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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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

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

1. Almond Tree Inn Hotel - Adults Only

Downtown Key West, 1.3 km from Waterfront Playhouse

John

AED 766

AED 862 total

includes taxes & fees

13 Oct - 14 Oct

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.

A wooden deck with lush greenery and a pool area.

2. Douglas House - Adults Only

Uptown - Upper Duval, 1.4 km from Waterfront Playhouse

Maricela

AED 491

AED 608 total

includes taxes & fees

7 Oct - 8 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 bar area with a counter, chairs, and a clock.

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

3. The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Forrest

AED 961

AED 1,081 total

includes taxes & fees

7 Oct - 8 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.

4. H2O Suites - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Corey

AED 1,172

AED 1,566 total

includes taxes & fees

12 Oct - 13 Oct

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

5. The Marquesa Hotel

Old Town Key West, 0.7 km from Waterfront Playhouse

Darrell

AED 1,245

AED 1,607 total

includes taxes & fees

12 Oct - 13 Oct

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 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.

6. Alexander's Guesthouse - Adult Exclusive

Old Town Key West, 1.2 km from Waterfront Playhouse

Nestor

AED 796

AED 1,047 total

includes taxes & fees

7 Oct - 8 Oct

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

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.

7. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

Nicholas

AED 752

AED 846 total

includes taxes & fees

13 Oct - 14 Oct

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

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

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

8. The Conch House Heritage Inn

Old Town Key West, 1.3 km from Waterfront Playhouse

John

AED 785

AED 883 total

includes taxes & fees

7 Oct - 8 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 hallway with a white door, a wooden bench, a blue sofa, and a staircase with a white railing.

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

9. Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

Christopher

AED 470

AED 607 total

includes taxes & fees

14 Oct - 15 Oct

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

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

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

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

10. Island City House Hotel

Historic Seaport, 0.8 km from Waterfront Playhouse

Osvaldo

AED 683

AED 769 total

includes taxes & fees

7 Oct - 8 Oct

A room with a bed, a ceiling fan, and a window with blinds.

A spacious kitchen with wooden cabinets, a granite countertop, and a ceiling fan.

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.

11. The Mermaid & Alligator

Old Town Key West, 1.3 km from Waterfront Playhouse

Adam

AED 879

AED 989 total

includes taxes & fees

8 Oct - 9 Oct

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 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.

12. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

yessy

AED 512

AED 1,040 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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.

13. Westwinds Inn

Historic Seaport, 0.9 km from Waterfront Playhouse

Anthony

AED 595

AED 669 total

includes taxes & fees

8 Oct - 9 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.

14. Ambrosia Key West

Old Town Key West, 0.7 km from Waterfront Playhouse

Tricia

AED 537

AED 604 total

includes taxes & fees

11 Oct - 12 Oct

A gated entrance with lush green foliage and a white picket fence.

A white colonial-style building with a balcony, surrounded by palm trees 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.

15. Coco Plum Inn

Downtown Key West, 0.8 km from Waterfront Playhouse

Riley

AED 521

AED 586 total

includes taxes & fees

12 Oct - 13 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 pool area with a circular pool, lounge chairs, and a gazebo.

A yellow building with a door marked '7'.

16. Alexander Palms Court

Casa Marina, 1.8 km from Waterfront Playhouse

Andrew

AED 521

AED 586 total

includes taxes & fees

11 Oct - 12 Oct

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.

17. Ella's Cottages - Key West Historic Inns

Old Town Key West, 1.1 km from Waterfront Playhouse

tracy

AED 918

AED 1,219 total

includes taxes & fees

7 Oct - 8 Oct

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

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

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 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

AED 327

AED 616 total

includes taxes & fees

7 Oct - 8 Oct

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

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

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.

19. Marrero's Guest Mansion

Downtown Key West, 0.6 km from Waterfront Playhouse

Michael

AED 1,153

AED 1,297 total

includes taxes & fees

7 Oct - 8 Oct

An aerial view of a coastal town with a marina, waterfront buildings, and a prominent red-roofed structure.

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

20. Opal Key Resort & Marina, Key West

Old Town Key West, 0.1 km from Waterfront Playhouse

Susan

AED 951

AED 1,215 total

includes taxes & fees

7 Oct - 8 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 1,003 reviews	View
Douglas House - Adults Only	9.8 Exceptional 548 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

Ridley House - Key West Historic Inns

10/10 Excellent

"Clean rooms and the staff was great"

Pier House Resort & Spa

10/10 Excellent

"Love pier house resort"

Amsterdam's Curry Mansion Inn

8/10 Good

"Good value compared to other locations we have stayed at the past 25 years. Great location and in easy walking distance of most bars, restaurants and points of interest on the island. Room was clean and well supplied with everything you need. There is no on site host, so if you have questions or concerns you must call the guest experience manager. Everything is self service from gaining access to your room, obtaining extra towels, removing trash, etc.. Our room was upstairs in the main mansion. The only issue we had with our stay was that the stairway was not well lit at night. Somewhat dangerous!"

La Concha Key West, Autograph Collection

10/10 Excellent

"The location on Duval is perfect, the hotel is top notch, and the staff can't do enough for you. Everyone from the GM to the housekeeping staff always wish you a good day and ask if there is anything they can do for you no matter how many times they see you. Perfect place to stay in Key West and we will be returning for sure!"

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!"

The Marquesa Hotel

10/10 Excellent

"Fabulous room with the most comfortable bed and pillows. Staff were so friendly and helpful. The pool area cosy and welcoming. Oasis of paradise. Overall our stay at this hotel was fabulous. Mark on reception was very welcoming."

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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 AED 586

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. Alexander's Guesthouse - Adult Exclusive

7. Orchid Key Inn - Adults Only

8. The Conch House Heritage Inn

9. Duval House

10. Island City House Hotel

11. The Mermaid & Alligator

12. Southernmost House - Adult Exclusive

13. Westwinds Inn

14. Ambrosia Key West

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. Opal Key Resort & Marina, Key West

Compare popular hotels close to Waterfront Playhouse

Top Waterfront Playhouse Hotel Reviews

Ridley House - Key West Historic Inns

Pier House Resort & Spa

Amsterdam's Curry Mansion Inn

La Concha Key West, Autograph Collection

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...

The Marquesa Hotel

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

DARLING OF DUVAL @ OLD TOWN Cottage + Spa + Last Key White Glove Service...