Hotels with Entertainment in Old Town, FL

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  2. Hotels with Entertainment
  3.  USA
  4.  Florida
  5.  Key West
  6.  Old Town
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Explore 73 Hotels with Entertainment in Old Town from $232

Truman Hotel
Truman Hotel
Hotel
Key West, FL, USA
0.1k from Old Town 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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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 Old Town 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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Paradise Inn - Adult Exclusive
Paradise Inn - Adult Exclusive
Hotel
Key West, FL, USA
0.2k from Old Town 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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Lighthouse Hotel - Key West Historic Inns
Lighthouse Hotel - Key West Historic Inns
Hotel
902 Whitehead St, Key West, FL, 33040, United States
0.4k from Old Town 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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Almond Tree Inn - Adults Only
Almond Tree Inn - Adults Only
Hotel
Old Town, Key West, Florida, USA
0.2k from Old Town 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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Southwinds Motel
Southwinds Motel
Hotel
1321 Simonton Street, Key West, FL, 33040, United States
0.4k from Old Town center

AC, Bar, Breakfast Included, Crib, Frontdesk 24 Hour, Laundry, Microwave, Outdoor Space, Parking Available

8.6

Fabulous

1298 reviews

$304
Average price / night
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The Mermaid & The Alligator
The Mermaid & The Alligator
Hotel
Key West, FL, USA
0.2k from Old Town center

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

9.3

Superb

148 reviews

$2197
Average price / night
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Southernmost House
Southernmost House
Hotel
1400 Duval Street, Key West, FL, 33040, United States
0.6k from Old Town center

AC, Bar, Breakfast Included, Housekeeping, Internet, No Smoking, Outdoor Space, Parking Available, Pool

9.4

Superb

1001 reviews

$394
Average price / night
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La Te Da - Adult Only, 21 or older
La Te Da - Adult Only, 21 or older
Hotel
Old Town, Key West, Florida, USA
0.3k from Old Town center

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

9.0

Fabulous

156 reviews

$285
Average price / night
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Island City House Hotel
Island City House Hotel
Hotel
411 William Street, Key West, FL, 33040, United States
0.8k from Old Town center

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

9.6

Exceptional

1000 reviews

$349
Average price / night
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H2O Suites- Adults Only
H2O Suites- Adults Only
Resort
Old Town, Key West, Florida, USA
0.3k from Old Town center

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

9.5

Superb

508 reviews

$1688
Average price / night
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Southernmost Inn Adult Exclusive
Southernmost Inn Adult Exclusive
Hotel
Key West, FL, USA
0.3k from Old Town center

B&bs, Accommodations, Pools, Inns, Romantic, 3-star, Lodgings, Hot tubs, Places to stay

7.8

Good

1411 reviews

$546
Average price / night
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Wicker Guesthouse
Wicker Guesthouse
Hotel
Key West, FL, USA
0.3k from Old Town 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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Orchid Key Inn - Adults Only
Orchid Key Inn - Adults Only
Hotel
Old Town, Key West, Florida, USA
0.3k from Old Town 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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Douglas House
Douglas House
Hotel
Key West, FL, USA
0.3k from Old Town center

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

9.0

Fabulous

2665 reviews

$260
Average price / night
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La Pensione Inn - Adult Exclusive
La Pensione Inn - Adult Exclusive
Hotel
Old Town, Key West, Florida, USA
0.3k from Old Town 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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The Gardens Hotel
The Gardens Hotel
Hotel
Old Town, Key West, Florida, USA
0.4k from Old Town 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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Duval Inn - Key West
Duval Inn - Key West
Hotel
Old Town, Key West, Florida, USA
0.5k from Old Town center

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

8.1

Very Good

902 reviews

$460
Average price / night
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Santa Maria Suites Resort
Santa Maria Suites Resort
Resort
Key West, FL, USA
0.5k from Old Town center

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

9.3

Superb

674 reviews

$432
Average price / night
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The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton
Resort
Key West, FL, USA
0.6k from Old Town center

Accommodations, Pools, Resorts, Parking, Spa, Pet-friendly, 4-star, Lodgings, Beach

7.6

Good

287 reviews

$418
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
0.7k from Old Town 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

Pro Tip for Travelers:
HotelsWithSuites simplifies your search by aggregating premium inventory from global leaders like Booking.com, Expedia, and Vrbo. Whether you need oceanfront hotels, a private pool, or a pet-friendly suite, use our Advanced Filters to instantly compare the top-rated Hotels with Entertainment in Old Town.

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Old Town 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 Old Town 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 Pool, Entertainment, and Guest Services for a more complete stay experience.