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Oct 4 - Oct 5
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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 breakfast table with various food items and drinks, a pool in the background, and a tiled wall.
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
John
NT$7,145
NT$8,038 total
includes taxes & fees
Oct 5 - Oct 6
Almond Tree Inn Hotel - Adults Only
A tropical outdoor area with palm trees, hanging plants, and string lights.
An outdoor patio with a table and chairs, surrounded by lush greenery and string lights.
A hotel room with a bed, a wooden floor, a seating area with a table and chairs, and a view of greenery outside.
A wooden deck with lush greenery and a pool area.

2. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 1.4 km from Waterfront Playhouse
United States
Maricela
NT$4,259
NT$5,270 total
includes taxes & fees
Oct 5 - Oct 6
Douglas House - 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.

3. H2O Suites - Adults Only

H2O Suites - Adults Only
Uptown - Upper Duval, 1.6 km from Waterfront Playhouse
United States
Carmen
NT$9,845
NT$13,226 total
includes taxes & fees
Oct 5 - Oct 6
H2O Suites - Adults Only
A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.
A narrow room with a bed, a potted plant, and a window with blinds.
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.

4. Alexander's Guesthouse - Adult Exclusive

Alexander's Guesthouse - Adult Exclusive
Old Town Key West, 1.2 km from Waterfront Playhouse
United States
Nestor
NT$6,906
NT$9,079 total
includes taxes & fees
Oct 6 - Oct 7
Alexander's Guesthouse - Adult Exclusive
A pool area with lounge chairs and a table, surrounded by palm trees.
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 neon sign for Orchid Key Inn with a 'VACANCY' sign below it.
A building with a neon sign that reads "Orchid Key Inn."

5. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
United States
Nicholas
NT$7,145
NT$8,038 total
includes taxes & fees
Oct 5 - Oct 6
Orchid Key Inn - Adults Only
A porch with a white railing, a bench, and a flag.
A pool area with lounge chairs and a dining table, surrounded by palm trees and a house with a porch.
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.

6. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 1.3 km from Waterfront Playhouse
United States
John
NT$6,041
NT$6,796 total
includes taxes & fees
Oct 6 - Oct 7
The Conch House Heritage Inn
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.
A garden with a pond, rocks, and various plants.
A covered walkway with a wooden ceiling, white railings, and a brick path.
A compact kitchen with wooden cabinets, a microwave, stove, and refrigerator. There is a dining area with a table and chairs, and a sofa.

7. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.8 km from Waterfront Playhouse
United States
Osvaldo
NT$5,793
NT$6,518 total
includes taxes & fees
Oct 11 - Oct 12
Island City House 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 hallway with a white door, a wooden bench, a blue sofa, and a staircase with a white railing.
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
Christopher
NT$3,154
NT$4,234 total
includes taxes & fees
Oct 5 - Oct 6
Duval House
A pool area with lounge chairs 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.
A neatly made bed with patterned pillows, a bedside table with a bottle and glasses, and a window with orchids.

9. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Anthony
NT$9,845
NT$13,226 total
includes taxes & fees
Oct 25 - Oct 26
Santa Maria Suites
A room with a bed, a ceiling fan, and a window with blinds.
A spacious kitchen with wooden cabinets, a granite countertop, and a ceiling fan.
A cozy outdoor seating area with a wooden bench and a table, surrounded by potted plants and a coffee and tea sign.
A poolside area with lounge chairs, a covered seating area, and a small pool.

10. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 1.3 km from Waterfront Playhouse
United Kingdom
Adam
NT$7,322
NT$8,238 total
includes taxes & fees
Oct 8 - Oct 9
The Mermaid & Alligator
A large, ornate hotel with a pool, palm trees, and a view of the ocean.
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.
A gated entrance with a blue metal gate, palm trees, and a building with a red roof in the background.

11. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
yessy
NT$4,438
NT$9,025 total
includes taxes & fees
Oct 26 - Oct 27
Southernmost House - Adult Exclusive
A wooden deck with wicker furniture and a white railing, surrounded by lush tropical vegetation.
A breakfast tray with croissants, orange juice, and coffee on a table by a window with a view of a pool and greenery.
A swimming pool with a white picket fence, surrounded by lounge chairs and potted plants.
A pathway leading to a building with a white facade, surrounded by lush greenery and palm trees.

12. Weatherstation Inn

Weatherstation Inn
Truman Annex, 0.5 km from Waterfront Playhouse
United States
Svetlana
NT$5,703
NT$6,416 total
includes taxes & fees
Oct 5 - Oct 6
Weatherstation Inn
A reception area with a curved marble counter, ceiling fans, large windows, and a staircase.
A breakfast table with a variety of food items, including fruits, pastries, and a coffee mug.
A two-story house with a white exterior, a green roof, and a staircase leading to the upper floor.
A bedroom with a bed, two bedside lamps, a ceiling fan, and a view of a balcony with plants.

13. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.9 km from Waterfront Playhouse
United States
Anthony
NT$5,161
NT$5,807 total
includes taxes & fees
Oct 6 - Oct 7
Westwinds Inn
A gated entrance with lush green foliage and a white picket fence.
A white colonial-style building with a balcony, surrounded by palm trees and a white picket fence.
A swimming pool with lounge chairs, a covered deck, and a view of lush greenery.
A covered outdoor dining area with white chairs and tables, surrounded by lush greenery and a wooden deck.

14. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.8 km from Waterfront Playhouse
United States
Riley
NT$4,516
NT$5,081 total
includes taxes & fees
Oct 12 - Oct 13
Coco Plum 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 wicker outdoor seating area with two chairs and a table, surrounded by lush tropical foliage.
A hotel room with a bed, a nightstand, a chair, a small table, and a ceiling fan.

15. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
Tricia
NT$4,660
NT$5,242 total
includes taxes & fees
Oct 5 - Oct 6
Ambrosia Key West
A room with a door featuring horizontal blinds, a visible outdoor view through the window, and a patterned carpet.
A room with a bed, a desk, a chair, a lamp, a painting of a boat on water, and a view of the sea.
A yellow building with a door marked '7'.
A garden with a stone pathway, a wooden fence, and various tropical plants.

16. Alexander Palms Court

Alexander Palms Court
Casa Marina, 1.8 km from Waterfront Playhouse
United States
Andrew
NT$3,799
NT$4,274 total
includes taxes & fees
Oct 5 - Oct 6
Alexander Palms Court
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
A hotel with a pool, bicycles, and lush greenery.
The entrance to Silver Palms Inn with a reception desk, a seating area, and a glass door.
A two-story yellow house with a porch, white railings, and green shutters.

17. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 1.4 km from Waterfront Playhouse
United States
sam
NT$2,839
NT$5,345 total
includes taxes & fees
Oct 7 - Oct 8
Silver Palms Inn & Historic Homes
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.
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 living room with a spiral staircase, a sofa, a chair, a coffee table, and a view of an outdoor seating area.

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
tracy
NT$7,328
NT$9,857 total
includes taxes & fees
Oct 5 - Oct 6
Ella's Cottages - Key West Historic Inns
A covered porch with white railings, wooden benches, and a hanging light fixture.
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.
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.

19. Marrero's Guest Mansion

Marrero's Guest Mansion
Downtown Key West, 0.6 km from Waterfront Playhouse
United States
Michael
NT$10,004
NT$11,255 total
includes taxes & fees
Oct 7 - Oct 8
Marrero's Guest Mansion
A bedroom with a four-poster bed, a wooden desk, wicker chairs, and a view of the outdoors.
A pool area with lounge chairs and candles, surrounded by palm trees and a building in the background.
A breakfast buffet with a variety of fruits, pastries, and beverages on a wooden deck with a view of a lush garden and a pool.
A wooden door with glass panels, leading to an interior space with furniture and plants.

20. Tropical Inn

Tropical Inn
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Natalie
NT$4,850
NT$6,252 total
includes taxes & fees
Oct 5 - Oct 6
Tropical Inn
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
1,001 reviews
View
A tropical outdoor area with palm trees, hanging plants, and string lights.
Douglas House - Adults Only
9.8
Exceptional
547 reviews
View
A modern outdoor area with a pool, lounge chairs, and a bar area.
H2O Suites - Adults Only
9.8
Exceptional
662 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
170 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

Top Waterfront Playhouse Hotel Reviews

Ambrosia Key West

Ambrosia Key West

10/10 Excellent
"Very nice for a getaway . Lovely room . Breakfast nice . Very close to Duval street . Our second time staying and will Stay again ."
Karen 3-night trip
Posted 22 hours ago
Ambrosia Key West
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"The location on Duval is perfect, the hotel is top notch, and the staff can't do enough for you. Everyone from the GM to the housekeeping staff always wish you a good day and ask if there is anything they can do for you no matter how many times they see you. Perfect place to stay in Key West and we will be returning for sure!"
Alan 4-night trip
Posted 1 day ago
La Concha Key West, Autograph Collection
Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

10/10 Excellent
"Staff was very attentive to our needs and the hotel was very clean."
Patrick 2-night trip
Posted 2 days ago
Ocean Key Resort - A Noble House Resort
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

10/10 Excellent
"Clean.helpful staff.good a/c.good location.will definitely stay here again."
GREGORY 4-night trip
Posted 3 days ago
The Marker Key West Harbor Resort
Heron House - Adult Only

Heron House - Adult Only

10/10 Excellent
"I’ve been to Key West many times, the Heron House is by far the best property we have stayed at. Perfect location to walk to Duval, Mallory Square. Great pool, friendly staff."
Erin 3-night trip
Posted 4 days ago
Heron House - Adult Only
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

10/10 Excellent
"Room was great breakfast was plentiful and staff great. Would definitely recommend and stay there again"
Jack 1-night trip
Posted 5 days ago
The Cabana Inn Key West - Adults Only
The Marquesa Hotel

The Marquesa Hotel

10/10 Excellent
"Fabulous room with the most comfortable bed and pillows. Staff were so friendly and helpful. The pool area cosy and welcoming. Oasis of paradise. Overall our stay at this hotel was fabulous. Mark on reception was very welcoming."
sharon 2-night trip
Posted 2 weeks ago
The Marquesa Hotel
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 1 month ago
Ocean Key Resort & Spa

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 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.
See properties
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)
Visit a house named after famed naturalist John James Audubon. Learn the history of why the house came to be here.
See properties
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 during your trip to Key West. Stroll along the area's seaside, or simply savor 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.
See properties

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.

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