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

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.

Popular amenities

  • Balcony
  • Spa pool on site
  • Outdoor pool
  • Outdoor barbecue
  • Air-conditioning
  • Refrigerator

Explore the area

View 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

Add dates for prices

Similar properties

Soak up sunshine with a bird’s-eye view of serenity.
Three Rooms w/ 2 Queen beds at Blue Flamingo Resort Key West l 2 Pools & Shuttle
New Town
  • Pool
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning
9.4 out of 10, Exceptional, (3 reviews)
Three Rooms w/ 2 Queen beds at Blue Flamingo Resort Key West l 2 Pools & Shuttle

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
  • Duval Street - 15 min drive - 8.3 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
  • ‪Starbucks - ‬15 min walk

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 4 November 2026, prices found for a 1-night stay for 2 adults at Thompson Island - Private Island Estate in Key West on 4 May 2027 start from NZ$10,699, 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 Regal Key West are also within 2 miles (3 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 18 out of 20 reviews
Rating 8 - Good. 2 out of 20 reviews
Rating 6 - Okay. 0 out of 20 reviews
Rating 4 - Poor. 0 out of 20 reviews
Rating 2 - Terrible. 0 out of 20 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very cool experience, like having your own private island. Great for huge groups, no neighbors, host was very helpful and responded very quickly.
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent property. The host was very accommodating and anticipated every need.
Stayed 2 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was the perfect property for our multigenerational family to be together. We had the best time playing volleyball, basketball, paddle boarding, swimming, sitting in the hot tub, grilling and looking for sea creatures together! Thank you so much for allowing us to stay on this beautiful island. We loved every second of our trip!
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful property for a large group.

We had an amazing time on Thompson Island for my big birthday! Plenty of room for our 15 friends. The property was clean and the kitchen was well stocked. We really enjoyed our stay.
Stayed 4 nights in Feb 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Historical bliss

Thompson island was an absolute perfect setting for my wife’s 40th. The week there was filled with so much activities(both on and off the island) and the history of the home was beautiful.
Stayed 5 nights in Jul 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

We had such a GREAT time!

My whole family and I stayed for a week. Everything was so perfect that besides going to the grocery store we didnt leave the house the whole time.
Stayed 4 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Memorable stay

The Thompson Island home was amazing for us to celebrate our wedding! Thanks so much to the host for being responsive and helpful. It was a great experience all around
Stayed 2 nights in Dec 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Happy Get Together

Wonderful communication. Lovely home. Thoroughly enjoyed our time and would return
Stayed 6 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect property for family, friends and wedding party

Thompson Island, private island, estate was just perfect for housing our friends and wedding guests of 20 people, and Andrew and Scott were super accommodating and easy to work with. Perfect combination of soaking in Key West and all that it has to offer, and a private estate to relax in and enjoy connections with those that you love.
Stayed 4 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome Experience

Andrew and Co. are the best. They make you feel right at home and can connect you with local businesses if you are looking to plan some fun when in KW
Stayed 2 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding celebration weekend

The property is large and private. It gears to large groups looking to celebrate any occasion. Water access is provided for kayaking and paddle boarding.
Stayed 2 nights in Nov 2023
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Historic Key West Vibe with Gatsby Flare

Very nice property with appropriate accoutrements to the time and period for the property. Very quiet location with excellent views. This is not a property for a party with anyone with accessibility needs.
Stayed 3 nights in Jul 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding of our dreams

We got married on Thompson Island and it was truly the wedding of our dreams. We got to have our closest friends and family stay on the Island with us for a long weekend and it was absolutely the best weekend ever. The place was so beautiful to take pictures at as well. And Andrew and his wife are so sweet and helpful. Couldn’t recommend enough.
Stayed 3 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing spot in the Keys for a professional meeting and social event.

We had a group of 20 dentists and meet ever year in a tropical or snow setting. The accomodations were ideal for us on Thompson island. Staff and owners were very attentive. One of our guest misplaced her wallet and phone. The staff located it and she was able to get it before flying out. First class!
Stayed 3 nights in Feb 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful family Christmas stay here at this charming, historic home! Loved the location as it is close to the airport, grocery, the beach and has a beautiful water view. We traveled with my 86 year old mom and I’d like to caution others that this is an old house that is not handicap accessible and does not have a shower on the main floor. For the younger ones, however, it was nice being on an island where they could talk and laugh and not bother any neighbors and there was a lot for them to do. Andrew is a very nice, accommodating, responsive host. Scott was great with orientation and any needs we had throughout the week. Overall a very positive stay!
Stayed 7 nights in Dec 2025
Response from VrboOwner on 14 January 2026
Thanks for the great review. Lovely group ! If the stairs are an issue with any guests there is an opportunity to add 1 or 2 cottages ( 3 steps off the ground each) with king beds and baths. Please reach out for additional information! Ty.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Incredible & Perfect!

We hosted an executive leadership retreat and rented the entire property. It was the most positive experience from beginning to end! The host's communication and the grounds team that greeted us were impeccable. The house & cottages were beautiful and surpassed our expectations. There is everything you need: kayaks, paddle boards, bikes, volleyball! I can't say enough how much we all enjoyed it. Thank you so much!! Highly recommend!
Stayed 4 nights in Apr 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spectacular location and property

The property manager was wonderful to work with from the moment we booked to the moment we left always was extremely responsive and professional the property itself is just wow wow wow what a location all the amenities all the kids stayed busy I would recommend this property to anyone that is looking for a dream vacation in the keys thank you Andrew to you and your staff a real Jem thank you.
Stayed 3 nights in May 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Our Island Off the Island

I had a milestone birthday and had family celebrate with me. Andrew's estate was conveniently close to the airport and was easy to find. All fifteen adults had comfortable beds and use of seven and a half bathrooms. We especially loved the size of the dining room and how we were all able to sit at the same table. The home itself is close to 100 years old, so do not expect perfection. It has its unique charm and a compelling history that is worth knowing. Everyone had a great stay in Key West, thanks in good part to this property.
Stayed 4 nights in Jan 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key West Wedding Weekend

We rented this home for our son And daughter in law to “tie the knot” on a sunset sailboat with just 16 family members. This home was perfect for what we needed so we could all hang out and Celebrate the weekend and getting to get to know each other’s family. The home is very large with a lot of space. If you like history then this home has it but you need to understand the home is close to 100 years old and not updated but had a lot of Charm. The owner was extremely easy to work with and very helpful and answered all questions very quickly.
Stayed 3 nights in Oct 2022
Verified review

10/10 Excellent

Stayed 3 nights in Nov 2024
Tell us how we can improve our siteShare feedback