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Historical hotels in Key West

Find and book your ideal hotel in Key West for a great vacation

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Historical hotels

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24 properties found in Key West

  • Westwinds Inn

    Westwinds Inn

    Downtown Key West Steps from Duval Street - 300m
    "Relax and unwind"
    Best for Couples

    • On-site massage services available

    • Two heated outdoor pools

    • Complimentary breakfast included

    from

    US$ 210 price for 1 night
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  • Weatherstation Inn Circa 1911

    Weatherstation Inn Circa 1911

    Downtown Key West Near historic sites - 500m
    "Relax by the pool"
    Best for Adults Only

    • Outdoor swimming pool available

    • Complimentary continental breakfast

    • Free Wi-Fi throughout the property

    from

    US$ 169 price for 1 night
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  • Southernmost Hotel

    Southernmost Hotel

    1319 Duval Street Close to attractions - 300m
    4.5
    8321 reviews
    Best for Couples

    • On-site spa for relaxation

    • Two white sand beaches

    • Three heated swimming pools

    from

    US$ 166 price for 1 night
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  • Parrot Key Hotel & Villas

    Parrot Key Hotel & Villas

    2801 North Roosevelt Boulevard Close to attractions - 1.5km
    4
    793 reviews
    Best for Families

    • Four sparkling outdoor pools

    • Complimentary shuttle service available

    • Spacious villas with water views

    from

    US$ 490 price for 1 night
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  • Doubletree By Hilton Grand Key Resort

    Doubletree By Hilton Grand Key Resort

    3990 S. Roosevelt Blvd Close to beach - 1.5km
    4
    4052 reviews
    Best for Families

    • Free airport shuttle service available

    • On-site restaurant with outdoor seating

    • Outdoor pool with cabanas

    from

    US$ 186 price for 1 night
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  • The Gates Hotel Key West

    The Gates Hotel Key West

    3820 North Roosevelt Boulevard Gateway to Key West - 6.5km
    4
    1962 reviews
    Best for Couples

    • Newly renovated stylish rooms

    • Four sparkling swimming pools

    • Poolside dining with fun vibes

    from

    US$ 140 price for 1 night
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  • Margaritaville Beach House Key West

    Margaritaville Beach House Key West

    2001 South Roosevelt Blvd Adjacent to beach - 0.1km
    4.5
    953 reviews
    Best for Beach Lovers

    • Lagoon-style pool access

    • On-site dining options

    • Beach access steps away

    from

    US$ 182 price for 1 night
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  • Ibis Bay Resort

    Ibis Bay Resort

    3101 North Roosevelt Boulevard Close to Bay Beach - 300m
    "Enjoy beach activities"
    Best for Families

    • Private beach with sun loungers

    • Outdoor saltwater swimming pool

    • Bicycle and kayak rentals available

    from

    US$ 364 price for 1 night
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  • Blue Flamingo Resort Key West

    Blue Flamingo Resort Key West

    3820 North Roosevelt Boulevard Gateway to Key West - 6.5km
    "Relax by the pool"
    Best for Couples

    • Newly renovated stylish rooms

    • Two lively pools with cabanas

    • On-site dining with island flair

    from

    US$ 293 price for 1 night
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  • Hilton Garden Inn Key West / The Keys Collection

    Hilton Garden Inn Key West / The Keys Collection

    3850 North Roosevelt Boulevard Proximity to attractions - 3 miles
    "Family-friendly leisure hotel"
    Best for Families

    • Outdoor pool with tiki bar

    • On-site restaurant serving breakfast

    • Complimentary shuttle to Old Town

    from

    US$ 87 price for 1 night
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  • Silver Palms Inn

    Silver Palms Inn

    Downtown Key West Three blocks from Duval - 300m
    "Charming island-style décor"
    Best for Couples

    • Outdoor heated saltwater pool

    • Complimentary continental breakfast

    • Private balconies in guest rooms

    from

    US$ 139 price for 1 night
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  • Fairfield Inn and Suites By Marriott Key West

    Fairfield Inn and Suites By Marriott Key West

    2400 North Roosevelt Boulevard Close to Smathers Beach - 3.2km
    4
    1956 reviews
    Best for Couples

    • Large outdoor pool with cabanas

    • Daily hot breakfast served poolside

    • On-site scooter and bicycle hire

    from

    US$ 193 price for 1 night
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  • Santa Maria Suites Resort

    Santa Maria Suites Resort

    Downtown Key West Close to Duval Street - 200m
    "Luxury poolside experience"
    Best for Luxury Travelers

    • Two heated outdoor pools

    • Spacious two-bedroom suites

    • Gourmet dining at Milagro

    from

    US$ 190 price for 1 night
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  • Hampton Inn Key West Fl

    Hampton Inn Key West Fl

    3755 S. Roosevelt Boulevard Close to Smathers Beach - 1.5km
    "Enjoy heated pool"
    Best for Couples

    • Heated pool with ocean view

    • Complimentary breakfast every day

    • Free Wi-Fi in all rooms

    from

    US$ 130 price for 1 night
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  • Fairfield By Marriott Inn & Suites Key West At The Keys Collection

    Fairfield By Marriott Inn & Suites Key West At The Keys Collection

    3852 North Roosevelt Boulevard Near local hotspots - 1.8km
    "Relax by the pool"
    Best for Couples

    • Newly renovated hotel experience

    • Outdoor pool and Tiki bar

    • 11,000 sq ft event space

    from

    US$ 112 price for 1 night
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  • The Laureate Key West

    The Laureate Key West

    3444 N Roosevelt Boulevard 33040 Key West Fl Us Near waterfront activities - 300m
    4.5
    107 reviews
    Best for Families

    • Luxury all-suite accommodations

    • Bi-level suites for groups

    • Grocery delivery for convenience

    from

    US$ 272 price for 1 night
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  • The Artist House

    The Artist House

    Downtown Key West Steps from Duval Street - 300m
    "Historic and charming"
    Best for Romantic Getaways

    • Complimentary daily gourmet breakfast

    • Historic Victorian architecture charm

    • Signature afternoon happy hour

    from

    US$ 125 price for 1 night
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  • Courtyard By Marriott Key West Waterfront

    Courtyard By Marriott Key West Waterfront

    3031-41 North Roosevelt Boulevard Key West attractions - 2.9 miles
    4
    1083 reviews
    Best for Beach Lovers

    • Heated outdoor swimming pool

    • Tiki Bar by the pool

    • Access to private beach area

    from

    US$ 184 price for 1 night
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  • El Patio Motel

    El Patio Motel

    Downtown Key West Close to beach - 300m
    3.5
    663 reviews
    Best for Couples

    • Private rooftop sun deck

    • Outdoor saltwater pool

    • Bicycle rentals available

    from

    US$ 109 price for 1 night
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  • Beachside Resort & Residences

    Beachside Resort & Residences

    3841 North Roosevelt Boulevard Direct beach access - 50m
    4.5
    3526 reviews
    Best for Couples

    • Private beach with lounge chairs

    • Oceanfront suites with direct beach access

    • Onsite marina offering water adventures

    from

    US$ 375 price for 1 night
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