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Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool

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4 bedrooms, desk, iron/ironing board, free WiFi
4 bedrooms, desk, iron/ironing board, free WiFi
Pool
Fridge, microwave, oven, stovetop
Fridge, microwave, oven, stovetop

Entire home

4 bedrooms4 bathrooms232 sq m

Popular amenities

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

Explore the area

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Key West, Florida
  • Place, Duval Street
    ‪14 min walk‬
  • Place, Southernmost Point
    ‪17 min walk‬
  • Place, Mallory Square
    ‪4 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪7 min drive‬

Room options

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About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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!
During your stay at this vacation home, you're just a quick walk from The Unitarian Universalist Fellowship of Key West. Enjoy your stay with amenities like free WiFi and a private pool in the vacation home.
  • Air-conditioned home with private pool, kitchen, and washing machine
  • Free WiFi (speed: 500+ Mbps (good for 6+ people or 10+ devices))
  • Onsite recreation includes tennis courts
  • 14 minutes by foot from Duval Street and a 3-minute drive from Ernest Hemingway Home and Museum

Property amenities

Pool/Spa

  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 3.5 bathrooms
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony

Laundry

  • Laundromat nearby
  • Washing machine

Work spaces

  • Computer monitor
  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Housekeeping (on request)
  • Iron/ironing board

Location highlights

  • In the city centre
  • Near a hospital
  • Near the marina
  • Near the sea

Things to do

  • Bicycles
  • Golf
  • Tennis
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Snorkelling nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Bicycles
  • Housekeeping (on request)
  • Unit size: 2,500 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Check-out instructions

The host requires you 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 trash
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.

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
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
Onsite 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

Property is also known as

1680-275424

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