Title: Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool - Latest Reviews, Deals & Photos 2026 - 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 # Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool Vacation home with private pool, near Duval Street ## Photo gallery for Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool ![Fridge, microwave, oven, stovetop - Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool (Key West)](https://images.trvl-media.com/lodging/120000000/119370000/119368500/119368408/16ae1184.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Terrace/patio - Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool (Key West)](https://images.trvl-media.com/lodging/120000000/119370000/119368500/119368408/3d2c7440.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop - Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool (Key West)](https://images.trvl-media.com/lodging/120000000/119370000/119368500/119368408/64b6e8da.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Pool - Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool (Key West)](https://images.trvl-media.com/lodging/120000000/119370000/119368500/119368408/678dfb20.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop - Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool (Key West)](https://images.trvl-media.com/lodging/120000000/119370000/119368500/119368408/292e2514.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Close to Duval Street and Ernest Hemingway Home and Museum, Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool provides amenities like golfing on site. Active travelers can enjoy bicycling at this vacation home. Guests can connect to free in-room WiFi. ### Entire home 4 bedrooms4 bathrooms2500 sq ft ## Popular amenities - Pool - Kitchen - Washer - Dryer - Free WiFi - Air conditioning ## 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. ### Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool Island Dreaming – Your Luxury Key West Getaway Welcome to Paradise Discover the ultimate island retreat at Island Dreaming, a spectacular Key West vacation home nestled between the charm of Old Town and the tranquility of the Meadows District. Whether you're traveling with family or friends, this private oasis blends upscale amenities with the laid-back lifestyle of the Keys. Property Highlights Location: Quiet yet central – walk to downtown, yet enjoy serene privacy Bedrooms: 4 spacious bedrooms including two primary suites Bathrooms: 3.5 modern bathrooms Parking: Off-street parking for 1 vehicle Size: Comfortably sleeps 8+ guests Outdoor Oasis Private Saltwater Pool: 12’ x 18’, heated (by request), custom-tiled with waterfall & in-pool loungers Outdoor Kitchen: BBQ grill, sink, and ice-maker – perfect for entertaining Multiple Outdoor Living Spaces: Expansive front porch for morning coffee Back deck for cocktails under the stars Shaded & sunny lounging areas Lush Landscaping: Tropical flora, paver walkways, irrigation, and outdoor lighting Interior Features Seamless Indoor-Outdoor Living: 9-ft ceilings & 16-ft glass doors connect the living area to the poolside deck Gourmet Kitchen: Fully equipped for all your culinary needs Wine Lovers’ Dream: 600-bottle, walk-in, climate-controlled wine room Two Primary Suites: First-floor suite with private bath Second-floor suite with vaulted pine ceiling & private balcony Bright Living Room: Natural light and pool views with wall-to-wall glass doors Additional Amenities Whole-house water filtration system Custom-designed staircase Pool heat available (fee applies; must be requested in advance) High-speed WiFi & smart TVs Washer & dryer Perfect Location Located in a diverse, upbeat neighborhood, Island Dreaming puts you close to: Duval Street nightlife Local restaurants & bars Art galleries, shops, and attractions Beaches & marinas Ideal For Families Groups of friends Extended stays Guests seeking a luxury, peaceful vacation with easy access to the action Additional fees may be added after booking: Pool heating fee of $300 per month for the months of November-March(optional) Reservations of more than a month require a mid stay cleaning fee \*\*\* Please note the from Nov - April rentals are required to start on the 1st of the calendar month, Any month that includes February has to be either Jan/Feb or Feb/March. We are unable to split the month. The house is available to rent from November 1st 2025\. Book Your Stay Today and Start Living the Island Dream! ## Property amenities ### Pool/Spa - Private pool ### Internet - Available in the house: Free WiFi ### Parking and transportation - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Ice maker - Kitchen island - Microwave - Oven - Refrigerator - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 4 bedrooms - Bedsheets provided ### Bathroom - 3.5 bathrooms - Hair dryer - Shower - Towels provided ### Living spaces - Dining table - Living room ### Entertainment - Smart TV with cable/satellite channels ### Outdoor areas - Balcony ### Laundry - Laundromat nearby - Washing machine ### Work spaces - Computer monitor - Desk - Desk chair ### Comfort - Air conditioning - Heating ### Pets - No pets allowed ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Housekeeping (on request) - Iron/ironing board ### Location highlights - In the city center - Near a hospital - Near the marina - Near the sea ### Things to do - Bicycles - Golf - Tennis - Basketball nearby - Birdwatching nearby - Cycling nearby - Ecotours nearby - Fishing nearby - Golfing nearby - Jet skiing nearby - Sailing nearby - Snorkeling nearby - Swimming nearby - Water skiing nearby - Water tubing 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) - First aid kit - Fire extinguisher - Deadbolt lock ### General - Bicycles - Housekeeping (on request) - Unit size: 2,500 square feet ## Similar properties ![A heated pool](https://images.trvl-media.com/lodging/103000000/102300000/102290800/102290750/6ed0df86.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### \*\*SPIRIT OF KEY WEST @ OLD TOWN\*\* Exquisite Home & Pool + LAST KEY SERVICES… Old Town Key West - Pool - Kitchen - Washer - Dryer [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-05&endDate=2026-02-06&selected=102290750&PinnedHotelID=102290750&HadPinnedHotel=true®ionId=-1&adults=2) ![A heated pool](https://images.trvl-media.com/lodging/37000000/36040000/36035500/36035493/bad4b65e.