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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, 1.3 km from Waterfront Playhouse
United States
John
CA $294
CA $331 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.
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.
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
CA $190
CA $236 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 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.
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
Corey
CA $425
CA $574 total
includes taxes & fees
Oct 11 - Oct 12
H2O Suites - 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 wooden ceiling, white sofas, a patterned armchair, a glass coffee table, and a large painting on the wall.
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.

4. Alexander's Guesthouse - Adult Exclusive

Alexander's Guesthouse - Adult Exclusive
Old Town Key West, 1.2 km from Waterfront Playhouse
United States
Nestor
CA $309
CA $406 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
CA $320
CA $360 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 spacious bedroom with a large bed, a sitting area with a sofa and armchairs, and a dining area with a table and chairs.
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.

6. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 1.3 km from Waterfront Playhouse
United States
John
CA $270
CA $304 total
includes taxes & fees
Oct 6 - Oct 7
The Conch House Heritage Inn
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
A bar area with a counter, chairs, and a clock.
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.

7. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Forrest
CA $319
CA $359 total
includes taxes & fees
Oct 6 - Oct 7
The Gardens Hotel
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.

8. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.8 km from Waterfront Playhouse
United States
Osvaldo
CA $262
CA $295 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 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 swimming pool with a mural of a dolphin and a butterfly, surrounded by lounge chairs and palm trees.

9. Duval House

Duval House
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Christopher
CA $130
CA $177 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 sign for Santa Maria Resort surrounded by lush greenery 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.

10. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Anthony
CA $396
CA $542 total
includes taxes & fees
Oct 28 - Oct 29
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 poolside area with lounge chairs, a covered seating area, and a small pool.
A room with a yellow armchair, a glass coffee table, and a view of a wooden deck and tropical plants.

11. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 1.3 km from Waterfront Playhouse
United Kingdom
Adam
CA $328
CA $368 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 gated entrance with a blue metal gate, palm trees, and a building with a red roof in the background.
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.

12. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
yessy
CA $199
CA $404 total
includes taxes & fees
Oct 26 - Oct 27
Southernmost House - Adult Exclusive
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 bedroom with a bed, two bedside lamps, a ceiling fan, and a view of a balcony with plants.
A two-story house with a white exterior, a green roof, and a staircase leading to the upper floor.

13. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.9 km from Waterfront Playhouse
United States
Anthony
CA $231
CA $260 total
includes taxes & fees
Oct 6 - Oct 7
Westwinds Inn
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 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.

14. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
Tricia
CA $208
CA $234 total
includes taxes & fees
Oct 5 - Oct 6
Ambrosia Key West
A gated entrance with lush green foliage and a white picket fence.
A swimming pool with lounge chairs, a covered deck, and a view of lush greenery.
A white colonial-style building with a balcony, surrounded by palm trees 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.

15. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.8 km from Waterfront Playhouse
United States
Riley
CA $202
CA $227 total
includes taxes & fees
Oct 12 - Oct 13
Coco Plum Inn
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 pathway leading to a building with a white facade, surrounded by lush greenery and palm trees.
A two-story building with a white picket fence, palm trees, and a clear blue sky.

16. Weatherstation Inn

Weatherstation Inn
Truman Annex, 0.5 km from Waterfront Playhouse
United States
Svetlana
CA $255
CA $287 total
includes taxes & fees
Oct 5 - Oct 6
Weatherstation Inn
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 room with a bed, a desk, a chair, a lamp, a painting of a boat on water, and a view of the sea.

17. Alexander Palms Court

Alexander Palms Court
Casa Marina, 1.8 km from Waterfront Playhouse
United States
Andrew
CA $170
CA $191 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.
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 two-story yellow house with a porch, white railings, and green shutters.
A hotel with a pool, bicycles, and lush greenery.

18. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 1.4 km from Waterfront Playhouse
United States
sam
CA $153
CA $268 total
includes taxes & fees
Oct 5 - Oct 6
Silver Palms Inn & Historic Homes
A poolside area with lounge chairs, umbrellas, and a pergola.
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.
A living room with a spiral staircase, a sofa, a chair, a coffee table, and a view of an outdoor seating area.

19. 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
CA $328
CA $441 total
includes taxes & fees
Oct 5 - Oct 6
Ella's Cottages - Key West Historic Inns
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 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.

20. Tropical Inn

Tropical Inn
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Natalie
CA $217
CA $280 total
includes taxes & fees
Oct 6 - Oct 7
Tropical Inn
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
1,001 reviews
View
A tropical outdoor area with palm trees, hanging plants, and string lights.
Douglas House - Adults Only
9.8
Exceptional
546 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

Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Great location and clean room! Easy to walk to restaurants, bars, and Mallory Square. The Chart Room Cocktail Lounge in hotel was also a fun late night stop."
Jennifer 2-night trip
Posted 15 hours ago
Pier House Resort & Spa
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 18 hours 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 2 days ago
The Marker Key West Harbor Resort
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 days ago
Heart of Downtown Key West Cottage With Off-Street Parking
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 3 days ago
Heron House - Adult Only
The Penthouse at Custom House Inn | New!

The Penthouse at Custom House Inn | New!

10/10 Excellent
"Nice week in Key West"
Anonymous traveller 3-night trip
Posted 2 weeks ago
The Penthouse at Custom House Inn | New!
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
Harbor House Penthouse- B

Harbor House Penthouse- B

10/10 Excellent
"Great location"
Megan M. 3-night trip
Posted 1 month ago
Harbor House Penthouse- B

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.
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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.
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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