Entire home
Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool
Photo gallery for Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool





4 bedrooms 3+ bathrooms Sleeps 10 232.3 sq m
Popular amenities
Explore the area

Key West, FL
- Duval Street14 min walk
- Southernmost Point17 min walk
- Mallory Square4 min drive
- Key West, FL (EYW-Key West Intl.)7 min drive
Rooms & beds
4 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
Bedroom 3
2 Single Beds
Bedroom 4
1 King Bed
3 bathrooms, 1 half bathroom
Bathroom 1
Toilet · Shower only
Bathroom 2
Toilet · Shower only
Bathroom 3
Toilet
Bathroom 4
Toilet · Shower only
Spaces
Deck or patio
Kitchen
Balcony
Dining area
About this property
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!
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 manager
All Florida Keys Property Management
Premier Host
Languages
English, Spanish
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

**BELLE OF THE BEACH @ CASA EAST** Beach House + LAST KEY SERVICES…
**BELLE OF THE BEACH @ CASA EAST** Beach House + LAST KEY SERVICES…
- Pool
- Kitchen
- Washer
- Dryer
10.0 out of 10, (59 reviews)
House Rules
Check in after 4:00 PM
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Check-out instructions
The host requires you to 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 rubbish
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.
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
On-site 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 that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Key West
Located by the sea, this holiday home is in Key West Historic District, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Fort Zachary Taylor Historic State Park and Florida Keys Beaches. The Kite House and Sails To Rails Museum at Flagler Station are also worth visiting. Jet skiing and snorkelling offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.

Key West, FL
What's nearby
- Duval Street - 14 min walk - 1.2 km
- Ernest Hemingway Home and Museum - 15 min walk - 1.3 km
- South Beach - 16 min walk - 1.3 km
- Southernmost Point - 17 min walk - 1.5 km
- Mallory Square - 4 min drive - 2.0 km
Getting around
Restaurants
- Sandy's Cafe - 6 min walk
- Thai Island Restaurant - 14 min walk
- Mac’s Sunset and Tiki Bar - 8 min walk
- Dairy Queen - 9 min walk
- El Siboney Restaurant - 11 min walk
Frequently asked questions
Reviews
Reviews
No reviews yet
Be the first to leave a review for this property after your stay.
About the host
Hosted by All Florida Keys Property Management

Languages:
English, Spanish
Premier Host
They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback