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

AED 893

AED 1,004 total

includes taxes & fees

1 Nov - 2 Nov

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 wooden deck with lush greenery and a pool area.

A large, two-story building with a balcony, surrounded by dense tropical foliage.

2. Douglas House - Adults Only

Uptown - Upper Duval, 1.4 km from Waterfront Playhouse

Maricela

AED 520

AED 644 total

includes taxes & fees

29 Oct - 30 Oct

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

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.

An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.

3. H2O Suites - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Kimberly

AED 1,649

AED 2,103 total

includes taxes & fees

8 Nov - 9 Nov

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 couple walking along a poolside pathway surrounded by lush greenery.

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

4. The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Gisele

AED 1,236

AED 1,390 total

includes taxes & fees

24 Nov - 25 Nov

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 white building with a porch, a sign reading 'Simonton Court,' and a 'Vacancy' sign.

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

5. Simonton Court Historic Inn & Cottages

Historic Seaport, 0.5 km from Waterfront Playhouse

William

AED 547

AED 616 total

includes taxes & fees

27 Oct - 28 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 neon sign for Orchid Key Inn with a 'VACANCY' sign below it.

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

6. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

ben

AED 939

AED 1,057 total

includes taxes & fees

27 Oct - 28 Oct

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

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.

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

7. Alexander's Guesthouse - Adult Exclusive

Old Town Key West, 1.2 km from Waterfront Playhouse

Nestor

AED 889

AED 1,154 total

includes taxes & fees

28 Oct - 29 Oct

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

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

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 covered porch with white wicker furniture and a blue floor, surrounded by lush tropical plants.

8. The Marquesa Hotel

Old Town Key West, 0.7 km from Waterfront Playhouse

Josh

AED 1,652

AED 2,065 total

includes taxes & fees

9 Nov - 10 Nov

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

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.

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

9. The Conch House Heritage Inn

Old Town Key West, 1.3 km from Waterfront Playhouse

Jennifer

AED 1,137

AED 1,279 total

includes taxes & fees

27 Oct - 28 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 covered walkway with a wooden ceiling, white railings, and a brick path.

10. Island City House Hotel

Historic Seaport, 0.8 km from Waterfront Playhouse

Elise

AED 729

AED 820 total

includes taxes & fees

27 Oct - 28 Oct

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

A row of blue bicycles parked under a tree, with a white fence and a building in the background.

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.

11. The Grand Guesthouse

Old Town Key West, 1.7 km from Waterfront Playhouse

Justyn

AED 571

AED 734 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 modern outdoor seating area with a sofa, chairs, and a small table, surrounded by glass doors and a view of greenery.

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

AED 1,098

AED 1,483 total

includes taxes & fees

27 Oct - 28 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 spacious kitchen with wooden cabinets, a granite countertop, and a ceiling fan.

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

13. The Mermaid & Alligator

Old Town Key West, 1.3 km from Waterfront Playhouse

Adam

AED 817

AED 919 total

includes taxes & fees

27 Oct - 28 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.

14. Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

Cathrine

AED 470

AED 608 total

includes taxes & fees

27 Oct - 28 Oct

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

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

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.

15. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

Janet

AED 769

AED 1,330 total

includes taxes & fees

8 Nov - 9 Nov

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

A bathroom with a vanity, a mirror, and a window with blinds.

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 bedroom with a large bed, a sofa, a nightstand, and a painting on the wall.

16. L'Habitation Guest House - Adults Only

Historic Seaport, 0.5 km from Waterfront Playhouse

Richard

AED 533

AED 599 total

includes taxes & fees

27 Oct - 28 Oct

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 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.

17. Westwinds Inn

Historic Seaport, 0.9 km from Waterfront Playhouse

Shari

AED 595

AED 669 total

includes taxes & fees

27 Oct - 28 Oct

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

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

AED 659

AED 742 total

includes taxes & fees

27 Oct - 28 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.

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

A bright kitchen with white cabinetry, a white island, wicker pendant lights, and geometric patterned backsplash.

19. Ella's Cottages - Key West Historic Inns

Old Town Key West, 1.1 km from Waterfront Playhouse

Lisa and David

AED 918

AED 1,219 total

includes taxes & fees

27 Oct - 28 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.

A two-story yellow house with a porch, white railings, and green shutters.

A hotel with a pool, bicycles, and lush greenery.

20. Silver Palms Inn & Historic Homes

Old Town Key West, 1.4 km from Waterfront Playhouse

sam

AED 493

AED 802 total

includes taxes & fees

27 Oct - 28 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 1,008 reviews	View
Douglas House - Adults Only	9.8 Exceptional 568 reviews	View
H2O Suites - Adults Only	9.8 Exceptional 670 reviews	View
The Gardens Hotel	9.8 Exceptional 1,000 reviews	View
Simonton Court Historic Inn & Cottages	9.8 Exceptional 1,001 reviews	View

Top Waterfront Playhouse Hotel Reviews

Opal Key Resort & Marina, Key West

10/10 Excellent

"Amazing property located at the tip of the keys. Very convenient to the strip and also a lot of shops."

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"Breakfast was varied and fresh. Housekeeping did a great job keeping our room clean. Would definitely stay again."

Pier House Resort & Spa

10/10 Excellent

"Great parking. Very central. Room was big and staying in the Spa building was quiet and great!"

Amsterdam's Curry Mansion Inn

10/10 Excellent

"if staying in old town is important to you, this is a great place."

The Marker Key West Harbor Resort

10/10 Excellent

"Love this place!!!"

Ridley House - Key West Historic Inns

10/10 Excellent

"Great staff and location"

The Marquesa Hotel

10/10 Excellent

"Everything"

Ocean Key Resort - A Noble House Resort

10/10 Excellent

"Loved! And the remodeling revamp is on point! The styling and decor has been done very well. The lobby area is perfect! Loved every bit of my stay!"

Chicken Run at Custom House Inn | Unbeatable Location!

10/10 Excellent

"Perfect location andni crdibly nice place."

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 599

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. The Gardens Hotel

5. Simonton Court Historic Inn & Cottages

6. Orchid Key Inn - Adults Only

7. Alexander's Guesthouse - Adult Exclusive

8. The Marquesa Hotel

9. The Conch House Heritage Inn

10. Island City House Hotel

11. The Grand Guesthouse

12. Santa Maria Suites

13. The Mermaid & Alligator

14. Duval House

15. Southernmost House - Adult Exclusive

16. L'Habitation Guest House - Adults Only

17. Westwinds Inn

18. Ambrosia Key West

19. Ella's Cottages - Key West Historic Inns

20. Silver Palms Inn & Historic Homes

Compare popular hotels close to Waterfront Playhouse

Top Waterfront Playhouse Hotel Reviews

Opal Key Resort & Marina, Key West

Winslow's Bungalows - Key West Historic Inns

Pier House Resort & Spa

Amsterdam's Curry Mansion Inn

The Marker Key West Harbor Resort

Ridley House - Key West Historic Inns

The Marquesa Hotel

Ocean Key Resort - A Noble House Resort

Chicken Run at Custom House Inn | Unbeatable Location!

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