Key West Resorts: Waterfront Stays in Old Town and Beyond

Find 15 top-rated Key West resorts with private beaches, spas, and Old Town access. Compare rates and book now for exclusive deals.

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Rooms and Guests2 Guests, 1 room
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Check-in
Fri, 06 Nov
-
Check-out
Sat, 07 Nov
Rooms and Guests2 Guests, 1 room
1Filter & Sort
View map
View map
1-17 out of 17
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
8.6
Great
Map
5.5 km from City Centre500 m from Safe Harbor
Full-Service MarinaHeated PoolsComplimentary Shuttle
  • Six heated saltwater pools
  • Free kayak and bike rentals
  • Complimentary shuttle to Key West
From£ 103 /nightSelect
8.3
Great
Map
2.5 km from City Centre200 m from Mallory Square
Sunset PierSpaTerreLIQUID Pool
  • Zero Duval Street location
  • Private balconies overlooking Gulf
  • On-site SpaTerre exotic treatments
From£ 275 /nightSelect
8.3
Great
Map
2.3 km from City Centre400 m from Mallory Square
Jala SpaShor RestaurantWaterfront Pool
  • Waterfront sunset views from pool
  • Gulf seafood dining at Shor
  • Full-service Jala Spa
From£ 190 /nightSelect
7.7
Very good
Private BeachOceanfront PoolsWater Sports
  • Largest private beach in Key West
  • Historic 1920s Spanish architecture
  • Complimentary water sports rentals
From£ 221 /nightSelect
8.3
Great
Map
1.5 km from City Centre1.6 km from Smathers Beach
Heated PoolsPool BarWater Sports
  • Forbes Best Family Hotel
  • Four distinct pool areas
  • Complimentary shuttle service
From£ 109 /nightSelect
8.5
Great
Map
2.4 km from City Centre200 m from Mallory Square
Private BeachFull-service SpaBeach Bar
  • Private white sand beach
  • Only full-service spa in Key West
  • Former headquarters of local legends
From£ 237 /nightSelect
8.3
Great
Map
3.2 km from City Centre1000 m from Kayak Kings Key West
Complimentary ShuttlePoolside CabanasTiki Bar
  • Free shuttle to downtown and airport
  • Warm cookies at check-in
  • Zero-entry pool & tiki bar
From£ 112 /nightSelect
8.3
Great
Pool ClubPerla RestaurantFitness Center
  • Historic hotel on Duval Street
  • Hemingway & Capone stayed here
  • Cuban-inspired dining & mojitos
From£ 167 /nightSelect
9.2
Perfect
Map
2.6 km from City Centre200 m from Mallory Square
Latitudes RestaurantFull-Service SpaTennis Court
  • Private island accessible only by ferry
  • Award-winning Latitudes on-site restaurant
  • Complimentary breakfast basket delivered daily
From£ 520 /nightSelect
8.7
Great
Map
2.0 km from City Centre700 m from San Carlos Institute Casa Cuba
Serenity PoolPeloton BikesCovered Parking
  • Three pools including adults-only
  • State-of-the-art fitness center
  • Rare onsite covered parking
From£ 307 /nightSelect
9.2
Perfect
Map
1.5 km from City Centre300 m from Key West Butterfly and Nature Conservatory
Saltwater PoolsFull KitchensBike Rentals
  • All two-bedroom suites with full kitchens
  • Two heated saltwater pools with gardens
  • Complimentary daily happy hour with wine
From£ 141 /nightSelect
7.2
Very good
Map
1.5 km from City Centre300 m from Key West Butterfly and Nature Conservatory
Private BeachOceanfront DiningSunset Sails
  • Only private natural sand beach
  • Award-winning Key Lime Pie
  • On-site sunset sailing excursions
From£ 126 /nightSelect
8.6
Great
Heated PoolSpa CenterWater Sports
  • Waterfront adjacent to aquarium
  • On-site spa with couples massage
  • Complimentary shuttle service
From£ 225 /nightSelect
Map
2.0 km from City Centre600 m from San Carlos Institute Casa Cuba
Indoor PoolFitness CenterPool Bar
  • 24-hour concierge and security service
  • On-site yoga classes and local culture tours
  • Extensive garden and outdoor leisure spaces
From£ 690 /nightSelect
7.8
Very good
Map
3.5 km from City Centre500 m from Kayak Kings Key West
Private BeachHeated PoolOn-site Marina
  • Private beach with Gulf views
  • Complimentary champagne on arrival
  • Free daily shuttle downtown
From£ 115 /nightSelect
9.2
Perfect
Map
1.5 km from City Centre200 m from Duval Street
Rooftop PoolPlunge PoolsBike Rental
  • Adults-only luxury suites
  • Private plunge pools in suites
  • Complimentary happy hour daily
From£ 222 /nightSelect
7.6
Very good
Map
2.0 km from City Centre1.9 km from Smathers Beach
Private BeachSaltwater PoolWildlife Feedings
  • On-site wildlife feedings and encounters
  • Complimentary shuttle to Duval Street
  • 1960s retro decor throughout
From£ 308 /nightSelect

Key West resorts range from beachfront properties with private sand to historic hotels steps off Duval Street. The Marker Waterfront Resort, for instance, sits just one block from the action, offering all-suite accommodations with full kitchens and two heated pools surrounded by gardens. Meanwhile, The Reach Key West, Curio Collection by Hilton, provides a 137-meter private beach and a spa, with the Ernest Hemingway House only a 10-minute walk away.

Rates vary by season and property type. Expect to pay from $200 to over $500 per night for resort rooms, with beachfront and spa resorts commanding higher prices. For the best value, consider Parrot Key Hotel & Villas, which features four swimming pools and a mobile pool bar, or the DoubleTree by Hilton Grand Key Resort, which offers free shuttle service to Old Town and the airport. Book in advance, especially during peak season (December-April), and check for package deals that include parking or resort credits.