Title: PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! - Latest Reviews, Deals & Photos 2025 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/ Shared Heated Pool! Cottage with kitchen, steps from Ernest Hemingway Home and Museum ![A heated pool](https://images.trvl-media.com/lodging/37000000/36180000/36177500/36177468/b6002627.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Interior](https://images.trvl-media.com/lodging/37000000/36180000/36177500/36177468/fc5c4ad7.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36180000/36177500/36177468/177c4224.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/37000000/36180000/36177500/36177468/8be7ef69.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36180000/36177500/36177468/64979ae9.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location 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. 9.6 Exceptional ### Entire home 1 bedroom1 bathroom544 sq ft ## Popular amenities - Dryer - Pool - Washer - Barbecue grill - Kitchen - Outdoor space ## Add dates for prices Check-in Check-out Travellers ## 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 - Golfing 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 ## Similar properties ![Pool](https://images.trvl-media.com/lodging/65000000/64570000/64564200/64564122/w1076h1183x1y0-39d4407c.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### A Stones Throw Away from Duval - Downtown -Caroline's Cottage KW Old Town Key West - Kitchen - Washer - Dryer - Free WiFi 9.6 Exceptional 12 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-22&endDate=2025-11-23&selected=64564122&PinnedHotelID=64564122&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/28000000/27690000/27682400/27682303/79d0a981.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Steps from Duval, Pool on Site & Bikes Included! Old Town Key West - Pool - Hot tub - Kitchen - Washer 9.6 Exceptional 408 reviews CA $125 CA $317 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&selected=27682303&PinnedHotelID=27682303&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21700000/21690900/21690843/81510f43.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC Old Town Key West - Kitchen - Pet-friendly - Free WiFi - Air conditioning 8.8 Excellent 235 reviews CA $94 CA $308 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-16&endDate=2025-11-17&selected=21690843&PinnedHotelID=21690843&HadPinnedHotel=true®ionId=-1&adults=2) ![Restaurant](https://images.trvl-media.com/lodging/90000000/89840000/89832400/89832384/d6422035.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Aqua Lodges at Hurricane Hole Marina Stock Island - Parking included - Free WiFi - Air conditioning 8.8 Excellent 165 reviews CA $156 CA $411 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-11&endDate=2025-11-12&selected=89832384&PinnedHotelID=89832384&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor dining](https://images.trvl-media.com/lodging/22000000/21630000/21626200/21626103/c33b1989.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### \*\*SWEPT AWAY @ OLD TOWN\*\* Dreamy Private Home & Pool + LAST KEY SERVICES... 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Old Town Key West - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 11 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-22&endDate=2025-11-23&selected=74975454&PinnedHotelID=74975454&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95840000/95837000/95836923/8876df94.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Prime Old Town Location w/ Pool, Walk to Duval Steet | Blue Heron by AvantStay Old Town Key West - Pool - Kitchen - Washer - Dryer 10 Exceptional 1 review [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-22&endDate=2025-11-23&selected=95836923&PinnedHotelID=95836923&HadPinnedHotel=true®ionId=-1&adults=2) ![A heated pool](https://images.trvl-media.com/lodging/107000000/106650000/106644800/106644767/4b8d1d94.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Tropical Cottage w/ Private Pool--Two blocks from Duval - Near Hemingway House! Old Town Key West - Pool - Kitchen - Washer - Dryer [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-22&endDate=2025-11-23&selected=106644767&PinnedHotelID=106644767&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 4:00 PM Contactless check-in 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 ### 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 ### Property is also known as 2450-154416 ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C24.55158%2C-81.80152&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=TEhAg4dTHwu6DHS2ESj3urTfGSI=) Key West, Florida #### What's nearby - Duval Street - 1 min walk - 0.2 km - Ernest Hemingway Home and Museum - 2 min walk - 0.2 km - South Beach - 9 min walk - 0.8 km - Southernmost Point - 11 min walk - 0.9 km - Mallory Square - 15 min walk - 1.3 km #### Getting around - Key West Intl. Airport (EYW) - 12 min drive #### Restaurants - ‪Blue Heaven - ‬2 min walk - ‪Moondog Cafe & Bakery - ‬2 min walk - ‪Bourbon Street Pub - ‬3 min walk - ‪Old Town Tavern - ‬4 min walk - ‪801 Bourbon Bar - ‬3 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!? > 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. Southernmost Point and Florida Keys Beaches are also within 15 minutes. ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. 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