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Key West Hotel Guide - Waterfront Playhouse hotels in Key West, United States of America.

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Check prices for these dates

Tonight
27 Aug - 28 Aug
Tomorrow
28 Aug - 29 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

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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 breakfast table with various food items and drinks, a pool in the background, and a tiled wall.
A reception area with a wooden herringbone wall, teal chairs, a wooden bench, and two framed sunset paintings.
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
Michelle
€141
includes taxes & fees
1 Sept - 2 Sept
Almond Tree Inn Hotel - Adults Only
A pool area with lounge chairs and a table, surrounded by palm trees.
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.
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.

2. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
United States
Nicholas
€141
includes taxes & fees
31 Aug - 1 Sept
Orchid Key Inn - 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 pathway flanked by lush green foliage leading to a gated entrance.
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, 0.5 km from Waterfront Playhouse
United States
Robin
€144
includes taxes & fees
30 Aug - 31 Aug
Simonton Court Historic Inn & Cottages
A room with a bed, a ceiling fan, and a window with blinds.
A poolside area with lounge chairs, a covered seating area, and a small pool.
A cozy outdoor seating area with a wooden bench and a table, surrounded by potted plants and a coffee and tea sign.
A spacious kitchen with wooden cabinets, a granite countertop, and a ceiling fan.

4. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 1.3 km from Waterfront Playhouse
United States
Johnny
€190
includes taxes & fees
1 Sept - 2 Sept
The Mermaid & Alligator
A covered porch with white railings, a ceiling fan, and a table with chairs.
A bedroom with a wooden headboard, a bed with white bedding, a blue patterned throw, and a view through a window with blinds.
A tree with green foliage and red flowers.
A room with a wooden floor, a sofa with patterned cushions, a table, a chair, a lamp, and a window with blinds.

5. The Porch on Frances Inn

The Porch on Frances Inn
Old Town Key West, 1.2 km from Waterfront Playhouse
United States
Corrynne
€138
includes taxes & fees
1 Sept - 2 Sept
The Porch on Frances Inn
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 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.

6. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Brian
€194
includes taxes & fees
31 Aug - 1 Sept
The Gardens Hotel
A two-story house with a covered porch, a brick pathway, and a large tree.
A hotel room with two beds, a ceiling fan, a large window with a view of palm trees, and a painting on the wall.
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
Darrell
€266
includes taxes & fees
13 Sept - 14 Sept
The Marquesa Hotel
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 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.

8. Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Old Town Key West, 1.2 km from Waterfront Playhouse
United States
RAFAEL
€145
includes taxes & fees
31 Aug - 1 Sept
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
A porch with a white railing, a bench, and a flag.
A two-story white house with green shutters, a wooden door, and a white picket fence.
A pool area with lounge chairs and a dining table, surrounded by palm trees and a house with a porch.
A spacious bedroom with a large bed, a sitting area with a sofa and armchairs, and a dining area with a table and chairs.

9. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 1.3 km from Waterfront Playhouse
United States
John
€183
includes taxes & fees
2 Sept - 3 Sept
The Conch House Heritage Inn
A modern outdoor area with a pool, lounge chairs, and a bar area.
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.
A modern hotel room with a bed, sofa, coffee table, and artwork.
An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.

10. H2O Suites - Adults Only

H2O Suites - Adults Only
Uptown - Upper Duval, 1.6 km from Waterfront Playhouse
United States
Shermeka
€327
includes taxes & fees
8 Sept - 9 Sept
H2O Suites - Adults Only
A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.
A hallway with a white door, a wooden bench, a blue sofa, and a staircase with a white railing.
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.

11. Duval House

Duval House
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Melissa
€114
includes taxes & fees
31 Aug - 1 Sept
Duval House
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.
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 garden with a pond, rocks, and various plants.
A covered walkway with a wooden ceiling, white railings, and a brick path.

12. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.8 km from Waterfront Playhouse
United States
Paul
€152
includes taxes & fees
16 Sept - 17 Sept
Island City House Hotel
A bedroom with a four-poster bed, a wooden desk, wicker chairs, and a view of the outdoors.
A cozy room with a wicker chair, a small table with a bottle and glasses, and a view of a yellow room through an open door.
A pool area with lounge chairs and candles, surrounded by palm trees and a building in the background.
A wooden door with glass panels, leading to an interior space with furniture and plants.

13. Tropical Inn

Tropical Inn
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Joel
€146
includes taxes & fees
1 Sept - 2 Sept
Tropical Inn
A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.
A two-story building with a porch, a sign reading "The Grand Guesthouse," and a purple flag.
A covered outdoor area with a wooden staircase, seating, and potted plants.
A bedroom with a bed, nightstand, lamp, air conditioning unit, and a no smoking sign.

14. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West, 1.7 km from Waterfront Playhouse
United States
Travis
€180
includes taxes & fees
1 Sept - 2 Sept
The Grand Guesthouse
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.

15. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
June Young
€327
includes taxes & fees
8 Sept - 9 Sept
Santa Maria Suites
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.

16. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 1.4 km from Waterfront Playhouse
United Kingdom
Dylan
€125
includes taxes & fees
8 Sept - 9 Sept
Douglas House - Adults Only
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.
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.

17. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 1.4 km from Waterfront Playhouse
United States
Shawn
€131
includes taxes & fees
31 Aug - 1 Sept
Silver Palms Inn & Historic Homes
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 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.

18. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.9 km from Waterfront Playhouse
United States
Karen
€134
includes taxes & fees
31 Aug - 1 Sept
Westwinds 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 breakfast tray with croissants, orange juice, and coffee on a table by a window with a view of a pool and greenery.
A pathway leading to a building with a white facade, surrounded by lush greenery and palm trees.

19. Weatherstation Inn

Weatherstation Inn
Truman Annex, 0.5 km from Waterfront Playhouse
United States
Svetlana
€172
includes taxes & fees
8 Sept - 9 Sept
Weatherstation Inn
A rectangular pool with a white deck, surrounded by lush greenery and a gazebo.
A spacious living room with a high ceiling, a ceiling fan, a large painting, a sofa, a coffee table, and a dining area with a table and chairs.
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.

20. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.7 km from Waterfront Playhouse
United Kingdom
Kate
€182
includes taxes & fees
8 Sept - 9 Sept
Ambrosia Key West
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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
1,024 reviews
View
A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
9.8
Exceptional
1,021 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
1,000 reviews
View
A room with a bed, a ceiling fan, and a window with blinds.
The Mermaid & Alligator
9.8
Exceptional
314 reviews
View
A covered porch with white railings, a ceiling fan, and a table with chairs.
The Porch on Frances Inn
9.8
Exceptional
138 reviews
View

Top Waterfront Playhouse Hotel Reviews

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Beautiful updated hotel, loved the bar and the lobby . Our room was perfect after we moved to the 6th floor . The first room was not great . We liked the newer section much better . Loved the bikes and the location. Elevators need to be updated and they need to add another one . Would stay here again ."
lisa 4-night trip
Posted 10 hours ago
La Concha Key West, Autograph Collection
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

10/10 Excellent
"This is our second time staying at The Marker and we will definitely be back! It is convenient to everything Key West has to offer. The staff goes above and beyond to accommodate whatever you need and we couldn't be happier with our stay!"
Emily 5-night trip
Posted 19 hours ago
The Marker Key West Harbor Resort
Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

10/10 Excellent
"Everything was top notch!! Entire staff was amazing!!"
Michael 6-night trip
Posted 1 day ago
Ocean Key Resort - A Noble House Resort
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

10/10 Excellent
"Location was nice and close to the activities we wanted to do."
Stacey 1-night trip
Posted 2 days ago
Hyatt Vacation Club at Sunset Harbor, Key West
Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages

10/10 Excellent
"."
Calita 3-night trip
Posted 2 days ago
Simonton Court Historic Inn & Cottages
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

8/10 Good
"Inside of room was very nice, no view at all, I mean ground level and just bushes. Love the pool, drinks are not cheap. Free 2 hours on bikes was very enjoyable. Always seems to be something being repaired, drilling. Our Ac had to be replaced after first night. A lot of noise, up by about 330am. But, give em credit, they had it replaced within 2-3 hours of me going to office! Very good location. Have stayed at this place probably 8-10 times, one of my favorites."
Dale 4-night trip
Posted 2 days ago
Hyatt Centric Key West Resort and Spa
Weatherstation Inn

Weatherstation Inn

10/10 Excellent
"Great location, clean property. Continental breakfast was a plus!"
Donna 5-night trip
Posted 3 days ago
Weatherstation Inn
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

10/10 Excellent
"We had a really lovely one night stay"
Vicky 1-night trip
Posted 6 days ago
Amsterdam's Curry Mansion Inn
The Key West Hotel

The Key West Hotel

10/10 Excellent
"Great place to stay - highly recommend."
Preston 2-night trip
Posted 7 days ago
The Key West Hotel

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.
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, take a look at the 1405 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 Ocean Key Resort - A Noble House Resort.
How many hotels will I find near Waterfront Playhouse?
Expedia has 1405 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?
Key West Shipwreck Museum, Mel Fisher Maritime Museum and Harry S. Truman Little White House feature a variety of fascinating exhibits to see while you're in town. Sights like Ernest Hemingway Home and Museum, Key West Lighthouse and Keeper's Quarters Museum and Fort Zachary Taylor Historic State Park 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.