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

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.

1. Almond Tree Inn Hotel - Adults Only

Downtown Key West, 1.3 km from Waterfront Playhouse

John

SAR 1,044

SAR 1,174 total

includes taxes & fees

27 Oct - 28 Oct

A modern outdoor area with a pool, lounge chairs, and a bar area.

A modern hotel room with a bed, sofa, coffee table, and artwork.

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.

2. H2O Suites - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Corey

SAR 1,235

SAR 1,642 total

includes taxes & fees

27 Oct - 28 Oct

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

A spacious bedroom with a large bed, a sitting area with a sofa and armchairs, and a dining area with a table and chairs.

3. The Conch House Heritage Inn

Old Town Key West, 1.3 km from Waterfront Playhouse

Jennifer

SAR 1,072

SAR 1,206 total

includes taxes & fees

26 Oct - 27 Oct

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 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."

4. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

ben

SAR 954

SAR 1,073 total

includes taxes & fees

27 Oct - 28 Oct

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 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.

5. The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Gisele

SAR 1,262

SAR 1,420 total

includes taxes & fees

27 Oct - 28 Oct

A modern interior with a staircase, a sofa set, a wooden table, and a television.

A spacious room with a large bed, a sofa, a chair, a small table, and a television.

A courtyard with two green lounge chairs, a palm tree, and a building with a white facade and lattice window design.

A pathway flanked by lush green foliage leading to a gated entrance.

6. Simonton Court Historic Inn & Cottages

Historic Seaport, 0.5 km from Waterfront Playhouse

William

SAR 634

SAR 714 total

includes taxes & fees

25 Oct - 26 Oct

A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.

A two-story building with a porch, a sign reading "The Grand Guesthouse," and a purple flag.

A bedroom with a bed, nightstand, lamp, air conditioning unit, and a no smoking sign.

A covered outdoor area with a wooden staircase, seating, and potted plants.

7. The Grand Guesthouse

Old Town Key West, 1.7 km from Waterfront Playhouse

Justyn

SAR 591

SAR 758 total

includes taxes & fees

27 Oct - 28 Oct

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

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.

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

8. Island City House Hotel

Historic Seaport, 0.8 km from Waterfront Playhouse

Elise

SAR 799

SAR 899 total

includes taxes & fees

27 Oct - 28 Oct

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

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

9. Santa Maria Suites

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

Anthony

SAR 1,122

SAR 1,516 total

includes taxes & fees

26 Oct - 27 Oct

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 swimming pool with a mural of a dolphin and a butterfly, surrounded by lounge chairs and palm trees.

10. Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

Cathrine

SAR 634

SAR 794 total

includes taxes & fees

26 Oct - 27 Oct

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

SAR 898

SAR 1,011 total

includes taxes & fees

19 Oct - 20 Oct

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.

12. Silver Palms Inn & Historic Homes

Old Town Key West, 1.4 km from Waterfront Playhouse

sam

SAR 334

SAR 630 total

includes taxes & fees

25 Oct - 26 Oct

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 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.

13. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

Amy

SAR 672

SAR 1,231 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

A wicker outdoor seating area with two chairs and a table, surrounded by lush tropical foliage.

14. Ambrosia Key West

Old Town Key West, 0.7 km from Waterfront Playhouse

RICHARD

SAR 847

SAR 953 total

includes taxes & fees

10 Nov - 11 Nov

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

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

SAR 559

SAR 629 total

includes taxes & fees

27 Oct - 28 Oct

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 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.

16. Coco Plum Inn

Downtown Key West, 0.8 km from Waterfront Playhouse

Riley

SAR 752

SAR 845 total

includes taxes & fees

19 Oct - 20 Oct

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.

17. Alexander Palms Court

Casa Marina, 1.8 km from Waterfront Playhouse

Andrew

SAR 844

SAR 950 total

includes taxes & fees

19 Oct - 20 Oct

A covered outdoor area with a pool, wicker furniture, and a red umbrella.

