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 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

￥38,590

￥43,414 total

includes taxes & fees

Oct 25 - Oct 26

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.

2. H2O Suites - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Kimberly

￥46,967

￥63,428 total

includes taxes & fees

Oct 28 - Oct 29

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 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.

3. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

ben

￥39,766

￥44,737 total

includes taxes & fees

Oct 25 - Oct 26

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

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.

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

￥35,119

￥39,508 total

includes taxes & fees

Oct 27 - Oct 28

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.

5. Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

Cathrine

￥20,061

￥25,939 total

includes taxes & fees

Oct 27 - Oct 28

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

6. Coco Plum Inn

Downtown Key West, 0.8 km from Waterfront Playhouse

August

￥24,844

￥27,950 total

includes taxes & fees

Oct 25 - Oct 26

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'.

7. Alexander Palms Court

Casa Marina, 1.8 km from Waterfront Playhouse

Brenda

￥25,272

￥28,433 total

includes taxes & fees

Oct 26 - Oct 27

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

8. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

Janet

￥22,405

￥45,042 total

includes taxes & fees

Oct 27 - Oct 28

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.

9. Ella's Cottages - Key West Historic Inns

Old Town Key West, 1.1 km from Waterfront Playhouse

Lisa and David

￥31,346

￥43,200 total

includes taxes & fees

Oct 27 - Oct 28

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 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.

10. The Marker Key West Harbor Resort

Historic Seaport, 0.6 km from Waterfront Playhouse

Lynne

￥28,440

￥42,231 total

includes taxes & fees

Oct 25 - Oct 26

A two-story building with a white picket fence, palm trees, and a sign that reads 'DUVAL GARDENS.'

A porch with wicker chairs and a table, white railings, and a window with a view of a palm tree.

11. Duval Gardens - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

JoAnn

￥23,860

￥37,433 total

includes taxes & fees

Oct 25 - Oct 26

A pool area with a brick patio, potted plants, and a covered seating area.

A white picket fence, a palm tree, and a sign reading "Garden House Key West".

A porch with a white chair, a wooden door, and a small indoor dining area visible through the door.

A house with a porch, a sign reading "Garden House," and a number "329" on the door.

12. The Garden House

Historic Seaport, 0.6 km from Waterfront Playhouse

Brad

￥15,530

￥20,845 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

13. Ridley House - Key West Historic Inns

Historic Seaport, 0.4 km from Waterfront Playhouse

Jeffrey

￥31,346

￥43,200 total

includes taxes & fees

Oct 27 - Oct 28

A covered porch with wicker furniture, potted plants, and a sign for the "Office" at the Palm Hotel.

A pink building with a white door, a balcony with a white railing, and a view of a pool area.

A hotel with a white facade, multiple balconies, and lush tropical landscaping.

A row of bicycles parked in front of a building with a white balcony and a palm tree.

14. The Palms Hotel

The Meadows, 1.5 km from Waterfront Playhouse

Jerry

￥23,442

￥29,901 total

includes taxes & fees

Oct 25 - Oct 26

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

A spacious living area with a wooden staircase, a ceiling fan, a TV, and a view of the beach through an open door.

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

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

15. Eden House

Historic Seaport, 1.1 km from Waterfront Playhouse

Michelle

￥19,538

￥24,618 total

includes taxes & fees

Oct 25 - Oct 26

A poolside area with lounge chairs, a small pool, and a white building with a balcony.

A white building with a sign reading "The StarCare Inn" and a "No Vacancies" sign.

A pool area with lounge chairs, a hot tub, and a deck with a railing.

A reception area with a wooden reception desk, a brown leather couch, and a mural of palm trees on the wall.

16. Seascape Tropical Inn - Adult Exclusive

Downtown Key West, 1.1 km from Waterfront Playhouse

Evan

￥29,779

￥41,436 total

includes taxes & fees

Nov 2 - Nov 3

A swimming pool with clear water, surrounded by lush greenery and palm trees.

A covered porch with white columns and wicker furniture.

A yellow building with a blue door and shutters, a number '302' on the wall, and a small porch area.

A bathroom with a shower, sink, and toilet.

17. Tranquility Guest House

Bahama Village, 0.9 km from Waterfront Playhouse

Sandra

￥14,229

￥29,950 total

includes taxes & fees

Oct 25 - Oct 26

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

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

A pathway leading to a white gazebo with a view of a lighthouse in the distance.

