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

Hotels with Entertainment in Florida Keys

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Check availability on Florida Keys Hotels with Entertainment

Tonight
28 Sept - 29 Sept
Tomorrow
29 Sept - 30 Sept
This weekend
2 Oct - 4 Oct
Next weekend
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 waterfront property with a large building, a smaller structure with a thatched roof, and several boats docked.
A balcony with a view of the ocean, a round table, and two chairs.
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
S$193
includes taxes & fees
4 Oct - 5 Oct
Fairfield Inn & Suites by Marriott Marathon Florida Keys
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.
A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.
A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.

2. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
United States
Esteban
S$242
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 clear view of turquoise ocean water and a blue sky with clouds.
A breakfast setting with a table, chairs, a vase with flowers, and a city view.
A hotel room with a balcony overlooking a marina and the ocean.

3. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
United States
Molly
S$258
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 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.
A beach wedding setup with white chairs, a wooden arch, and lanterns.
A balcony with a view of the ocean, a table, chairs, and a railing.

4. Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
United States
yendy
S$424
includes taxes & fees
4 Oct - 5 Oct
Hyatt Centric Key West Resort and Spa
A swimming pool with lounge chairs and palm trees.
A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'
A modern living room with a sectional sofa, a small round table, and a potted plant.

5. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
New Town
United States
Walt
S$187
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 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.
A waterfront hotel with multiple balconies, a dock, and boats.

6. Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
Old Town Key West
United States
Susan
S$422
includes taxes & fees
29 Sept - 30 Sept
Opal Key Resort & Marina, Key West
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
A balcony with a view of the ocean, a sofa, and a massage table.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.
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
S$385
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 rectangular swimming pool with a tiled deck, surrounded by lounge chairs and thatched umbrellas.
A hotel room with a large bed, a desk with a chair, a television, and a window with curtains.
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
S$250
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 spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.
A tropical resort with a swimming pool, palm trees, and a waterfall.
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
S$275
includes taxes & fees
30 Sept - 1 Oct
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
S$141
includes taxes & fees
11 Oct - 12 Oct
Artist House Key West
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Top Florida Keys Hotel Reviews

Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

10/10 Excellent
"Place was great!! Can’t wait to go back!!"
Cory 1-night trip
Posted 1 hour ago
Hampton Inn Key Largo Manatee Bay
Bayside Inn Key Largo

Bayside Inn Key Largo

8/10 Good
"The floor of the room was dirty. Dust, leaves and mud on the floor."
Ryoko 1-night trip
Posted 1 hour ago
Bayside Inn Key Largo
Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"i loved this place beautiful hotel full kitchen perfect for a little trip 100% recommend"
Ysabella 2-night trip
Posted 2 hours ago
Waterside Suites & Marina
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 4 hours 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 5 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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 5 hours ago
Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"All was nice!!"
Luis 1-night trip
Posted 6 hours ago
Amara Cay Resort
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