8 best hotels with a pool in Key West

Hotels with a pool in Key West are a smart pick for travellers who want to cool off between ocean air, sun-soaked walks, and late-afternoon waterfront entertainment. Key West is compact, so staying near the island’s action helps: many guests base themselves around Old Town and Duval Street, the lively main strip lined with restaurants, bars and boutiques. For iconic evenings, Mallory Square is where the famous Sunset Celebration draws crowds nightly, with performers and vendors by the water.

A genuinely “pool hotel” in Key West goes beyond a token dip. Look for properties with a proper on-site swimming area that’s usable year-round, plus spaces that suit the island’s pace—loungers for downtime, and a relaxed setting for morning coffee or post-walk recovery. This makes pool hotels especially appealing to couples wanting a romantic base, families who value breaks in the day, and friends planning beach days but still craving a calm retreat on return.

If your priority is a central, stroll-friendly stay, the Duval Street / Old Town area suits most itineraries; if you’re chasing sunsets and waterfront vibes, anchoring closer to Mallory Square is ideal. From our bookable options, you can consider well-rated pool-friendly stays such as The Marker Waterfront Resort Key West (4★) and Orchid Key Inn (4★) for a fuller resort feel, while H2O Suites (3★) and Santa Maria Suites (4★) can also be strong choices depending on your desired balance of comfort and location.