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Check prices for these dates

Tonight
22 Sep - 23 Sep
Tomorrow
23 Sep - 24 Sep
This weekend
25 Sep - 27 Sep
Next weekend
2 Oct - 4 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 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.
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
John
฿5,584
฿6,282 total
includes taxes & fees
27 Sept - 28 Sept
Almond Tree Inn Hotel - Adults Only
A modern interior with a staircase, a sofa set, a wooden table, and a television.
A pool area with a clear view of a house in the background, surrounded by palm trees and greenery.
A pathway flanked by lush green foliage leading to a gated entrance.
A courtyard with two green lounge chairs, a palm tree, and a building with a white facade and lattice window design.

2. Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
Historic Seaport, 0.5 km from Waterfront Playhouse
United States
Robin
฿5,950
฿6,693 total
includes taxes & fees
23 Sept - 24 Sept
Simonton Court Historic Inn & Cottages
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 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.

3. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
United States
Nicholas
฿5,335
฿6,002 total
includes taxes & fees
27 Sept - 28 Sept
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 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.

4. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 1.3 km from Waterfront Playhouse
United States
John
฿4,627
฿5,205 total
includes taxes & fees
29 Sept - 30 Sept
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 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.

5. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Robert
฿7,466
฿8,399 total
includes taxes & fees
30 Sept - 1 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 narrow room with a bed, a potted plant, and a window with blinds.
A pool area with lounge chairs, a pool, and a building with a balcony and outdoor seating.

6. Alexander's Guesthouse - Adult Exclusive

Alexander's Guesthouse - Adult Exclusive
Old Town Key West, 1.2 km from Waterfront Playhouse
United States
Nestor
฿7,204
฿9,471 total
includes taxes & fees
27 Sept - 28 Sept
Alexander's Guesthouse - Adult Exclusive
A two-story house with a covered porch, a brick pathway, and a large tree.
A covered porch with white wicker furniture and a blue floor, surrounded by lush tropical plants.
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 poolside area with a swimming pool, a staircase leading to a deck, and a building with multiple windows and balconies.

7. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
Darrell
฿7,600
฿10,419 total
includes taxes & fees
23 Sept - 24 Sept
The Marquesa Hotel
A gated entrance to Villas Key West with a brick pathway leading to the gate.
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'.
A covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.

8. Key West Villas

Key West Villas
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Margaret
฿8,645
฿9,726 total
includes taxes & fees
15 Oct - 16 Oct
Key West Villas
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 with a prominent glass facade, palm trees, and a clear sky.

9. H2O Suites - Adults Only

H2O Suites - Adults Only
Uptown - Upper Duval, 1.6 km from Waterfront Playhouse
United States
Kourosh
฿9,273
฿12,676 total
includes taxes & fees
27 Sept - 28 Sept
H2O Suites - 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.
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.

10. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 1.4 km from Waterfront Playhouse
United States
michael
฿3,391
฿4,196 total
includes taxes & fees
24 Sept - 25 Sept
Douglas House - Adults Only
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
Anne
฿3,291
฿4,417 total
includes taxes & fees
27 Sept - 28 Sept
Duval House
A bedroom with a four-poster bed, a wooden desk, wicker chairs, and a view of the outdoors.
A wooden door with glass panels, leading to an interior space with furniture and plants.
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.
A pool area with lounge chairs and candles, surrounded by palm trees and a building in the background.

12. Tropical Inn

Tropical Inn
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Molly
฿3,206
฿4,438 total
includes taxes & fees
27 Sept - 28 Sept
Tropical Inn
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 covered walkway with a wooden ceiling, white railings, and a brick path.

13. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.8 km from Waterfront Playhouse
United States
Osvaldo
฿5,110
฿5,749 total
includes taxes & fees
23 Sept - 24 Sept
Island City House Hotel
A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.
A two-story building with a porch, a sign reading "The Grand Guesthouse," and a purple flag.
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.

14. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West, 1.7 km from Waterfront Playhouse
United States
Alissa
฿3,750
฿5,049 total
includes taxes & fees
23 Sept - 24 Sept
The Grand Guesthouse
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 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.

15. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 1.3 km from Waterfront Playhouse
United States
Brian
฿5,983
฿6,731 total
includes taxes & fees
28 Sept - 29 Sept
The Mermaid & Alligator
A pool area with lounge chairs and palm trees.
A sign for Santa Maria Resort surrounded by lush greenery and palm trees.
A hotel named "Santa Maria" with a prominent illuminated sign, a glass entrance, and a view of the ocean.
A modern outdoor seating area with a sofa, chairs, and a small table, surrounded by glass doors and a view of greenery.

16. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Anthony
฿9,273
฿12,676 total
includes taxes & fees
27 Sept - 28 Sept
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 breakfast table with a variety of food items, including fruits, pastries, and a coffee mug.
A bedroom with a bed, two bedside lamps, a ceiling fan, and a view of a balcony with plants.

17. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.9 km from Waterfront Playhouse
United States
Tricia
฿3,864
฿4,347 total
includes taxes & fees
23 Sept - 24 Sept
Westwinds Inn
A room with a door featuring horizontal blinds, a visible outdoor view through the window, and a patterned carpet.
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.
A pool area with a covered seating area, palm trees, and a small pavilion.

18. Alexander Palms Court

Alexander Palms Court
Casa Marina, 1.8 km from Waterfront Playhouse
United States
Andrew
฿3,964
฿4,459 total
includes taxes & fees
23 Sept - 24 Sept
Alexander Palms Court
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.

19. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 1.4 km from Waterfront Playhouse
United States
sam
฿2,662
฿5,239 total
includes taxes & fees
23 Sept - 24 Sept
Silver Palms Inn & Historic Homes
A large, ornate hotel with a pool, palm trees, and a view of the ocean.
A grand staircase with ornate railings and a chandelier.
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.

20. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
yessy
฿4,763
฿9,576 total
includes taxes & fees
24 Sept - 25 Sept
Southernmost House - Adult Exclusive
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
1,006 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
1,000 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 porch with a white railing, a bench, and a flag.
The Conch House Heritage Inn
9.8
Exceptional
189 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
1,004 reviews
View

Top Waterfront Playhouse Hotel Reviews

Weatherstation Inn

Weatherstation Inn

10/10 Excellent
"The property was charming, a little rough around the edges but that added to the charm. If you like the standard chain hotels then this place isn't for you. The staff were all helpful and friendly. The pool is small but sufficient for a dip in the heat, one morning we were joined by a large iguana but he just sat in the sunshine. Breakfast was plentiful and location was perfect, quiet but close to Duval Street. I would stay again"
Julia 3-night trip
Posted less than an hour ago
Weatherstation Inn
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Overall an excellent stay. Pool is somewhat small but nice. Staff is overall top notch. Location is about as good as you can get if your plan is to hang in Old Town. Would definitely recommend."
David 5-night trip
Posted 2 hours ago
La Concha Key West, Autograph Collection
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Todo estaba perfecto menos la playa estaba extremadamente sucia"
Daimary 2-night trip
Posted 8 hours ago
Southernmost Beach Resort and Guesthouses
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

10/10 Excellent
"Great stay. Clean and well Maintained. Friendly staff."
ALEASE 3-night trip
Posted 16 hours ago
The Cabana Inn Key West - Adults Only
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"The room was clean and decorated for the keys. Breakfast was amazing. Take advantage of that. The location is great for getting to so many hotspots."
Michael 2-night trip
Posted 22 hours ago
Winslow's Bungalows - Key West Historic Inns
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

10/10 Excellent
"4th time we have stayed here and you can’t beat the location, pool with 3pm free sangria is a awesome break in the heat of the day. Highly recommend"
Todd 2-night trip
Posted 22 hours ago
Ridley House - Key West Historic Inns
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"Always love staying at the Opal."
SHANNON 6-night trip
Posted 1 day ago
Opal Key Resort & Marina, Key West
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

10/10 Excellent
"The Curry is so convenient to everyiwe want to do while in Key West."
Catherine Elizabeth 4-night trip
Posted 2 days ago
Amsterdam's Curry Mansion Inn
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

10/10 Excellent
"Staff: friendly, attentive and professional. Location : excellent. Cleanliness: impeccable, very clean, Overall experience: exceptional, wonderful, highly recommended."
Abel 2-night trip
Posted 5 days ago
Hyatt Vacation Club at Sunset Harbor, Key West

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.
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 1399 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 1399 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?
Mel Fisher Maritime Museum, Harry S. Truman Little White House and Florida Keys Eco - Discovery Center feature a variety of fascinating exhibits to see while you're in town. Sights like Ernest Hemingway Home and Museum, Key West Lighthouse and Keeper's Quarters Museum and Fort Zachary Taylor Historic State Park 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.