18. The Independent Inn-Adults only

Historic Seaport, 1.1 km from Waterfront Playhouse

Michael

SAR 566

SAR 767 total

includes taxes & fees

18 Oct - 19 Oct

A building with a white exterior, a large red awning, and a gated entrance.

A paved pathway lined with various plants and trees, leading to a building with a beige exterior.

A small, enclosed porch with a chair and a table, surrounded by lush greenery and a white lattice fence.

A spacious kitchen with a dining area, large windows, and a view of the outdoors.

19. Authors of Key West Guest House

The Meadows, 1.5 km from Waterfront Playhouse

Robbie

SAR 571

SAR 642 total

includes taxes & fees

27 Oct - 28 Oct

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.

20. Opal Key Resort & Marina, Key West

Old Town Key West, 0.1 km from Waterfront Playhouse

Susan

SAR 972

SAR 1,241 total

includes taxes & fees

26 Oct - 27 Oct

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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 1,001 reviews	View
H2O Suites - Adults Only	9.8 Exceptional 667 reviews	View
The Conch House Heritage Inn	9.8 Exceptional 194 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,000 reviews	View
The Gardens Hotel	9.8 Exceptional 1,001 reviews	View

Hotels recommended for families near Waterfront Playhouse

A pool area with lounge chairs and a cabana.

A dining area with a glass table, clear glass bottles, a bowl of fruit, and a wicker chair.

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

A waterfront hotel with a long pier, multiple balconies, and a view of the ocean.

Ocean Key Resort - A Noble House Resort

Key West Historic District

SAR 1,122

SAR 1,566 total

includes taxes & fees

18 Oct - 19 Oct

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

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.

A balcony with a view of the ocean, a sofa, and a massage table.

A view through a white-framed window with a decorative white fence, leading to a tiled patio area with a round table.

Pier House Resort & Spa

Key West Historic District

SAR 973

SAR 1,357 total

includes taxes & fees

2 Nov - 3 Nov

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

A marina with jet skis docked in front of a hotel with a dock and a boat in the background.

A balcony with a view of the ocean, a table, chairs, and a railing.

A beach wedding setup with white chairs, a wooden arch, and lanterns.

Hyatt Centric Key West Resort and Spa

Key West Historic District

SAR 949

SAR 1,330 total

includes taxes & fees

2 Nov - 3 Nov

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

A modern kitchen with white cabinetry, a central island, and a view of the outdoors.

A hotel room with a large bed, a sitting area, and multiple bookshelves filled with books.

A pool area with lounge chairs, a small table, and a thatched umbrella.

Ridley House - Key West Historic Inns

Key West Historic District

SAR 751

SAR 1,034 total

includes taxes & fees

25 Oct - 26 Oct

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 marina with various boats docked, including a green and white boat named 'Jolly Roger'.

A tropical setting with palm trees and a building with a white facade and dark roof.

The Marker Key West Harbor Resort

Key West Historic District

SAR 707

SAR 1,031 total

includes taxes & fees

25 Oct - 26 Oct

A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.

A cozy cabin with a wooden interior, a bed, a TV, and a kitchenette.

A pool area with lounge chairs and umbrellas, surrounded by buildings with balconies and a clear blue sky.

A spacious living area with a gray sofa, wooden staircase, and a kitchen in the background.

Eden House

Key West Historic District

SAR 532

SAR 670 total

includes taxes & fees

28 Oct - 29 Oct

Island City House Hotel

Key West Historic District

SAR 799

SAR 899 total

includes taxes & fees

27 Oct - 28 Oct

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.

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.

Ella's Cottages - Key West Historic Inns

Old Town Key West

SAR 751

SAR 1,034 total

includes taxes & fees

18 Oct - 19 Oct

Top Waterfront Playhouse Hotel Reviews

Pier House Resort & Spa

10/10 Excellent

"This resort has everything with the best hospitality! I highly recommend this resort for anyone that wants to enjoy Key West with total relaxation! 😎"

The Marquesa Hotel

10/10 Excellent

"Fantastic hotel, very clean, helpful staff, awesome Key West vibes, and great location! We were so happy with everything- breakfast at the Cafe featured friendly staff and the best bacon EVER, pool was delightful, room was great. Highly recommend if you are coming to Key West!"

