The 10 Best Hotels Near Waterfront Playhouse, Key West from CA $157

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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

John

CA $220

CA $247 total

includes taxes & fees

Sep 29 - Sep 30

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 patio area with white metal tables and chairs, surrounded by potted plants and palm trees.

2. Artist House Key West

Historic Seaport, 0.5 km from Waterfront Playhouse

NATHAN

CA $139

CA $157 total

includes taxes & fees

Oct 11 - Oct 12

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.

3. The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Forrest

CA $343

CA $386 total

includes taxes & fees

Sep 30 - Oct 1

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 spacious living room with a wooden ceiling, white sofas, a patterned armchair, a glass coffee table, and a large painting on the wall.

4. Alexander's Guesthouse - Adult Exclusive

Old Town Key West, 1.2 km from Waterfront Playhouse

Nestor

CA $307

CA $403 total

includes taxes & fees

Sep 28 - Sep 29

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.

5. The Conch House Heritage Inn

Old Town Key West, 1.3 km from Waterfront Playhouse

John

CA $268

CA $302 total

includes taxes & fees

Sep 28 - Sep 29

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 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.

6. H2O Suites - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Corey

CA $363

CA $504 total

includes taxes & fees

Sep 28 - Sep 29

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 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.

7. The Marquesa Hotel

Old Town Key West, 0.7 km from Waterfront Playhouse

Darrell

CA $380

CA $508 total

includes taxes & fees

Sep 28 - Sep 29

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 garden with a pond, rocks, and various plants.

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

8. Island City House Hotel

Historic Seaport, 0.8 km from Waterfront Playhouse

Osvaldo

CA $217

CA $245 total

includes taxes & fees

Sep 28 - Sep 29

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 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.

9. Douglas House - Adults Only

Uptown - Upper Duval, 1.4 km from Waterfront Playhouse

michael

CA $167

CA $206 total

includes taxes & fees

Sep 28 - Sep 29

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

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.

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

10. The Grand Guesthouse

Old Town Key West, 1.7 km from Waterfront Playhouse

Travis

CA $160

CA $215 total

includes taxes & fees

Sep 30 - Oct 1

A bedroom with a four-poster bed, a wooden desk, wicker chairs, and a view of the outdoors.

A breakfast buffet with a variety of fruits, pastries, and beverages on a wooden deck with a view of a lush garden and a pool.

A pool area with lounge chairs and candles, surrounded by palm trees and a building in the background.

A wooden door with glass panels, leading to an interior space with furniture and plants.

11. Tropical Inn

Downtown Key West, 1.1 km from Waterfront Playhouse

Molly

CA $136

CA $189 total

includes taxes & fees

Sep 28 - Sep 29

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

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

12. The Mermaid & Alligator

Old Town Key West, 1.3 km from Waterfront Playhouse

Brian

CA $255

CA $286 total

includes taxes & fees

Sep 28 - Sep 29

A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.

A hallway with a white door, a wooden bench, a blue sofa, and a staircase with a white railing.

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.

13. Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

Christopher

CA $141

CA $188 total

includes taxes & fees

Oct 5 - Oct 6

A pool area with lounge chairs and palm trees.

A sign for Santa Maria Resort surrounded by lush greenery and palm trees.

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

A hotel named "Santa Maria" with a prominent illuminated sign, a glass entrance, and a view of the ocean.

14. Santa Maria Suites

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

Anthony

CA $352

CA $492 total

includes taxes & fees

Sep 28 - Sep 29

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 covered seating area, palm trees, and a small pavilion.

A yellow building with a door marked '7'.

15. Alexander Palms Court

Casa Marina, 1.8 km from Waterfront Playhouse

Andrew

CA $169

CA $190 total

includes taxes & fees

Sep 28 - Sep 29

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 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.

16. Ambrosia Key West

Old Town Key West, 0.7 km from Waterfront Playhouse

Tricia

CA $190

CA $214 total

includes taxes & fees

Sep 28 - Sep 29

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

A covered outdoor dining area with white chairs and tables, surrounded by lush greenery and a wooden deck.

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

A hotel room with a large bed, two bedside tables, a ceiling fan, and two framed pictures on the wall.

17. Coco Plum Inn

Downtown Key West, 0.8 km from Waterfront Playhouse

Riley

CA $190

CA $214 total

includes taxes & fees

Sep 29 - Sep 30

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

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

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

CA $113

CA $223 total

includes taxes & fees

Sep 28 - Sep 29

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 bedroom with a bed, two bedside lamps, a ceiling fan, and a view of a balcony with plants.

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

19. Westwinds Inn

Historic Seaport, 0.9 km from Waterfront Playhouse

Anthony

CA $197

CA $222 total

includes taxes & fees

Sep 28 - Sep 29

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.

20. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

yessy

CA $197

CA $401 total

includes taxes & fees

Oct 25 - Oct 26

View all properties

Compare popular hotels close to Waterfront Playhouse

Property	Star rating	Guest rating
Almond Tree Inn Hotel - Adults Only	10.0 Exceptional 1,007 reviews	View
Artist House Key West	9.8 Exceptional 456 reviews	View
The Gardens Hotel	9.8 Exceptional 1,003 reviews	View
Alexander's Guesthouse - Adult Exclusive	9.8 Exceptional 169 reviews	View
The Conch House Heritage Inn	9.8 Exceptional 190 reviews	View

Top Waterfront Playhouse Hotel Reviews

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"We loved the property, staff, room, but was unable to enjoy the beach at the hotel and was not notified beach was not going to be opened. We picked this hotel for the beach access and didn’t find out the beach was not available until we went down to the beach to relax."

La Concha Key West, Autograph Collection

10/10 Excellent

"Great location"

The Marker Key West Harbor Resort

10/10 Excellent

"Always solid"

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"From before we arrived we already knew we chose the right place to stay! We had questions about parking our motorcycle on property and there was no hesitation to share information and also connect with us. The staff is great. We are recommending this location and properties to friends and family. Next time we’re in town, 100% this will be the place we stay. Location is great and the property is fun to explore. Thank you all for making our stay memorable!"

Simonton Court Historic Inn & Cottages

10/10 Excellent

"Staff was great rooms are older but quite charming. Would definitely stay again."

The Penthouse at Custom House Inn | New!

10/10 Excellent

"Nice week in Key West"

Heart of Downtown Key West Cottage With Off-Street Parking

10/10 Excellent

"We go to Key West, once a year and have been staying in different places, trying to find that special place. This is it. If you want 5 star, Hilton Hotel style. Not it. If you want 5 star old town Key West. This is it. It's a gem. Literally in the heart of downtown. A block walk to everything going on, on Duval Street. But the Key, you'd never know it. It is so quiet (maybe during a festival it might be a bit more noise). It's tucked away, very private. Free parking (that right there will save you over 50 a day). Restaurants close by. Pan Am house, literally next door. Mel Fisher museum, 5-7 min walk. Mallory square maybe 12. Need to pick something up. CVS is a 10 min walk. If that. The owners are respond very quickly. For us, it was so good, we only corresponded about Key West, nothing to do with the cottage. If you are going to Key West and you WANT Key West, this is the place."

Hyatt Vacation Club at Sunset Harbor, Key West

10/10 Excellent

"Staff: friendly, attentive and professional. Location : excellent. Cleanliness: impeccable, very clean, Overall experience: exceptional, wonderful, highly recommended."

Ocean Key Resort & Spa

10/10 Excellent

"This resort was amazing! The best area and most beautiful in Old Town. Craig and the whole staff were lovely! Would def return!"

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 1399 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 1399 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.

What can I see and do near Waterfront Playhouse?

Mel Fisher Maritime Museum, Harry S. Truman Little White House, and Florida Keys Eco - Discovery Center feature a variety of fascinating exhibits to see while you're in town. Sights like Ernest Hemingway Home and Museum, Key West Lighthouse and Keeper's Quarters Museum, and Fort Zachary Taylor Historic State Park 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.

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Key West Vacation Rentals

Find hotels near Waterfront Playhouse, Key West from CA $157

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. Artist House Key West

3. The Gardens Hotel

4. Alexander's Guesthouse - Adult Exclusive

5. The Conch House Heritage Inn

6. H2O Suites - Adults Only

7. The Marquesa Hotel

8. Island City House Hotel

9. Douglas House - Adults Only

10. The Grand Guesthouse

11. Tropical Inn

12. The Mermaid & Alligator

13. Duval House

14. Santa Maria Suites

15. Alexander Palms Court

16. Ambrosia Key West

17. Coco Plum Inn

18. Silver Palms Inn & Historic Homes

19. Westwinds Inn

20. Southernmost House - Adult Exclusive

Compare popular hotels close to Waterfront Playhouse

Top Waterfront Playhouse Hotel Reviews

Southernmost Beach Resort and Guesthouses

La Concha Key West, Autograph Collection

The Marker Key West Harbor Resort

Winslow's Bungalows - Key West Historic Inns

Simonton Court Historic Inn & Cottages

The Penthouse at Custom House Inn | New!

Heart of Downtown Key West Cottage With Off-Street Parking

Hyatt Vacation Club at Sunset Harbor, Key West

Ocean Key Resort & Spa

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

Explore a world of travel with Expedia