The Best Hotels Closest to Waterfront Playhouse in Key West for 2026

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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

Downtown Key West, 1.3 km from Waterfront Playhouse

Teresa

₩308,470

₩347,029 total

includes taxes & fees

Oct 27 - Oct 28

A tropical outdoor area with palm trees, hanging plants, and string lights.

A wooden deck with lush greenery and a pool area.

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.

2. Douglas House - Adults Only

Uptown - Upper Duval, 1.4 km from Waterfront Playhouse

Maricela

₩210,000

₩259,875 total

includes taxes & fees

Oct 27 - Oct 28

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 modern hotel with a prominent glass facade, palm trees, and a clear sky.

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.

3. H2O Suites - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Kimberly

₩417,529

₩559,782 total

includes taxes & fees

Oct 28 - Oct 29

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

A building with a neon sign that reads "Orchid Key Inn."

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

4. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

ben

₩281,904

₩317,142 total

includes taxes & fees

Oct 27 - Oct 28

A gated entrance to Villas Key West with a brick pathway leading to the gate.

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'.

A swimming pool with a hot tub, surrounded by a wooden deck and lush greenery.

5. Key West Villas

Downtown Key West, 0.9 km from Waterfront Playhouse

Margaret

₩406,103

₩456,883 total

includes taxes & fees

Nov 18 - Nov 19

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 bar area with a counter, chairs, and a clock.

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

6. The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Gisele

₩357,886

₩402,622 total

includes taxes & fees

Oct 27 - Oct 28

A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.

A narrow room with a bed, a potted plant, and a window with blinds.

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.

7. Alexander's Guesthouse - Adult Exclusive

Old Town Key West, 1.2 km from Waterfront Playhouse

Nestor

₩322,247

₩418,176 total

includes taxes & fees

Oct 28 - Oct 29

A two-story house with a covered porch, a brick pathway, and a large tree.

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.

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

8. The Marquesa Hotel

Old Town Key West, 0.7 km from Waterfront Playhouse

Josh

₩571,020

₩717,276 total

includes taxes & fees

Oct 26 - Oct 27

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 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.

9. The Conch House Heritage Inn

Old Town Key West, 1.3 km from Waterfront Playhouse

Jennifer

₩380,148

₩427,666 total

includes taxes & fees

Oct 25 - Oct 26

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 compact kitchen with wooden cabinets, a microwave, stove, and refrigerator. There is a dining area with a table and chairs, and a sofa.

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

10. Island City House Hotel

Historic Seaport, 0.8 km from Waterfront Playhouse

Elise

₩264,027

₩297,031 total

includes taxes & fees

Oct 25 - Oct 26

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 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.

11. Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

Cathrine

₩211,637

₩266,710 total

includes taxes & fees

Oct 25 - Oct 26

A pool area with lounge chairs 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.

A neatly made bed with patterned pillows, a bedside table with a bottle and glasses, and a window with orchids.

A sign for Santa Maria Resort surrounded by lush greenery and palm trees.

12. Santa Maria Suites

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

Anthony

₩397,984

₩537,578 total

includes taxes & fees

Oct 26 - Oct 27

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 two-story house with a white exterior, a green roof, and a staircase leading to the upper floor.

A bedroom with a bed, two bedside lamps, a ceiling fan, and a view of a balcony with plants.

13. Westwinds Inn

Historic Seaport, 0.9 km from Waterfront Playhouse

Anthony

₩215,630

₩242,584 total

includes taxes & fees

Oct 25 - Oct 26

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

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 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.

14. Ambrosia Key West

Old Town Key West, 0.7 km from Waterfront Playhouse

RICHARD

₩289,569

₩325,765 total

includes taxes & fees

Oct 25 - Oct 26

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 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.

15. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

Amy

₩238,964

₩437,701 total

includes taxes & fees

Oct 27 - Oct 28

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

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

16. Coco Plum Inn

Downtown Key West, 0.8 km from Waterfront Playhouse

August

₩266,556

₩299,872 total

includes taxes & fees

Oct 25 - Oct 26

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

17. Silver Palms Inn & Historic Homes

Old Town Key West, 1.4 km from Waterfront Playhouse

sam

₩118,597

₩223,284 total

includes taxes & fees

Oct 25 - Oct 26

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

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.

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

18. Opal Key Resort & Marina, Key West

Old Town Key West, 0.1 km from Waterfront Playhouse

Ann

₩344,742

₩440,258 total

includes taxes & fees

Oct 26 - Oct 27

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

A garden with a stone pathway, a wooden fence, and various tropical plants.

19. Alexander Palms Court

Casa Marina, 1.8 km from Waterfront Playhouse

Brenda

₩238,391

₩268,207 total

includes taxes & fees

Oct 21 - Oct 22

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.

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

An open door leading to a pool area with a wicker chair and a sofa inside a room with a view of the pool.

20. Ella's Cottages - Key West Historic Inns

Old Town Key West, 1.1 km from Waterfront Playhouse

Henry

₩332,763

₩441,750 total

includes taxes & fees

Oct 25 - Oct 26

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Compare popular hotels close to Waterfront Playhouse

Property	Property class	Guest rating
Almond Tree Inn Hotel - Adults Only	10.0 Exceptional 1,002 reviews	View
Douglas House - Adults Only	9.8 Exceptional 562 reviews	View
H2O Suites - Adults Only	9.8 Exceptional 669 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,001 reviews	View
Key West Villas	9.8 Exceptional 279 reviews	View

Top Waterfront Playhouse Hotel Reviews

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!"

Weatherstation Inn

10/10 Excellent

"This place is excellent. Very quiet. Nice amenities. Close to old town"

Hyatt Centric Key West Resort and Spa

10/10 Excellent

"Excellent all around."

Ambrosia Key West

10/10 Excellent

"Beautiful and quiet. Staff was very helpful"

Simonton Court Historic Inn & Cottages

10/10 Excellent

"This was a perfect couples oasis. The hotel is within walking distance to all the major restaurants and attractions. The Continental breakfast was a perfect way to start the day. The staff was extremely friendly. Having access to the pools 24/7 was great since it was hot."

Opal Key Resort & Marina, Key West

10/10 Excellent

"Great hotel will definitely stay again"

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!"

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."

Heron House - Adult Only

10/10 Excellent

"The property was wonderfully located, clean, and beautiful. Highly recommend."

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.

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.

Find hotels near Waterfront Playhouse, Key West from ₩223,284

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

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Our top choices for Waterfront Playhouse hotels

1. Almond Tree Inn Hotel - Adults Only

2. Douglas House - Adults Only

3. H2O Suites - Adults Only

4. Orchid Key Inn - Adults Only

5. Key West Villas

6. The Gardens Hotel

7. Alexander's Guesthouse - Adult Exclusive

8. The Marquesa Hotel

9. The Conch House Heritage Inn

10. Island City House Hotel

11. Duval House

12. Santa Maria Suites

13. Westwinds Inn

14. Ambrosia Key West

15. Southernmost House - Adult Exclusive

16. Coco Plum Inn

17. Silver Palms Inn & Historic Homes

18. Opal Key Resort & Marina, Key West

19. Alexander Palms Court

20. Ella's Cottages - Key West Historic Inns

Compare popular hotels close to Waterfront Playhouse

Top Waterfront Playhouse Hotel Reviews

Ocean Key Resort - A Noble House Resort

Weatherstation Inn

Hyatt Centric Key West Resort and Spa

Ambrosia Key West

Simonton Court Historic Inn & Cottages

Opal Key Resort & Marina, Key West

Pier House Resort & Spa

Ridley House - Key West Historic Inns

Heron House - Adult Only

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