Best Hotels with Rooftop Bars & Pools in Key West (2026)

Key West's most romantic address — a collection of four historic buildings connected by half an acre of private tropical gardens with a freshwater pool, koi ponds, and a 60-year-old bronze orchid collection. The 17 rooms are individually furnished with antiques, and the absence of TVs is a feature rather than an oversight.

• Old Town
• Boutique
• Honeymoon

★ 9.4 Hotelier's Choice score, 40+ criteria · Many rooms include free cancellation

Key West's finest full-service waterfront resort sits at the foot of Duval Street with a private dock, sunset-view pool, and 100 suites facing the Gulf of Mexico — the preferred address for those who want resort facilities without sacrificing the soul of Old Town. The rooftop Hot Tin Roof bar is one of Key West's best sunset perches.

• Old Town
• Waterfront
• Couples

★ 9.1 Hotelier's Choice score, 40+ criteria · Many rooms include free cancellation

A modern boutique resort on the harbor designed with a zero-waste philosophy — solar panels, electric boat charters, and a marine conservation partnership — without sacrificing any luxury amenity. Three pools, a water sports center, and 96 rooms with harbor views make it Key West's most thoughtfully conceived newer property.

• Harbor
• Boutique
• Couples

★ 9.0 Hotelier's Choice score, 40+ criteria · Many rooms include free cancellation

A Key West institution since 1968, anchoring the corner where Duval Street meets the Gulf with a private beach, full-service spa, and 142 rooms ranging from poolside cottages to Gulf-view balcony suites. The Chart Room bar — a wood-paneled mariner's bar that hasn't changed in 50 years — is where every Key West visit should begin.

• Old Town
• Historic
• Beach

★ 8.9 Hotelier's Choice score, 40+ criteria · Many rooms include free cancellation

The only resort on Key West with direct Atlantic Ocean beach access — a Hilton Curio Collection property with a distinctive Caribbean colonial design, three pools, a full-service dive shop, and 150 rooms facing the most swimmable ocean water on the island. The Rêve Spa and beachfront dining at their best here.

• South Beach
• Beach
• Couples

★ 8.9 Hotelier's Choice score, 40+ criteria · Many rooms include free cancellation

Key West's most family-friendly full-service resort, straddling Atlantic and Gulf beaches at the island's southern tip with three pools, a poolside tiki bar, and direct access to both Southernmost Beach and the Atlantic. The rooms in the Beach House are the finest, with private balconies facing the water.

• South Beach
• Families
• Beach

★ 8.7 Hotelier's Choice score, 40+ criteria · Many rooms include free cancellation