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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 building with a sign reading "ALMOND Frog & Toad Inn" and a "VACANCY" sign below it.
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
John
CA $249
CA $280 total
includes taxes & fees
Sep 29 - Sep 30
Almond Tree Inn Hotel - 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 colonial-style building with a porch, surrounded by lush tropical vegetation.
A bar area with a counter, chairs, and a clock.

2. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Forrest
CA $343
CA $386 total
includes taxes & fees
Sep 30 - Oct 1
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 building with a neon sign that reads "Orchid Key Inn."
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.

3. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
United States
Nicholas
CA $260
CA $292 total
includes taxes & fees
Sep 30 - Oct 1
Orchid Key Inn - Adults Only
A two-story house with a covered porch, a brick pathway, and a large tree.
A restaurant with multiple tables set for dining, a wine bottle, and a glass of wine on the table.
A poolside area with a swimming pool, a staircase leading to a deck, and a building with multiple windows and balconies.
A covered porch with white wicker furniture and a blue floor, surrounded by lush tropical plants.

4. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
Darrell
CA $380
CA $508 total
includes taxes & fees
Sep 29 - Sep 30
The Marquesa Hotel
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 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.
A spacious living room with a wooden ceiling, white sofas, a patterned armchair, a glass coffee table, and a large painting on the wall.

5. Alexander's Guesthouse - Adult Exclusive

Alexander's Guesthouse - Adult Exclusive
Old Town Key West, 1.2 km from Waterfront Playhouse
United States
Nestor
CA $307
CA $403 total
includes taxes & fees
Sep 29 - Sep 30
Alexander's Guesthouse - Adult Exclusive
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 pathway flanked by lush green foliage leading to a gated entrance.
A pool area with a clear view of a house in the background, surrounded by palm trees and greenery.

6. Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
Historic Seaport, 0.5 km from Waterfront Playhouse
United States
William
CA $281
CA $317 total
includes taxes & fees
Sep 29 - Sep 30
Simonton Court Historic Inn & Cottages
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 spacious bedroom with a large bed, a sitting area with a sofa and armchairs, and a dining area with a table and chairs.
A living room with a sofa, a glass coffee table, a TV, and a painting on the wall.

7. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 1.3 km from Waterfront Playhouse
United States
John
CA $268
CA $302 total
includes taxes & fees
Sep 29 - Sep 30
The Conch House Heritage Inn
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 room with a bed, sofa, coffee table, and artwork.

8. H2O Suites - Adults Only

H2O Suites - Adults Only
Uptown - Upper Duval, 1.6 km from Waterfront Playhouse
United States
Corey
CA $363
CA $504 total
includes taxes & fees
Sep 29 - Sep 30
H2O Suites - 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 hotel room with a bed, a wooden floor, a seating area with a table and chairs, and a view of greenery outside.

9. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 1.4 km from Waterfront Playhouse
United States
michael
CA $189
CA $234 total
includes taxes & fees
Sep 30 - Oct 1
Douglas House - Adults Only
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 pool area with lounge chairs and candles, surrounded by palm trees and a building in the background.
A breakfast buffet with a variety of fruits, pastries, and beverages on a wooden deck with a view of a lush garden and a pool.

10. Tropical Inn

Tropical Inn
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Molly
CA $136
CA $189 total
includes taxes & fees
Sep 29 - Sep 30
Tropical Inn
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 bedroom with a bed, nightstand, lamp, air conditioning unit, and a no smoking sign.
A covered outdoor area with a wooden staircase, seating, and potted plants.

11. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West, 1.7 km from Waterfront Playhouse
United States
Travis
CA $160
CA $215 total
includes taxes & fees
Sep 30 - Oct 1
The Grand Guesthouse
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 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.

12. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.8 km from Waterfront Playhouse
United States
Osvaldo
CA $217
CA $245 total
includes taxes & fees
Sep 29 - Sep 30
Island City House 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 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.

13. Duval House

Duval House
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Christopher
CA $133
CA $180 total
includes taxes & fees
Oct 1 - Oct 2
Duval House
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.

14. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 1.3 km from Waterfront Playhouse
United Kingdom
Adam
CA $255
CA $286 total
includes taxes & fees
Sep 29 - Sep 30
The Mermaid & Alligator
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 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.

15. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Anthony
CA $352
CA $492 total
includes taxes & fees
Sep 29 - Sep 30
Santa Maria Suites
A room with a door featuring horizontal blinds, a visible outdoor view through the window, and a patterned carpet.
A pool area with a covered seating area, palm trees, and a small pavilion.
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.

