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!
One bedroom on the main level with a king. The other three bedrooms are on the first floor of the home. The Primary features a walk in closet and a full en suite bathroom.
Minimum number of persons: 1
Maximum number of persons: 10