A beach with palm trees, people relaxing on chairs, and colorful kayaks.

Search Hotels with Entertainment in Florida Keys

Check availability on Florida Keys Hotels with Entertainment

Tonight
27 Sept - 28 Sept
Tomorrow
28 Sept - 29 Sept
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

Our top choices for Florida Keys hotels with entertainment

A bottle of Marc's Reserve 12 FL. OZ. on a coaster with a metal table.
A front door with purple shutters, a small porch, and a doormat with 'The Artist House Circa 1890' text.
A patio area with white metal tables and chairs, surrounded by potted plants and palm trees.
A potted yellow orchid plant in a garden setting with a brick pathway, palm trees, and a white building in the background.

1. Artist House Key West

Artist House Key West
Key West Historic District
United States
NATHAN
£86
includes taxes & fees
11 Oct - 12 Oct
Artist House Key West
A poolside area with lounge chairs, a staircase leading to a balcony, and a pool.
An outdoor patio with tables and chairs, surrounded by trees and a house.
A Southernmost Inn with a porch, a sign indicating vacancy, and a staircase leading to the entrance.
A dining area with round tables and wicker chairs, a ceiling fan, and a bar area in the background.

2. The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only
Old Town Key West
United States
jeff
£101
includes taxes & fees
29 Sept - 30 Sept
The Southernmost Inn - Adults Only
A gated entrance with a gazebo, palm trees, and a brick pathway leading to a building with a red roof.
A garden with a statue of two figures, lush greenery, and a building in the background.
A bedroom with a large bed, wooden headboard, two bedside lamps, and a floral wall art piece.
A poolside area with lounge chairs and umbrellas, a bar, and a staircase leading to a house.

3. Duval Inn

Duval Inn
Old Town Key West
United States
Arnold J
£129
includes taxes & fees
1 Oct - 2 Oct
Duval Inn
A swimming pool with clear water, surrounded by lush greenery and palm trees.
A bathroom with a white sink, three bottles of body lotion, and a white towel.
A bedroom with a bed, a ceiling fan, an air conditioning unit, a bedside table, a lamp, and a window with blinds.
A yellow building with a blue door and shutters, a number '302' on the wall, and a small porch area.

4. Tranquility Guest House

Tranquility Guest House
Old Town Key West
United States
Sandra
£127
includes taxes & fees
29 Sept - 30 Sept
Tranquility Guest House
A pool area with lounge chairs and a cabana.
A waterfront hotel with a long pier, multiple balconies, and a view of the ocean.
A hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.
A balcony with a table set for breakfast, overlooking the sea.

5. Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
Key West Historic District
United States
Brian
£224
includes taxes & fees
29 Sept - 30 Sept
Ocean Key Resort - A Noble House Resort
A large, ornate hotel with a pool, palm trees, and a view of the ocean.
A large, two-story house with a prominent tower and a covered porch.
A balcony with white railings and a table, overlooking a beach with palm trees and a clear blue sky.
A grand staircase with ornate railings and a chandelier.

6. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Old Town Key West
United States
yessy
£214
includes taxes & fees
25 Oct - 26 Oct
Southernmost House - Adult Exclusive
A wooden deck with wicker furniture, a white staircase, and a lush garden area.
A hotel room with a large bed, a view of a swimming pool, and a balcony with outdoor seating.
A bedroom with a large bed, a view of a swimming pool, and an open door leading to an outdoor seating area.
A hotel entrance with a sign reading "Heron House Office."

7. Heron House - Adult Only

Heron House - Adult Only
Old Town Key West
United States
Fernando
£124
includes taxes & fees
29 Sept - 30 Sept
Heron House - Adult Only
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.
A bar area with a thatched roof, wooden chairs, and a view of the ocean.
A tropical resort with a swimming pool, palm trees, and a waterfall.
A spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.

8. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
RAIBEL
£167
includes taxes & fees
29 Sept - 30 Sept
Cheeca Lodge & Spa
A marina with boats docked, a pool area, and a building with a white facade.
A marina with numerous boats docked, a swimming pool, and palm trees.
A hotel room with a balcony overlooking a marina and the ocean.
A clear view of turquoise ocean water and a blue sky with clouds.

9. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
United States
Molly
£152
includes taxes & fees
4 Oct - 5 Oct
Hilton Key West Resort & Marina
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.
A canal with boats docked on both sides, surrounded by lush greenery and trees.
A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.

10. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
United States
Michel
£58
includes taxes & fees
7 Oct - 8 Oct
Looe Key Reef Resort
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Top Florida Keys Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Very beautiful place. Besides breakfast but we didn't stay hungry. Beside that, everything was perfect"
Roy 2-night trip
Posted less than an hour ago
Chesapeake Beach Resort
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

10/10 Excellent
"The place is a awesome"
Micheal 3-night trip
Posted 1 hour ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Bayside Inn Key Largo

Bayside Inn Key Largo

10/10 Excellent
"Great place to watch the sun set at the bar on the beach"
Anthony 1-night trip
Posted 1 hour ago
Bayside Inn Key Largo
Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"We booked this last minute traveling through the keys on our way to Key West. It was a fantastic place to stay. The staff were so friendly and helpful and the property was beautiful. Highly recommend. I hope we can come back and stay longer next time."
Rebecca 1-night trip
Posted 1 hour ago
Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"All was nice!!"
Luis 1-night trip
Posted 2 hours ago
Amara Cay Resort
Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

10/10 Excellent
"Breakfast was good. large. The pool was very excellent. The beach area was great,a lovely view pver the water,and saw manatees.Our room had been refurbed and was amazing, large size and looked over the pool"
Elizabeth 4-night trip
Posted 4 hours ago
Hampton Inn Key Largo Manatee Bay
Sunset Cove Beach Resort

Sunset Cove Beach Resort

10/10 Excellent
"Great getaway for weekend and bring the dog"
Brian 4-night trip
Posted 1 day ago
Sunset Cove Beach Resort
Hawks Cay Resort

Hawks Cay Resort

10/10 Excellent
"Family friendly"
Victor 4-night trip
Posted 2 days ago
Hawks Cay Resort

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