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

18. Lighthouse Hotel - Key West Historic Inns

Bahama Village, 1.2 km from Waterfront Playhouse

Jill

￥31,346

￥43,200 total

includes taxes & fees

Oct 27 - Oct 28

A white building with a grey roof, surrounded by potted plants and a blue umbrella.

A patio with sun loungers, a table with an umbrella, and potted plants.

A breakfast setup with wine bottles, fruits, and pastries on a tray by a door with a view of a staircase and greenery.

A spacious kitchen with wooden cabinets and a dining area with a round table and chairs.

19. The Cabana Inn Key West - Adults Only

Downtown Key West, 0.7 km from Waterfront Playhouse

Donna

￥25,250

￥35,458 total

includes taxes & fees

Oct 26 - Oct 27

A deck with sun loungers and a railing overlooking the sea.

A poolside area with lounge chairs and umbrellas, palm trees, and a view of the sea.

A beach scene with two people relaxing under a white umbrella, a palm tree, and a clear blue sky.

A room with a view of the beach and ocean, a bed with a white and blue blanket, and a small table with a potted plant.

20. Southernmost Beach Resort and Guesthouses

Uptown - Upper Duval, 1.7 km from Waterfront Playhouse

Jacob Stuart

￥18,558

￥32,879 total

includes taxes & fees

Oct 25 - Oct 26

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Compare popular hotels close to Waterfront Playhouse

Property	Star rating	Guest rating
Almond Tree Inn Hotel - Adults Only	10.0 Exceptional 1,005 reviews	View
H2O Suites - Adults Only	9.8 Exceptional 669 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,003 reviews	View
The Gardens Hotel	9.8 Exceptional 1,000 reviews	View
Duval House	9.6 Exceptional 1,126 reviews	View

Top Waterfront Playhouse Hotel Reviews

Opal Key Resort & Marina, Key West

10/10 Excellent

"Proximity to downtown and perfect walking distance to restaurants. Great pool."

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"The resort was amazing. Staff was friendly and went out of their way to make you feel welcomed all week, not just when you checked in. The property was clean and the room was very comfortable. I would definitely go back."

Hyatt Centric Key West Resort and Spa

10/10 Excellent

"Friendly staff, when mentioned an allergy issue was offered several options to remedy, staff was very kind and helpful. Bar and pool staff were also very attentive and mixed fantastic drinks"

The Marker Key West Harbor Resort

8/10 Good

"Everyone is friendly and does their best"

Amsterdam's Curry Mansion Inn

8/10 Good

"The location is amazing. The pool was cleaned daily. They provide washer and dryer and supplies to wash clothes. A couple days there were no clean towels to get for the rooms or pool. They do not clean your room daily which is fine. It’s very relaxed atmosphere. The staff is not present very much."

Ridley House - Key West Historic Inns

10/10 Excellent

"The staff were incredibly helpful and friendly. Breakfast was good. Location of the hotel would be hard to beat. Even all the people staying here were great."

Heron House - Adult Only

10/10 Excellent

"Great location. Nice place. Would absolutely stay again"

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!"

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)

This interactive museum is home to unbelievable relics pulled from the bottom of the sea and a watchtower with views across the Gulf of Mexico.

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Mallory Square

9.2/10 (15,939 reviews)

Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.

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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)

Visit a house named after famed naturalist John James Audubon. Learn the history of why the house came to be here.

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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)

Key West’s definitive maritime museum is an important attraction for anyone wanting to learn about early life in the Keys. Hear stories of slavery, pirates and fishermen.

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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 ￥20,845

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Our top choices for Waterfront Playhouse hotels

1. Almond Tree Inn Hotel - Adults Only

2. H2O Suites - Adults Only

3. Orchid Key Inn - Adults Only

4. The Gardens Hotel

5. Duval House

6. Coco Plum Inn

7. Alexander Palms Court

8. Southernmost House - Adult Exclusive

9. Ella's Cottages - Key West Historic Inns

10. The Marker Key West Harbor Resort

11. Duval Gardens - Adults Only

12. The Garden House

13. Ridley House - Key West Historic Inns

14. The Palms Hotel

15. Eden House

16. Seascape Tropical Inn - Adult Exclusive

17. Tranquility Guest House

18. Lighthouse Hotel - Key West Historic Inns

19. The Cabana Inn Key West - Adults Only

20. Southernmost Beach Resort and Guesthouses

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

Hyatt Centric Key West Resort and Spa

The Marker Key West Harbor Resort

Amsterdam's Curry Mansion Inn

Ridley House - Key West Historic Inns

Heron House - Adult Only

The Marquesa Hotel

Ocean Key Resort - A Noble House Resort

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