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Key West Hotel Guide - Waterfront Playhouse hotels in Key West, United States of America.

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Check prices for these dates

Tonight
11 Oct - 12 Oct
Tomorrow
12 Oct - 13 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

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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 breakfast table with various food items and drinks, a pool in the background, and a tiled wall.
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
John
€279
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 hotel room with a bed, a wooden floor, a seating area with a table and chairs, and a view of greenery outside.
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
€165
includes taxes & fees
13 Oct - 14 Oct
Douglas House - Adults Only
A modern interior with a staircase, a sofa set, a wooden 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.
A spacious room with a large bed, a sofa, a chair, a small table, and a television.

3. Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
Historic Seaport, 0.5 km from Waterfront Playhouse
United States
William
€200
includes taxes & fees
13 Oct - 14 Oct
Simonton Court Historic Inn & Cottages
A pool area with lounge chairs and a table, surrounded by palm trees.
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.
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
€233
includes taxes & fees
13 Oct - 14 Oct
Orchid Key Inn - 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 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.

5. Alexander's Guesthouse - Adult Exclusive

Alexander's Guesthouse - Adult Exclusive
Old Town Key West, 1.2 km from Waterfront Playhouse
United States
Nestor
€262
includes taxes & fees
15 Oct - 16 Oct
Alexander's Guesthouse - Adult Exclusive
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 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.

6. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Gisele
€338
includes taxes & fees
14 Oct - 15 Oct
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.

7. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 1.3 km from Waterfront Playhouse
United States
John
€287
includes taxes & fees
25 Oct - 26 Oct
The Conch House Heritage Inn
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 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
Darrell
€411
includes taxes & fees
15 Oct - 16 Oct
The Marquesa Hotel
A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.
A swimming pool with a mural of a dolphin and a butterfly, surrounded by lounge chairs and palm trees.
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.

9. Duval House

Duval House
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Cliff
€199
includes taxes & fees
26 Oct - 27 Oct
Duval House
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 bedroom with a bed, nightstand, lamp, air conditioning unit, and a no smoking sign.

10. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West, 1.7 km from Waterfront Playhouse
United States
Justyn
€142
includes taxes & fees
13 Oct - 14 Oct
The Grand Guesthouse
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 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
Osvaldo
€224
includes taxes & fees
25 Oct - 26 Oct
Island City House Hotel
A room with a bed, a ceiling fan, and a window with blinds.
A cozy outdoor seating area with a wooden bench and a table, surrounded by potted plants and a coffee and tea sign.
A room with a yellow armchair, a glass coffee table, and a view of a wooden deck and tropical plants.
A spacious kitchen with wooden cabinets, a granite countertop, and a ceiling fan.

12. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 1.3 km from Waterfront Playhouse
United Kingdom
Adam
€253
includes taxes & fees
13 Oct - 14 Oct
The Mermaid & Alligator
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 neatly made bed with patterned pillows, a bedside table with a bottle and glasses, and a window with orchids.
A reception area with a modern design, featuring a reception desk, a sofa, and a potted plant.

13. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Anthony
€371
includes taxes & fees
25 Oct - 26 Oct
Santa Maria Suites
A reception area with a curved marble counter, ceiling fans, large windows, and a staircase.
A two-story house with a white exterior, a green roof, and a staircase leading to the upper floor.
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.

14. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.9 km from Waterfront Playhouse
United States
Anthony
€325
includes taxes & fees
8 Nov - 9 Nov
Westwinds Inn
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
A hotel with a pool, bicycles, and lush greenery.
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.

15. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 1.4 km from Waterfront Playhouse
United States
sam
€150
includes taxes & fees
25 Oct - 26 Oct
Silver Palms Inn & Historic Homes
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.

16. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Amy
€253
includes taxes & fees
25 Oct - 26 Oct
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 swimming pool with lounge chairs, a covered deck, and a view of lush greenery.
A hotel room with a large bed, two bedside tables, a ceiling fan, and two framed pictures on the wall.

17. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.8 km from Waterfront Playhouse
United States
Riley
€190
includes taxes & fees
13 Oct - 14 Oct
Coco Plum 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 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.

18. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
Tricia
€181
includes taxes & fees
13 Oct - 14 Oct
Ambrosia Key West
A green house with a white porch, a flag, and a sign advertising a property for sale.
A bathroom with a vanity, a mirror, and a window with blinds.
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.

19. L'Habitation Guest House - Adults Only

L'Habitation Guest House - Adults Only
Historic Seaport, 0.5 km from Waterfront Playhouse
United States
Richard
€162
includes taxes & fees
26 Oct - 27 Oct
L'Habitation Guest House - Adults Only
A poolside area with lounge chairs, umbrellas, and a pergola.
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 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
€296
includes taxes & fees
13 Oct - 14 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
1,001 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
1,003 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 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
171 reviews
View

Top Waterfront Playhouse Hotel Reviews

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

10/10 Excellent
"Great place and so convenient to everything! Kendra our bartender was the best part of our stay! She was so helpful and attentive and made our time here so memorable!"
Stacie 4-night trip
Posted 2 hours ago
Ocean Key Resort - A Noble House Resort
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

8/10 Good
"Muy bueno y muy buen precio la localización perfecto"
Yureisi 2-night trip
Posted 4 hours ago
Amsterdam's Curry Mansion Inn
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

10/10 Excellent
"Great property. Stayed one night as part of a boy’s trip to the keys."
Bernt 1-night trip
Posted 6 hours 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 7 hours ago
Opal Key Resort & Marina, Key West
Heron House - Adult Only

Heron House - Adult Only

10/10 Excellent
"The staff was exceptional. Greg at the desk made us feel welcome and showed us around the resort. I would highly recommend this resort. We will be staying again."
Steven 1-night trip
Posted 9 hours ago
Heron House - Adult Only
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 1 day ago
Weatherstation Inn
The Marquesa Hotel

The Marquesa Hotel

10/10 Excellent
"We had such a good time; it was the highlight of our trip. We would have liked to be able to swim later than sunset..."
Jeffrey 3-night trip
Posted 2 days ago
The Marquesa Hotel
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 4 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 6 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.
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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.
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, 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.