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Check prices for these dates

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 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 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.
A building with a sign reading "ALMOND Frog & Toad Inn" and a "VACANCY" sign below it.

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 897
SAR 1,010 total
includes taxes & fees
25 Oct - 26 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 hotel room with a bed, a wooden floor, a seating area with a table and chairs, and a view of greenery outside.
An outdoor patio with a table and chairs, surrounded by lush greenery and string lights.

2. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 1.4 km from Waterfront Playhouse
United States
Maricela
SAR 591
SAR 731 total
includes taxes & fees
27 Oct - 28 Oct
Douglas House - Adults Only
A pool area with lounge chairs and a table, surrounded by palm trees.
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.
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.

3. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
United States
ben
SAR 926
SAR 1,041 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 couple walking along a poolside pathway surrounded by lush greenery.
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 1,009
SAR 1,135 total
includes taxes & fees
27 Oct - 28 Oct
The Gardens Hotel
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 pool area with a clear view of a house in the background, surrounded by palm trees and greenery.
A courtyard with two green lounge chairs, a palm tree, and a building with a white facade and lattice window design.

5. Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
Historic Seaport, 0.5 km from Waterfront Playhouse
United States
William
SAR 559
SAR 629 total
includes taxes & fees
27 Oct - 28 Oct
Simonton Court Historic Inn & Cottages
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.
A covered walkway with a wooden ceiling, white railings, and a brick path.
A garden with a pond, rocks, and various plants.
A pool area with lounge chairs and a wooden building with balconies.

6. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.8 km from Waterfront Playhouse
United States
Elise
SAR 743
SAR 835 total
includes taxes & fees
26 Oct - 27 Oct
Island City House Hotel
A two-story house with a covered porch, a brick pathway, and a large tree.
A poolside area with a swimming pool, a staircase leading to a deck, and a building with multiple windows and balconies.
A restaurant with multiple tables set for dining, a wine bottle, and a glass of wine on the table.
A covered porch with white wicker furniture and a blue floor, surrounded by lush tropical plants.

7. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
Josh
SAR 1,610
SAR 2,022 total
includes taxes & fees
26 Oct - 27 Oct
The Marquesa 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 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.

8. Duval House

Duval House
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Cathrine
SAR 521
SAR 667 total
includes taxes & fees
26 Oct - 27 Oct
Duval House
A pool area with lounge chairs and palm trees.
A modern outdoor seating area with a sofa, chairs, and a small table, surrounded by glass doors and a view of greenery.
A reception area with a modern design, featuring a reception desk, a sofa, and a potted plant.
A sign for Santa Maria Resort surrounded by lush greenery and palm trees.

9. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Anthony
SAR 1,122
SAR 1,515 total
includes taxes & fees
26 Oct - 27 Oct
Santa Maria Suites
A reception area with a curved marble counter, ceiling fans, large windows, and a staircase.
A poolside area with lounge chairs and a clear blue pool surrounded by lush tropical vegetation.
A breakfast table with a variety of food items, including fruits, pastries, and a coffee mug.
A bedroom with a bed, two bedside lamps, a ceiling fan, and a view of a balcony with plants.

10. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.9 km from Waterfront Playhouse
United States
Anthony
SAR 608
SAR 684 total
includes taxes & fees
25 Oct - 26 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 balcony with white railings and a table, overlooking a beach with palm trees and a clear blue sky.
A large, two-story house with a prominent tower and a covered porch.

11. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Amy
SAR 672
SAR 1,231 total
includes taxes & fees
25 Oct - 26 Oct
Southernmost House - Adult Exclusive
A gated entrance with lush green foliage and a white picket fence.
A covered outdoor dining area with white chairs and tables, surrounded by lush greenery and a wooden deck.
A swimming pool with lounge chairs, a covered deck, and a view of lush greenery.
A hotel room with a large bed, two bedside tables, a ceiling fan, and two framed pictures on the wall.

12. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.8 km from Waterfront Playhouse
United States
August
SAR 751
SAR 845 total
includes taxes & fees
25 Oct - 26 Oct
Coco Plum Inn
A wooden deck with wicker furniture and a white railing, surrounded by lush tropical vegetation.
A two-story building with a white picket fence, palm trees, and a clear blue sky.
A pathway leading to a building with a white facade, surrounded by lush greenery and palm trees.
A swimming pool with a white picket fence, surrounded by lounge chairs and potted plants.

13. Weatherstation Inn

Weatherstation Inn
Truman Annex, 0.5 km from Waterfront Playhouse
United States
Robert
SAR 746
SAR 840 total
includes taxes & fees
25 Oct - 26 Oct
Weatherstation Inn
A rectangular pool with a white deck, surrounded by lush greenery and a gazebo.
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.
A wicker outdoor seating area with two chairs and a table, surrounded by lush tropical foliage.

14. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
RICHARD
SAR 816
SAR 918 total
includes taxes & fees
25 Oct - 26 Oct
Ambrosia Key West
A green house with a white porch, a flag, and a sign advertising a property for sale.
A covered porch with wicker furniture, potted plants, and a view of the house.
A bathroom with a vanity, a mirror, and a window with blinds.
A bedroom with a large bed, a sofa, a nightstand, and a painting on the wall.

15. L'Habitation Guest House - Adults Only

L'Habitation Guest House - Adults Only
Historic Seaport, 0.5 km from Waterfront Playhouse
United States
Richard
SAR 638
SAR 718 total
includes taxes & fees
28 Oct - 29 Oct
L'Habitation Guest House - Adults Only
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
A two-story yellow house with a porch, white railings, and green shutters.
The entrance to Silver Palms Inn with a reception desk, a seating area, and a glass door.
The exterior of the Silver Palms Inn with a two-story structure, a green awning over the entrance, and a palm tree to the right.

16. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 1.4 km from Waterfront Playhouse
United States
sam
SAR 334
SAR 629 total
includes taxes & fees
25 Oct - 26 Oct
Silver Palms Inn & Historic Homes
A room with a door featuring horizontal blinds, a visible outdoor view through the window, and a patterned carpet.
A garden with a stone pathway, a wooden fence, and various tropical plants.
A yellow building with a door marked '7'.
A pool area with a circular pool, lounge chairs, and a gazebo.

17. Alexander Palms Court

Alexander Palms Court
Casa Marina, 1.8 km from Waterfront Playhouse
United States
Brenda
SAR 1,212
SAR 1,364 total
includes taxes & fees
25 Oct - 26 Oct
Alexander Palms Court
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.
A bright kitchen with white cabinetry, a white island, wicker pendant lights, and geometric patterned backsplash.
An open door leading to a pool area with a wicker chair and a sofa inside a room with a view of the pool.

18. 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 807
SAR 1,098 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 tropical setting with palm trees and a building with a white facade and dark roof.
A covered outdoor area with a pool, palm trees, and lounge chairs.

19. 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 707
SAR 1,031 total
includes taxes & fees
25 Oct - 26 Oct
The Marker Key West Harbor Resort
A covered porch with white railings, wooden benches, and a hanging light fixture.
A living room with a large mirror, a wicker chair, a television on a wooden cabinet, and a window with a view of palm trees.
A sign for Marrero's Guest Mansion in Key West, FL, by Verdigris Hotels.
A bedroom with a four-poster bed, a wicker chair, a wooden dresser, and a television.

20. Marrero's Guest Mansion

Marrero's Guest Mansion
Downtown Key West, 0.6 km from Waterfront Playhouse
United States
Michael
SAR 1,215
SAR 1,367 total
includes taxes & fees
26 Oct - 27 Oct
Marrero's Guest Mansion
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
1,003 reviews
View
A tropical outdoor area with palm trees, hanging plants, and string lights.
Douglas House - Adults Only
9.8
Exceptional
563 reviews
View
A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
9.8
Exceptional
1,001 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
1,001 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
1,007 reviews
View

Hotels recommended for families near Waterfront Playhouse

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 balcony with a table set for breakfast, overlooking the sea.
A dining area with a glass table, clear glass bottles, a bowl of fruit, and a wicker chair.

