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

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Fridge, microwave, oven, stovetop - Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool (Key West)
Pool - Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool (Key West)
Fridge, microwave, oven, stovetop - Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool (Key West)
Fridge, microwave, oven, stovetop - Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool (Key West)
Terrace/patio - Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool (Key West)
Close to Duval Street and Ernest Hemingway Home and Museum, Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool provides amenities such as golfing on-site. Guests can connect to free in-room WiFi.

Entire home

4 bedrooms4 bathrooms232 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Add dates for prices

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

*** Please note for 2027 High Season rentals Jan- February - Arrival after the 5th of January for 6 week minimum is required in order to get accurate pricing***

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

Book Your Stay Today and Start Living the Island Dream!

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

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  • Washing machine
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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are 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
Information provided by the property may be translated using automated translation tools

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.

Pets

Pets not 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
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
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
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

About the area

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 cycling and ecotours nearby. Visit our Key West travel guide
View more Holiday homes in Key West
Map
Key West, FL

What's nearby

  • #TroveOn A couple miles north of Key West, on the right is Boca Chica Rd, follow that road as far as you can and you'll get to the beach at Geiger Key. The road comes to an abrupt stop, the rest of it was destroyed in a hurricane years ago but you can park there and walk out. The beach is secluded and quiet, except when the Navy is holding flight practices. The planes are so close, you can see the pilots!
    Key West Naval Station
    2 min walk - 0.2 km
  • Duval Street featuring signage
    Duval Street
    12 min walk - 1.1 km
  • Ernest Hemingway Home and Museum featuring heritage elements and a house
    Ernest Hemingway Home and Museum
    15 min walk - 1.3 km
  • South Beach featuring a sandy beach and general coastal views as well as a small group of people
    South Beach
    15 min walk - 1.3 km
  • Southernmost Point featuring signage
    Southernmost Point
    17 min walk - 1.5 km

Getting around

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

Restaurants

  • Dions Truman & White
    4 min walk
  • Square Grouper Key West
    13 min walk
  • Sandy's Café
    6 min walk
  • The Dive Bar Shirt Club - Grub House
    11 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.

How much is parking at Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool?

On-site parking is available at the 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).

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