Hotels with Entertainment in Key West Historic District, FL

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  3.  USA
  4.  Florida
  5.  Key West
  6.  Key West Historic District
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Explore 73 Hotels with Entertainment in Key West Historic District from $232

Duval Inn - Key West
Duval Inn - Key West
Hotel
Key West Historic District, Key West, Florida, USA
0.3k from Key West Historic District center

Accommodations, Pools, Motels, Parking, Romantic, Lodgings, Places to stay

8.1

Very Good

902 reviews

$460
Average price / night
Check Availability
Island City House Hotel
Island City House Hotel
Hotel
411 William Street, Key West, FL, 33040, United States
0.3k from Key West Historic District center

AC, Housekeeping, Internet, Kitchen, Laundry, Microwave, Outdoor Space, Pool, TV

9.6

Exceptional

1000 reviews

$349
Average price / night
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Paradise Inn - Adult Exclusive
Paradise Inn - Adult Exclusive
Hotel
Key West, FL, USA
0.3k from Key West Historic District center

B&bs, Accommodations, Pools, Parking, Inns, Romantic, 3-star, Lodgings, Hot tubs

8.4

Very Good

715 reviews

$270
Average price / night
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Ella's Cottages - Key West Historic Inns
Ella's Cottages - Key West Historic Inns
Hotel
811 Simonton Street, Key West, FL, 33040, United States
0.3k from Key West Historic District center

AC, Breakfast Included, Heater, Housekeeping, Internet, Microwave, No Smoking, Outdoor Space, Parking Available

9.4

Superb

457 reviews

$498
Average price / night
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The Gardens Hotel
The Gardens Hotel
Hotel
Key West Historic District, Key West, Florida, USA
0.3k from Key West Historic District center

Accommodations, Pools, Parking, Romantic, 4-star, Lodgings, Places to stay, Accessible hotels

9.7

Exceptional

141 reviews

$1074
Average price / night
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Westwinds Inn
Westwinds Inn
Hotel
914 Eaton St, Key West, FL, 33040, United States
0.4k from Key West Historic District center

AC, Barbecue, Breakfast Included, Housekeeping, Internet, Laundry, No Smoking, Outdoor Space, Pool

9.4

Superb

1001 reviews

$371
Average price / night
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Truman Hotel
Truman Hotel
Hotel
Key West, FL, USA
0.4k from Key West Historic District center

Accommodations, Pools, Parking, Romantic, Boutique, 3-star, Lodgings, Places to stay, Family

8.9

Fabulous

3248 reviews

$244
Average price / night
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Eden House
Eden House
Hotel
1015 Fleming St, Key West, FL, 33040, United States
0.5k from Key West Historic District center

AC, Bar, Business Services, Crib, Frontdesk 24 Hour, Hot Tub, Housekeeping, Internet, Laundry

9.0

Fabulous

1002 reviews

$401
Average price / night
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La Pensione Inn - Adult Exclusive
La Pensione Inn - Adult Exclusive
Hotel
Key West Historic District, Key West, Florida, USA
0.4k from Key West Historic District center

Accommodations, Pools, Parking, Romantic, 3-star, Lodgings, Vacation rentals, Places to stay, Accessible hotels

8.7

Fabulous

644 reviews

$511
Average price / night
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Lighthouse Hotel - Key West Historic Inns
Lighthouse Hotel - Key West Historic Inns
Hotel
902 Whitehead St, Key West, FL, 33040, United States
0.6k from Key West Historic District center

AC, Bar, Breakfast Included, Crib, Heater, Housekeeping, Internet, No Smoking, Outdoor Space

9.0

Fabulous

922 reviews

$431
Average price / night
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The Mermaid & The Alligator
The Mermaid & The Alligator
Hotel
Key West, FL, USA
0.4k from Key West Historic District center

Accommodations, Pools, Lodgings, Hot tubs, Places to stay

9.3

Superb

148 reviews

$2197
Average price / night
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La Concha Key West, Autograph Collection
La Concha Key West, Autograph Collection
Resort
Key West, FL, USA
0.5k from Key West Historic District center

