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Find hotels near Waterfront Playhouse, Key West from CA $203

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    • Check prices for these dates

    Check prices for these dates, December 13–14, 2026

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    Our top choices for Waterfront Playhouse hotels

    1. Almond Tree Inn Hotel - Adults Only

    A swimming pool with lounge chairs, surrounded by palm trees and greenery.

    2. Douglas House - Adults Only

    A wooden deck leading to a pool area with a building in the background.

    3. Orchid Key Inn - Adults Only

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

    4. Ambrosia Key West

    A rectangular pool with a white deck, surrounded by lush greenery and a gazebo.

    5. Alexander Palms Court

    A garden pathway leading to a building with a door, surrounded by lush greenery and a palm tree.

    6. Silver Palms Inn & Historic Homes

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

    7. Opal Key Resort & Marina, Key West

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

    8. The Marker Key West Harbor Resort

    A large, white, two-story building with a balcony and a sign reading "The Marker Resort."

    9. Hyatt Centric Key West Resort and Spa

    A hotel with a swimming pool, balconies, and a view of the sea.

    10. Heron House - Adult Only

    A building with a sign reading "HERON HOUSE OFFICE" at the entrance, surrounded by lush greenery and palm trees.

    11. Duval Gardens - Adults Only

    A two-story building with a white picket fence, palm trees, and a sign that reads 'DUVAL GARDENS.'

    12. The Key West Hotel

    A narrow brick pathway flanked by large potted plants and a pink wall.

    13. Seascape Tropical Inn - Adult Exclusive

    A pool area with lounge chairs, a hot tub, and a deck with a railing.

    14. Eden House

    A porch with white railings, a rocking chair, and a covered area with a teal awning.

    15. Tranquility Guest House

    A swimming pool with clear water, surrounded by lush greenery and palm trees.

    16. The Independent Inn

    Room

    17. The Saint Hotel Key West, Autograph Collection, Adult Only

    A pool area with lounge chairs and a staircase leading to a balcony.

    18. Duval Inn

    A gated entrance with a gazebo, palm trees, and a brick pathway leading to a building with a red roof.

    19. Coconut Beach Resort

    A pool area with palm trees, lounge chairs, and umbrellas.

    20. Southernmost Beach Resort and Guesthouses

    A deck with sun loungers and a railing overlooking the sea.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Compare popular hotels close to Waterfront Playhouse

    PropertyStar ratingGuest ratingBreakfast includedPoolSpaPet-friendlyWiFi included
    A swimming pool with lounge chairs, surrounded by palm trees and greenery.
    Almond Tree Inn Hotel - Adults Only    		10.0Exceptional1,000 reviewsView
    A wooden deck leading to a pool area with a building in the background.
    Douglas House - Adults Only    		9.8Exceptional593 reviewsView
    A pool area with lounge chairs and a table, surrounded by palm trees.
    Orchid Key Inn - Adults Only    		9.8Exceptional1,000 reviewsView
    A rectangular pool with a white deck, surrounded by lush greenery and a gazebo.
    Ambrosia Key West    		9.4Exceptional1,000 reviewsView
    A garden pathway leading to a building with a door, surrounded by lush greenery and a palm tree.
    Alexander Palms Court    		9.4Exceptional1,007 reviewsView

    Hotels recommended for families near Waterfront Playhouse

    Ocean Key Resort - A Noble House Resort

    A balcony with a table set for breakfast, overlooking the sea.

    Pier House Resort & Spa

    A beachfront hotel with a covered patio, palm trees, and a boat on the sand.

    Ridley House - Key West Historic Inns

    A white building with green shutters and a white picket fence.

    Hyatt Centric Key West Resort and Spa

    A hotel with a swimming pool, balconies, and a view of the sea.

    The Marker Key West Harbor Resort

    A large, white, two-story building with a balcony and a sign reading "The Marker Resort."

    Island City House Hotel

    A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.

    Eden House

    A porch with white railings, a rocking chair, and a covered area with a teal awning.

    Banana's Foster Guesthouse

    A pool area with a blue table and chairs, surrounded by palm trees and a white building.

    Other attractions near Waterfront Playhouse

    A historic building with a tall tower, palm trees, and a vintage trolley.

    Key West Shipwreck Museum

    Rating: 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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    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

    Rating: 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

    Rating: 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

    Rating: 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

    Rating: 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

    Rating: 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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    Top Waterfront Playhouse Hotel Reviews

    Artist House Key West

    A two-story building with a balcony, white columns, and hanging flower baskets.

    The Gardens Hotel

    A white house with blue shutters, a front porch, and potted plants.

    Simonton Court Historic Inn & Cottages

    A rooftop pool with clear water, surrounded by palm trees and lounge chairs.

    The Marquesa Hotel

    A poolside area with a swimming pool, a staircase leading to a deck, and a building with multiple windows and balconies.

    Key West Villas

    A covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.

    Orchid Key Inn - Adults Only

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

    Douglas House - Adults Only

    A wooden deck leading to a pool area with a building in the background.

    Island City House Hotel

    A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.

    H2O Suites - Adults Only

    An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.

    Tropical Inn

    A pool area with lounge chairs and candles, surrounded by palm trees and a building in the background.

    L'Habitation Guest House - Adults Only

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

    The Mermaid & Alligator

    A covered porch with wicker furniture, potted plants, and a ceiling fan.

    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.

    Where can I learn more about changing or cancelling my trip in the area near Waterfront Playhouse?

    To access more information about rescheduling or cancelling your stay near Waterfront Playhouse, go to https://www.expedia.com/service/.

    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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