16. Alexander Palms Court

Alexander Palms Court
Casa Marina, 1.8 km from Waterfront Playhouse
United States
Andrew
CA $169
CA $190 total
includes taxes & fees
Sep 29 - Sep 30
Alexander Palms Court
A rectangular pool with a white deck, surrounded by lush greenery and a gazebo.
A wicker outdoor seating area with two chairs and a table, surrounded by lush tropical foliage.
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 hotel room with a bed, a nightstand, a chair, a small table, and a ceiling fan.

17. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
Tricia
CA $190
CA $214 total
includes taxes & fees
Sep 29 - Sep 30
Ambrosia Key West
A wooden deck with wicker furniture and a white railing, surrounded by lush tropical vegetation.
A swimming pool with a white picket fence, surrounded by lounge chairs and potted plants.
A pathway leading to a building with a white facade, surrounded by lush greenery and palm trees.
A two-story building with a white picket fence, palm trees, and a clear blue sky.

18. Weatherstation Inn

Weatherstation Inn
Truman Annex, 0.5 km from Waterfront Playhouse
United States
Svetlana
CA $253
CA $285 total
includes taxes & fees
Oct 5 - Oct 6
Weatherstation Inn
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.

19. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.8 km from Waterfront Playhouse
United States
Riley
CA $190
CA $214 total
includes taxes & fees
Sep 29 - Sep 30
Coco Plum Inn
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.

20. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
yessy
CA $197
CA $401 total
includes taxes & fees
Oct 25 - Oct 26
Southernmost House - Adult Exclusive
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
1,007 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
A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
9.8
Exceptional
1,005 reviews
View
A two-story house with a covered porch, a brick pathway, and a large tree.
The Marquesa Hotel
9.8
Exceptional
1,001 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
169 reviews
View

Top Waterfront Playhouse Hotel Reviews

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

10/10 Excellent
"Loved the decor! The lobby, lobby bar and deck were so cute! I specially picked this resort and the room fur the decor-very tropical and fabulous! But honestly, the staff is what made this resort so great! From the front desk, to concierge, to the staff at Hot Tin Roof, to the pool bartender/ they all went above and beyond!"
Mary Ann 3-night trip
Posted 4 hours ago
Ocean Key Resort - A Noble House Resort
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Great location and superb private beach"
Stian 3-night trip
Posted 6 hours ago
Pier House Resort & Spa
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Great location"
Mary 5-night trip
Posted 1 day ago
La Concha Key West, Autograph Collection
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

10/10 Excellent
"Always solid"
Jeff 6-night trip
Posted 1 day ago
The Marker Key West Harbor Resort
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"From before we arrived we already knew we chose the right place to stay! We had questions about parking our motorcycle on property and there was no hesitation to share information and also connect with us. The staff is great. We are recommending this location and properties to friends and family. Next time we’re in town, 100% this will be the place we stay. Location is great and the property is fun to explore. Thank you all for making our stay memorable!"
Rebecca 2-night trip
Posted 3 days ago
Winslow's Bungalows - Key West Historic Inns
Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages

10/10 Excellent
"Staff was great rooms are older but quite charming. Would definitely stay again."
William 4-night trip
Posted 3 days ago
Simonton Court Historic Inn & Cottages
The Penthouse at Custom House Inn | New!

The Penthouse at Custom House Inn | New!

10/10 Excellent
"Nice week in Key West"
Anonymous traveller 3-night trip
Posted 8 days ago
The Penthouse at Custom House Inn | New!
Heart of Downtown Key West Cottage With Off-Street Parking

Heart of Downtown Key West Cottage With Off-Street Parking

10/10 Excellent
"We go to Key West, once a year and have been staying in different places, trying to find that special place. This is it. If you want 5 star, Hilton Hotel style. Not it. If you want 5 star old town Key West. This is it. It's a gem. Literally in the heart of downtown. A block walk to everything going on, on Duval Street. But the Key, you'd never know it. It is so quiet (maybe during a festival it might be a bit more noise). It's tucked away, very private. Free parking (that right there will save you over 50 a day). Restaurants close by. Pan Am house, literally next door. Mel Fisher museum, 5-7 min walk. Mallory square maybe 12. Need to pick something up. CVS is a 10 min walk. If that. The owners are respond very quickly. For us, it was so good, we only corresponded about Key West, nothing to do with the cottage. If you are going to Key West and you WANT Key West, this is the place."
Matthew A. 6-night trip
Posted 9 days ago
Heart of Downtown Key West Cottage With Off-Street Parking
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 10 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.
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.
See properties
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.
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, check out the 1399 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 1399 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?
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 theater.

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