Accommodations, Pools, Resorts, Parking, Romantic, 4-star, Lodgings, Places to stay, Accessible hotels

8.3

Very Good

54 reviews

$306
Average price / night
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Wicker Guesthouse
Wicker Guesthouse
Hotel
Key West, FL, USA
0.5k from Key West Historic District center

B&bs, Accommodations, Pools, Parking, Inns, Romantic, Pet-friendly, 3-star, Lodgings

8.0

Good

2911 reviews

$242
Average price / night
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Almond Tree Inn - Adults Only
Almond Tree Inn - Adults Only
Hotel
Key West Historic District, Key West, Florida, USA
0.5k from Key West Historic District center

Accommodations, Pools, Parking, Romantic, Boutique, 3-star, Lodgings, Hot tubs, Places to stay

9.4

Superb

278 reviews

$889
Average price / night
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The Cabana Inn Key West - Adult Exclusive
The Cabana Inn Key West - Adult Exclusive
Hotel
Key West, FL, USA
0.5k from Key West Historic District center

B&bs, Accommodations, Pools, Parking, Inns, Romantic, 3-star, Lodgings, Hot tubs

8.2

Very Good

843 reviews

$232
Average price / night
Check Availability
The Porch on Frances Inn - Adults Exclusive
The Porch on Frances Inn - Adults Exclusive
Hotel
Key West, FL, USA
0.5k from Key West Historic District center

B&bs, Cheap, Accommodations, Parking, Inns, Lodgings, Places to stay

9.0

Fabulous

125 reviews

$484
Average price / night
Check Availability
The Saint Hotel Key West, Autograph Collection, Adult Only
The Saint Hotel Key West, Autograph Collection, Adult Only
Hotel
Key West, FL, USA
0.6k from Key West Historic District center

Accommodations, Pools, Parking, 4-star, Lodgings, Places to stay, Family, Accessible hotels

8.8

Fabulous

44 reviews

$268
Average price / night
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Orchid Key Inn - Adults Only
Orchid Key Inn - Adults Only
Hotel
Key West Historic District, Key West, Florida, USA
0.6k from Key West Historic District center

Accommodations, Pools, Parking, Boutique, 3-star, Lodgings, Hot tubs, Places to stay

9.4

Superb

285 reviews

$848
Average price / night
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La Te Da - Adult Only, 21 or older
La Te Da - Adult Only, 21 or older
Hotel
Key West Historic District, Key West, Florida, USA
0.7k from Key West Historic District center

Accommodations, Pools, 3-star, Lodgings, Places to stay, Accessible hotels

9.0

Fabulous

156 reviews

$285
Average price / night
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Douglas House
Douglas House
Hotel
Key West, FL, USA
0.7k from Key West Historic District center

B&bs, Accommodations, Pools, Parking, Inns, Romantic, Pet-friendly, 3-star, Lodgings

9.0

Fabulous

2665 reviews

$260
Average price / night
Check Availability
The Palms Hotel
The Palms Hotel
Hotel
Key West Historic District, Key West, Florida, USA
0.7k from Key West Historic District center

Accommodations, Pools, Romantic, Pet-friendly, 3-star, Lodgings, Places to stay

8.3

Very Good

2374 reviews

$252
Average price / night
Check Availability

Pro Tip for Travelers:
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Key West Historic District Hotels with Entertainment on the Map

Frequently Asked Questions

Entertainment offerings may include live music, cultural shows, game rooms, or on-site events depending on the hotel’s category and facilities.

Some hotels include basic entertainment at no extra cost, while others may charge separately for premium shows or special events.

Hotels with entertainment in Key West Historic District generally start from around $232 per night, depending on the level of facilities and activities offered.

Yes, many entertainment-focused hotels are designed for families and groups, offering activities suitable for both adults and children.

Along with entertainment options, many properties also offer Guest Services, Entertainment, and Pool for a more complete stay experience.