Skip to main content

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.
A covered outdoor area with a view of a body of water and boats.
A checkered floor, a staircase with ornate railings, a dining area with chairs, and a console table with decorative items.
A coastal property with multiple white buildings, a well-maintained lawn, and a view of the ocean.
A spacious living room with a grey and white color scheme, featuring a large sofa, armchairs, a coffee table, and a fireplace.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Dive into relaxation
    Unwind in the top-rated pool, your perfect spot for relaxation.
  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
9 bedrooms8+ bathroomsSleeps 20

Popular amenities

  • Outdoor pool
  • Hot tub on site
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View in a map
Key West, FL
  • Place, Key West Tropical Forest and Botanical Garden
    ‪17 min walk‬
  • Place, Key West Golf Club
    ‪4 min drive‬
  • Place, Fort East Martello Museum and Gallery
    ‪5 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪6 min drive‬

Rooms & beds

9 bedrooms (sleeps 20)

1 Master Bedroom

2 King Beds

2 Turtle Bedroom

1 King Bed

3 Ocean Bedroom

1 King Bed

4 Coral Bedroom

1 King Bed

5 Gatsby Bedroom

1 King Bed

6 Flamingo Bedroom

1 King Bed

7 Dolphin Bedroom

2 King Beds

8 Beach Bedroom

1 King Bed

9 Mermaid Bedroom

1 King Bed

8 bathrooms, 1 half bathroom

1.1 Master Bathroom

Towels provided · Bathtub · Toilet · Shower only · Hair dryer

2.1 Turtle Bathroom

Towels provided · Toilet · Shower only · Hair dryer

3.1 Ocean Bathroom

Towels provided · Bathtub · Toilet · Hair dryer

4.1 Coral Bathroom

Towels provided · Bathtub · Toilet · Hair dryer

5.1 Gatsby Bathroom

Towels provided · Toilet · Hair dryer

6.1 Flamingo Bathroom

Towels provided · Toilet · Shower only · Hair dryer

7.1 Dolphin Bathroom

Towels provided · Toilet · Shower only · Hair dryer

8.1 Beach Bathroom

Towels provided · Toilet · Shower only · Hair dryer

9.1 Mermaid Bathroom

Towels provided · Toilet · Shower only · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Garden

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

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Living Area
Evershore Estate at Lunara Bay | Wellness Home
Key Haven
  • Pool
  • Kitchen
  • Washing machine
  • Dryer
9.8 out of 10, Exceptional, (28 reviews)
Evershore Estate at Lunara Bay | Wellness Home

House Rules

Check in after 4:00 PM
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
ALL CHILDREN ARE COUNTED FOR MAX OCCUPANCY
default

Events

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

Pets

No pets allowed
default

Smoking

Smoking is not permitted

Important information

You need to know

Property # 2737769vb
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

About the area

Key West

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.
View more Holiday homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Key West Tropical Forest and Botanical Garden - 17 min walk - 1.4 km
  • Key West Golf Club - 4 min drive - 2.8 km
  • Fort East Martello Museum and Gallery - 5 min drive - 3.0 km
  • Regal Key West - 5 min drive - 2.7 km
  • Museum of Art & History at the Custom House - 6 min drive - 3.4 km

Getting around

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

Restaurants

  • ‪Hogfish Bar & Grill - ‬5 min drive
  • ‪Hurricane Hole Marina - ‬19 min walk
  • ‪Goldman's Deli - ‬5 min drive
  • ‪Domino's Pizza - ‬4 min drive
  • ‪The Conch Flyer Restaurant & Lounge - ‬3 min drive

Frequently asked questions

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

Yes, this property has an outdoor pool.

How much does it cost to stay at Thompson Island - Private Island Estate in Key West?

As of 21 Aug, 2026, prices found for a 1-night stay for 2 adults at Thompson Island - Private Island Estate in Key West on 1 Dec, 2026 start from S$6,741, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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 Key West Art and Historical Society are also within 2 miles (3 km).

About the host

Hosted by Andrew

Host profile image
Tell us how we can improve our siteShare feedback