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Check prices for these dates

Tonight
20 Oct - 21 Oct
Tomorrow
21 Oct - 22 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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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 breakfast table with various food items and drinks, a pool in the background, and a tiled wall.

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
฿7,783
฿8,756 total
includes taxes & fees
27 Oct - 28 Oct
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 large, two-story building with a balcony, surrounded by dense tropical foliage.
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
฿5,286
฿6,541 total
includes taxes & fees
27 Oct - 28 Oct
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 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.

3. H2O Suites - Adults Only

H2O Suites - Adults Only
Uptown - Upper Duval, 1.6 km from Waterfront Playhouse
United States
Kimberly
฿10,459
฿14,023 total
includes taxes & fees
28 Oct - 29 Oct
H2O Suites - Adults Only
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 building with a neon sign that reads "Orchid Key Inn."
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.

4. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
United States
ben
฿7,113
฿8,002 total
includes taxes & fees
27 Oct - 28 Oct
Orchid Key Inn - Adults Only
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 house with a porch, a table, and a door with a number '6'.
A swimming pool with a hot tub, surrounded by a wooden deck and lush greenery.

5. Key West Villas

Key West Villas
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Margaret
฿10,247
฿11,528 total
includes taxes & fees
19 Nov - 20 Nov
Key West Villas
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 bar area with a counter, chairs, and a clock.
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
Gisele
฿8,987
฿10,110 total
includes taxes & fees
27 Oct - 28 Oct
The Gardens Hotel
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 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.

7. Alexander's Guesthouse - Adult Exclusive

Alexander's Guesthouse - Adult Exclusive
Old Town Key West, 1.2 km from Waterfront Playhouse
United States
Nestor
฿8,131
฿10,551 total
includes taxes & fees
28 Oct - 29 Oct
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 restaurant with multiple tables set for dining, a wine bottle, and a glass of wine on the table.
A hotel room with two beds, a ceiling fan, a large window with a view of palm trees, and a painting on the wall.

8. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
Josh
฿14,408
฿18,098 total
includes taxes & fees
26 Oct - 27 Oct
The Marquesa 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 pool area with lounge chairs and a wooden building with balconies.
A garden with a pond, rocks, and various plants.

9. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.8 km from Waterfront Playhouse
United States
Elise
฿6,738
฿7,581 total
includes taxes & fees
21 Oct - 22 Oct
Island City House Hotel
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 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.

10. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 1.3 km from Waterfront Playhouse
United States
Jennifer
฿9,592
฿10,791 total
includes taxes & fees
25 Oct - 26 Oct
The Conch House Heritage Inn
A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.
A lush garden with a variety of tropical plants and a paved walkway.
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.

11. Duval House

Duval House
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Cathrine
฿5,340
฿6,730 total
includes taxes & fees
25 Oct - 26 Oct
Duval House
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 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.

12. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Anthony
฿10,042
฿13,564 total
includes taxes & fees
26 Oct - 27 Oct
Santa Maria Suites
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
฿5,441
฿6,121 total
includes taxes & fees
25 Oct - 26 Oct
Westwinds 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 wicker outdoor seating area with two chairs and a table, surrounded by lush tropical foliage.
A hotel room with a bed, a nightstand, a chair, a small table, and a ceiling fan.

14. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
RICHARD
฿7,306
฿8,220 total
includes taxes & fees
25 Oct - 26 Oct
Ambrosia Key West
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.

15. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Amy
฿5,986
฿10,965 total
includes taxes & fees
25 Oct - 26 Oct
Southernmost House - Adult Exclusive
A gated entrance with lush green foliage 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 covered outdoor dining area with white chairs and tables, surrounded by lush greenery and a wooden deck.
A white colonial-style building with a balcony, surrounded by palm trees and a white picket fence.

16. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.8 km from Waterfront Playhouse
United States
August
฿6,726
฿7,566 total
includes taxes & fees
25 Oct - 26 Oct
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 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.

17. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 1.4 km from Waterfront Playhouse
United States
sam
฿3,597
฿6,314 total
includes taxes & fees
26 Oct - 27 Oct
Silver Palms Inn & Historic Homes
A hotel with a covered entrance, multiple balconies, and palm trees.
A room with a stone wall, a wooden bench, a cactus, and a framed painting.
A waterfront hotel with multiple balconies, a dock, and boats.
A covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.

18. 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
฿8,657
฿11,055 total
includes taxes & fees
26 Oct - 27 Oct
Opal Key Resort & Marina, Key West
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 pool area with a circular pool, lounge chairs, and a gazebo.

19. Alexander Palms Court

Alexander Palms Court
Casa Marina, 1.8 km from Waterfront Playhouse
United States
Brenda
฿6,015
฿6,767 total
includes taxes & fees
21 Oct - 22 Oct
Alexander Palms Court
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.
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.

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
฿8,396
฿11,146 total
includes taxes & fees
25 Oct - 26 Oct
Ella's Cottages - Key West Historic Inns
View all properties

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
1,002 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 pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
9.8
Exceptional
1,001 reviews
View
A gated entrance to Villas Key West with a brick pathway leading to the gate.
Key West Villas
9.8
Exceptional
279 reviews
View

Top Waterfront Playhouse Hotel Reviews

Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages

8/10 Good
"The rooms were extremely nice , but mine was at the top of a very long flight of stairs. Just steps from Duval street.It is in the perfect location. Staff is extremely nice and very helpful. Pool area could use some TLC, but still a relief on a hot day. Very convenient to wake up and have coffee and breakfast by the pool."
Wayne 2-night trip
Posted less than an hour ago
Simonton Court Historic Inn & Cottages
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
Ambrosia Key West

Ambrosia Key West

10/10 Excellent
"Beautiful and quiet. Staff was very helpful"
TIMOTHY 2-night trip
Posted 18 hours ago
Ambrosia Key West
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

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.
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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, take a look at the 1400 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 Opal Key Resort & Marina, Key West.
How many hotels will I find near Waterfront Playhouse?
Expedia has 1400 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?
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 theatre.