lighthouse and Keeper's Quarters Museum
    2 min walk - 0.2 km
  • A beachside resort with palm trees, a large white building, and a checkered pattern on the sand.
    South Beach
    9 min walk - 0.8 km
  • A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.
    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
  • Mangoes Restaurant
    4 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.

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.

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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.
More informationOpens 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

Cleanliness

9.6

Location

Reviews

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!
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.
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.
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
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

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.
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
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
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
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!
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
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.
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
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.
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.
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.