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Check prices for these dates

Tonight
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 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 building with a sign reading "ALMOND Frog & Toad Inn" and a "VACANCY" sign below it.
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.

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
6.188.440 ₫
6.961.995 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Almond Tree Inn Hotel - Adults Only
A modern outdoor area with a pool, lounge chairs, and a bar area.
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.
An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.
A modern hotel with a prominent glass facade, palm trees, and a clear sky.

2. H2O Suites - Adults Only

H2O Suites - Adults Only
Uptown - Upper Duval, 1.6 km from Waterfront Playhouse
United States
Kimberly
8.094.290 ₫
10.852.031 ₫ 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 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 building with a neon sign that reads "Orchid Key Inn."
A neon sign for Orchid Key Inn with a 'VACANCY' sign below it.

3. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
United States
ben
6.382.435 ₫
7.180.240 ₫ total
includes taxes & fees
25 Oct - 26 Oct
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 couple walking along a poolside pathway surrounded by lush greenery.
A colonial-style building with a porch, surrounded by lush tropical vegetation.

4. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Gisele
6.954.721 ₫
7.824.061 ₫ total
includes taxes & fees
27 Oct - 28 Oct
The Gardens Hotel
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.
A covered walkway with a wooden ceiling, white railings, and a brick path.
A garden with a pond, rocks, and various plants.
A compact kitchen with wooden cabinets, a microwave, stove, and refrigerator. There is a dining area with a table and chairs, and a sofa.

5. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.8 km from Waterfront Playhouse
United States
Elise
5.130.780 ₫
5.772.128 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Island City House Hotel
A pool area with lounge chairs and palm trees.
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.
A neatly made bed with patterned pillows, a bedside table with a bottle and glasses, and a window with orchids.

6. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Anthony
7.733.934 ₫
10.446.631 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Santa Maria Suites
A gated entrance with lush green foliage 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.
A white colonial-style building with a balcony, surrounded by palm trees and a white picket fence.

7. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.8 km from Waterfront Playhouse
United States
August
4.096.398 ₫
4.608.545 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Coco Plum 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 balcony with white railings and a table, overlooking a beach with palm trees and a clear blue sky.
A grand staircase with ornate railings and a chandelier.

8. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Amy
4.632.601 ₫
8.485.343 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Southernmost House - Adult Exclusive
A green house with a white porch, a flag, and a sign advertising a property for sale.
A bedroom with a large bed, a sofa, a nightstand, and a painting on the wall.
A covered porch with wicker furniture, potted plants, and a view of the house.
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.

9. L'Habitation Guest House - Adults Only

L'Habitation Guest House - Adults Only
Historic Seaport, 0.5 km from Waterfront Playhouse
United States
Richard
4.399.807 ₫
4.949.977 ₫ total
includes taxes & fees
28 Oct - 29 Oct
L'Habitation Guest House - Adults Only
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 garden with a stone pathway, a wooden fence, and various tropical plants.
A room with a bed, a desk, a chair, a lamp, a painting of a boat on water, and a view of the sea.

10. Alexander Palms Court

Alexander Palms Court
Casa Marina, 1.8 km from Waterfront Playhouse
United States
Brenda
5.237.865 ₫
5.892.792 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Alexander Palms Court
A covered porch with white railings, wooden benches, and a hanging light fixture.
A sign for Marrero's Guest Mansion in Key West, FL, by Verdigris Hotels.
A living room with a large mirror, a wicker chair, a television on a wooden cabinet, and a window with a view of palm trees.
A bedroom with a four-poster bed, a wicker chair, a wooden dresser, and a television.

11. Marrero's Guest Mansion

Marrero's Guest Mansion
Downtown Key West, 0.6 km from Waterfront Playhouse
United States
Michael
8.380.584 ₫
9.428.157 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Marrero's Guest Mansion
A wooden deck with wicker furniture and a white railing, surrounded by lush tropical vegetation.
A two-story building with a white picket fence, palm trees, and a clear blue sky.
A breakfast tray with croissants, orange juice, and coffee on a table by a window with a view of a pool and greenery.
A pathway leading to a building with a white facade, surrounded by lush greenery and palm trees.

12. Weatherstation Inn

Weatherstation Inn
Truman Annex, 0.5 km from Waterfront Playhouse
United States
Robert
4.630.014 ₫
5.208.766 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Weatherstation Inn
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'.

13. The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Historic Seaport, 0.6 km from Waterfront Playhouse
United States
Dana Nicole
4.689.506 ₫
6.905.252 ₫ total
includes taxes & fees
25 Oct - 26 Oct
The Marker Key West Harbor Resort
Lobby
A two-story building with a balcony, a flag, and a palm tree.
Exterior
Room

14. The Independent Inn

The Independent Inn
Historic Seaport, 1.1 km from Waterfront Playhouse
United States
Michael
3.903.955 ₫
5.396.685 ₫ total
includes taxes & fees
25 Oct - 26 Oct
The Independent Inn
A modern bathroom with a freestanding bathtub, a vanity with a mirror, and a chair.
A poolside area with lounge chairs, umbrellas, and a covered seating area with hanging lights.
A white picket fence, a wooden bench with cushions, and a concrete pathway surrounded by lush greenery.
A white building with a sign reading 'Kimpton Key West Winslow's Bungalow.'

15. Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns
Old Town Key West, 1.3 km from Waterfront Playhouse
United States
Elizabeth
5.949.180 ₫
8.002.424 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Winslow's Bungalows - Key West Historic Inns
A two-story building with a white picket fence, palm trees, and a sign that reads 'DUVAL GARDENS.'
Pool
A porch with wicker chairs and a table, white railings, and a window with a view of a palm tree.
Room

16. Duval Gardens - Adults Only

Duval Gardens - Adults Only
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
United States
JoAnn
5.197.971 ₫
7.594.476 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Duval Gardens - Adults Only
A pool area with a brick patio, potted plants, and a covered seating area.
A white picket fence, a palm tree, and a sign reading "Garden House Key West".
A house with a porch, a sign reading "Garden House," and a number "329" on the door.
A porch with a white chair, a wooden door, and a small indoor dining area visible through the door.

17. The Garden House

The Garden House
Historic Seaport, 0.6 km from Waterfront Playhouse
United States
Brad
2.560.734 ₫
3.437.074 ₫ total
includes taxes & fees
26 Oct - 27 Oct
The Garden House
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.

18. Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns
Bahama Village, 1.2 km from Waterfront Playhouse
United States
Jill
5.949.180 ₫
8.002.424 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Lighthouse Hotel - Key West Historic Inns
A covered porch with wicker furniture, potted plants, and a sign for the "Office" at the Palm Hotel.
A pink building with a white door, a balcony with a white railing, and a view of a pool area.
A hotel with a white facade, multiple balconies, and lush tropical landscaping.
A row of bicycles parked in front of a building with a white balcony and a palm tree.

19. The Palms Hotel

The Palms Hotel
The Meadows, 1.5 km from Waterfront Playhouse
United States
Jerry
4.025.447 ₫
5.110.613 ₫ total
includes taxes & fees
25 Oct - 26 Oct
The Palms Hotel
A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.
A cozy cabin with a wooden interior, a bed, a TV, and a kitchenette.
A pool area with lounge chairs and umbrellas, surrounded by buildings with balconies and a clear blue sky.
A spacious living area with a wooden staircase, a ceiling fan, a TV, and a view of the beach through an open door.

20. Eden House

Eden House
Historic Seaport, 1.1 km from Waterfront Playhouse
United States
Michelle
3.947.720 ₫
4.974.128 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Eden House
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
1,004 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
1,003 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
1,000 reviews
View
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.
Island City House Hotel
9.6
Exceptional
1,000 reviews
View

Top Waterfront Playhouse Hotel Reviews

Pier House Resort & Spa

Pier House Resort & Spa

8/10 Good
"The property is lovely but it needs updating. The beach was the best part but it should’ve been raked of the seaweed daily."
Rhonda 6-night trip
Posted 2 hours ago
Pier House Resort & Spa
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

10/10 Excellent
"Place was amazing. Perfect location to everything"
Toby 6-night trip
Posted 5 hours ago
Amsterdam's Curry Mansion Inn
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

10/10 Excellent
"The staff were incredibly helpful and friendly. Breakfast was good. Location of the hotel would be hard to beat. Even all the people staying here were great."
Steven 3-night trip
Posted 5 hours ago
Ridley House - Key West Historic Inns
Heron House - Adult Only

Heron House - Adult Only

10/10 Excellent
"Great location. Nice place. Would absolutely stay again"
Jeffrey 2-night trip
Posted 18 hours ago
Heron House - Adult Only
The Marquesa Hotel

The Marquesa Hotel

10/10 Excellent
"Everything"
Mike 4-night trip
Posted 20 hours ago
The Marquesa Hotel
Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

10/10 Excellent
"Loved! And the remodeling revamp is on point! The styling and decor has been done very well. The lobby area is perfect! Loved every bit of my stay!"
haley 3-night trip
Posted 1 day ago
Ocean Key Resort - A Noble House Resort
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

10/10 Excellent
"Great location between duval and seaport. Our only issue was the AC intermittently didn’t work due to the patio door malfunction, but the staff was very attentive in making sure it was fixed. The front desk staff was amazing. Paul was extremely helpful."
Robert 3-night trip
Posted 1 day ago
The Marker Key West Harbor Resort
Weatherstation Inn

Weatherstation Inn

10/10 Excellent
"Location, Everything within walking distance"
Constance 2-night trip
Posted 2 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 2 weeks 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)
You can spend an afternoon studying the exhibits at Key West Shipwreck Museum during your trip to Key West. In the area, take in the lively festivals and beautiful sunsets.
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)
You can find out about the history of Key West with a trip to Mallory Square. Stroll along the area's seaside or experience its lively festivals.
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 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.
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 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)
You can spend an afternoon browsing the exhibits at Audubon House and Tropical Gardens during your trip to Key West. Discover the area's lively bars and its lively festivals.
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)
You can spend time studying the exhibits at Mel Fisher Maritime Museum in Key West. Wander the seaside and beautiful beaches in the area.
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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.
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.