Top Resorts in Key West

Find the Top Resorts in Key West – 100+ Quality Options from Leading Providers

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22 Guests, 1 Room
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61-80 out of 109 resorts
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Bed & Breakfast
8.2
Great183 reviews
MapView on map1.2 mi from City Center300 yd from San Carlos Institute Casa Cuba
From   US$ 299 /nightSelect
  • Unique themed accommodations
  • Lush tropical garden setting
  • Multiple outdoor pools
8.2
Great591 reviews
MapView on map1.1 mi from City Center300 yd from Duval Street
From   US$ 205 /nightSelect
  • Charming tropical gardens for relaxation
  • Delightfully dog-friendly accommodations
  • Newly renovated Superior King Suites
8.4
Great94 reviews
  • Tiki Bar
  • Saltwater Pool
  • Private Courtyard
1.3 mi from City Center200 yd from Jackson Square
From   US$ 235 /nightSelect
  • Historic Victorian boutique hotel charm
  • Private courtyard oasis and pool
  • Complimentary wine and beer Happy Hour
Guest house
8.4
Great674 reviews
  • On-site Spa
  • Bike Rentals
  • Tropical Gardens
1.0 mi from City Center600 yd from Key West Cemetery
From   US$ 210 /nightSelect
  • Two sparkling outdoor pools
  • On-site massage services available
  • Complimentary continental breakfast offered
8.2
Great82 reviews
  • Outdoor Pool
  • Complimentary Breakfast
  • Private Parking
1.5 mi from City Center300 yd from Jackson Square
From   US$ 237 /nightSelect
  • Adults-only retreat with historic charm
  • Distinct island-inspired guest rooms
  • Outdoor pool surrounded by lush gardens
8.4
Great69 reviews
  • Cabaret Venue
  • Piano Bar
  • Outdoor Pool
1.1 mi from City Center200 yd from Duval Street
From   US$ 360 /nightSelect
  • Live cabaret shows by Randy Roberts
  • Gourmet dining on Duval Street
  • Adults-only atmosphere
8.0
Great199 reviews
  • Saltwater pool
  • Marina access
  • BBQ facilities
2.1 mi from City Center500 yd from Kayak Kings Key West
From   US$ 265 /nightSelect
  • Private access to fishing opportunities
  • Spacious two-bedroom units for families
  • Gumbos bar next to the water
8.4
Great167 reviews
  • Heated Pool
  • Seaside Café
  • Spa Services
1.1 mi from City Center200 yd from US Southernmost Point
From   US$ 450 /nightSelect
  • Heated adults-only swimming pool
  • On-site Seaside Café for dining
  • Cultural walking tours available
8.6
Great49 reviews
  • Hot Tub
  • Pool
  • Sundecks
1600 yd from City Center700 yd from Key West Cemetery
From   US$ 344 /nightSelect
  • Clothing-optional sundecks with great views
  • Complimentary cocktail happy hour daily
  • Historic Conch-style house from 1902
8.4
Great366 reviews
  • Plunge Pool
  • Private Beach
  • Outdoor Dining
1.0 mi from City Center100 yd from Key West Butterfly and Nature Conservatory
From   US$ 273 /nightSelect
  • Unique beach access for guests
  • Complimentary homemade cookies daily
  • Quiet pool area for relaxation
8.2
Great86 reviews
  • Clean Pool
  • Central Courtyard
  • Complimentary Breakfast
From   US$ 632 /nightSelect
  • Lush tropical gardens enhance relaxation
  • Adults-only atmosphere for tranquility
  • Resident cats add unique charm
8.4
Great235 reviews
  • Garden Bar
  • Spa Pool
  • Bicycle Rentals
1.1 mi from City Center200 yd from Key West Butterfly and Nature Conservatory
From   US$ 303 /nightSelect
  • Complimentary happy hour drinks daily
  • Historic Victorian era architecture
  • Adjacent to Southernmost Point monument
8.6
Great52 reviews
  • Plunge Pool
  • Garden Terrace
  • On-site Spa
1500 yd from City Center300 yd from Key West Cemetery
From   US$ 354 /nightSelect
  • Lush tropical gardens and exotic birds
  • Adults-only retreat with personalized service
  • Charming Victorian-style accommodations
Bed & Breakfast
8.2
Great151 reviews
  • Tropical Courtyard
  • Swimming Pool
  • Private Balconies
1.1 mi from City Center100 yd from Ernest Hemingway House
From   US$ 139 /nightSelect
  • Historic hotel on famous Duval Street
  • Charming inner courtyard with tropical plants
  • Rooms with air conditioning and balconies
8.2
Great268 reviews
  • Swimming Pool
  • BBQ Grills
  • Coin Laundry
800 yd from City Center1100 yd from Key West Cemetery
From   US$ 159 /nightSelect
  • Spectacular waterfront views by Garrison Bight
  • Docking access for fishing boats available
  • Houseboat accommodations with stunning marina views
8.4
Great294 reviews
  • Outdoor pool
  • Hot tub
  • Spacious suites
1.2 mi from City Center100 yd from San Carlos Institute Casa Cuba
From   US$ 114 /nightSelect
  • Centrally located on vibrant Duval Street
  • Elegant Art Deco style accommodations
  • Heated outdoor swimming pool and spa
8.4
Great167 reviews
  • Heated Pool
  • Tropical Garden
  • Outdoor Seating
From   US$ 164 /nightSelect
  • Complimentary bike rentals for exploration
  • Charming cottage-style accommodations
  • Pet-friendly policy for furry friends
Guest house
8.2
Great219 reviews
  • Bicycle rental
  • Flat-screen TV
  • Private bathrooms
1.3 mi from City Center300 yd from Classic Harbor Line
From   US$ 142 /nightSelect
  • Adults-only relaxation environment
  • Bicycle rental for local exploration
  • Air-conditioned rooms with refrigerators
8.4
Great123 reviews
  • Outdoor pool
  • Garden bar
  • Fitness center
1.2 mi from City Center300 yd from Ernest Hemingway House
From   US$ 163 /nightSelect
  • Clothing-optional sundeck and garden bar
  • Complimentary happy hour every evening
  • Adult-only heated outdoor pool
8.4
Great199 reviews
  • Cocktail Hour
  • Garden Terrace
  • Air Conditioning
1.4 mi from City Center300 yd from Jackson Square
From   US$ 199 /nightSelect
  • Adults-only ambiance and tranquility
  • Inviting garden and terrace areas
  • Daily cocktail hour for relaxation