See all properties
Entire home

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

Choose dates to view prices

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

A modern kitchen with a central island, built-in appliances, and pendant lighting.
A kitchen with a stainless steel refrigerator, a built-in oven, and a gas stove.
A covered porch with two chairs, a potted plant, and a house number sign.
A two-story house with a swimming pool, outdoor seating, and a covered patio area.
A modern kitchen with a central island, a dining area with a round table, and a living area with a sofa and TV.

Entire home

4 bedrooms4 bathrooms2500 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Key West, FL
  • Place, Key West Naval Station
    ‪2 min walk‬
  • Place, Duval Street
    ‪13 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪17 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪8 min drive‬

Room options

You may also like

Ad
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

New Town
  • Pool
  • Breakfast included
  • Parking included
  • Restaurant
8.6 out of 10, Excellent, 1,188 reviews
$152 nightly
The price is $171
Nov 15 - Nov 16
Total with taxes and fees
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

About the neighborhood

Key West

Located in Key West Historic District within a short walk of Duval Street, this vacation home is within a mile (2 km) of other popular sights such as Florida Keys Beaches. The vacation home includes a private pool, a kitchen, and a balcony.
View more Vacation Homes in Key WestOpens in a new window

What's nearby

  • Key West Naval Station - 2 min walk - 0.1 miles
  • Key West Cemetery - 6 min walk - 0.4 miles
  • Duval Street - 13 min walk - 0.7 miles
  • Ernest Hemingway Home and Museum - 17 min walk - 0.9 miles
  • South Beach - 18 min walk - 1.0 mile

Getting around

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

Restaurants

  • ‪Cuban Coffee Queen Waterfront - ‬14 min walk
  • ‪Circle K - ‬13 min walk
  • ‪Square Grouper Key West - ‬13 min walk
  • ‪Harpoon Harry's Restaurant and Bar - ‬13 min walk
  • ‪Pepe's Cafe - ‬14 min walk

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 - MONTHLY RENTAL
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!
The vacation home is air-conditioned and features a kitchen, 3.5 bathrooms, and a balcony, and there's space to spread out with 4 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a private pool, a washing machine, and a coffee maker. Housekeeping is available on request.

Similar properties

A two-story house with a swimming pool, a covered patio, and a dining area visible through large sliding glass doors.
**SOUTHERN STAR @ THE MEADOWS** Home & Pool + Last Key White Glove Service...
Key West Historic District
  • Pool
  • Hot tub
  • Kitchen
  • Washer
**SOUTHERN STAR @ THE MEADOWS** Home & Pool + Last Key White Glove Service...

Property amenities

Pool/Spa

  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bed sheets 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

  • Smoking not allowed

Services and conveniences

  • Housekeeping (on request)
  • Iron/ironing board

Location highlights

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

Things to do

  • Bicycles
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Snorkeling 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)
  • Deadbolt lock
  • Fire extinguisher
  • First aid kit

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
Information provided by the property may be translated using automated translation tools

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

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

Smoking

Smoking is not permitted

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
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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.

Property is also known as

1680-275424

Frequently asked questions

What can I see close to this vacation home?

This vacation home is situated in Key West Historic District within a short 14-minute walk of Duval Street and also 19 minutes on foot from Florida Keys Beaches. You'll also find Mallory Square and Ernest Hemingway Home and Museum within a short drive.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home; however, the accommodation features a private pool.

Does this vacation home include breakfast service?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

Where is the closest airport to this vacation home?

The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 3.1 mi away (8 minutes by car).

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

More to Explore