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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 swimming pool with lounge chairs, surrounded by palm trees and greenery.
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
John
CA $212
CA $239 total
includes taxes & fees
Sep 15 - Sep 16
Almond Tree Inn Hotel - Adults Only
A modern interior with a staircase, a sofa set, a wooden table, and a television.
A pool area with a clear view of a house in the background, surrounded by palm trees and greenery.
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.

2. Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
Historic Seaport, 0.5 km from Waterfront Playhouse
United States
Robin
CA $262
CA $295 total
includes taxes & fees
Sep 15 - Sep 16
Simonton Court Historic Inn & Cottages
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 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 neon sign for Orchid Key Inn with a 'VACANCY' sign below it.

3. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
United States
Nicholas
CA $206
CA $232 total
includes taxes & fees
Sep 20 - Sep 21
Orchid Key Inn - Adults Only
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.

4. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
LISA
CA $266
CA $378 total
includes taxes & fees
Sep 28 - Sep 29
The Marquesa Hotel
A covered porch with white railings, a ceiling fan, and a table with chairs.
A two-story house with a porch, a large tree, and a fire hydrant.
A bedroom with a wooden headboard, a bed with white bedding, a blue patterned throw, and a view through a window with blinds.
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
Marcos
CA $161
CA $223 total
includes taxes & fees
Sep 15 - Sep 16
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 bar area with a counter, chairs, and a clock.
A bedroom with a large bed, a television on a dresser, and a view of the outdoors through a sliding door.

6. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Robert
CA $233
CA $262 total
includes taxes & fees
Sep 21 - Sep 22
The Gardens Hotel
A modern outdoor area with a pool, lounge chairs, and a bar area.
A modern hotel room with a bed, sofa, coffee table, and artwork.
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.

7. H2O Suites - Adults Only

H2O Suites - Adults Only
Uptown - Upper Duval, 1.6 km from Waterfront Playhouse
United States
Kourosh
CA $348
CA $485 total
includes taxes & fees
Sep 27 - Sep 28
H2O Suites - 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 living room with a sofa, a glass coffee table, a TV, and a painting on the wall.

8. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 1.3 km from Waterfront Playhouse
United States
John
CA $246
CA $277 total
includes taxes & fees
Sep 29 - Sep 30
The Conch House Heritage Inn
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 narrow room with a bed, a potted plant, and a window with blinds.
A spacious living room with a wooden ceiling, white sofas, a patterned armchair, a glass coffee table, and a large painting on the wall.

9. Alexander's Guesthouse - Adult Exclusive

Alexander's Guesthouse - Adult Exclusive
Old Town Key West, 1.2 km from Waterfront Playhouse
United States
Justin
CA $124
CA $191 total
includes taxes & fees
Sep 16 - Sep 17
Alexander's Guesthouse - Adult Exclusive
A bedroom with a four-poster bed, a wooden desk, wicker chairs, and a view of the outdoors.
A wooden door with glass panels, leading to an interior space with furniture and plants.
A pool area with lounge chairs and candles, surrounded by palm trees and a building in the background.
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.

10. Tropical Inn

Tropical Inn
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Anthony
CA $134
CA $185 total
includes taxes & fees
Sep 14 - Sep 15
Tropical 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 compact kitchen with wooden cabinets, a microwave, stove, and refrigerator. There is a dining area with a table and chairs, and a sofa.
A pool area with lounge chairs and a wooden building with balconies.

11. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.8 km from Waterfront Playhouse
United States
Paul
CA $213
CA $240 total
includes taxes & fees
Sep 14 - Sep 15
Island City House Hotel
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.

12. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 1.4 km from Waterfront Playhouse
United States
michael
CA $109
CA $134 total
includes taxes & fees
Sep 15 - Sep 16
Douglas House - 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 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.

13. Duval House

Duval House
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Robert
CA $135
CA $181 total
includes taxes & fees
Sep 16 - Sep 17
Duval House
A gated entrance to Villas Key West with a brick pathway leading to the gate.
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'.
A covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.

