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

Florida Keys Hotels with Entertainment

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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 bar area with a long counter, bar stools, and a view of the water.
A balcony with a view of the ocean, a round table, and two chairs.
A Marriott Fairfield Inn & Suites with a modern design, featuring a covered entrance and palm trees.
A balcony with a view of a body of water, a pool, and outdoor seating.

1. Fairfield Inn & Suites by Marriott Marathon Florida Keys

Fairfield Inn & Suites by Marriott Marathon Florida Keys
Marathon
United States
JOSE
RM546
RM615 total
includes taxes & fees
4 Oct - 5 Oct
Fairfield Inn & Suites by Marriott Marathon Florida Keys
A couple holding hands in a tropical setting with palm trees and greenery.
A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

2. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
United States
Esteban
RM481
RM771 total
includes taxes & fees
29 Sept - 30 Sept
Blue Flamingo Resort Key West
A marina with boats docked, a pool area, and a building with a white facade.
A breakfast setting with a table, chairs, a vase with flowers, and a city view.
A marina with numerous boats docked, a swimming pool, and palm trees.
A clear view of turquoise ocean water and a blue sky with clouds.

3. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
United States
Molly
RM514
RM823 total
includes taxes & fees
4 Oct - 5 Oct
Hilton Key West Resort & Marina
A hotel with a swimming pool, balconies, and a view of the sea.
A beach wedding setup with white chairs, a wooden arch, and lanterns.
A marina with jet skis docked in front of a hotel with a dock and a boat in the background.
A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.

4. Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
United States
yendy
RM949
RM1,352 total
includes taxes & fees
4 Oct - 5 Oct
Hyatt Centric Key West Resort and Spa
A swimming pool with lounge chairs and palm trees.
A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.
A modern living room with a sectional sofa, a small round table, and a potted plant.
A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'

5. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
New Town
United States
Walt
RM427
RM596 total
includes taxes & fees
4 Oct - 5 Oct
Hilton Garden Inn Key West / The Keys Collection
A hotel with a covered entrance, multiple balconies, and palm trees.
A waterfront hotel with multiple balconies, a dock, and boats.
A restaurant interior with wooden beams, a bar area, and a colorful ceiling mural.
A room with a stone wall, a wooden bench, a cactus, and a framed painting.

6. Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
Old Town Key West
United States
Susan
RM1,055
RM1,348 total
includes taxes & fees
30 Sept - 1 Oct
Opal Key Resort & Marina, Key West
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.
A resort with a beach, a dock, and a water view.
A view through a white-framed window with a decorative white fence, leading to a tiled patio area with a round table.

7. Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
United States
Cheryl
RM838
RM1,227 total
includes taxes & fees
4 Oct - 5 Oct
Pier House Resort & Spa
A balcony with two white chairs overlooking a marina with boats, a building with a green roof, and palm trees.
A hotel room with a large bed, a desk with a chair, a television, and a window with curtains.
A bar area with a thatched roof, wooden furniture, and a variety of bottles.
A restaurant with indoor seating, a long counter, and large windows.

8. Holiday Inn Key Largo by IHG

Holiday Inn Key Largo by IHG
Key Largo
United States
suany
RM709
RM797 total
includes taxes & fees
1 Oct - 2 Oct
Holiday Inn Key Largo by IHG
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.
A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.
A spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.
A bar area with a thatched roof, wooden chairs, and a view of the ocean.

9. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
RAIBEL
RM607
RM981 total
includes taxes & fees
29 Sept - 30 Sept
Cheeca Lodge & Spa
A bottle of Marc's Reserve 12 FL. OZ. on a coaster with a metal table.
A patio area with white metal tables and chairs, surrounded by potted plants and palm trees.
A front door with purple shutters, a small porch, and a doormat with 'The Artist House Circa 1890' text.
A potted yellow orchid plant in a garden setting with a brick pathway, palm trees, and a white building in the background.

10. Artist House Key West

Artist House Key West
Key West Historic District
United States
NATHAN
RM401
RM451 total
includes taxes & fees
11 Oct - 12 Oct
Artist House Key West
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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 1 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 2 hours 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 2 hours 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 3 hours ago
Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"All was nice!!"
Luis 1-night trip
Posted 3 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 5 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