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Check prices for these dates

Tonight
24 Oct - 25 Oct
Tomorrow
25 Oct - 26 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

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Our top choices for Waterfront Playhouse hotels

A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.
A building with a sign reading "ALMOND Frog & Toad Inn" and a "VACANCY" sign below it.
A reception area with a wooden herringbone wall, teal chairs, a wooden bench, and two framed sunset paintings.
A swimming pool with lounge chairs, surrounded by palm trees and greenery.

1. Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
Downtown Key West, 1.3 km from Waterfront Playhouse
United States
Teresa
SAR 923
SAR 1,039 total
includes taxes & fees
25 Oct - 26 Oct
Almond Tree Inn Hotel - Adults Only
A modern outdoor area with a pool, lounge chairs, and a bar area.
A modern hotel with a prominent glass facade, palm trees, and a clear sky.
An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.
A bar area with a modern design, featuring a flat-screen TV mounted on a textured wall, two stools, and a bar stocked with various bottles.

2. H2O Suites - Adults Only

H2O Suites - Adults Only
Uptown - Upper Duval, 1.6 km from Waterfront Playhouse
United States
Kimberly
SAR 1,124
SAR 1,518 total
includes taxes & fees
28 Oct - 29 Oct
H2O Suites - Adults Only
A pool area with lounge chairs and a table, surrounded by palm trees.
A building with a neon sign that reads "Orchid Key Inn."
A neon sign for Orchid Key Inn with a 'VACANCY' sign below it.
A hotel room with a large bed, a nightstand, a desk, a bathroom with a shower, and a painting of a pier over water on the wall.

3. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
United States
ben
SAR 951
SAR 1,070 total
includes taxes & fees
25 Oct - 26 Oct
Orchid Key Inn - Adults Only
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
A bedroom with a large bed, a television on a dresser, and a view of the outdoors through a sliding door.
A colonial-style building with a porch, surrounded by lush tropical vegetation.
A bar area with a counter, chairs, and a clock.

4. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Gisele
SAR 840
SAR 945 total
includes taxes & fees
27 Oct - 28 Oct
The Gardens Hotel
A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.
A lush garden with a variety of tropical plants and a paved walkway.
A two-story building with a white picket fence, a mailbox, and a small tree in front.
A swimming pool with a mural of a dolphin and a butterfly, surrounded by lounge chairs and palm trees.

5. Duval House

Duval House
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Cathrine
SAR 480
SAR 621 total
includes taxes & fees
25 Oct - 26 Oct
Duval House
A room with a door featuring horizontal blinds, a visible outdoor view through the window, and a patterned carpet.
A pool area with a circular pool, lounge chairs, and a gazebo.
A yellow building with a door marked '7'.
A garden with a stone pathway, a wooden fence, and various tropical plants.

6. Alexander Palms Court

Alexander Palms Court
Casa Marina, 1.8 km from Waterfront Playhouse
United States
Brenda
SAR 605
SAR 680 total
includes taxes & fees
26 Oct - 27 Oct
Alexander Palms Court
A gated entrance with lush green foliage and a white picket fence.
A swimming pool with lounge chairs, a covered deck, and a view of lush greenery.
A white colonial-style building with a balcony, surrounded by palm trees and a white picket fence.
A hotel room with a large bed, two bedside tables, a ceiling fan, and two framed pictures on the wall.

7. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.8 km from Waterfront Playhouse
United States
August
SAR 594
SAR 669 total
includes taxes & fees
25 Oct - 26 Oct
Coco Plum Inn
A large, ornate hotel with a pool, palm trees, and a view of the ocean.
A grand staircase with ornate railings and a chandelier.
A large, two-story house with a prominent tower and a covered porch.
A gated entrance with a blue metal gate, palm trees, and a building with a red roof in the background.

8. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Janet
SAR 537
SAR 1,079 total
includes taxes & fees
27 Oct - 28 Oct
Southernmost House - Adult Exclusive
A poolside area with lounge chairs, umbrellas, and a pergola.
A living room with a spiral staircase, a sofa, a chair, a coffee table, and a view of an outdoor seating area.
An open door leading to a pool area with a wicker chair and a sofa inside a room with a view of the pool.
A bright kitchen with white cabinetry, a white island, wicker pendant lights, and geometric patterned backsplash.

9. Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
Old Town Key West, 1.1 km from Waterfront Playhouse
United States
Lisa and David
SAR 751
SAR 1,035 total
includes taxes & fees
25 Oct - 26 Oct
Ella's Cottages - Key West Historic Inns
A large, white, two-story building with a balcony and a sign reading "The Marker Resort."
A marina with various boats docked, including a green and white boat named 'Jolly Roger'.
A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.
A tropical setting with palm trees and a building with a white facade and dark roof.

10. The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Historic Seaport, 0.6 km from Waterfront Playhouse
United States
Dana Nicole
SAR 680
SAR 1,010 total
includes taxes & fees
25 Oct - 26 Oct
The Marker Key West Harbor Resort
A two-story building with a white picket fence, palm trees, and a sign that reads 'DUVAL GARDENS.'
A porch with wicker chairs and a table, white railings, and a window with a view of a palm tree.
Pool
A kitchen counter with a coffee maker, a bottle of champagne, and various fruits and pastries.

11. Duval Gardens - Adults Only

Duval Gardens - Adults Only
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
United States
JoAnn
SAR 691
SAR 925 total
includes taxes & fees
25 Oct - 26 Oct
Duval Gardens - Adults Only
A pool area with a brick patio, potted plants, and a covered seating area.
A view through a glass door with a metal handle, leading to a white fence and a blue car parked outside.
A house with a porch, a sign reading "Garden House," and a number "329" on the door.
A white picket fence, a palm tree, and a sign reading "Garden House Key West".

12. The Garden House

The Garden House
Historic Seaport, 0.6 km from Waterfront Playhouse
United States
Brad
SAR 372
SAR 499 total
includes taxes & fees
26 Oct - 27 Oct
The Garden House
A white building with green shutters and a white picket fence.
A pool area with lounge chairs, a small table, and a thatched umbrella.
A modern kitchen with white cabinetry, a central island, and a view of the outdoors.
A hotel room with a large bed, a sitting area, and multiple bookshelves filled with books.

13. Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns
Historic Seaport, 0.4 km from Waterfront Playhouse
United States
Jeffrey
SAR 751
SAR 1,035 total
includes taxes & fees
25 Oct - 26 Oct
Ridley House - Key West Historic Inns
A covered porch with wicker furniture, potted plants, and a sign for the "Office" at the Palm Hotel.
A pink building with a white door, a balcony with a white railing, and a view of a pool area.
A row of bicycles parked in front of a building with a white balcony and a palm tree.
A compact kitchen with white cabinets, a microwave, and a small dining area with two wicker chairs.

14. The Palms Hotel

The Palms Hotel
The Meadows, 1.5 km from Waterfront Playhouse
United States
Jerry
SAR 657
SAR 824 total
includes taxes & fees
25 Oct - 26 Oct
The Palms Hotel
A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.
A spacious living area with a wooden staircase, a ceiling fan, a TV, and a view of the beach through an open door.
A cozy cabin with a wooden interior, a bed, a TV, and a kitchenette.
A spacious living area with a gray sofa, wooden staircase, and a kitchen in the background.

15. Eden House

Eden House
Historic Seaport, 1.1 km from Waterfront Playhouse
United States
Michelle
SAR 532
SAR 670 total
includes taxes & fees
25 Oct - 26 Oct
Eden House
A poolside area with lounge chairs, a small pool, and a white building with a balcony.
A white building with a sign reading "The StarCare Inn" and a "No Vacancies" sign.
A reception area with a wooden reception desk, a brown leather couch, and a mural of palm trees on the wall.
A bedroom with a bed, a ceiling fan, a window with blinds, a painting, and a nightstand with a lamp.

