The 10 Best Hotels Near Waterfront Playhouse, Key West from CA $180

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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 breakfast table with various food items and drinks, a pool in the background, and a tiled wall.

1. Almond Tree Inn Hotel - Adults Only

Downtown Key West, 1.3 km from Waterfront Playhouse

John

CA $297

CA $334 total

includes taxes & fees

Oct 6 - Oct 7

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 large, two-story building with a balcony, surrounded by dense tropical foliage.

2. Douglas House - Adults Only

Uptown - Upper Duval, 1.4 km from Waterfront Playhouse

Maricela

CA $145

CA $180 total

includes taxes & fees

Oct 6 - Oct 7

A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.

A colonial-style building with a porch, surrounded by lush tropical vegetation.

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.

3. The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Forrest

CA $319

CA $359 total

includes taxes & fees

Oct 6 - Oct 7

A porch with a white railing, a bench, and a flag.

A pool area with lounge chairs and a dining table, surrounded by palm trees and a house with a porch.

A living room with a sofa, a glass coffee table, a TV, and a painting on the wall.

A two-story white house with green shutters, a wooden door, and a white picket fence.

4. The Conch House Heritage Inn

Old Town Key West, 1.3 km from Waterfront Playhouse

John

CA $270

CA $304 total

includes taxes & fees

Oct 6 - Oct 7

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 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.

5. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

Nicholas

CA $309

CA $348 total

includes taxes & fees

Oct 12 - Oct 13

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 wooden ceiling, white sofas, a patterned armchair, a glass coffee table, and a large painting on the wall.

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.

6. Alexander's Guesthouse - Adult Exclusive

Old Town Key West, 1.2 km from Waterfront Playhouse

Nestor

CA $309

CA $406 total

includes taxes & fees

Oct 6 - Oct 7

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 restaurant with multiple tables set for dining, a wine bottle, and a glass of wine on the table.

A hotel room with two beds, a ceiling fan, a large window with a view of palm trees, and a painting on the wall.

7. The Marquesa Hotel

Old Town Key West, 0.7 km from Waterfront Playhouse

Darrell

CA $483

CA $624 total

includes taxes & fees

Oct 12 - Oct 13

A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.

A lush garden with a variety of tropical plants and a paved walkway.

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.

8. Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

Christopher

CA $182

CA $236 total

includes taxes & fees

Oct 14 - Oct 15

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 pool area with lounge chairs and a wooden building with balconies.

A garden with a pond, rocks, and various plants.

9. Island City House Hotel

Historic Seaport, 0.8 km from Waterfront Playhouse

Osvaldo

CA $262

CA $295 total

includes taxes & fees

Oct 11 - Oct 12

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 modern outdoor seating area with a sofa, chairs, and a small table, surrounded by glass doors and a view of greenery.

10. Santa Maria Suites

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

Anthony

CA $396

CA $542 total

includes taxes & fees

Oct 28 - Oct 29

A room with a bed, a ceiling fan, and a window with blinds.

A room with a yellow armchair, a glass coffee table, and a view of a wooden deck and tropical plants.

A cozy outdoor seating area with a wooden bench and a table, surrounded by potted plants and a coffee and tea sign.

A spacious kitchen with wooden cabinets, a granite countertop, and a ceiling fan.

11. The Mermaid & Alligator

Old Town Key West, 1.3 km from Waterfront Playhouse

Adam

CA $328

CA $368 total

includes taxes & fees

Oct 8 - Oct 9

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 hotel room with a bed, a nightstand, a chair, a small table, and a ceiling fan.

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.

12. Ambrosia Key West

Old Town Key West, 0.7 km from Waterfront Playhouse

Tricia

CA $208

CA $234 total

includes taxes & fees

Oct 6 - Oct 7

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 balcony with white railings and a table, overlooking a beach with palm trees and a clear blue sky.

A large, two-story house with a prominent tower and a covered porch.

13. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

yessy

CA $199

CA $404 total

includes taxes & fees

Oct 26 - Oct 27

A gated entrance with lush green foliage and a white picket fence.

A covered outdoor dining area with white chairs and tables, surrounded by lush greenery and a wooden deck.

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.

14. Coco Plum Inn

Downtown Key West, 0.8 km from Waterfront Playhouse

Riley

CA $202

CA $227 total

includes taxes & fees

Oct 12 - Oct 13

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 breakfast table with a variety of food items, including fruits, pastries, and a coffee mug.

15. Westwinds Inn

Historic Seaport, 0.9 km from Waterfront Playhouse

Anthony

CA $231

CA $260 total

includes taxes & fees

Oct 6 - Oct 7

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 room with a bed, a desk, a chair, a lamp, a painting of a boat on water, and a view of the sea.

A yellow building with a door marked '7'.

16. Alexander Palms Court

Casa Marina, 1.8 km from Waterfront Playhouse

Andrew

CA $170

CA $191 total

includes taxes & fees

Oct 7 - Oct 8

A hotel with a covered entrance, multiple balconies, and palm trees.

A covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.

A room with a stone wall, a wooden bench, a cactus, and a framed painting.

A waterfront hotel with multiple balconies, a dock, and boats.

17. Opal Key Resort & Marina, Key West

Old Town Key West, 0.1 km from Waterfront Playhouse

Susan

CA $369

CA $471 total

includes taxes & fees

Oct 6 - Oct 7

A poolside area with lounge chairs, umbrellas, and a pergola.

A bright kitchen with white cabinetry, a white island, wicker pendant lights, and geometric patterned backsplash.

