Entire home

Thompson Island - Private Island Estate in Key West

Photo gallery for Thompson Island - Private Island Estate in Key West

A large building with a fountain in the center, surrounded by lush greenery. - Thompson Island - Private Island Estate in Key West (Key West)
A checkered floor, a staircase with ornate railings, a dining area with chairs, and a console table with decorative items. - Thompson Island - Private Island Estate in Key West (Key West)
A coastal property with multiple white buildings, a well-maintained lawn, and a view of the ocean. - Thompson Island - Private Island Estate in Key West (Key West)
A covered outdoor area with a view of a body of water and boats. - Thompson Island - Private Island Estate in Key West (Key West)
A spacious living room with a grey and white color scheme, featuring a large sofa, armchairs, a coffee table, and a fireplace. - Thompson Island - Private Island Estate in Key West (Key West)
You can look forward to a garden, a playground and laundry facilities at Thompson Island - Private Island Estate in Key West. For some rest and relaxation, visit the hot tub. Stay connected with free in-room WiFi.

Reviews

9.8 out of 10
Exceptional

Entire home

9 bedrooms9 bathroomsSleeps 20743 sq m

Popular amenities

  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Add dates for prices

About this property

Thompson Island - Private Island Estate in Key West

  • Thompson Island is the only private island in Key West with direct bridge access. Guests drive across a private bridge, pass through gated entry, and arrive at a completely secluded historic estate — no boats, ferries, or shared access required.
    This nearly century-old property has hosted U.S. Presidents, Governors, and distinguished guests. The main house and private cottages comfortably accommodate 16–20 guests. Amenities include a saltwater oceanside pool, jacuzzi, a separate freshwater pool, deep-water dockage, waterfront decks, kayaks, paddle boards, volleyball, basketball hoop, high-speed Wi-Fi, air conditioning, and ample on-island parking. The setting offers uninterrupted open-water views free from highway noise or commercial development.
    Located just 8–10 minutes from Duval Street, the estate provides rare privacy while remaining conveniently close to the heart of Key West. Ideal for large family gatherings, corporate retreats, and special celebrations.

    NOTE:
    The listing as booked through VRBO includes 7 bedrooms with 8 king beds (huge master bedroom has 2 king beds). 16 guests max. This means the Main House and the Mango Cottage.

    BEDROOM 8 and 9 (BOTH KINGS) are in 2 OPTIONAL COTTAGES that cost $300 per night each.

    NOTE WE DO NOT RENT TO OTHER GROUPS WHILE YOU ARE STAYING ON THE ISLAND!!

    PLEASE NOTE: Visitors are only allowed with the owner's permission. No parties/events allowed without the owner's permission.

    ALSO STAFF (2) are on the property daily for regular maintenance and separate housing

    PLEASE CALL FOR MORE INFO
    Thanks Andrew cell 305 923 6480

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Hot tub
  • Outdoor pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 9 bedrooms
  • Bedsheets provided

Bathroom

  • 8.5 bathrooms
  • Bathtub
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the ocean
  • On the waterfront

Things to do

  • Billiards/pool table
  • Foosball table
  • Kayak

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 not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Garden
  • Unit size: 8,000 square feet

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM

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

Pets

Pets not allowed

Children and extra beds

Children are welcome
Note from host: ALL CHILDREN ARE COUNTED FOR MAX OCCUPANCY

Events

Events allowed: family gatherings, birthday parties, weddings
PEOPLE ATTENDING NOT STAYING SUBJECT TO ADDED FEE

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
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 99
Note from host: PEOPLE ATTENDING NOT STAYING SUBJECT TO ADDED FEE
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 not indicated whether there is a smoke detector on the property
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

About the area

Located in Key West, this holiday home is on the waterfront. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Smathers Beach. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Visit our Key West travel guide
View more Holiday homes in Key West
Map
Key West, FL

What's nearby

  • A stone pathway through a tropical forest with dense foliage and a stone wall.
    Key West Tropical Forest and Botanical Garden
    17 min walk - 1.4 km
  • A serene landscape with a pond, palm trees, and a golf course.
    Key West Golf Club
    4 min drive - 2.8 km
  • A brick building with a central archway, palm trees, and a gravel path.
    Fort East Martello Museum and Gallery
    5 min drive - 3.0 km
  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    15 min drive - 8.3 km
  • Regal Key West
    5 min drive - 2.7 km

Getting around

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

Restaurants

  • McDonald's
    17 min walk
  • Hurricane Hole Marina
    19 min walk
  • Hurricane Hole Waterfront Bar & Grill
    19 min walk
  • Bad Boy Taqueria & Tequila
    5 min drive
  • Matt’s Stock Island Kitchen
    5 min drive

Frequently asked questions

Does Thompson Island - Private Island Estate in Key West have a pool?

Yes, this property has an outdoor pool.

Is Thompson Island - Private Island Estate in Key West pet-friendly?

No, pets are not allowed at this property.

How much is parking at Thompson Island - Private Island Estate in Key West?

On-site parking is available at the property.

What time is check-in at Thompson Island - Private Island Estate in Key West?

Check-in begins at 4:00 PM.

What time is check-out at Thompson Island - Private Island Estate in Key West?

Checkout is at 10:00 AM.

Where is Thompson Island - Private Island Estate in Key West located?

Situated on the waterfront, this holiday home is 0.9 mi (1.5 km) from Key West Tropical Forest and Botanical Garden and 2.7 mi (4.3 km) from Florida Keys Beaches. Fort East Martello Museum and Gallery and Regal Key West are also within 2 miles (3 km).

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Thompson Island - Private Island Estate in Key West Reviews