16. Seascape Tropical Inn - Adult Exclusive

Seascape Tropical Inn - Adult Exclusive
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Evan
SAR 713
SAR 992 total
includes taxes & fees
1 Nov - 2 Nov
Seascape Tropical Inn - Adult Exclusive
A swimming pool with clear water, surrounded by lush greenery and palm trees.
A bathroom with a shower, sink, and toilet.
A covered porch with white columns and wicker furniture.
A yellow building with a blue door and shutters, a number '302' on the wall, and a small porch area.

17. Tranquility Guest House

Tranquility Guest House
Bahama Village, 0.9 km from Waterfront Playhouse
United States
Sandra
SAR 348
SAR 725 total
includes taxes & fees
25 Oct - 26 Oct
Tranquility Guest House
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with a white facade.
A pathway leading to a white gazebo with a view of a lighthouse in the distance.
A modern kitchen with a wooden counter, two stools, a wicker chair, and a hanging light fixture.
A table with chairs in a lush indoor garden setting.

18. Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns
Bahama Village, 1.2 km from Waterfront Playhouse
United States
Jill
SAR 751
SAR 1,035 total
includes taxes & fees
25 Oct - 26 Oct
Lighthouse Hotel - Key West Historic Inns
A breakfast setup with wine bottles, fruits, and pastries on a tray by a door with a view of a staircase and greenery.
A spacious kitchen with wooden cabinets and a dining area with a round table and chairs.
A patio with sun loungers, a table with an umbrella, and potted plants.
A pool area with lounge chairs, a wicker basket, and a staircase leading to an upper level.

19. The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only
Downtown Key West, 0.7 km from Waterfront Playhouse
United States
Donna
SAR 605
SAR 849 total
includes taxes & fees
25 Oct - 26 Oct
The Cabana Inn Key West - Adults Only
A deck with sun loungers and a railing overlooking the sea.
A poolside area with lounge chairs and umbrellas, palm trees, and a view of the sea.
A beach scene with two people relaxing under a white umbrella, a palm tree, and a clear blue sky.
A beachside hotel with rows of blue lounge chairs and white umbrellas, palm trees, and a clear blue sky.

20. Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
Uptown - Upper Duval, 1.7 km from Waterfront Playhouse
United States
Jacob Stuart
SAR 444
SAR 787 total
includes taxes & fees
25 Oct - 26 Oct
Southernmost Beach Resort and Guesthouses
View all properties

Compare popular hotels close to Waterfront Playhouse

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.
Almond Tree Inn Hotel - Adults Only
10.0
Exceptional
1,005 reviews
View
A modern outdoor area with a pool, lounge chairs, and a bar area.
H2O Suites - Adults Only
9.8
Exceptional
669 reviews
View
A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
9.8
Exceptional
1,003 reviews
View
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
The Gardens Hotel
9.8
Exceptional
1,000 reviews
View
A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.
Duval House
9.6
Exceptional
1,126 reviews
View

Hotels recommended for families near Waterfront Playhouse

A pool area with lounge chairs and a cabana.
A reception area with a wooden reception desk, a tiled wall, and a hanging light fixture.
A balcony with a table set for breakfast, overlooking the sea.
A waterfront hotel with a long pier, multiple balconies, and a view of the ocean.

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
Key West Historic District
SAR 1,050
SAR 1,485 total
includes taxes & fees
23 Nov - 24 Nov
Ocean Key Resort - A Noble House Resort
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
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.
A balcony with a view of the ocean, a sofa, and a massage table.

Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
SAR 589
SAR 924 total
includes taxes & fees
26 Oct - 27 Oct
Pier House Resort & Spa
A white building with green shutters and a white picket fence.
A pool area with lounge chairs, a small table, and a thatched umbrella.
A modern kitchen with white cabinetry, a central island, and a view of the outdoors.
A hotel room with a large bed, a sitting area, and multiple bookshelves filled with books.

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns
Key West Historic District
SAR 751
SAR 1,035 total
includes taxes & fees
25 Oct - 26 Oct
Ridley House - Key West Historic Inns
A hotel with a swimming pool, balconies, and a view of the sea.
A marina with jet skis docked in front of a hotel with a dock and a boat in the background.
A balcony with a view of the ocean, a table, chairs, and a railing.
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.

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
SAR 860
SAR 1,241 total
includes taxes & fees
25 Oct - 26 Oct
Hyatt Centric Key West Resort and Spa
A large, white, two-story building with a balcony and a sign reading "The Marker Resort."
A marina with various boats docked, including a green and white boat named 'Jolly Roger'.
A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.
A tropical setting with palm trees and a building with a white facade and dark roof.

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Key West Historic District
SAR 680
SAR 1,010 total
includes taxes & fees
25 Oct - 26 Oct
The Marker Key West Harbor Resort
A poolside area with lounge chairs, umbrellas, and a pergola.
A living room with a spiral staircase, a sofa, a chair, a coffee table, and a view of an outdoor seating area.
An open door leading to a pool area with a wicker chair and a sofa inside a room with a view of the pool.
A bright kitchen with white cabinetry, a white island, wicker pendant lights, and geometric patterned backsplash.

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
Old Town Key West
SAR 751
SAR 1,035 total
includes taxes & fees
25 Oct - 26 Oct
Ella's Cottages - Key West Historic Inns
A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.
A spacious living area with a wooden staircase, a ceiling fan, a TV, and a view of the beach through an open door.
A cozy cabin with a wooden interior, a bed, a TV, and a kitchenette.
A spacious living area with a gray sofa, wooden staircase, and a kitchen in the background.

Eden House

Eden House
Key West Historic District
SAR 532
SAR 670 total
includes taxes & fees
25 Oct - 26 Oct
Eden House
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with a white facade.
A pathway leading to a white gazebo with a view of a lighthouse in the distance.
A modern kitchen with a wooden counter, two stools, a wicker chair, and a hanging light fixture.
A table with chairs in a lush indoor garden setting.

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
SAR 751
SAR 1,035 total
includes taxes & fees
25 Oct - 26 Oct
Lighthouse Hotel - Key West Historic Inns

Top Waterfront Playhouse Hotel Reviews

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"The resort was amazing. Staff was friendly and went out of their way to make you feel welcomed all week, not just when you checked in. The property was clean and the room was very comfortable. I would definitely go back."
Jennifer 5-night trip
Posted 1 day ago
Winslow's Bungalows - Key West Historic Inns
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

8/10 Good
"Everyone is friendly and does their best"
Robert 3-night trip
Posted 1 day ago
The Marker Key West Harbor Resort
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

8/10 Good
"The location is amazing. The pool was cleaned daily. They provide washer and dryer and supplies to wash clothes. A couple days there were no clean towels to get for the rooms or pool. They do not clean your room daily which is fine. It’s very relaxed atmosphere. The staff is not present very much."
matt 5-night trip
Posted 1 day ago
Amsterdam's Curry Mansion Inn
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

10/10 Excellent
"The staff were incredibly helpful and friendly. Breakfast was good. Location of the hotel would be hard to beat. Even all the people staying here were great."
Steven 3-night trip
Posted 2 days ago
Ridley House - Key West Historic Inns
The Marquesa Hotel

The Marquesa Hotel

10/10 Excellent
"Everything"
Mike 4-night trip
Posted 3 days ago
The Marquesa Hotel
Heart of Downtown Key West Cottage With Off-Street Parking

Heart of Downtown Key West Cottage With Off-Street Parking

10/10 Excellent
"Excellent location, private parking, and great communication from host!"
Laura L. 4-night trip
Posted 3 weeks ago
Heart of Downtown Key West Cottage With Off-Street Parking
Ocean Key Resort & Spa

Ocean Key Resort & Spa

10/10 Excellent
"This resort was amazing! The best area and most beautiful in Old Town. Craig and the whole staff were lovely! Would def return!"
Lola 1-night trip
Posted 2 months ago
Ocean Key Resort & Spa
Chicken Run at Custom House Inn | Unbeatable Location!