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
Key West Historic District
SAR 1,122
SAR 1,566 total
includes taxes & fees
28 Oct - 29 Oct
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 pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.

Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
SAR 682
SAR 1,029 total
includes taxes & fees
25 Oct - 26 Oct
Pier House Resort & Spa
A white building with green shutters and a white picket fence.
A hotel room with a large bed, a sitting area, and multiple bookshelves filled with books.
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.

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns
Key West Historic District
SAR 750
SAR 1,034 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 balcony with a view of the ocean, a table, chairs, and a railing.
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.

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
SAR 878
SAR 1,262 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 tropical setting with palm trees and a building with a white facade and dark roof.
A covered outdoor area with a pool, palm trees, and lounge chairs.

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Key West Historic District
SAR 707
SAR 1,031 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.
A bright kitchen with white cabinetry, a white island, wicker pendant lights, and geometric patterned backsplash.
An open door leading to a pool area with a wicker chair and a sofa inside a room with a view of the pool.

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
Old Town Key West
SAR 807
SAR 1,098 total
includes taxes & fees
25 Oct - 26 Oct
Ella's Cottages - Key West Historic Inns
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 bedroom with a sloped ceiling, a bed, two chairs, a hanging light fixture, and a window with a view of greenery.

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
SAR 750
SAR 1,034 total
includes taxes & fees
25 Oct - 26 Oct
Lighthouse Hotel - Key West Historic Inns
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.
A covered walkway with a wooden ceiling, white railings, and a brick path.
A garden with a pond, rocks, and various plants.
A pool area with lounge chairs and a wooden building with balconies.

Island City House Hotel

Island City House Hotel
Key West Historic District
SAR 743
SAR 835 total
includes taxes & fees
26 Oct - 27 Oct
Island City House Hotel

Top Waterfront Playhouse Hotel Reviews

Weatherstation Inn

Weatherstation Inn

10/10 Excellent
"Location, Everything within walking distance"
Constance 2-night trip
Posted 6 hours ago
Weatherstation Inn
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Close to everything!!"
David S 5-night trip
Posted 8 hours ago
Pier House Resort & Spa
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

10/10 Excellent
"We love staying at The Marker in Key West! The location is perfect, the grounds are beautiful and clean, and the stuff is amazing! This was our 2nd time saying at The Marker and we’ve already got our 3rd trip planned, for our honeymoon!"
Jessica 4-night trip
Posted 15 hours ago
The Marker Key West Harbor Resort
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"We had no issues. Room clean, restaurant good!"
Michael 4-night trip
Posted 18 hours ago
Opal Key Resort & Marina, Key West
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

10/10 Excellent
"The property manager was very helpful and the breakfast organizer (Sonya) provided the very best display and variety of food with warm greeting."
Carolyn 4-night trip
Posted 3 days ago
Ridley House - Key West Historic Inns
Heron House - Adult Only

Heron House - Adult Only

10/10 Excellent
"The property was wonderfully located, clean, and beautiful. Highly recommend."
Lance 3-night trip
Posted 4 days ago
Heron House - Adult Only
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Loved our stay at La Concha. Staff was excellent and constantly focused on our comfort and enjoyment. Upon arrival (kind of late), we were unsure if the bar was still serving food. Once staff became aware that we wanted food, they did everything they could think of to ensure we got what we needed. Top-notch customer service! The location of the hotel could not be beat, for our purposes. Easy to explore many different areas that we wanted to see…particularly Old Town and the seaport district. Everything is very walkable; however, if you have people in your party who cannot walk much distance, it is very easy to rent a golf cart to haul them around. An extremely enjoyable trip, made all the better by the staff and quality of La Concha."
LEE 7-night trip
Posted 5 days ago
La Concha Key West, Autograph Collection
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 13 days ago
Hyatt Vacation Club at Sunset Harbor, Key West
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

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.
See properties
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.
See properties

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.