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Oct 13 - Oct 14
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Oct 14 - Oct 15
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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 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.

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 $397
CA $447 total
includes taxes & fees
Oct 27 - Oct 28
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 wooden deck with lush greenery and a pool area.
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
CA $225
CA $278 total
includes taxes & fees
Oct 15 - Oct 16
Douglas House - 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 courtyard with two green lounge chairs, a palm tree, and a building with a white facade and lattice window design.
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
William
CA $284
CA $320 total
includes taxes & fees
Oct 14 - Oct 15
Simonton Court Historic Inn & Cottages
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.

4. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
United States
ben
CA $363
CA $408 total
includes taxes & fees
Oct 27 - Oct 28
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 colonial-style building with a porch, surrounded by lush tropical vegetation.
A bar area with a counter, chairs, and a clock.

5. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Gisele
CA $427
CA $480 total
includes taxes & fees
Oct 28 - Oct 29
The Gardens Hotel
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 living room with a sofa, a glass coffee table, a TV, and a painting on the wall.
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
CA $408
CA $459 total
includes taxes & fees
Oct 25 - Oct 26
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 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.

7. Alexander's Guesthouse - Adult Exclusive

Alexander's Guesthouse - Adult Exclusive
Old Town Key West, 1.2 km from Waterfront Playhouse
United States
Nestor
CA $320
CA $419 total
includes taxes & fees
Oct 15 - Oct 16
Alexander's Guesthouse - Adult Exclusive
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 hotel room with two beds, a ceiling fan, a large window with a view of palm trees, and a painting on the wall.
A covered porch with white wicker furniture and a blue floor, surrounded by lush tropical plants.

8. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
Anna
CA $513
CA $657 total
includes taxes & fees
Oct 15 - Oct 16
The Marquesa Hotel
A gated entrance to Villas Key West with a brick pathway leading to the gate.
A covered porch with wicker furniture, a large potted plant, and a sign for Villas Key West.
A covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.
A swimming pool with a hot tub, surrounded by a wooden deck and lush greenery.

9. Key West Villas

Key West Villas
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Margaret
CA $371
CA $417 total
includes taxes & fees
Oct 15 - Oct 16
Key West Villas
A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.
A row of blue bicycles parked under a tree, with a white fence and a building in the background.
A covered outdoor area with a wooden staircase, seating, and potted plants.
A two-story building with a porch, a sign reading "The Grand Guesthouse," and a purple flag.

10. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West, 1.7 km from Waterfront Playhouse
CA $210
CA $272 total
includes taxes & fees
Oct 15 - Oct 16
The Grand Guesthouse
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.

11. Duval House

Duval House
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Cliff
CA $256
CA $319 total
includes taxes & fees
Oct 26 - Oct 27
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 covered walkway with a wooden ceiling, white railings, and a brick path.
A pool area with lounge chairs and a wooden building with balconies.

12. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.8 km from Waterfront Playhouse
United States
Osvaldo
CA $266
CA $299 total
includes taxes & fees
Oct 15 - Oct 16
Island City House Hotel
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.

13. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Anthony
CA $427
CA $577 total
includes taxes & fees
Oct 14 - Oct 15
Santa Maria Suites
A room with a bed, a ceiling fan, and a window with blinds.
A room with a yellow armchair, a glass coffee table, and a view of a wooden deck and tropical plants.
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.

14. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 1.3 km from Waterfront Playhouse
United Kingdom
Adam
CA $330
CA $371 total
includes taxes & fees
Oct 15 - Oct 16
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 grand staircase with ornate railings and a chandelier.

15. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Amy
CA $199
CA $405 total
includes taxes & fees
Oct 28 - Oct 29
Southernmost House - Adult Exclusive
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.

16. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.9 km from Waterfront Playhouse
CA $231
CA $260 total
includes taxes & fees
Oct 25 - Oct 26
Westwinds Inn
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 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.

17. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 1.4 km from Waterfront Playhouse
United States
sam
CA $127
CA $239 total
includes taxes & fees
Oct 25 - Oct 26
Silver Palms Inn & Historic Homes
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 wicker outdoor seating area with two chairs and a table, surrounded by lush tropical foliage.
A cozy living room with a wooden ceiling, a sofa set, two side tables with lamps, and framed artwork on the wall.

18. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.7 km from Waterfront Playhouse
CA $338
CA $380 total
includes taxes & fees
Oct 15 - Oct 16
Ambrosia Key West
A green house with a white porch, a flag, and a sign advertising a property for sale.
A room with a ceiling fan, an air conditioning unit, a window with blinds, a sofa with patterned cushions, a small round table, and a floor lamp.
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.

19. L'Habitation Guest House - Adults Only

L'Habitation Guest House - Adults Only
Historic Seaport, 0.5 km from Waterfront Playhouse
United States
Richard
CA $243
CA $273 total
includes taxes & fees
Oct 28 - Oct 29
L'Habitation Guest House - Adults Only
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.

20. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.8 km from Waterfront Playhouse
United States
Riley
CA $256
CA $289 total
includes taxes & fees
Oct 15 - Oct 16
Coco Plum 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
1,004 reviews
View
A tropical outdoor area with palm trees, hanging plants, and string lights.
Douglas House - Adults Only
9.8
Exceptional
555 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
1,006 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
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
1,008 reviews
View

Hotels recommended for families near Waterfront Playhouse

A pool area with lounge chairs and a cabana.
A hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.
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
CA $448
CA $620 total
includes taxes & fees
Oct 27 - Oct 28
Ocean Key Resort - A Noble House Resort
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
A balcony with a view of the ocean, a sofa, and a massage table.
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
CA $487
CA $648 total
includes taxes & fees
Oct 15 - Oct 16
Pier House Resort & Spa
A hotel with a swimming pool, balconies, and a view of the sea.
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.
A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
CA $344
CA $487 total
includes taxes & fees
Oct 26 - Oct 27
Hyatt Centric Key West Resort and Spa
A white building with green shutters and a white picket fence.
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.
A brick pathway leading to a green door, surrounded by lush tropical plants and a white fence.

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns
Key West Historic District
CA $314
CA $426 total
includes taxes & fees
Oct 15 - Oct 16
Ridley House - Key West Historic Inns
A large, white, two-story building with a balcony and a sign reading "The Marker Resort."
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.
A marina with various boats docked, including a green and white boat named 'Jolly Roger'.

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Key West Historic District
CA $279
CA $404 total
includes taxes & fees
Oct 25 - Oct 26
The Marker Key West Harbor Resort
A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.
A spacious living area with a wooden staircase, a ceiling fan, a TV, and a view of the beach through an open door.
A pool area with lounge chairs and umbrellas, surrounded by buildings with balconies and a clear blue sky.
A spacious living area with a gray sofa, wooden staircase, and a kitchen in the background.

Eden House

Eden House
Key West Historic District
CA $187
CA $235 total
includes taxes & fees
Oct 15 - Oct 16
Eden 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 covered walkway with a wooden ceiling, white railings, and a brick path.
A pool area with lounge chairs and a wooden building with balconies.

Island City House Hotel

Island City House Hotel
Key West Historic District
CA $266
CA $299 total
includes taxes & fees
Oct 15 - Oct 16
Island City House Hotel
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
CA $357
CA $474 total
includes taxes & fees
Oct 15 - Oct 16
Ella's Cottages - Key West Historic Inns

Top Waterfront Playhouse Hotel Reviews

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

10/10 Excellent
"My husband and I loved our stay at Ridley house. The property is beautiful and well maintained and our room was a nice size with a comfortable bed. We were served a breakfast spread every morning with plenty of food choices. The manager Angel was so helpful and knowledgeable, and he asked us every time he saw us if we needed anything. I don't remember the person's name who filled in for him, but she helped us set up rentals and a sandbar sunset cruise. We used the pool every day, to soak up some sun before heading out for the day. Duval street was an easy two blocks away."
Mary 5-night trip
Posted 2 hours ago
Ridley House - Key West Historic Inns
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

8/10 Good
"Great location. Large rooms. Pool area is nice. Only gripes are the limited parking, and the fact that you can’t ever check in before 4pm, even though you can see the room sitting there empty. Also, the 10am checkout in an area known for nightlife is downright criminal."
Edmond 3-night trip
Posted 20 hours ago
Amsterdam's Curry Mansion Inn
Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

10/10 Excellent
"The property is located in an excellent location, walking all restaurants, boats, nightlife. The vibe is island, great pool, good food and the staff is wonderful. Could use some maintenance in the rooms, but it’s pretty good. Overall, it’s a fun place!"
Gregory D 3-night trip
Posted 1 day ago
Ocean Key Resort - A Noble House Resort
The Marquesa Hotel

The Marquesa Hotel

10/10 Excellent
"The staff was friendly and my room was clean , and the hotel was very nice!"
Anna 4-night trip
Posted 1 day ago
The Marquesa Hotel
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

10/10 Excellent
"Nice clean room and close to all the attractions"
Brian 4-night trip
Posted 2 days ago
The Marker Key West Harbor Resort
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"Great location. Walking distance to Anything you’d want to do in Key West. Housekeeping staff very attentive. Valets very friendly and quick to attend. Room was clean spacious and bed comfortable. Restaurant was just OK. Staff there not as friendly and attentive. Pool was ok."
Amy 3-night trip
Posted 2 days ago
Opal Key Resort & Marina, Key West
Weatherstation Inn

Weatherstation Inn

10/10 Excellent
"We liked how close the Inn was to everything we wanted to do. Very walkable and in a quiet area. Staff was friendly, the breakfast bake goods were great."
Sarah 2-night trip
Posted 3 days ago
Weatherstation Inn
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 5 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
"Wonderful place at a great location"
THOMAS 2-night trip
Posted 7 days ago
La Concha Key West, Autograph Collection

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.
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.
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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