Hotels with Entertainment in Midtown, FL

Booking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Hotels with Entertainment
  3.  USA
  4.  Florida
  5.  Key West
  6.  Midtown
Refine your search

Price per night

Amenity Filter

Rating

Explore 73 Hotels with Entertainment in Midtown from $192

Casa Marina Key West, Curio Collection by Hilton
Casa Marina Key West, Curio Collection by Hilton
Resort
Key West, FL, USA
1.0k from Midtown center

Accommodations, Pools, Resorts, Parking, Spa, Romantic, Pet-friendly, 5-star, Lodgings

7.6

Good

261 reviews

$416
Average price / night
Check Availability
Southwinds Motel
Southwinds Motel
Hotel
1321 Simonton Street, Key West, FL, 33040, United States
1.4k from Midtown center

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

8.6

Fabulous

1298 reviews

$304
Average price / night
Check Availability
The Palms Hotel
The Palms Hotel
Hotel
Midtown, Key West, Florida, USA
1.0k from Midtown center

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

8.3

Very Good

2374 reviews

$252
Average price / night
Check Availability
Eden House
Eden House
Hotel
1015 Fleming St, Key West, FL, 33040, United States
1.5k from Midtown center

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

9.0

Fabulous

1002 reviews

$401
Average price / night
Check Availability
Margaritaville Beach House Key West
Margaritaville Beach House Key West
Hotel
Key West, FL, USA
1.1k from Midtown center

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

8.2

Very Good

921 reviews

$311
Average price / night
Check Availability
3BR Villas for Your Beach Getaway with Shuttle Service, Onsite Parking, Pools!
3BR Villas for Your Beach Getaway with Shuttle Service, Onsite Parking, Pools!
Hotel
Key West, FL, 33040, United States
1.6k from Midtown center

AC, Balcony, Barbecue, Fitness Equipment, Free Parking, Heater, Internet, No Smoking, Outdoor Space

New to Booking
$2137
Average price / night
Check Availability
Fairfield Inn & Suites by Marriott Key West
Fairfield Inn & Suites by Marriott Key West
Hotel
Key West, FL, USA
1.1k from Midtown center

Accommodations, Pools, Parking, Pet-friendly, 3-star, Lodgings, Places to stay, Family, Accessible hotels

7.3

Good

1118 reviews

$192
Average price / night
Check Availability
Tropics Escape in Key West with Onsite Pools!
Tropics Escape in Key West with Onsite Pools!
Hotel
Key West, FL, 33040, United States
1.6k from Midtown center

AC, Balcony, Barbecue, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Microwave

10.0

Exceptional

1 reviews

$1426
Average price / night
Check Availability
La Pensione Inn - Adult Exclusive
La Pensione Inn - Adult Exclusive
Hotel
Midtown, Key West, Florida, USA
1.2k from Midtown center

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

8.7

Fabulous

644 reviews

$511
Average price / night
Check Availability
Southernmost House
Southernmost House
Hotel
1400 Duval Street, Key West, FL, 33040, United States
1.6k from Midtown center

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

9.4

Superb

1001 reviews

$394
Average price / night
Check Availability
The Mermaid & The Alligator
The Mermaid & The Alligator
Hotel
Key West, FL, USA
1.3k from Midtown center

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

9.3

Superb

148 reviews

$2197
Average price / night
Check Availability
The Porch on Frances Inn - Adults Exclusive
The Porch on Frances Inn - Adults Exclusive
Hotel
Key West, FL, USA
1.3k from Midtown center

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

9.0

Fabulous

125 reviews

$484
Average price / night
Check Availability
The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton
Resort
Key West, FL, USA
1.4k from Midtown center

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

7.6

Good

287 reviews

$418
Average price / night
Check Availability
H2O Suites- Adults Only
H2O Suites- Adults Only
Resort
Midtown, Key West, Florida, USA
1.4k from Midtown center

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

9.5

Superb

508 reviews

$1688
Average price / night
Check Availability
Santa Maria Suites Resort
Santa Maria Suites Resort
Resort
Key West, FL, USA
1.4k from Midtown center

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

9.3

Superb

674 reviews

$432
Average price / night
Check Availability
Southernmost Inn Adult Exclusive
Southernmost Inn Adult Exclusive
Hotel
Key West, FL, USA
1.5k from Midtown center

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

7.8

Good

1411 reviews

$546
Average price / night
Check Availability
Truman Hotel
Truman Hotel
Hotel
Key West, FL, USA
1.5k from Midtown center

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

8.9

Fabulous

3248 reviews

$244
Average price / night
Check Availability
La Te Da - Adult Only, 21 or older
La Te Da - Adult Only, 21 or older
Hotel
Midtown, Key West, Florida, USA
1.6k from Midtown center

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

9.0

Fabulous

156 reviews

$285
Average price / night
Check Availability
Parrot Key Hotel & Villas
Parrot Key Hotel & Villas
Resort
Key West, FL, USA
1.6k from Midtown center

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

8.4

Very Good

3303 reviews

$255
Average price / night
Check Availability
Paradise Inn - Adult Exclusive
Paradise Inn - Adult Exclusive
Hotel
Key West, FL, USA
1.6k from Midtown center

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

8.4

Very Good

715 reviews

$270
Average price / night
Check Availability
Almond Tree Inn - Adults Only
Almond Tree Inn - Adults Only
Hotel
Midtown, Key West, Florida, USA
1.6k from Midtown center

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

9.4

Superb

278 reviews

$889
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 Midtown.

Where to stay in Midtown? Best neighborhoods & areas

Stay Near Midtown's Top Attractions

HotelsWithSuites can help you find hotels, resorts, and suites near many of 's top attractions, neighborhoods, and points of interest.

Midtown 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 Midtown generally start from around $192 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 Entertainment, Balcony/Terrace, and Guest Services for a more complete stay experience.