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Check prices for these dates

Tonight
10 Oct - 11 Oct
Tomorrow
11 Oct - 12 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

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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, 0.8 mi from Waterfront Playhouse
United States
John
£187
includes taxes & fees
12 Oct - 13 Oct
Almond Tree Inn Hotel - Adults Only
A tropical outdoor area with palm trees, hanging plants, and string lights.
A large, two-story building with a balcony, surrounded by dense tropical foliage.
A wooden deck with lush greenery and a pool area.
A hotel room with a bed, a wooden floor, a seating area with a table and chairs, and a view of greenery outside.

2. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 0.9 mi from Waterfront Playhouse
United States
Maricela
£124
includes taxes & fees
12 Oct - 13 Oct
Douglas House - Adults Only
A modern interior with a staircase, a sofa set, a wooden table, and a television.
A spacious room with a large bed, a sofa, a chair, a small table, and a television.
A courtyard with two green lounge chairs, a palm tree, and a building with a white facade and lattice window design.
A pool area with a clear view of a house in the background, surrounded by palm trees and greenery.

3. Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
Historic Seaport, 0.3 mi from Waterfront Playhouse
United States
William
£195
includes taxes & fees
12 Oct - 13 Oct
Simonton Court Historic Inn & Cottages
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 patio with a white wicker lounge chair, a wooden table with a book and a potted plant, surrounded by lush tropical foliage and palm trees.

4. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 0.8 mi from Waterfront Playhouse
United States
ben
£197
includes taxes & fees
12 Oct - 13 Oct
Orchid Key Inn - Adults Only
A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.
A spacious living room with a sofa, chairs, and a dining table. There are large windows with blinds, a door leading to a patio, and a ceiling with exposed beams.
A pool area with lounge chairs, a pool, and a building with a balcony and outdoor seating.
A spacious living room with a wooden ceiling, white sofas, a patterned armchair, a glass coffee table, and a large painting on the wall.

5. Alexander's Guesthouse - Adult Exclusive

Alexander's Guesthouse - Adult Exclusive
Old Town Key West, 0.8 mi from Waterfront Playhouse
United States
Nestor
£214
includes taxes & fees
12 Oct - 13 Oct
Alexander's Guesthouse - Adult Exclusive
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
A colonial-style building with a porch, surrounded by lush tropical vegetation.
A couple walking along a poolside pathway surrounded by lush greenery.
A bar area with a counter, chairs, and a clock.

6. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.6 mi from Waterfront Playhouse
United States
Gisele
£254
includes taxes & fees
27 Oct - 28 Oct
The Gardens Hotel
A porch with a white railing, a bench, and a flag.
A living room with a sofa, a glass coffee table, a TV, and a painting on the wall.
A two-story white house with green shutters, a wooden door, and a white picket fence.
A spacious bedroom with a large bed, a sitting area with a sofa and armchairs, and a dining area with a table and chairs.

7. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 0.8 mi from Waterfront Playhouse
United States
John
£202
includes taxes & fees
12 Oct - 13 Oct
The Conch House Heritage Inn
A gated entrance to Villas Key West with a brick pathway leading to the gate.
A covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.
A swimming pool with a hot tub, surrounded by a wooden deck and lush greenery.
A house with a porch, a table, and a door with a number '6'.

8. Key West Villas

Key West Villas
Downtown Key West, 0.6 mi from Waterfront Playhouse
United States
Margaret
£221
includes taxes & fees
15 Oct - 16 Oct
Key West Villas
A two-story house with a covered porch, a brick pathway, and a large tree.
A covered porch with white wicker furniture and a blue floor, surrounded by lush tropical plants.
A restaurant with multiple tables set for dining, a wine bottle, and a glass of wine on the table.
A poolside area with a swimming pool, a staircase leading to a deck, and a building with multiple windows and balconies.

9. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.4 mi from Waterfront Playhouse
United States
Darrell
£331
includes taxes & fees
12 Oct - 13 Oct
The Marquesa Hotel
A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.
A swimming pool with a mural of a dolphin and a butterfly, surrounded by lounge chairs and palm trees.
A two-story building with a white picket fence, a mailbox, and a small tree in front.
A lush garden with a variety of tropical plants and a paved walkway.

