The 10 Best Hotels Near Waterfront Playhouse, Key West from CA $227

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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 building with a sign reading "ALMOND Frog & Toad Inn" and a "VACANCY" sign below it.

1. Almond Tree Inn Hotel - Adults Only

Downtown Key West, 1.3 km from Waterfront Playhouse

John

CA $301

CA $338 total

includes taxes & fees

Oct 13 - Oct 14

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.

An outdoor patio with a table and chairs, surrounded by lush greenery and string lights.

2. Douglas House - Adults Only

Uptown - Upper Duval, 1.4 km from Waterfront Playhouse

Maricela

CA $191

CA $236 total

includes taxes & fees

Oct 7 - Oct 8

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

A couple walking along a poolside pathway surrounded by lush greenery.

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.

3. The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Forrest

CA $373

CA $420 total

includes taxes & fees

Oct 7 - Oct 8

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.

4. H2O Suites - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Carmen

CA $455

CA $608 total

includes taxes & fees

Oct 12 - Oct 13

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.

5. 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 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 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 neon sign for Orchid Key Inn with a 'VACANCY' sign below it.

6. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

Nicholas

CA $292

CA $328 total

includes taxes & fees

Oct 13 - Oct 14

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 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.

7. 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 7 - Oct 8

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

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

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.

8. The Conch House Heritage Inn

Old Town Key West, 1.3 km from Waterfront Playhouse

John

CA $305

CA $343 total

includes taxes & fees

Oct 7 - Oct 8

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 two-story building with a white picket fence, a mailbox, and a small tree in front.

A hallway with a white door, a wooden bench, a blue sofa, and a staircase with a white railing.

9. Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

Christopher

CA $210

CA $267 total

includes taxes & fees

Oct 13 - Oct 14

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 covered walkway with a wooden ceiling, white railings, and a brick path.

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

10. 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 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 poolside area with lounge chairs, a covered seating area, and a small pool.

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 $341

CA $384 total

includes taxes & fees

Oct 8 - Oct 9

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.

12. 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 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 cozy living room with a wooden ceiling, a sofa set, two side tables with lamps, and framed artwork on the wall.

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.

13. Ambrosia Key West

Old Town Key West, 0.7 km from Waterfront Playhouse

Tricia

CA $209

CA $235 total

includes taxes & fees

Oct 11 - Oct 12

A reception area with a curved marble counter, ceiling fans, large windows, and a staircase.

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.

A poolside area with lounge chairs and a clear blue pool surrounded by lush tropical vegetation.

14. Westwinds Inn

Historic Seaport, 0.9 km from Waterfront Playhouse

Anthony

CA $231

CA $260 total

includes taxes & fees

Oct 8 - Oct 9

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 hotel room with a large bed, two bedside tables, a ceiling fan, and two framed pictures on the wall.

A swimming pool with lounge chairs, a covered deck, and a view of lush greenery.

15. 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 room with a door featuring horizontal blinds, a visible outdoor view through the window, and a patterned carpet.

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'.

A pool area with a circular pool, lounge chairs, and a gazebo.

16. Alexander Palms Court

Casa Marina, 1.8 km from Waterfront Playhouse

Andrew

CA $202

CA $227 total

includes taxes & fees

Oct 11 - Oct 12

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

A wooden bench with a cushion and a small table, surrounded by bamboo plants and a wooden deck.

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

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

17. Ella's Cottages - Key West Historic Inns

Old Town Key West, 1.1 km from Waterfront Playhouse

tracy

CA $357

CA $473 total

includes taxes & fees

Oct 7 - Oct 8

A swimming pool with water splashing, surrounded by palm trees and a building in the background.

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 two-story yellow house with a porch, white railings, and green shutters.

A hotel with a pool, bicycles, and lush greenery.

18. 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 7 - Oct 8

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

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 pool area with lounge chairs and a small palm tree.

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

19. Marrero's Guest Mansion

Downtown Key West, 0.6 km from Waterfront Playhouse

Michael

CA $447

CA $503 total

includes taxes & fees

Oct 12 - Oct 13

A green house with a white porch, a flag, and a sign advertising a property for sale.

A covered porch with wicker furniture, potted plants, and a view of the house.

A bedroom with a large bed, a sofa, a nightstand, and a painting on the wall.

A bathroom with a vanity, a mirror, and a window with blinds.

20. L'Habitation Guest House - Adults Only

Historic Seaport, 0.5 km from Waterfront Playhouse

Richard

CA $243

CA $273 total

includes taxes & fees

Oct 26 - Oct 27

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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 1,003 reviews	View
Douglas House - Adults Only	9.8 Exceptional 549 reviews	View
The Gardens Hotel	9.8 Exceptional 1,006 reviews	View
H2O Suites - Adults Only	9.8 Exceptional 663 reviews	View
The Marquesa Hotel	9.8 Exceptional 1,000 reviews	View

Top Waterfront Playhouse Hotel Reviews

Amsterdam's Curry Mansion Inn

8/10 Good

"Great location & easy check-in! We enjoyed our room and the beautiful inn! Improvements would be: communication - we did not see a single person who works there the entire stay and no response to inquiries. For example, we had a great jacuzzi tub but could not use it as there was no plug, Door to balcony was blocked and could not open. Laundry was always full of inn towels and sheets. Side doors were left open, so security was limited. Despite these things, we most likely would stay again!"

Pier House Resort & Spa

10/10 Excellent

"Location is great. Room was very clean. Beds were great and the rain shower was amazing."

The Marker Key West Harbor Resort

10/10 Excellent

"Very nice room with lots of space. Comfortable bed. Nice pool area with an outdoor bar and live music/entertainment. Good food. Friendly, helpful staff. Great location next to the historic seaport and 3 blocks from Duval Street. Lots of shops, restaurants, and bars within easy walking distance. Would definitely stay here again."

La Concha Key West, Autograph Collection

10/10 Excellent

"Wonderful place at a great location"

Ridley House - Key West Historic Inns

10/10 Excellent

"Clean rooms and the staff was great"

Ocean Key Resort - A Noble House Resort

10/10 Excellent

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

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!"

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 $227

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. H2O Suites - Adults Only

5. The Marquesa Hotel

6. Orchid Key Inn - Adults Only

7. Alexander's Guesthouse - Adult Exclusive

8. The Conch House Heritage Inn

9. Duval House

10. Island City House Hotel

11. The Mermaid & Alligator

12. Southernmost House - Adult Exclusive

13. Ambrosia Key West

14. Westwinds Inn

15. Coco Plum Inn

16. Alexander Palms Court

17. Ella's Cottages - Key West Historic Inns

18. Silver Palms Inn & Historic Homes

19. Marrero's Guest Mansion

20. L'Habitation Guest House - Adults Only

Compare popular hotels close to Waterfront Playhouse

Top Waterfront Playhouse Hotel Reviews

Amsterdam's Curry Mansion Inn

Pier House Resort & Spa

The Marker Key West Harbor Resort

La Concha Key West, Autograph Collection

Ridley House - Key West Historic Inns

Ocean Key Resort - A Noble House 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...

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...