Private Island Estate in Key West — Sleeps 16–20.
Thompson Island — the only private island in Key West with direct bridge access. Gated, secluded, and steeped in nearly a century of history — yet just 8–10 minutes from Duval Street.
"Your own private island in Key West — drive across the bridge."
A historic private island in Key West — hosted by Presidents, Governors, and business leaders.
Thompson Island is a storied private island in Key West. For nearly a century, this historic private estate has quietly hosted U.S. Presidents, Governors, and prominent business leaders — a rare, gated piece of Key West you can actually stay on.
Unlike almost every other private island in the Florida Keys, Thompson Island offers direct bridge access. No boat. No ferry. No shuttle. You drive across a private bridge, pass through the gate, and step onto your own island — while Old Town Key West and Duval Street remain just 8–10 minutes away.
Whether it's a wedding, a family reunion, a corporate retreat, or a milestone celebration, this gated private island Key West estate delivers something almost impossible to find on the island: complete privacy at true Key West scale.
A True Private Island
Vs. Every Other Key West Rental
Most "luxury" Key West rentals share a street, a subdivision, or a dock. Thompson Island shares nothing. You get your own island — gated, historic, and reached only by a private bridge — while still being minutes from Duval.
Bridge, Not a Boat
The only private island in Key West you can reach by car. No ferry, no shuttle, no dinghy — drive across your own bridge and park inside the gates.
Gated & Truly Secluded
No neighboring rentals, no shared driveway, no public access. The entire island is yours for the duration of your stay — the definition of a secluded Key West estate.
Historic Legacy
Nearly a century of hosting Presidents, Governors, and business leaders. Thompson Island is a rare, historic private island in Key West with a real story — not a new build.
A True Island Sanctuary
Vs. Highway-Adjacent Developments
Not all Key West luxury rentals are created equal. While many large corporate developments squeeze 20+ rental houses into tight tracts right along busy commercial corridors, our estate offers something money can’t usually buy: absolute peace, quiet, and space.
No Highway Noise
Tucked away from commercial traffic, your mornings are filled with the sounds of the ocean — not heavy delivery trucks or highway engine braking off US-1.
Uncompromising Views
Enjoy 100% pristine open-water and island vistas. You will never look out your master suite window at a gas station, parking lot, or neighboring rental driveway.
Unmatched Gated Privacy
Instead of sharing a cramped subdivision with dozens of other vacationing groups, you enjoy a sprawling, self-contained private estate with deep-water dockage, sports facilities, and complete security.
The main house and private cottages — a Key West private island that sleeps 20.
Thompson Island is one of the largest private island rentals in Key West, purpose-built for groups that want the whole island to themselves.
The centerpiece of the estate — spacious living, dining, and gathering rooms with multiple bedrooms and en-suite baths.
Separate cottages on the island offer additional bedrooms and private space for extended family, wedding parties, or executive teams.
The main house and cottages combine to comfortably sleep 16–20 guests across the private island — reunions, weddings, retreats.
A private island resort in Key West — everything on-site, nothing shared.
The only private island in Key West you can reach by car — a gated, secluded estate on its own island.
Private bridge — no boat, no ferry, no shuttle. Drive straight onto the island and park inside the gates.
Oceanside saltwater pool set against the private island shoreline.
A separate freshwater pool for the group — two pools, one private island.
Historic main house plus private cottages — one of the largest private island rentals in Key West.
Complete privacy behind private gates. No neighboring rentals, no shared driveways, no public access.
Nearly a century of hosting Presidents, Governors, and business leaders — a rare piece of Key West history.
Secluded island living — minutes from Old Town Key West, Duval Street, and the Key West airport.
Fast Wi-Fi across the estate, central AC, and abundant on-island parking for the whole group.
A private island — 8–10 minutes from Duval Street.
Thompson Island offers something no other Key West estate can match: direct bridge access. You get the full seclusion of an offshore estate without ever needing a boat, and Old Town Key West is a short drive away.
Gallery
Aerials, gated entry, and the historic main house of Thompson Island — a private estate with direct bridge access to Key West.
Frequently asked questions about Thompson Island
Is Thompson Island really a private island in Key West?
Yes. Thompson Island is the only private island in Key West with direct bridge access — no boat required. The estate is gated and completely secluded, yet you can drive across the private bridge in a car and be on Duval Street in Old Town Key West in about 8–10 minutes.
How do you get to Thompson Island — do you need a boat?
No boat needed. Thompson Island is the only private island in Key West you can reach by car via a private bridge. Guests drive directly onto the island and park inside the gated estate.
How many guests can Thompson Island sleep?
The private island estate sleeps 16–20 guests across the historic main house and adjacent cottages — making it one of the largest private island rentals in Key West, ideal for weddings, family reunions, corporate retreats, and milestone celebrations.
Where is Thompson Island located?
Thompson Island sits just off 4095 South Roosevelt Boulevard, Key West, FL 33040. It is a gated private island only 8–10 minutes from Duval Street, Old Town Key West, and the Key West International Airport (EYW).
What is the history of Thompson Island?
Thompson Island is a historic private estate in Key West that has quietly hosted U.S. Presidents, Governors, and prominent business leaders for nearly a century. It is a storied private island in Key West — a rare piece of Key West history you can actually stay on.
Does the estate have a pool?
Yes — two. Thompson Island features both a saltwater pool and a separate freshwater pool, along with waterfront decks and lounge areas throughout the private island.
Is Thompson Island good for a Key West wedding or private event?
It is one of the best venues in Key West for a truly private wedding or corporate retreat. Because it is a gated private island, you get complete exclusivity — no neighboring rentals, no shared amenities, no public traffic — while still being minutes from Old Town Key West.
How do I book Thompson Island directly?
Book direct with owner Andrew at (305) 923-6480 or andrewlippi@gmail.com. Booking direct means no third-party service fees and flexible communication about dates, group size, and event needs.
Ready to book Thompson Island?
Book direct with Andrew — no third-party service fees and flexible group and event pricing.