Chicken Run at Custom House Inn | Unbeatable Location!

8/10 Good
"Nice basic room, convenient location, comfortable."
Mike W. 5-night trip
Posted 3 months ago
Chicken Run at Custom House Inn | Unbeatable Location!

Other attractions near Waterfront Playhouse

A historic building with a tall tower, palm trees, and a vintage trolley.

Key West Shipwreck Museum

8.6/10 (361 reviews)
You can spend an afternoon studying the exhibits at Key West Shipwreck Museum during your trip to Key West. In the area, take in the lively festivals and beautiful sunsets.
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A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.

Mallory Square

9.2/10 (15,939 reviews)
You can find out about the history of Key West with a stop at Mallory Square. Stroll along the area's seaside or experience its lively festivals.
See properties
A large cruise ship docked at a pier with palm trees and a clear sky.

Mallory Dock

8.8/10 (1,152 reviews)
You can search for that perfect souvenir at Mallory Dock during your visit to Key West. Wander the area's seaside or simply enjoy one of its lively bars.
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A red brick building with arched windows and a clock on the facade.

Museum of Art & History at the Custom House

8.4/10 (15 reviews)
You can spend time exploring the galleries in Museum of Art & History at the Custom House during your trip to Key West. Discover the area's lively bars and its lively festivals.
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A two-story house with green shutters and a wooden balcony.

Audubon House and Tropical Gardens

8.8/10 (378 reviews)
You can spend an afternoon exploring the galleries in Audubon House and Tropical Gardens in Key West. Discover the area's lively bars and its lively festivals.
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A historic building with maritime museum banners, a rusty boat, and a tree-lined street.

Mel Fisher Maritime Museum

9.2/10 (56 reviews)
You can spend time studying the exhibits at Mel Fisher Maritime Museum in Key West. Wander the seaside and beautiful beaches in the area.
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Roy John-Karl Gallery

You can spend time browsing the exhibits at Roy John-Karl Gallery during your trip to Key West. Stroll along the area's seaside, or simply savor its lively bars.
See properties

Sloppy Joe's Bar

Sloppy Joe's Bar is just one of the places to see in Key West, so why not enjoy the other things to explore during your travels? Experience the area's great live music and entertainment choices.
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Frequently asked questions

What's the area like around Waterfront Playhouse?
Waterfront Playhouse is located in an area of Key West known for its beautiful ocean views, sailing, and lively festivals. If you're looking for a convenient place to stay, check out the 1400 hotels and other accommodations you'll find within a mile.
What's the best hotel to stay near Waterfront Playhouse?
Adjacent to Waterfront Playhouse, Pier House Resort & Spa is one of the top choices for your stay based on our traveler data, and this resort offers a full-service spa and a private beach. Other good options within a short distance include Hyatt Centric Key West Resort and Spa and Opal Key Resort & Marina, Key West.
How many hotels will I be able to find near Waterfront Playhouse?
Expedia has 1400 hotels and other accommodations within a mile from Waterfront Playhouse.
If I need to cancel the hotel reservation for my stay near Waterfront Playhouse, will I receive a refund?
Yes, you'll find most hotel reservations are refundable if you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before your arrival date. If your reservation is non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of booking. Add your dates and click on "Search", then you can use the "fully refundable" filter to get the top deals on offer near Waterfront Playhouse.
Where can I learn more about changing or cancelling my trip in the area near Waterfront Playhouse?
To access more information about rescheduling or cancelling your stay near Waterfront Playhouse, go to https://www.expedia.com/service/.
What can I see and do near Waterfront Playhouse?
Harry S. Truman Little White House, Florida Keys Eco - Discovery Center, and Ernest Hemingway Home and Museum feature a variety of fascinating exhibits to see while you're in town. Sights like Key West Lighthouse and Keeper's Quarters Museum, Fort Zachary Taylor Historic State Park, and Fort East Martello Museum and Gallery are landmarks to visit in the area. You can watch performances at Red Barn Theater, Key West Film Society, and The Key West Theater if you're interested in local theater.