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
- Adult-only pool for tranquility
- Beachside cafe with live music
- Diverse room types for every guest
From
US$ 192
/night
- Beachfront access to Smathers Beach
- Tropical lagoon-style pool
- On-site Tin Cup Chalice Bar
Hotel
- Private Pool
- In-suite Kitchens
- Furnished Balconies
2.9 km from City Centre1.3 km from Kayak Kings Key West
From
US$ 214
/night
- Bi-level suites for up to 10 guests
- Outdoor pool with serene bay-front views
- Pet-friendly with special amenities for dogs
9.6
Perfect11 review10
- Outdoor Pool
- On-site Restaurant
- Fitness Center
3.2 km from City Centre1000 m from Kayak Kings Key West
From
US$ 168
/night
- Complimentary shuttle to downtown attractions
- Poolside bar with specialty drinks available
- Warm chocolate chip cookies upon check-in
Hotel
- Food Truck
- Pool Bar
- Cigar Lounge
3.4 km from City Centre700 m from Kayak Kings Key West
From
US$ 140
/night
- Onsite food truck with local cuisine
- Live music events by the pool
- Dog-friendly without weight restrictions
Resort
- Outdoor Pool
- Seafood Restaurant
- Wildlife Exhibits
1.9 km from City Centre1.8 km from Smathers Beach
From
US$ 144
/night
- Unique wildlife interactions with marine species
- On-site fresh seafood restaurant for convenience
- Vibrant 1960s decor and atmosphere
Resort
- Tropical Gardens
- Swimming Pools
- On-site Dining
1.5 km from City Centre1.6 km from Smathers Beach
From
US$ 170
/night
- Four distinct pool areas for leisure
- Unique culinary offerings and cocktails
- Spacious villas with private outdoor terraces
Hotel
- Saltwater Pool
- Bicycle Rentals
- Tesla Charging
1.3 km from City Centre300 m from Key West Cemetery
From
US$ 139
/night
- Outdoor heated saltwater swimming pool
- Designer rooms with chic island décor
- Eco-friendly certified green lodging
Resort
- Saltwater Pools
- Private Balconies
- Gourmet Kitchen
1.5 km from City Centre300 m from Key West Butterfly and Nature Conservatory
From
US$ 190
/night
- Private saltwater pools surrounded by gardens
- Turn-down service with daily gourmet snacks
- Spacious two-bedroom suites with full kitchens
5.0
Guest rating11 review10
3.3 km from City Centre800 m from Kayak Kings Key West
From
US$ 123
/night
Featuring fitness classes and various recreational opportunities, the 4-star 24 North Hotel in a museum neighbourhood is located within 4.5 km of Key West Butterfly and Nature Conservatory.
Hotel
10.0
Perfect11 review10
- Heated Pool
- Concierge Service
- Poolside Bar
3.4 km from City Centre1.6 km from Kayak Kings Key West
From
US$ 130
/night
- Heated outdoor pool with ocean views
- Daily shuttle service to downtown Key West
- Complimentary drinks at the pool bar
Bed & Breakfast
- Happy Hour
- Jacuzzi
- Garden
2.0 km from City Centre300 m from San Carlos Institute Casa Cuba
From
US$ 125
/night
- Historic Victorian architecture
- Daily happy hour with complimentary drinks
- Charming garden with jacuzzi
Motel
- Rooftop deck
- Swimming pool
- Bicycle rentals
1.2 km from City Centre300 m from Dog Beach
From
US$ 109
/night
- Rooftop deck for sunbathing and stargazing
- 30-room motel in Art Deco style
- Swimming pool with spacious sunbathing area
Guest house
- Outdoor pools
- Massage services
- Private balconies
1.7 km from City Centre600 m from Key West Cemetery
From
US$ 210
/night
- Two sparkling outdoor pools
- On-site massage services available
- Complimentary continental breakfast offered
Bed & Breakfast
- Outdoor pool
- Private bath
- Complimentary breakfast
2.4 km from City Centre300 m from Jackson Square
From
US$ 213
/night
- Historic hotel built in 1911
- Adults-only bed and breakfast atmosphere
- Outdoor pool surrounded by lush gardens
9.6
Perfect11 review10
- Pool Bar
- Tiki Bar
- Outdoor Pool
3.4 km from City Centre600 m from Kayak Kings Key West
From
US$ 112
/night
- Complimentary drink coupons for pool bar
- Personalized concierge service by Donna
- Live music enhances poolside atmosphere
- Infinity Pool
- Private Beach
- Kitchen Suites
3.2 km from City Centre1.7 km from Kayak Kings Key West
From
US$ 250
/night
- Ocean-view infinity pool
- Full kitchens in every unit
- Private beach access
- Private Beach
- On-site Marina
- Presidential Suite
3.5 km from City Centre500 m from Kayak Kings Key West
From
US$ 194
/night
- Presidential Suite with panoramic ocean views
- Private beach for peaceful relaxation
- Exciting sandbar and sunset cruises available
- Heated Pool
- Bicycle Rentals
- Private Cottages
1.7 km from City Centre300 m from Fury Water Adventures Key West
From
US$ 291
/night
- Adult-only environment for serene retreats
- Complimentary evening wine and cheese hour
- Tropical gardens with relaxing lounge areas
- Outdoor Pool
- Hot Tub
- Private Balcony
3.7 km from City Centre400 m from Kayak Kings Key West
From
US$ 359
/night
- Fully equipped kitchen in suites
- Outdoor swimming pool with hot tub
- Snorkeling and windsurfing activities
- Outdoor Pool
- Tiki Bar
- Fitness Center
1.9 km from City Centre1.8 km from Smathers Beach
From
US$ 184
/night
- Complimentary shuttle to downtown Key West
- Scenic waterfront promenade with beach access
- Tiki bar serving cocktails by the pool
- Saltwater Pool
- Gumbos Bar
- Fishing Dock
3.4 km from City Centre400 m from Kayak Kings Key West
From
US$ 244
/night
- Saltwater pools enhance relaxation experience
- Complimentary bicycles offered for exploration
- Gas grills for outdoor cooking available
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