10. Duval House

Duval House
Downtown Key West, 0.7 mi from Waterfront Playhouse
United States
Cliff
£167
includes taxes & fees
25 Oct - 26 Oct
Duval House
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.
A garden with a pond, rocks, and various plants.
A compact kitchen with wooden cabinets, a microwave, stove, and refrigerator. There is a dining area with a table and chairs, and a sofa.
A covered walkway with a wooden ceiling, white railings, and a brick path.

11. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.5 mi from Waterfront Playhouse
United States
Osvaldo
£177
includes taxes & fees
15 Oct - 16 Oct
Island City House Hotel
A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.
A covered outdoor area with a wooden staircase, seating, and potted plants.
A row of blue bicycles parked under a tree, with a white fence and a building in the background.
A two-story building with a porch, a sign reading "The Grand Guesthouse," and a purple flag.

12. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West, 1 mi from Waterfront Playhouse
United States
Justyn
£120
includes taxes & fees
13 Oct - 14 Oct
The Grand Guesthouse
A pool area with lounge chairs and palm trees.
A sign for Santa Maria Resort surrounded by lush greenery and palm trees.
A reception area with a modern design, featuring a reception desk, a sofa, and a potted plant.
A modern outdoor seating area with a sofa, chairs, and a small table, surrounded by glass doors and a view of greenery.

13. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.1 mi from Waterfront Playhouse
United States
Anthony
£314
includes taxes & fees
25 Oct - 26 Oct
Santa Maria Suites
A room with a bed, a ceiling fan, and a window with blinds.
A room with a yellow armchair, a glass coffee table, and a view of a wooden deck and tropical plants.
A spacious kitchen with wooden cabinets, a granite countertop, and a ceiling fan.
A poolside area with lounge chairs, a covered seating area, and a small pool.

14. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 0.8 mi from Waterfront Playhouse
United Kingdom
Adam
£214
includes taxes & fees
12 Oct - 13 Oct
The Mermaid & Alligator
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
The entrance to Silver Palms Inn with a reception desk, a seating area, and a glass door.
A hotel with a pool, bicycles, and lush greenery.
A two-story yellow house with a porch, white railings, and green shutters.

15. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 0.9 mi from Waterfront Playhouse
United States
sam
£127
includes taxes & fees
25 Oct - 26 Oct
Silver Palms Inn & Historic Homes
A reception area with a curved marble counter, ceiling fans, large windows, and a staircase.
A bedroom with a bed, two bedside lamps, a ceiling fan, and a view of a balcony with plants.
A breakfast table with a variety of food items, including fruits, pastries, and a coffee mug.
A poolside area with lounge chairs and a clear blue pool surrounded by lush tropical vegetation.

16. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.6 mi from Waterfront Playhouse
United States
Anthony
£138
includes taxes & fees
12 Oct - 13 Oct
Westwinds 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 balcony with white railings and a table, overlooking a beach with palm trees and a clear blue sky.

17. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.1 mi from Waterfront Playhouse
United States
Amy
£214
includes taxes & fees
25 Oct - 26 Oct
Southernmost House - Adult Exclusive
A rectangular pool with a white deck, surrounded by lush greenery and a gazebo.
A wicker outdoor seating area with two chairs and a table, surrounded by lush tropical foliage.
A cozy living room with a wooden ceiling, a sofa set, two side tables with lamps, and framed artwork on the wall.
A hotel room with a bed, a nightstand, a chair, a small table, and a ceiling fan.

18. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.4 mi from Waterfront Playhouse
United States
Tricia
£117
includes taxes & fees
13 Oct - 14 Oct
Ambrosia Key West
A gated entrance with lush green foliage 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.
A covered outdoor dining area with white chairs and tables, surrounded by lush greenery and a wooden deck.
A white colonial-style building with a balcony, surrounded by palm trees and a white picket fence.

19. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.5 mi from Waterfront Playhouse
United States
Riley
£151
includes taxes & fees
12 Oct - 13 Oct
Coco Plum Inn
A poolside area with lounge chairs, umbrellas, and a pergola.
A bright kitchen with white cabinetry, a white island, wicker pendant lights, and geometric patterned backsplash.
A wooden bench with a cushion and a small table, surrounded by bamboo plants and a wooden deck.
An open door leading to a pool area with a wicker chair and a sofa inside a room with a view of the pool.

20. Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
Old Town Key West, 0.7 mi from Waterfront Playhouse
United States
Henry
£251
includes taxes & fees
12 Oct - 13 Oct
Ella's Cottages - Key West Historic Inns
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
1,000 reviews
View
A tropical outdoor area with palm trees, hanging plants, and string lights.
Douglas House - Adults Only
9.8
Exceptional
552 reviews
View
A modern interior with a staircase, a sofa set, a wooden table, and a television.
Simonton Court Historic Inn & Cottages
9.8
Exceptional
1,003 reviews
View
A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
9.8
Exceptional
1,002 reviews
View
A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.
Alexander's Guesthouse - Adult Exclusive
9.8
Exceptional
171 reviews
View

Top Waterfront Playhouse Hotel Reviews

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"Very cute and clean place to stay"
Angelica 3-night trip
Posted 5 hours ago
Winslow's Bungalows - Key West Historic Inns
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

8/10 Good
"If you like an old historical place to stay, this is it. Great location, big rooms, great atmosphere, free parking (bonus)"
chris 2-night trip
Posted 5 hours ago
Amsterdam's Curry Mansion Inn
Weatherstation Inn

Weatherstation Inn

10/10 Excellent
"We liked how close the Inn was to everything we wanted to do. Very walkable and in a quiet area. Staff was friendly, the breakfast bake goods were great."
Sarah 2-night trip
Posted 6 hours ago
Weatherstation Inn
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

10/10 Excellent
"Fantastic as always!!"
LYNDA 5-night trip
Posted 8 hours ago
The Marker Key West Harbor Resort
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

8/10 Good
"Fantastic location next to the marina, cruise ship docks and shopping. Hotel needs updating but the location more than makes up for that. Lolita’s Restaurant, on hotel property, is fantastic for really breathtaking sunset dining! Our bathroom was dirty when we checked in but the staff were quick to address and correct. The A/C was really loud and couldn’t quite keep up. Overall very nice resort and great location. Would gladly stay here again."
Michael 2-night trip
Posted 8 hours ago
Opal Key Resort & Marina, Key West
The Marquesa Hotel

The Marquesa Hotel

10/10 Excellent
"We had such a good time; it was the highlight of our trip. We would have liked to be able to swim later than sunset..."
Jeffrey 3-night trip
Posted 1 day ago
The Marquesa Hotel
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

10/10 Excellent
"Had an excellent time. Absolutely beautiful hotel and amazing staff!"
Kertpal 1-night trip
Posted 3 days ago
Hyatt Vacation Club at Sunset Harbor, Key West
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Wonderful place at a great location"
THOMAS 2-night trip
Posted 5 days ago
La Concha Key West, Autograph Collection
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 9 days ago
Heart of Downtown Key West Cottage With Off-Street Parking

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)
This interactive museum is home to unbelievable relics pulled from the bottom of the sea and a watchtower with views across the Gulf of Mexico.
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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)
Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.
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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 find the perfect gifts to bring home at Mallory Dock during your trip 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 studying the exhibits at 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)
Visit a house named after famed naturalist John James Audubon. Learn the history of why the house came to be here.
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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)
Key West’s definitive maritime museum is an important attraction for anyone wanting to learn about early life in the Keys. Hear stories of slavery, pirates and fishermen.
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Roy John-Karl Gallery

You can spend time browsing the exhibits at Roy John-Karl Gallery in Key West. Stroll along the area's seaside or simply savour its lively bars.
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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, take a look at the 1400 hotels and other accommodation options you'll find within a mile.
Where is the best place 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 traveller 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 find near Waterfront Playhouse?
Expedia has 1400 hotels and other accommodation options 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 room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might be able to still cancel and be given a refund within a 24-hour period of booking. Add your dates and click on "Search", then use the filter option "fully refundable" to view the best deals near Waterfront Playhouse.
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 theatre.