House in Stock Island, FL
20 guests · 9 bedrooms · 8 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
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
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
Amenities at Thompson Island - Private Island Estate in Key West
Non-smoking
No pets allowed
Map of Stock Island, FL
Ratings and reviews
10 / 10Outstanding·Apr 2026
Very cool experience, like having your own private island. Great for huge groups, no neighbors, host was very helpful and responded very quickly.
10 / 10Outstanding·Apr 2026
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!
10 / 10Outstanding·Jan 2026
Excellent property. The host was very accommodating and anticipated every need.
10 / 10Outstanding·Dec 2025
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!
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Top rated by guests
9.8Outstanding
(20 Ratings)
"Very cool experience, like having your own private island. Great for huge groups, no neighbors, host was very helpful and responded very quickly."
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