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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 swimming pool with lounge chairs, surrounded by palm trees and greenery.
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
Teresa
CA $327
CA $368 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.
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.
A hotel room with a bed, a wooden floor, a seating area with a table and chairs, and a view of greenery outside.

2. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 1.4 km from Waterfront Playhouse
United States
Maricela
CA $222
CA $275 total
includes taxes & fees
Oct 27 - Oct 28
Douglas House - Adults Only
A modern outdoor area with a pool, lounge chairs, and a bar area.
An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.
A modern hotel room with a bed, sofa, coffee table, and artwork.
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
Kimberly
CA $464
CA $617 total
includes taxes & fees
Oct 28 - Oct 29
H2O Suites - Adults Only
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
A couple walking along a poolside pathway surrounded by lush greenery.
A bedroom with a large bed, a television on a dresser, and a view of the outdoors through a sliding door.
A bar area with a counter, chairs, and a clock.

4. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Gisele
CA $379
CA $427 total
includes taxes & fees
Oct 27 - Oct 28
The Gardens Hotel
A pool area with lounge chairs and a table, surrounded by palm trees.
A neon sign for Orchid Key Inn with a 'VACANCY' sign below it.
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 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
ben
CA $299
CA $336 total
includes taxes & fees
Oct 27 - Oct 28
Orchid Key Inn - Adults Only
A gated entrance to Villas Key West with a brick pathway leading to the gate.
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.
A house with a porch, a table, and a door with a number '6'.

6. Key West Villas

Key West Villas
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Margaret
CA $430
CA $484 total
includes taxes & fees
Nov 18 - Nov 19
Key West Villas
A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.
A pool area with lounge chairs, a pool, and a building with a balcony and outdoor seating.
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.

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 $342
CA $443 total
includes taxes & fees
Oct 28 - Oct 29
Alexander's Guesthouse - Adult Exclusive
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.

8. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
Josh
CA $605
CA $760 total
includes taxes & fees
Oct 26 - Oct 27
The Marquesa Hotel
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 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.

9. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 1.3 km from Waterfront Playhouse
United States
Jennifer
CA $403
CA $453 total
includes taxes & fees
Oct 27 - Oct 28
The Conch House Heritage Inn
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.
A pool area with lounge chairs and a wooden building with balconies.
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.

10. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.8 km from Waterfront Playhouse
United States
Elise
CA $265
CA $298 total
includes taxes & fees
Oct 26 - Oct 27
Island City House Hotel
A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.
A two-story building with a white picket fence, a mailbox, and a small tree in front.
A hallway with a white door, a wooden bench, a blue sofa, and a staircase with a white railing.
A lush garden with a variety of tropical plants and a paved walkway.

11. Duval House

Duval House
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Cathrine
CA $224
CA $283 total
includes taxes & fees
Oct 25 - Oct 26
Duval House
A pool area with lounge chairs and palm trees.
A sign for Santa Maria Resort surrounded by lush greenery and palm trees.
A reception area with a modern design, featuring a reception desk, a sofa, and a potted plant.
A neatly made bed with patterned pillows, a bedside table with a bottle and glasses, and a window with orchids.

12. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Anthony
CA $422
CA $570 total
includes taxes & fees
Oct 26 - Oct 27
Santa Maria Suites
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 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.

13. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
RICHARD
CA $235
CA $265 total
includes taxes & fees
Oct 25 - Oct 26
Ambrosia Key West
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 breakfast table with a variety of food items, including fruits, pastries, and a coffee mug.

14. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.9 km from Waterfront Playhouse
United States
Anthony
CA $229
CA $257 total
includes taxes & fees
Oct 25 - Oct 26
Westwinds Inn
A large, ornate hotel with a pool, palm trees, and a view of the ocean.
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.
A balcony with white railings and a table, overlooking a beach with palm trees and a clear blue sky.

15. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Amy
CA $253
CA $463 total
includes taxes & fees
Oct 27 - Oct 28
Southernmost House - Adult Exclusive
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 hotel room with a large bed, two bedside tables, a ceiling fan, and two framed pictures on the wall.
A swimming pool with lounge chairs, a covered deck, and a view of lush greenery.

16. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.8 km from Waterfront Playhouse
United States
August
CA $283
CA $318 total
includes taxes & fees
Oct 27 - Oct 28
Coco Plum Inn
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
The entrance to Silver Palms Inn with a reception desk, a seating area, and a glass door.
A hotel with a pool, bicycles, and lush greenery.
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
sam
CA $126
CA $237 total
includes taxes & fees
Oct 25 - Oct 26
Silver Palms Inn & Historic Homes
A room with a door featuring horizontal blinds, a visible outdoor view through the window, and a patterned carpet.
A pool area with a circular pool, lounge chairs, and a gazebo.
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 garden with a stone pathway, a wooden fence, and various tropical plants.

18. Alexander Palms Court

Alexander Palms Court
Casa Marina, 1.8 km from Waterfront Playhouse
United States
Brenda
CA $253
CA $284 total
includes taxes & fees
Oct 21 - Oct 22
Alexander Palms Court
A hotel with a covered entrance, multiple balconies, and palm trees.
A waterfront hotel with multiple balconies, a dock, and boats.
A restaurant interior with wooden beams, a bar area, and a colorful ceiling mural.
A room with a stone wall, a wooden bench, a cactus, and a framed painting.

19. Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
Old Town Key West, 0.1 km from Waterfront Playhouse
United States
Ann
CA $365
CA $467 total
includes taxes & fees
Oct 26 - Oct 27
Opal Key Resort & Marina, Key West
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.
A living room with a spiral staircase, a sofa, a chair, a coffee table, and a view of an outdoor seating area.
An open door leading to a pool area with a wicker chair and a sofa inside a room with a view of the pool.

20. 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
Henry
CA $307
CA $417 total
includes taxes & fees
Oct 29 - Oct 30
Ella's Cottages - Key West Historic Inns
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 tropical outdoor area with palm trees, hanging plants, and string lights.
Douglas House - Adults Only
9.8
Exceptional
562 reviews
View
A modern outdoor area with a pool, lounge chairs, and a bar area.
H2O Suites - Adults Only
9.8
Exceptional
669 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
1,006 reviews
View
A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
9.8
Exceptional
1,001 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 $422
CA $589 total
includes taxes & fees
Oct 26 - Oct 27
Ocean Key Resort - A Noble House Resort
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.
A view through a white-framed window with a decorative white fence, leading to a tiled patio area with a round table.
A resort with a beach, a dock, and a water view.

Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
CA $256
CA $387 total
includes taxes & fees
Oct 25 - Oct 26
Pier House Resort & Spa
A white building with green shutters and a white picket fence.
A hotel room with a large bed, a sitting area, and multiple bookshelves filled with books.
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 $271
CA $376 total
includes taxes & fees
Oct 25 - Oct 26
Ridley House - Key West Historic Inns
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 balcony with a view of the ocean, a table, chairs, and a railing.
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 $330
CA $470 total
includes taxes & fees
Oct 25 - Oct 26
Hyatt Centric Key West Resort and Spa
A large, white, two-story building with a balcony and a sign reading "The Marker Resort."
A marina with various boats docked, including a green and white boat named 'Jolly Roger'.
A covered outdoor area with a pool, palm trees, and lounge chairs.
A tropical setting with palm trees and a building with a white facade and dark roof.

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Key West Historic District
CA $266
CA $388 total
includes taxes & fees
Oct 25 - Oct 26
The Marker Key West Harbor Resort
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.
A living room with a spiral staircase, a sofa, a chair, a coffee table, and a view of an outdoor seating area.
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 $307
CA $417 total
includes taxes & fees
Oct 29 - Oct 30
Ella's Cottages - Key West Historic Inns
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with a white facade.
A table with chairs in a lush indoor garden setting.
A modern kitchen with a wooden counter, two stools, a wicker chair, and a hanging light fixture.
A pathway leading to a white gazebo with a view of a lighthouse in the distance.

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
CA $282
CA $389 total
includes taxes & fees
Oct 25 - Oct 26
Lighthouse Hotel - Key West Historic Inns
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.
A pool area with lounge chairs and a wooden building with balconies.
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.

Island City House Hotel

Island City House Hotel
Key West Historic District
CA $265
CA $298 total
includes taxes & fees
Oct 26 - Oct 27
Island City House Hotel

Top Waterfront Playhouse Hotel Reviews

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

10/10 Excellent
"Great location and the ocean facing suite was amazing and very clean. Staff was super friendly. We really enjoyed the in-room breakfast offering as well. The pool in particular was great for an afternoon dip and to watch the sunset. We would absolutely come back!"
Martine 5-night trip
Posted 6 hours ago
Ocean Key Resort - A Noble House Resort
Weatherstation Inn

Weatherstation Inn

10/10 Excellent
"This place is excellent. Very quiet. Nice amenities. Close to old town"
Chad 2-night trip
Posted 7 hours ago
Weatherstation Inn
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

10/10 Excellent
"Excellent all around."
Harvey 3-night trip
Posted 15 hours ago
Hyatt Centric Key West Resort and Spa
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

10/10 Excellent
"The Marker Resort. This place is one of the best places to stay in Key West! Great Location to everything we like to do. One of the swimming pools were closed for the week but highly recommend this resort."
Bob 4-night trip
Posted 22 hours ago
The Marker Key West Harbor Resort
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"Great hotel will definitely stay again"
Ann 2-night trip
Posted 1 day ago
Opal Key Resort & Marina, Key West
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Everything was exceptional at Pier House. Breakfast by the water every morning great music and drinks from the bar, well maintained property and beach! Staff went out of their way and were very kimd. Our room with lanai was fantastic! Thank you Pier House!"
Steven 3-night trip
Posted 2 days ago
Pier House Resort & Spa
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

10/10 Excellent
"The property manager was very helpful and the breakfast organizer (Sonya) provided the very best display and variety of food with warm greeting."
Carolyn 4-night trip
Posted 2 days ago
Ridley House - Key West Historic Inns
Heron House - Adult Only

Heron House - Adult Only

10/10 Excellent
"The property was wonderfully located, clean, and beautiful. Highly recommend."
Lance 3-night trip
Posted 3 days ago
Heron House - Adult Only
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Loved our stay at La Concha. Staff was excellent and constantly focused on our comfort and enjoyment. Upon arrival (kind of late), we were unsure if the bar was still serving food. Once staff became aware that we wanted food, they did everything they could think of to ensure we got what we needed. Top-notch customer service! The location of the hotel could not be beat, for our purposes. Easy to explore many different areas that we wanted to see…particularly Old Town and the seaport district. Everything is very walkable; however, if you have people in your party who cannot walk much distance, it is very easy to rent a golf cart to haul them around. An extremely enjoyable trip, made all the better by the staff and quality of La Concha."
LEE 7-night trip
Posted 4 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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