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Old Town Key West classic with private saltwater pool & enclosed patio- by shops Old Town Key West - Pool - Kitchen - Washer - Dryer 9.8 Exceptional 11 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-05&endDate=2026-02-06&selected=36035493&PinnedHotelID=36035493&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83680000/83674600/83674516/d7468b24.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Conch Republic Retreat Key West Historic District - Pool - Washer - Dryer - Free WiFi [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-05&endDate=2026-02-06&selected=83674516&PinnedHotelID=83674516&HadPinnedHotel=true®ionId=-1&adults=2) ![Dining](https://images.trvl-media.com/lodging/120000000/119160000/119153700/119153648/2e9dd029.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### \*\*THE ARTIST’S AVIARY @ OLD TOWN\*\* Newly Renovated Home & Pool + LAST KEY SERVIC Old Town Key West - Pool - Kitchen - Washer - Dryer [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-05&endDate=2026-02-06&selected=119153648&PinnedHotelID=119153648&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/121000000/120290000/120288800/120288800/3b4da04f.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### THE WRITER'S COTTAGE \~ Renovated Old Town 2 BR/2 Ba Home w/Parking! Old Town Key West - Kitchen - Washer - Dryer - Free WiFi [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-05&endDate=2026-02-06&selected=120288800&PinnedHotelID=120288800&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/97000000/96460000/96454700/96454624/41cf94eb.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Charming + Circa 1889 Historic Eyebrow Home Old Town Key West - Pool - Kitchen - Washer - Dryer 10 Exceptional 3 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-05&endDate=2026-02-06&selected=96454624&PinnedHotelID=96454624&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach](https://images.trvl-media.com/lodging/79000000/78490000/78486000/78485945/0d848011.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Conch Chateau: Stylishly Renovated Conch House in the Heart of Key West, Heated/Chilled Pool! 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Key West Historic District - Pool - Kitchen - Washer - Dryer 9.2 Wonderful 5 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-05&endDate=2026-02-06&selected=50936163&PinnedHotelID=50936163&HadPinnedHotel=true®ionId=-1&adults=2) ![Dining](https://images.trvl-media.com/lodging/46000000/45770000/45766900/45766815/7f9c0831.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### PINEAPPLE BREEZE \~ JUST RENOVATED Home in The Meadows with Pool! Key West Historic District - Pool - Kitchen - Washer - Dryer 10 Exceptional 4 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-05&endDate=2026-02-06&selected=45766815&PinnedHotelID=45766815&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 4:00 PM Contactless check-in available ### 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 ### Check-out instructions The host requires you complete the following before checking out: Load and start the dishwasher Strip any used beds and gather used towels Remove personal items, remove leftover food and drinks, and take out the trash Turn off the lights, lock the doors, and return the keys Please turn the AC back to 78 degrees Failure to complete these may result in a negative review from the host. ### 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, a first aid kit, and a deadbolt lock This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room 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 is also known as 1680-275424 ## About the area Located by the sea, this vacation home is in Key West Historic District, 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. The Kite House and Sails To Rails Museum at Flagler Station are also worth visiting. Jet skiing and snorkeling offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and ecotours nearby. [Visit our Key West travel guide](https://www.expedia.ca/Key-West.dx1187) [View more Vacation homes in Key West](https://www.expedia.ca/Key-West-Private-Vacation-Homes.d1187-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![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%7C24.55799%2C-81.79233&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=kJdmGw7MtVZueUklpBv9L88HlBI=) Key West, FL ### What's nearby - ![#TroveOn A couple miles north of Key West, on the right is Boca Chica Rd, follow that road as far as you can and you'll get to the beach at Geiger Key. The road comes to an abrupt stop, the rest of it was destroyed in a hurricane years ago but you can park there and walk out. The beach is secluded and quiet, except when the Navy is holding flight practices. The planes are so close, you can see the pilots!](https://images.trvl-media.com/place/553248635976481245/e66923bb-4dc7-449a-bbc6-f6b5c57b69c9.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Key West Naval Station 2 min walk \- 0.2 km - ![Duval Street featuring signage](https://images.trvl-media.com/place/6068616/5997ee0c-eca4-415b-b051-99f4d38fbc11.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Duval Street 12 min walk \- 1.1 km - ![Ernest Hemingway Home and Museum featuring heritage elements and a house](https://images.trvl-media.com/place/501376/3b4c31fa-338d-424b-aa0f-482ad359d16a.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Ernest Hemingway Home and Museum 15 min walk \- 1.3 km - ![South Beach featuring a sandy beach and general coastal views as well as a small group of people](https://images.trvl-media.com/place/6246827/42d13a3e-a933-4e9f-b857-cde9f4314a24.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) South Beach 16 min walk \- 1.3 km - ![Southernmost Point showing signage](https://images.trvl-media.com/place/501380/6b10fd25-a167-4157-b127-b099a5ff5ea1.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Southernmost Point 17 min walk \- 1.5 km ### Getting around - Key West Intl. Airport (EYW) 8 min drive ### Restaurants - Dions Truman & White 4 min walk - Sandy's Café 6 min walk - Mangia Mangia 8 min walk - Dairy Queen 9 min walk - Moose Lodge 6 min walk ## Frequently asked questions ### Is Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool pet-friendly? ### How much is parking? ### What time is check-in at Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool? ### What time is check-out at Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool? ### Where is Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. 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