A Flagler-era grande dame on the island's only private beach, a 27-acre private island, and Sunset Pier glowing at dusk. Key West's best stays trade glitz for Old Town character and the water's edge.
The full ranking
A Flagler-era grande dame on the island's only private beach, a 27-acre private island, and Sunset Pier glowing at dusk. Key West's best stays trade glitz for Old Town character and the water's edge.
Casa Marina Key West, Curio Collection by Hilton (Casa Marina)
Henry Flagler’s 1920 grande dame anchors the only true private beach in Key West, with twin oceanfront pools, a long swim dock and the Dorada restaurant on the Atlantic. A century on, it remains the island’s flagship resort address.
Ocean Key Resort & Spa (Old Town)
Planted at Zero Duval where the harbor meets Mallory Square, this island-style resort owns the famous string-lit Sunset Pier and the airy Hot Tin Roof. Rooms in playful tropical color open to balconies over the water.
Sunset Key Cottages (Sunset Key)
A seven-minute launch ride from Old Town delivers you to a private 27-acre island of beach-chic cottages, palm-shaded sand and the lauded Latitudes restaurant. It is the most exclusive, and most serene, address in Key West.
Hyatt Centric Key West Resort & Spa (Old Town)
A waterfront resort steps from Mallory Square with a waterfall pool, floating dock and direct Gulf views. Condé Nast Traveler readers voted it the No. 1 resort in the Florida Keys.
Marquesa Hotel (Old Town)
Four meticulously restored 1884 conch houses wrap two pools and lush courtyards a block off Duval, with the acclaimed Café Marquesa on site. Adults-oriented and deeply romantic, it is Old Town’s most polished boutique stay.
H2O Suites Hotel (Old Town)
An adults-only, all-suite hideaway where the top suites come with private plunge pools and rooftop soaking tubs. It is the highest-rated luxury hotel on the island across both Google and Tripadvisor.
The Gardens Hotel (Old Town)
Set on a rare full acre of mature tropical gardens, this historic, intimate hideaway hides cottages and a plunge pool a block and a half off Duval. Near-perfect guest reviews make it a perennial Key West favorite.
Santa Maria Suites Resort (Old Town)
A sleek, contemporary all-suite resort a few steps from both Duval Street and the Atlantic, with private heated pools and spacious suites built for longer stays. U.S. News ranks it the No. 1 hotel in Key West.
Pier House Resort & Spa (Old Town)
At One Duval, this resort reaches out over the water on wooden piles, pairing a rare private beach with a full spa and the legendary Chart Room bar. It is the original blend of Duval energy and waterfront calm.
The Marker Key West Harbor Resort (Old Town)
Key West’s first new-build resort in decades sits on the Historic Seaport with three pools and breezy, coastal rooms. Condé Nast Traveler readers named it the No. 1 resort in the Florida Keys.
Ranked across 5 sources: U.S. News & World Report · 25 Best Hotels in Key West 2026; Oyster · Best Luxury Hotels in Key West (unordered roundup); Condé Nast Traveler · The 13 Best Hotels in Key West 2025 (unordered roundup); Google Reviews · Ranked by Rating (June 2026); Live Pricing · 5 Months Out (November 2026). Full scoring is on the Methodology tab above.
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