Key West — Traveler Guide
A great pool transforms a hotel stay. Whether it's an infinity-edge marvel overlooking the skyline, a subterranean spa pool lit by candlelight, or a sun-drenched terrace pool with cabana service, these Key West hotels deliver exceptional aquatic experiences.
Quick Answer
A great pool transforms a hotel stay. Whether it's an infinity-edge marvel overlooking the skyline, a subterranean spa pool lit by candlelight, or a sun-drenched terrace pool with cabana service, these Key West hotels deliver exceptional aquatic experiences.
6 hotels reviewed · Price range: $$, $$$, $$$$ · Last updated March 2026
About This Guide
Key West offers exceptional options for travellers seeking pool hotels, and we've curated the very best. Each property has been selected for its outstanding facilities, prime location, and the quality of experience it delivers. Leading our list, Cypress House Hotel excels with its exceptional attention to detail and commitment to the pool experience. The Reach Key West, Curio Collection offers a compelling alternative with its unique approach and distinctive character. Whether you're a first-time visitor to Key West or returning for another stay, these hotels represent the gold standard for pool accommodation in the city. Each has been independently evaluated for quality, location, and value.
Insider Tips
Book directly with the hotel for the best rate guarantee and potential upgrades.
Read recent guest reviews for the most up-to-date assessment of facilities.
Consider visiting during shoulder season for better rates and fewer crowds.
Ask the concierge for local recommendations — they know Key West better than any guidebook.
Our Picks
6 hotels · Updated February 2026
Old Town
A magnificent 1888 Conch Republic Classic House listed on the National Register of Historic Places, with wraparound verandas, a clothing-optional pool area, and 18 rooms that retain genuine period character. The location on Caroline Street puts Sloppy Joe's, the Ernest Hemingway Home, and the Historic Seaport a five-minute stroll away.
South Beach
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.
New Town
Key West's largest hotel delivers a reliable Marriott experience with a private beachfront, rooftop infinity pool, full-service spa, and 220 rooms at prices that undercut Old Town equivalents by 30-40%. Ideal for families who want resort scale and water access without the Old Town premium.
Old Town
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
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.
Key West Harbor
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.
Keep Exploring
Common Questions
Some hotels offer day passes for pool access, especially in resort-style properties. Contact the hotel directly for availability and pricing.
Indoor pools are heated year-round. Many outdoor pools are heated seasonally, with some luxury properties maintaining them year-round under retractable roofs or with heating systems.
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Prices and availability change daily. Lock in the best rate by booking early — most of our top picks offer free cancellation.
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