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

Pool - 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

Similar properties

Pool
Kitchen
Washing machine
Dryer

Compare similar properties

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

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

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

Key West, FL

What's nearby

Key West Naval Station
2 min walk - 0.2 km
Duval Street
12 min walk - 1.1 km
Ernest Hemingway Home and Museum
15 min walk - 1.3 km
South Beach
15 min walk - 1.3 km
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).

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

Entire home

Popular amenities

Add dates for prices

About this property

Entire place

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

Property amenities

Pool/Spa

Internet

Parking and transport

Kitchen

Dining

Bedrooms

Bathroom

Living spaces

Entertainment

Outdoor areas

Laundry

Work spaces

Comfort

Pets

Suitability/Accessibility

Services and conveniences

Location highlights

Things to do

Safety features

General

Similar properties

Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches

Policies

Check-in

Check-out

Special check-in instructions

Check-out instructions

Pets

Children and extra beds

Events

Smoking

Important information

You need to know

Property is also known as

About the area

What's nearby

Getting around

Restaurants

Frequently asked questions

Have a question?

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

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