Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool | House in Key West
4 Bedroom House in The Meadows, Key West
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!
Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool is located in The Meadows. Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool provides accommodation, featuring View, Ocean View, Wellness Facilities, among other amenities. This House features View, Ocean View, Wellness Facilities, to make your stay a comfortable one.
Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool has 4 Bedrooms , 3 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the The Meadows has interesting places to visit. If you want to learn more about the House in The Meadows, such as places to visit and things to do nearby, you can check below to learn more.
This Property is OneKey Eligible
Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.
Amenities
Facility Overview
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Air conditioning
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Heating
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3+ bathrooms
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Shower
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Towels provided
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Hair dryer
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Bed sheets provided
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4 bedrooms
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Dining table
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Living room
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Toaster
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Coffee/tea maker
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Ice maker
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Oven
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Refrigerator
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Kitchen island
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Dishwasher
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Microwave
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Stovetop
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Washing machine and dryer
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Near laundromat
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Onsite parking
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No pets allowed
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Smoke-free property
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Bicycle on site
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Snorkeling nearby
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Marina nearby
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Windsurfing nearby
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Fitness facilities nearby
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Golf nearby
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Golfing on site
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Fishing nearby
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Tennis on site
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Swimming nearby
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Water skiing nearby
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Cycling nearby
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Ecotours nearby
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Smart TV with cable/satellite service
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Unit size: 2500 sq ft (232 sq m)
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English
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Spanish
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Near a hospital
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Near the sea
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In the city center
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Desk chair
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Computer monitor
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Desk
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Iron/ironing board
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Housekeeping (on request)
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Free WiFi, with speed of 500+ Mbps (good for 6+ people or 10+ devices)
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Balcony
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Smoke detector installed (host has indicated there is a smoke detector on the property)
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Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
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First aid kit
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Deadbolt lock
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Fire extinguisher
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Private pool
Policies
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 host has indicated there is a smoke detector on the property host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