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 living room with a spiral staircase, a sofa, a chair, a coffee table, and a view of an outdoor seating area.

18. Ella's Cottages - Key West Historic Inns

Old Town Key West, 1.1 km from Waterfront Playhouse

tracy

CA $328

CA $441 total

includes taxes & fees

Oct 6 - Oct 7

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.

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.

The entrance to Silver Palms Inn with a reception desk, a seating area, and a glass door.

19. Silver Palms Inn & Historic Homes

Old Town Key West, 1.4 km from Waterfront Playhouse

sam

CA $127

CA $239 total

includes taxes & fees

Oct 6 - Oct 7

A covered porch with white railings, wooden benches, and a hanging light fixture.

A bedroom with a four-poster bed, a wicker chair, a wooden dresser, and a television.

A pool area with lounge chairs and a small palm tree.

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.

20. Marrero's Guest Mansion

Downtown Key West, 0.6 km from Waterfront Playhouse

Michael

CA $447

CA $503 total

includes taxes & fees

Oct 7 - Oct 8

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Compare popular hotels close to Waterfront Playhouse

Property	Star rating	Guest rating
Almond Tree Inn Hotel - Adults Only	10.0 Exceptional 1,001 reviews	View
Douglas House - Adults Only	9.8 Exceptional 548 reviews	View
The Gardens Hotel	9.8 Exceptional 1,006 reviews	View
The Conch House Heritage Inn	9.8 Exceptional 191 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,002 reviews	View

Top Waterfront Playhouse Hotel Reviews

Amsterdam's Curry Mansion Inn

8/10 Good

"Good value compared to other locations we have stayed at the past 25 years. Great location and in easy walking distance of most bars, restaurants and points of interest on the island. Room was clean and well supplied with everything you need. There is no on site host, so if you have questions or concerns you must call the guest experience manager. Everything is self service from gaining access to your room, obtaining extra towels, removing trash, etc.. Our room was upstairs in the main mansion. The only issue we had with our stay was that the stairway was not well lit at night. Somewhat dangerous!"

Weatherstation Inn

8/10 Good

"Beautiful historic property! Loved our stay. Great location within walking distance of many local attractions. Just steps away from Little Whitehouse. Loved the spa like toiletries in large shower & the breakfast pastries from local bakery were wonderful as well."

La Concha Key West, Autograph Collection

10/10 Excellent

"The location on Duval is perfect, the hotel is top notch, and the staff can't do enough for you. Everyone from the GM to the housekeeping staff always wish you a good day and ask if there is anything they can do for you no matter how many times they see you. Perfect place to stay in Key West and we will be returning for sure!"

Ocean Key Resort - A Noble House Resort

10/10 Excellent

"Staff was very attentive to our needs and the hotel was very clean."

The Marker Key West Harbor Resort

10/10 Excellent

"Clean.helpful staff.good a/c.good location.will definitely stay here again."

Heart of Downtown Key West Cottage With Off-Street Parking

10/10 Excellent

"Excellent location, private parking, and great communication from host!"

Heron House - Adult Only

10/10 Excellent

"I’ve been to Key West many times, the Heron House is by far the best property we have stayed at. Perfect location to walk to Duval, Mallory Square. Great pool, friendly staff."

DARLING OF DUVAL @ OLD TOWN Cottage + Spa + Last Key White Glove Service...

10/10 Excellent

"Beautiful and private guest house close to Duval street and walking distance from restaurants and other attractions. Loved it!"

The Marquesa Hotel

10/10 Excellent

"Fabulous room with the most comfortable bed and pillows. Staff were so friendly and helpful. The pool area cosy and welcoming. Oasis of paradise. Overall our stay at this hotel was fabulous. Mark on reception was very welcoming."

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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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 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.

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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 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.

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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 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.

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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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Key West Vacation Rentals

Find hotels near Waterfront Playhouse, Key West from CA $180

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Waterfront Playhouse hotels

1. Almond Tree Inn Hotel - Adults Only

2. Douglas House - Adults Only

3. The Gardens Hotel

4. The Conch House Heritage Inn

5. Orchid Key Inn - Adults Only

6. Alexander's Guesthouse - Adult Exclusive

7. The Marquesa Hotel

8. Duval House

9. Island City House Hotel

10. Santa Maria Suites

11. The Mermaid & Alligator

12. Ambrosia Key West

13. Southernmost House - Adult Exclusive

14. Coco Plum Inn

15. Westwinds Inn

16. Alexander Palms Court

17. Opal Key Resort & Marina, Key West

18. Ella's Cottages - Key West Historic Inns

19. Silver Palms Inn & Historic Homes

20. Marrero's Guest Mansion

Compare popular hotels close to Waterfront Playhouse

Top Waterfront Playhouse Hotel Reviews

Amsterdam's Curry Mansion Inn

Weatherstation Inn

La Concha Key West, Autograph Collection

Ocean Key Resort - A Noble House Resort

The Marker Key West Harbor Resort

Heart of Downtown Key West Cottage With Off-Street Parking

Heron House - Adult Only

**DARLING OF DUVAL @ OLD TOWN** Cottage + Spa + Last Key White Glove Service...

The Marquesa Hotel

Other attractions near Waterfront Playhouse

Key West Shipwreck Museum

Mallory Square

Mallory Dock

Museum of Art & History at the Custom House

Audubon House and Tropical Gardens

Mel Fisher Maritime Museum

Roy John-Karl Gallery

Sloppy Joe's Bar

Frequently asked questions

Explore a world of travel with Expedia

DARLING OF DUVAL @ OLD TOWN Cottage + Spa + Last Key White Glove Service...