House in Key West, FL
10 guests · 4 bedrooms · 3 baths
Reasons to book
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
Includes essentialsFamily friendly and more
About this house rental
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!
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!
Amenities at Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool
Family friendly
Map of Key West, FL
Things to know
Additional fees to expect
Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All Expedia properties are professionally cleaned after each stay.
Booking feeNo booking fees, easy credit card payments.
Service feeThis helps Expedia provide a safer and more secure booking experience.
TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.
Customer support
Customer support is handled by our partner Expedia
$$$$
Don't miss out! Price and availability may change
