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 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.

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

6 Oct - 7 Oct

A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.

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

A bedroom with a large bed, a television on a dresser, and a view of the outdoors through a sliding door.

A couple walking along a poolside pathway surrounded by lush greenery.

2. The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Forrest

AED 823

AED 926 total

includes taxes & fees

6 Oct - 7 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 sofa, chairs, and a dining table. There are large windows with blinds, a door leading to a patio, and a ceiling with exposed beams.

A pool area with lounge chairs, a pool, and a building with a balcony and outdoor seating.

3. 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

4 Oct - 5 Oct

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 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.

4. H2O Suites - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Carmen

AED 1,021

AED 1,397 total

includes taxes & fees

4 Oct - 5 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."

5. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

Nicholas

AED 824

AED 927 total

includes taxes & fees

4 Oct - 5 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 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.

6. Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

Christopher

AED 335

AED 455 total

includes taxes & fees

5 Oct - 6 Oct

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

A poolside area with lounge chairs, a covered seating area, and a small pool.

A cozy outdoor seating area with a wooden bench and a table, surrounded by potted plants and a coffee and tea sign.

A room with a yellow armchair, a glass coffee table, and a view of a wooden deck and tropical plants.

7. The Mermaid & Alligator

Old Town Key West, 1.3 km from Waterfront Playhouse

Adam

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

A wooden deck with lush greenery and a pool area.

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.

8. Douglas House - Adults Only

Uptown - Upper Duval, 1.4 km from Waterfront Playhouse

Maricela

AED 491

AED 608 total

includes taxes & fees

5 Oct - 6 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 swimming pool with lounge chairs, a covered deck, and a view of lush greenery.

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

9. Coco Plum Inn

Downtown Key West, 0.8 km from Waterfront Playhouse

Riley

AED 576

AED 648 total

includes taxes & fees

4 Oct - 5 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 large, two-story house with a prominent tower and a covered porch.

A balcony with white railings and a table, overlooking a beach with palm trees and a clear blue sky.

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

11. Ambrosia Key West

Old Town Key West, 0.7 km from Waterfront Playhouse

Tricia

AED 537

AED 604 total

includes taxes & fees

5 Oct - 6 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

AED 393

AED 691 total

includes taxes & fees

4 Oct - 5 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 room with a stone wall, a wooden bench, a cactus, and a framed painting.

A waterfront hotel with multiple balconies, a dock, and boats.

13. 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

4 Oct - 5 Oct

A poolside area with lounge chairs, umbrellas, and a pergola.

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.

A living room with a spiral staircase, a sofa, a chair, a coffee table, and a view of an outdoor seating area.

14. Ella's Cottages - Key West Historic Inns

Old Town Key West, 1.1 km from Waterfront Playhouse

tracy

AED 845

AED 1,136 total

includes taxes & fees

4 Oct - 5 Oct

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

A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.

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.

15. The Marker Key West Harbor Resort

Historic Seaport, 0.6 km from Waterfront Playhouse

Keith

AED 829

AED 1,163 total

includes taxes & fees

26 Oct - 27 Oct

A bright green porch with hanging planters, a wooden chair, and a railing.

A bar area with a wooden counter, colorful decorations, and a sign with motivational ocean-themed text.

A brightly colored Caribbean house with a balcony, a sign indicating it's for rent, and bicycles parked outside.

16. Caribbean House

Bahama Village, 1 km from Waterfront Playhouse

David

AED 561

AED 723 total

includes taxes & fees

4 Oct - 5 Oct

A wooden deck with wicker furniture, a white staircase, and a lush garden area.

A hotel entrance with a sign reading "Heron House Office."

A two-story house with a balcony, surrounded by palm trees and a clear blue sky.

A bedroom with a large bed, a view of a swimming pool, and an open door leading to an outdoor seating area.

17. Heron House - Adult Only

Downtown Key West, 0.7 km from Waterfront Playhouse

Erin

AED 442

AED 620 total

includes taxes & fees

4 Oct - 5 Oct

A pool area with lounge chairs and a cabana.

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

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

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

18. Ocean Key Resort - A Noble House Resort

Historic Seaport, < 0.1 km from Waterfront Playhouse

Patrick

AED 1,172

AED 1,603 total

includes taxes & fees

4 Oct - 5 Oct

A spacious room with a wooden floor, white furniture, and large windows.

A white building with a covered porch, potted plants, and a white picket fence.

A paved pathway surrounded by lush greenery and palm trees.

A modern living room with a sofa, two armchairs, a coffee table, and a small table with a lamp. There is a large window with shutters, an air conditioning unit, and a view of greenery outside.

19. Paradise Inn Key West - Adults Only

Downtown Key West, 1.1 km from Waterfront Playhouse

Mary

AED 466

AED 705 total

includes taxes & fees

4 Oct - 5 Oct

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

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

20. Ridley House - Key West Historic Inns

Historic Seaport, 0.4 km from Waterfront Playhouse

STEVEN

AED 845

AED 1,136 total

includes taxes & fees

4 Oct - 5 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
The Gardens Hotel	9.8 Exceptional 1,003 reviews	View
Alexander's Guesthouse - Adult Exclusive	9.8 Exceptional 170 reviews	View
H2O Suites - Adults Only	9.8 Exceptional 661 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,000 reviews	View

Top Waterfront Playhouse Hotel Reviews

Pier House Resort & Spa

10/10 Excellent

"Great location and clean room! Easy to walk to restaurants, bars, and Mallory Square. The Chart Room Cocktail Lounge in hotel was also a fun late night stop."

Opal Key Resort & Marina, Key West

10/10 Excellent

"Location, location, location!"

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"Amazing!"

Ocean Key Resort - A Noble House Resort

10/10 Excellent

"Staff was very attentive to our needs and the hotel was very clean."

Hyatt Centric Key West Resort and Spa

10/10 Excellent

"Location is excellent. Very quiet. Pool and bar are quite relaxing and convenient."

The Marker Key West Harbor Resort

10/10 Excellent

"Clean.helpful staff.good a/c.good location.will definitely stay here again."

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."

The Penthouse at Custom House Inn | New!

10/10 Excellent

"Nice week in Key West"

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 AED 455

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Treat yourself

Be picky

Check prices for these dates

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Star rating

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Our top choices for Waterfront Playhouse hotels

1. Almond Tree Inn Hotel - Adults Only

2. The Gardens Hotel

3. Alexander's Guesthouse - Adult Exclusive

4. H2O Suites - Adults Only

5. Orchid Key Inn - Adults Only

6. Duval House

7. The Mermaid & Alligator

8. Douglas House - Adults Only

9. Coco Plum Inn

10. Southernmost House - Adult Exclusive

11. Ambrosia Key West

12. Silver Palms Inn & Historic Homes

13. Opal Key Resort & Marina, Key West

14. Ella's Cottages - Key West Historic Inns

15. The Marker Key West Harbor Resort

16. Caribbean House

17. Heron House - Adult Only

18. Ocean Key Resort - A Noble House Resort

19. Paradise Inn Key West - Adults Only

20. Ridley House - Key West Historic Inns

Compare popular hotels close to Waterfront Playhouse

Top Waterfront Playhouse Hotel Reviews

Pier House Resort & Spa

Opal Key Resort & Marina, Key West

Southernmost Beach Resort and Guesthouses

Ocean Key Resort - A Noble House Resort

Hyatt Centric Key West Resort and Spa

The Marker Key West Harbor Resort

Heart of Downtown Key West Cottage With Off-Street Parking

Heron House - Adult Only

The Penthouse at Custom House Inn | New!

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