14. Key West Villas

Key West Villas
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Margaret
CA $411
CA $462 total
includes taxes & fees
Oct 6 - Oct 7
Key West Villas
A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.
A bedroom with a bed, nightstand, lamp, air conditioning unit, and a no smoking sign.
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.

15. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West, 1.7 km from Waterfront Playhouse
United States
Alissa
CA $156
CA $211 total
includes taxes & fees
Sep 14 - Sep 15
The Grand Guesthouse
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 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.

16. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 1.3 km from Waterfront Playhouse
United States
Johnny
CA $250
CA $281 total
includes taxes & fees
Sep 14 - Sep 15
The Mermaid & Alligator
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 hotel named "Santa Maria" with a prominent illuminated sign, a glass entrance, and a view of the ocean.
A modern outdoor seating area with a sofa, chairs, and a small table, surrounded by glass doors and a view of greenery.

17. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
June Young
CA $387
CA $529 total
includes taxes & fees
Sep 14 - Sep 15
Santa Maria Suites
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 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.

18. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.9 km from Waterfront Playhouse
United States
Tricia
CA $161
CA $181 total
includes taxes & fees
Sep 22 - Sep 23
Westwinds Inn
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
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.
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.

19. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 1.4 km from Waterfront Playhouse
United States
Alexey
CA $111
CA $219 total
includes taxes & fees
Sep 14 - Sep 15
Silver Palms Inn & Historic Homes
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 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.

20. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.7 km from Waterfront Playhouse
United Kingdom
Kate
CA $186
CA $209 total
includes taxes & fees
Sep 27 - Sep 28
Ambrosia Key West
View all properties

Compare popular hotels close to Waterfront Playhouse

Property
Star rating
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
1,002 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 pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
9.8
Exceptional
1,000 reviews
View
A two-story house with a covered porch, a brick pathway, and a large tree.
The Marquesa Hotel
9.8
Exceptional
1,000 reviews
View
A covered porch with white railings, a ceiling fan, and a table with chairs.
The Porch on Frances Inn
9.8
Exceptional
142 reviews
View

Top Waterfront Playhouse Hotel Reviews

Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Best location in Key West. The private beach and service on the beach are the best"
Michael 4-night trip
Posted 6 hours ago
Pier House Resort & Spa
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Property was clean and well maintained. Only negative was the big pool closed to be resurfaced."
Jenine Shanks 5-night trip
Posted 8 hours ago
Southernmost Beach Resort and Guesthouses
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

8/10 Good
"No fresh coffee at a Resort Hotel is preposterous. A select few of the staff choose to be rude to patrons, which is odd as most are great."
Michael 6-night trip
Posted 1 day ago
Opal Key Resort & Marina, Key West
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

10/10 Excellent
"A"
Allison 2-night trip
Posted 2 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
"Love the history of La Concha, the vibe, bar, size and the location, almost mid-way on Duval Street, the hub of activity. It’s also one of the stops on the “hop-on hop-off “(every 30min) Old Town Trolley Key West Tours, which is a really big deal. There are no doubt other excellent properties in Key West, but La Concha was a great fit for me. I will definitely stay there on my next trip to the island."
Bonnie Gayle 5-night trip
Posted 2 days ago
La Concha Key West, Autograph Collection
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 3 days ago
Ocean Key Resort & Spa
Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages

10/10 Excellent
"The staff was very friendly and helpful. The lady working the breakfast was amazing! She had a wonderful attitude and smiled as she engaged us. Great location!"
Tim 4-night trip
Posted 4 days ago
Simonton Court Historic Inn & Cottages
Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

10/10 Excellent
"Great staff nice property"
Alidad 2-night trip
Posted 5 days ago
Ocean Key Resort - A Noble House Resort
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

10/10 Excellent
"Loved the stay. Definitely will be back"
Kelli 4-night trip
Posted 5 days ago
Hyatt Centric Key West Resort and 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.
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)
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.
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.
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.
See properties
A room with a harp, a round table with chairs, and a view of greenery outside.

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.
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.
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 1404 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 Ocean Key Resort - A Noble House Resort.
How many hotels will I be able to find near Waterfront Playhouse?
Expedia has 1404 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.
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 theater.

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