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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 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
CA $338
CA $380 total
includes taxes & fees
Oct 25 - Oct 26
Almond Tree Inn Hotel - 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 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
CA $222
CA $275 total
includes taxes & fees
Oct 27 - Oct 28
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
CA $464
CA $617 total
includes taxes & fees
Oct 28 - Oct 29
H2O Suites - 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 bar area with a counter, chairs, and a clock.
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
CA $379
CA $427 total
includes taxes & fees
Oct 27 - Oct 28
The Gardens Hotel
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 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."

5. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
United States
ben
CA $348
CA $391 total
includes taxes & fees
Oct 26 - Oct 27
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 covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.
A house with a porch, a table, and a door with a number '6'.

6. Key West Villas

Key West Villas
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Margaret
CA $430
CA $484 total
includes taxes & fees
Nov 18 - Nov 19
Key West Villas
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 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 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
CA $342
CA $443 total
includes taxes & fees
Oct 28 - Oct 29
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 restaurant with multiple tables set for dining, a wine bottle, and a glass of wine on the table.

8. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
Josh
CA $605
CA $760 total
includes taxes & fees
Oct 26 - Oct 27
The Marquesa 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 pool area with lounge chairs and a wooden building with balconies.

9. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.8 km from Waterfront Playhouse
United States
Elise
CA $265
CA $298 total
includes taxes & fees
Oct 27 - Oct 28
Island City House Hotel
A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.
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.
A hallway with a white door, a wooden bench, a blue sofa, and a staircase with a white railing.

10. Duval House

Duval House
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Cathrine
CA $210
CA $267 total
includes taxes & fees
Oct 25 - Oct 26
Duval House
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.

11. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Anthony
CA $422
CA $570 total
includes taxes & fees
Oct 26 - Oct 27
Santa Maria Suites
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.

12. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
RICHARD
CA $235
CA $264 total
includes taxes & fees
Oct 27 - Oct 28
Ambrosia Key West
A reception area with a curved marble counter, ceiling fans, large windows, and a staircase.
A bedroom with a bed, two bedside lamps, a ceiling fan, and a view of a balcony with plants.
A poolside area with lounge chairs and a clear blue pool surrounded by lush tropical vegetation.
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
CA $229
CA $257 total
includes taxes & fees
Oct 25 - Oct 26
Westwinds Inn
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 balcony with white railings and a table, overlooking a beach with palm trees and a clear blue sky.

14. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Amy
CA $253
CA $463 total
includes taxes & fees
Oct 25 - Oct 26
Southernmost House - Adult Exclusive
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 white colonial-style building with a balcony, surrounded by palm trees 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.

15. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.8 km from Waterfront Playhouse
United States
August
CA $283
CA $318 total
includes taxes & fees
Oct 25 - Oct 26
Coco Plum Inn
A poolside area with lounge chairs, umbrellas, and a pergola.
A living room with a spiral staircase, a sofa, a chair, a coffee table, and a view of an outdoor seating area.
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 wooden bench with a cushion and a small table, surrounded by bamboo plants and a wooden deck.

16. 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
CA $307
CA $417 total
includes taxes & fees
Oct 29 - Oct 30
Ella's Cottages - Key West Historic Inns
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.
A hotel with a pool, bicycles, and lush greenery.
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
CA $126
CA $237 total
includes taxes & fees
Oct 25 - Oct 26
Silver Palms Inn & Historic Homes
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.

18. Alexander Palms Court

Alexander Palms Court
Casa Marina, 1.8 km from Waterfront Playhouse
United States
Brenda
CA $253
CA $284 total
includes taxes & fees
Oct 21 - Oct 22
Alexander Palms Court
A hotel with a covered entrance, multiple balconies, and palm trees.
A restaurant interior with wooden beams, a bar area, and a colorful ceiling mural.
A waterfront hotel with multiple balconies, a dock, and boats.
A room with a stone wall, a wooden bench, a cactus, and a framed painting.

19. 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
CA $365
CA $467 total
includes taxes & fees
Oct 25 - Oct 26
Opal Key Resort & Marina, Key West
A pool area with lounge chairs and a cabana.
A waterfront hotel with a long pier, multiple balconies, and a view of the ocean.
A hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.
A dining area with a glass table, clear glass bottles, a bowl of fruit, and a wicker chair.

20. Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
Historic Seaport, < 0.1 km from Waterfront Playhouse
United States
Jeremy
CA $422
CA $589 total
includes taxes & fees
Oct 26 - Oct 27
Ocean Key Resort - A Noble House Resort
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
1,002 reviews
View
A tropical outdoor area with palm trees, hanging plants, and string lights.
Douglas House - Adults Only
9.8
Exceptional
563 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 garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
The Gardens Hotel
9.8
Exceptional
1,006 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

Hotels recommended for families near Waterfront Playhouse

A pool area with lounge chairs and a cabana.
A waterfront hotel with a long pier, multiple balconies, and a view of the ocean.
A hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.
A dining area with a glass table, clear glass bottles, a bowl of fruit, and a wicker chair.

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
Key West Historic District
CA $422
CA $589 total
includes taxes & fees
Oct 26 - Oct 27
Ocean Key Resort - A Noble House Resort
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
A view through a white-framed window with a decorative white fence, leading to a tiled patio area with a round table.
A resort with a beach, a dock, and a water view.
A balcony with a view of the ocean, a sofa, and a massage table.

Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
CA $256
CA $387 total
includes taxes & fees
Oct 26 - Oct 27
Pier House Resort & Spa
A white building with green shutters and a white picket fence.
A brick pathway leading to a green door, surrounded by lush tropical plants and a white fence.
A pool area with lounge chairs, a small table, and a thatched umbrella.
A modern kitchen with white cabinetry, a central island, and a view of the outdoors.

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns
Key West Historic District
CA $271
CA $376 total
includes taxes & fees
Oct 26 - Oct 27
Ridley House - Key West Historic Inns
A hotel with a swimming pool, balconies, and a view of the sea.
A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.
A marina with jet skis docked in front of a hotel with a dock and a boat in the background.
A beach wedding setup with white chairs, a wooden arch, and lanterns.

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
CA $330
CA $475 total
includes taxes & fees
Oct 25 - Oct 26
Hyatt Centric Key West Resort and Spa
A large, white, two-story building with a balcony and a sign reading "The Marker Resort."
A covered outdoor area with a pool, palm trees, and lounge chairs.
A tropical setting with palm trees and a building with a white facade and dark roof.
A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Key West Historic District
CA $266
CA $388 total
includes taxes & fees
Oct 25 - Oct 26
The Marker Key West Harbor Resort
A poolside area with lounge chairs, umbrellas, and a pergola.
A living room with a spiral staircase, a sofa, a chair, a coffee table, and a view of an outdoor seating area.
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 wooden bench with a cushion and a small table, surrounded by bamboo plants and a wooden deck.

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
Old Town Key West
CA $307
CA $417 total
includes taxes & fees
Oct 29 - Oct 30
Ella's Cottages - Key West Historic Inns
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with a white facade.
A bedroom with a sloped ceiling, a bed, two chairs, a hanging light fixture, and a window with a view of greenery.
A pathway leading to a white gazebo with a view of a lighthouse in the distance.
A table with chairs in a lush indoor garden setting.

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns
Old Town Key West
CA $282
CA $389 total
includes taxes & fees
Oct 25 - Oct 26
Lighthouse Hotel - Key West Historic Inns
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 pool area with lounge chairs and a wooden building with balconies.

Island City House Hotel

Island City House Hotel
Key West Historic District
CA $265
CA $298 total
includes taxes & fees
Oct 27 - Oct 28
Island City House Hotel

Top Waterfront Playhouse Hotel Reviews

Weatherstation Inn

Weatherstation Inn

10/10 Excellent
"The location is amazing...quiet neighborhood and walkable to everything, Amazing Free parking is also so great in Key West..each room gets one free parking space and it is wonderful, We stayed three nights and did not move the car because we could walk everywhere. Close to Duval street, shopping, restaurants, and all of the attractions. Close to the museums too and the aquarium. Staff were fabulous, kind helpful and attentive. Lovely Room was clean and amenities are great. Very pretty room. They offer cold bottled water which is great in a tropical environment. I would highly recommend...if we come back to Key West, I will absolutely stay at the Weatherstation Inn. They do have a few breakfast items..yogurt and bakery items that are nice. They also offer bottled lemonade. Just an FYI for those with mobility issues: I do not believe they have an elevator, so if you are on the second floor, the steps are steep. And we hand carried our duffle bags up approximately 25-30 steps. The stairs are also outdoors. Thank you to the Weatherstation Inn...thank you for a great stay."
Rebecca 3-night trip
Posted 1 hour ago
Weatherstation Inn
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

10/10 Excellent
"Wonderful property with wonderful staff"
Michael Joseph 4-night trip
Posted 1 hour ago
Hyatt Centric Key West Resort and Spa
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

10/10 Excellent
"We love staying at The Marker in Key West! The location is perfect, the grounds are beautiful and clean, and the stuff is amazing! This was our 2nd time saying at The Marker and we’ve already got our 3rd trip planned, for our honeymoon!"
Jessica 4-night trip
Posted 3 hours ago
The Marker Key West Harbor Resort
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"We had no issues. Room clean, restaurant good!"
Michael 4-night trip
Posted 6 hours ago
Opal Key Resort & Marina, Key West
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 13 hours ago
Ocean Key Resort - A Noble House Resort
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
Heron House - Adult Only

Heron House - Adult Only

10/10 Excellent
"The property was wonderfully located, clean, and beautiful. Highly recommend."
Lance 3-night trip
Posted 3 days ago
Heron House - Adult Only
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Loved our stay at La Concha. Staff was excellent and constantly focused on our comfort and enjoyment. Upon arrival (kind of late), we were unsure if the bar was still serving food. Once staff became aware that we wanted food, they did everything they could think of to ensure we got what we needed. Top-notch customer service! The location of the hotel could not be beat, for our purposes. Easy to explore many different areas that we wanted to see…particularly Old Town and the seaport district. Everything is very walkable; however, if you have people in your party who cannot walk much distance, it is very easy to rent a golf cart to haul them around. An extremely enjoyable trip, made all the better by the staff and quality of La Concha."
LEE 7-night trip
Posted 4 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.
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.
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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, check out the 1400 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 1400 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?
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 theater.

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