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

Pool
Exterior
Room
Terrace/patio
Pool
4 bedrooms3+ bathroomsSleeps 10232.3 sq m

Popular amenities

  • Dryer
  • Parking available
  • Washer
  • Free WiFi
  • Air conditioning
  • Kitchen

Explore the area

View map
Key West, FL
  • Duval Street
    ‪14 min walk‬
  • Southernmost Point
    ‪17 min walk‬
  • Mallory Square
    ‪4 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!

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?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

House Rules

Check in after 4:00 PM
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

No pets allowed
default

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.
Map
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

  • Key West, FL (EYW-Key West Intl.) - 8 min drive

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

Is Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool?

Check-in begins at 4:00 PM.

What time is check-out at Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool?

Checkout is at 10:00 AM.

Where is Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool located?

Located in Key West Historic District, this holiday home is within a 15-minute walk of The Unitarian Universalist Fellowship of Key West and Duval Street. Ernest Hemingway Home and Museum and Florida Keys Beaches are also within 1 mile (2 km).

Reviews

Rating 10 - Excellent. 0 out of 0 reviews
Rating 8 - Good. 0 out of 0 reviews
Rating 6 - Okay. 0 out of 0 reviews
Rating 4 - Poor. 0 out of 0 reviews
Rating 2 - Terrible. 0 out of 0 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

Host profile image

Languages:

English, Spanish

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback