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

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

Teresa

SAR 1,033

SAR 1,162 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

SAR 591

SAR 731 total

includes taxes & fees

27 Oct - 28 Oct

A bottle of Marc's Reserve 12 FL. OZ. on a coaster with a metal table.

A front door with purple shutters, a small porch, and a doormat with 'The Artist House Circa 1890' text.

A potted yellow orchid plant in a garden setting with a brick pathway, palm trees, and a white building in the background.

A pool with a lion head sculpture in the center.

3. Artist House Key West

Historic Seaport, 0.5 km from Waterfront Playhouse

Debbie

SAR 745

SAR 838 total

includes taxes & fees

29 Oct - 30 Oct

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

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

A pool area with a clear view of a house in the background, surrounded by palm trees and greenery.

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

4. Simonton Court Historic Inn & Cottages

Historic Seaport, 0.5 km from Waterfront Playhouse

William

SAR 634

SAR 713 total

includes taxes & fees

27 Oct - 28 Oct

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

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

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

5. H2O Suites - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Corey

SAR 1,174

SAR 1,574 total

includes taxes & fees

28 Oct - 29 Oct

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 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.

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

A covered porch with wicker furniture, a large potted plant, and a sign for Villas Key West.

7. Key West Villas

Downtown Key West, 0.9 km from Waterfront Playhouse

Margaret

SAR 1,145

SAR 1,288 total

includes taxes & fees

18 Nov - 19 Nov

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

8. Alexander's Guesthouse - Adult Exclusive

Old Town Key West, 1.2 km from Waterfront Playhouse

Nestor

SAR 909

SAR 1,179 total

includes taxes & fees

28 Oct - 29 Oct

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

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

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

9. The Marquesa Hotel

Old Town Key West, 0.7 km from Waterfront Playhouse

Josh

SAR 1,528

SAR 1,930 total

includes taxes & fees

3 Nov - 4 Nov

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.

10. 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

25 Oct - 26 Oct

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

11. Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

Cathrine

SAR 634

SAR 794 total

includes taxes & fees

25 Oct - 26 Oct

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.

12. Island City House Hotel

Historic Seaport, 0.8 km from Waterfront Playhouse

Elise

SAR 816

SAR 918 total

includes taxes & fees

21 Oct - 22 Oct

A pool area with lounge chairs and palm trees.

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.

A reception area with a modern design, featuring a reception desk, a sofa, and a potted plant.

13. 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 large, ornate hotel with a pool, palm trees, and a view of the ocean.

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

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.

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

A room with a ceiling fan, an air conditioning unit, a window with blinds, a sofa with patterned cushions, a small round table, and a floor lamp.

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.

15. L'Habitation Guest House - Adults Only

Historic Seaport, 0.5 km from Waterfront Playhouse

Richard

SAR 638

SAR 718 total

includes taxes & fees

28 Oct - 29 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.

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.

16. Ella's Cottages - Key West Historic Inns

Old Town Key West, 1.1 km from Waterfront Playhouse

Henry

SAR 863

SAR 1,161 total

includes taxes & fees

20 Oct - 21 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.

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

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

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

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

18. Ambrosia Key West

Old Town Key West, 0.7 km from Waterfront Playhouse

RICHARD

SAR 816

SAR 918 total

includes taxes & fees

25 Oct - 26 Oct

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 white colonial-style building with a balcony, surrounded by palm trees and a white picket fence.

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

19. Coco Plum Inn

Downtown Key West, 0.8 km from Waterfront Playhouse

August

SAR 752

SAR 845 total

includes taxes & fees

20 Oct - 21 Oct

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

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

20. Westwinds Inn

Historic Seaport, 0.9 km from Waterfront Playhouse

Anthony

SAR 608

SAR 684 total

includes taxes & fees

25 Oct - 26 Oct

View all properties

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 560 reviews	View
Artist House Key West	9.8 Exceptional 463 reviews	View
Simonton Court Historic Inn & Cottages	9.8 Exceptional 1,004 reviews	View
H2O Suites - Adults Only	9.8 Exceptional 668 reviews	View

Hotels recommended for families near Waterfront Playhouse

A pool area with lounge chairs and a cabana.

A hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.

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

20 Oct - 21 Oct

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

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

A resort with a beach, a dock, and a water view.

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

Pier House Resort & Spa

Key West Historic District

SAR 990

SAR 1,376 total

includes taxes & fees

2 Nov - 3 Nov

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

A brick pathway leading to a green door, surrounded by lush tropical plants and a white fence.

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

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

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.

A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.

Hyatt Centric Key West Resort and Spa

Key West Historic District

SAR 953

SAR 1,334 total

includes taxes & fees

20 Oct - 21 Oct

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

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

A covered outdoor area with a pool, palm trees, and lounge chairs.

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

Ella's Cottages - Key West Historic Inns

Old Town Key West

SAR 863

SAR 1,161 total

includes taxes & fees

20 Oct - 21 Oct

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

A bedroom with a sloped ceiling, a bed, two chairs, a hanging light fixture, and a window with a view of greenery.

A modern kitchen with a wooden counter, two stools, a wicker chair, and a hanging light fixture.

A table with chairs in a lush indoor garden setting.

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

SAR 751

SAR 1,034 total

includes taxes & fees

20 Oct - 21 Oct

Island City House Hotel

Key West Historic District

SAR 816

SAR 918 total

includes taxes & fees

21 Oct - 22 Oct

Top Waterfront Playhouse Hotel Reviews

The Marker Key West Harbor Resort

10/10 Excellent

"Excellent place to stay. Conveniently located to Duval Street."

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!"

Opal Key Resort & Marina, Key West

10/10 Excellent

"The hotel was in a great location. The staff was helpful. The room was spacious and clean."

The Marquesa Hotel

10/10 Excellent

"This is my favorite hotel in the world, and Key West"

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."

Weatherstation Inn

10/10 Excellent

"Our stay was for two nights in October 2026. This is a beautiful property in a wonderful neighborhood, the Truman Annex section of Key West. The hotel is historic, quite classic, with property filled with tropical plantings, all well maintained. The staff was so friendly, professional, polite and very helpful. Our room was spotless and nicely appointed, with extra thoughtful touches...cozy terry robes, and slippers. Bathroom was lovely, large and cheery. Additional cotton blankets and beach towels were so nice to have on hand. The self-serve breakfast included an assortment of croissant pastries and doughnuts, yogurt, fresh fruit and of course coffee, including hot chocolate and various teas. So delicious! The pool area is charming. Bicycles for rent were just inside the gate. The location couldn't be better. Quiet yet so close to everything. We love staying at historic properties. The Weatherstation Inn did not disappoint! We will definitely be back again. One more thing! Parking is included on property."

Heron House - Adult Only

10/10 Excellent

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

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."

Hyatt Vacation Club at Sunset Harbor, Key West

10/10 Excellent

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

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 630

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. Artist House Key West

4. Simonton Court Historic Inn & Cottages

5. H2O Suites - Adults Only

6. Orchid Key Inn - Adults Only

7. Key West Villas

8. Alexander's Guesthouse - Adult Exclusive

9. The Marquesa Hotel

10. The Conch House Heritage Inn

11. Duval House

12. Island City House Hotel

13. Santa Maria Suites

14. Southernmost House - Adult Exclusive

15. L'Habitation Guest House - Adults Only

16. Ella's Cottages - Key West Historic Inns

17. Silver Palms Inn & Historic Homes

18. Ambrosia Key West

19. Coco Plum Inn

20. Westwinds Inn

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

Ridley House - Key West Historic Inns

Hyatt Centric Key West Resort and Spa

The Marker Key West Harbor Resort

Ella's Cottages - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

Island City House Hotel

Top Waterfront Playhouse Hotel Reviews

The Marker Key West Harbor Resort

Pier House Resort & Spa

Opal Key Resort & Marina, Key West

The Marquesa Hotel

Ridley House - Key West Historic Inns

Weatherstation Inn

Heron House - Adult Only

La Concha Key West, Autograph Collection

Hyatt Vacation Club at Sunset Harbor, Key West

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