Historical hotels in Key West
Find the Top Historical hotels in Key West – 20+ Quality Options from Leading Providers
1-22 out of 22 hotels
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Hotel
From
US$ 166
/night
- Tanning pier with direct ocean access
- Luxury spa services on-site
- Diverse room types for every traveler
From
US$ 192
/night
- Beachfront access to Smathers Beach
- Lagoon-style pool with cabanas
- Tin Cup Chalice Bar & Chill dining
Resort
- Tropical Gardens
- Adults-Only Pool
- On-site Dining
1700 yd from City Center1.0 mi from Smathers Beach
From
US$ 170
/night
- Four unique pool areas for relaxation
- Luxurious villas with private terraces
- On-site water sports rentals available
- Infinity Pool
- Private Beach
- Full Kitchens
2.0 mi from City Center1.1 mi from Kayak Kings Key West
From
US$ 250
/night
- Infinity pool with ocean views
- Full kitchens in every unit
- Private beach access for guests
9.6
Perfect11 review10
- Outdoor Pool
- On-site Restaurant
- Pet-friendly Rooms
2.0 mi from City Center1100 yd from Kayak Kings Key West
From
US$ 181
/night
- Free shuttle to downtown attractions
- Iguanas around the pool area
- Warm chocolate chip cookies on arrival
- Tiki Bar
- Outdoor Pool
- Observation Boardwalk
1.2 mi from City Center1.1 mi from Smathers Beach
From
US$ 184
/night
- Complimentary downtown shuttle service
- On-site Tiki bar with tropical cocktails
- Scenic boardwalk for leisurely strolls
5.0
Guest rating11 review10
2.1 mi from City Center900 yd from Kayak Kings Key West
From
US$ 123
/night
Featuring a gym and a swimming pool, the 24 North Hotel Key West is located 10 minutes by car from Fort Zachary Taylor Historic State Park.
Hotel
- Food Truck
- Pool Bar
- Cigar Lounge
2.1 mi from City Center800 yd from Kayak Kings Key West
From
US$ 140
/night
- Onsite food truck with local cuisine
- Pet-friendly policies for larger dogs
- Live music at poolside bar
Hotel
- Bi-level suites
- Private pool
- Grocery delivery
1.8 mi from City Center1400 yd from Kayak Kings Key West
From
US$ 214
/night
- Bi-level suites accommodating up to 10 guests
- Tranquil pool with bay-front views
- Dog-friendly with special amenities
- Private Beach
- On-site Marina
- Rooftop Terrace
2.2 mi from City Center600 yd from Kayak Kings Key West
From
US$ 164
/night
- Private beach with exclusive access
- Luxury Presidential Suite with stunning views
- On-site marina with adventure cruises
- Heated Pool
- Private Cottages
- Wine Reception
1.0 mi from City Center300 yd from Fury Water Adventures Key West
From
US$ 291
/night
- Exclusive adults-only atmosphere
- Complimentary evening wine and cheese hour
- Beautifully landscaped gardens
Hotel
- Saltwater Pool
- Bicycle Rentals
- Continental Breakfast
1400 yd from City Center400 yd from Key West Cemetery
From
US$ 139
/night
- Outdoor heated saltwater swimming pool
- Eco-friendly green boutique hotel
- Rooms with private balconies
Motel
- Rooftop Deck
- Swimming Pool
- Tropical Garden
1300 yd from City Center300 yd from Dog Beach
From
US$ 109
/night
- Rooftop deck for sunbathing and stargazing
- Tropical garden with swimming pool
- Bicycle rentals for exploring the island
Resort
- Saltwater Pool
- Bicycle Rentals
- Outdoor Dining
1.2 mi from City Center1.1 mi from Smathers Beach
From
US$ 229
/night
- Unique wildlife interactions for families
- Free shuttle service to downtown attractions
- On-site fresh seafood restaurant option
Hotel
10.0
Perfect11 review10
- Heated Pool
- Tiki Bar
- Concierge Service
2.1 mi from City Center1800 yd from Kayak Kings Key West
From
US$ 130
/night
- Heated pool with ocean views
- Hourly shuttle to downtown attractions
- Two complimentary drinks daily
9.6
Perfect11 review10
- Poolside Bar
- Private Cabanas
- Fitness Center
2.1 mi from City Center600 yd from Kayak Kings Key West
From
US$ 112
/night
- Live music enhances poolside atmosphere
- Complimentary drink coupons at pool bar
- Accessible on-site parking options
Resort
- Saltwater Pools
- Full Kitchens
- Concierge Service
1700 yd from City Center300 yd from Key West Butterfly and Nature Conservatory
From
US$ 620
/night
- Saltwater pools surrounded by lush gardens
- Full kitchens for meal preparation convenience
- Complimentary daily happy hour with wine
- Outdoor Pool
- Hot Tub
- Bike Hire
2.3 mi from City Center400 yd from Kayak Kings Key West
From
US$ 359
/night
- Fully equipped suites with private balcony
- Outdoor pool with hot tub amenities
- On-site activities: snorkeling and fishing
Bed & Breakfast
- Outdoor Pool
- Complimentary Breakfast
- Private Parking
1.5 mi from City Center300 yd from Jackson Square
From
US$ 213
/night
- Adults-only retreat with historic charm
- Distinct island-inspired guest rooms
- Outdoor pool surrounded by lush gardens
Guest house
- On-site Spa
- Bike Rentals
- Tropical Gardens
1.0 mi from City Center600 yd from Key West Cemetery
From
US$ 210
/night
- Two sparkling outdoor pools
- On-site massage services available
- Complimentary continental breakfast offered
Bed & Breakfast
- Garden courtyard
- Private hot tub
- Happy hour
1.3 mi from City Center300 yd from San Carlos Institute Casa Cuba
From
US$ 125
/night
- Historic Victorian architecture and charm
- Social happy hour in garden courtyard
- Complimentary use of bicycles for guests
- Saltwater pool
- Marina access
- BBQ facilities
2.1 mi from City Center500 yd from Kayak Kings Key West
From
US$ 244
/night
- Private access to fishing opportunities
- Spacious two-bedroom units for families
- Gumbos bar next to the water
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