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."

Opal Key Resort & Marina, Key West

10/10 Excellent

"The hotel location, cleanliness and view are awesome. No complaints about anything. The unlimited cold water bottles were icing on the cake. If I’m so happy with a partial sea view room, I’ll be even happier with an oceanfront room. Maybe next time."

Ridley House - Key West Historic Inns

10/10 Excellent

"My husband and I loved our stay at Ridley house. The property is beautiful and well maintained and our room was a nice size with a comfortable bed. We were served a breakfast spread every morning with plenty of food choices. The manager Angel was so helpful and knowledgeable, and he asked us every time he saw us if we needed anything. I don't remember the person's name who filled in for him, but she helped us set up rentals and a sandbar sunset cruise. We used the pool every day, to soak up some sun before heading out for the day. Duval street was an easy two blocks away."

Weatherstation Inn

10/10 Excellent

"We liked how close the Inn was to everything we wanted to do. Very walkable and in a quiet area. Staff was friendly, the breakfast bake goods were great."

Hyatt Vacation Club at Sunset Harbor, Key West

10/10 Excellent

"Had an excellent time. Absolutely beautiful hotel and amazing staff!"

Heart of Downtown Key West Cottage With Off-Street Parking

10/10 Excellent

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

Ocean Key Resort & Spa

10/10 Excellent

"This resort was amazing! The best area and most beautiful in Old Town. Craig and the whole staff were lovely! Would def return!"

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)

You can spend an afternoon studying the exhibits at Key West Shipwreck Museum during your trip to Key West. In the area, take in the lively festivals and beautiful sunsets.

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Mallory Square

9.2/10 (15,939 reviews)

You can find out about the history of Key West with a stop at Mallory Square. Stroll along the area's seaside or experience its lively festivals.

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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)

You can spend an afternoon exploring the galleries in Audubon House and Tropical Gardens in Key West. Discover the area's lively bars and its lively festivals.

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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)

You can spend time studying the exhibits at Mel Fisher Maritime Museum in Key West. Wander the seaside and beautiful beaches in the area.

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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 SAR 629

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Star rating

Guest rating

Our top choices for Waterfront Playhouse hotels

1. Almond Tree Inn Hotel - Adults Only

2. H2O Suites - Adults Only

3. The Conch House Heritage Inn

4. Orchid Key Inn - Adults Only

5. The Gardens Hotel

6. Simonton Court Historic Inn & Cottages

7. The Grand Guesthouse

8. Island City House Hotel

9. Santa Maria Suites

10. Duval House

11. The Mermaid & Alligator

12. Silver Palms Inn & Historic Homes

13. Southernmost House - Adult Exclusive

14. Ambrosia Key West

15. Westwinds Inn

16. Coco Plum Inn

17. Alexander Palms Court

18. The Independent Inn-Adults only

19. Authors of Key West Guest House

20. Opal Key Resort & Marina, Key West

Compare popular hotels close to Waterfront Playhouse

Hotels recommended for families near Waterfront Playhouse

Ocean Key Resort - A Noble House Resort

Pier House Resort & Spa

Hyatt Centric Key West Resort and Spa

Ridley House - Key West Historic Inns

The Marker Key West Harbor Resort

Eden House

Island City House Hotel

Ella's Cottages - Key West Historic Inns

Top Waterfront Playhouse Hotel Reviews

Pier House Resort & Spa

The Marquesa Hotel

La Concha Key West, Autograph Collection

Opal Key Resort & Marina, Key West

Ridley House - Key West Historic Inns

Weatherstation Inn

Hyatt Vacation Club at Sunset Harbor, Key West

Heart of Downtown Key West Cottage With Off-Street Parking

Ocean Key Resort & Spa

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