The 10 Best Hotels Near Waterfront Playhouse, Key West from CA $136

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

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.

1. Almond Tree Inn Hotel - Adults Only

Downtown Key West, 1.3 km from Waterfront Playhouse

John

CA $249

CA $280 total

includes taxes & fees

Sep 23 - Sep 24

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."

2. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

Nicholas

CA $228

CA $256 total

includes taxes & fees

Sep 21 - Sep 22

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 hotel room with two beds, a ceiling fan, a large window with a view of palm trees, and a painting on the wall.

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

3. The Marquesa Hotel

Old Town Key West, 0.7 km from Waterfront Playhouse

LISA

CA $318

CA $436 total

includes taxes & fees

Sep 20 - Sep 21

A modern interior with a staircase, a sofa set, a wooden table, and a television.

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

A pathway flanked by lush green foliage leading to a gated entrance.

A courtyard with two green lounge chairs, a palm tree, and a building with a white facade and lattice window design.

4. Simonton Court Historic Inn & Cottages

Historic Seaport, 0.5 km from Waterfront Playhouse

Robin

CA $263

CA $296 total

includes taxes & fees

Sep 29 - Sep 30

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.

5. The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Robert

CA $312

CA $351 total

includes taxes & fees

Sep 30 - Oct 1

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

6. The Conch House Heritage Inn

Old Town Key West, 1.3 km from Waterfront Playhouse

John

CA $232

CA $261 total

includes taxes & fees

Sep 29 - Sep 30

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.

7. H2O Suites - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Kourosh

CA $346

CA $483 total

includes taxes & fees

Sep 27 - Sep 28

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.

8. Alexander's Guesthouse - Adult Exclusive

Old Town Key West, 1.2 km from Waterfront Playhouse

Justin

CA $188

CA $265 total

includes taxes & fees

Sep 20 - Sep 21

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 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.

9. Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

Robert

CA $127

CA $173 total

includes taxes & fees

Sep 20 - Sep 21

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

An outdoor patio with a table and chairs, surrounded by lush greenery 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.

10. Douglas House - Adults Only

Uptown - Upper Duval, 1.4 km from Waterfront Playhouse

michael

CA $110

CA $136 total

includes taxes & fees

Sep 21 - Sep 22

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

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

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 cozy room with a wicker chair, a small table with a bottle and glasses, and a view of a yellow room through an open door.

11. Tropical Inn

Downtown Key West, 1.1 km from Waterfront Playhouse

Anthony

CA $134

CA $186 total

includes taxes & fees

Sep 21 - Sep 22

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

A two-story building with a porch, a sign reading "The Grand Guesthouse," and a purple flag.

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.

12. The Grand Guesthouse

Old Town Key West, 1.7 km from Waterfront Playhouse

Alissa

CA $157

CA $211 total

includes taxes & fees

Sep 20 - Sep 21

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

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.

A covered walkway with a wooden ceiling, white railings, and a brick path.

13. Island City House Hotel

Historic Seaport, 0.8 km from Waterfront Playhouse

Osvaldo

CA $214

CA $241 total

includes taxes & fees

Sep 21 - Sep 22

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

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.

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

14. The Mermaid & Alligator

Old Town Key West, 1.3 km from Waterfront Playhouse

Johnny

CA $252

CA $283 total

includes taxes & fees

Sep 21 - Sep 22

A pool area with lounge chairs 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.

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

15. Santa Maria Suites

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

June Young

CA $388

CA $531 total

includes taxes & fees

Sep 27 - Sep 28

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

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.

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

16. Silver Palms Inn & Historic Homes

Old Town Key West, 1.4 km from Waterfront Playhouse

Sandra

CA $112

CA $219 total

includes taxes & fees

Sep 20 - Sep 21

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

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.

A grand staircase with ornate railings and a chandelier.

17. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

yessy

CA $195

CA $396 total

includes taxes & fees

Sep 30 - Oct 1

A wooden deck with wicker furniture and a white railing, surrounded by lush tropical vegetation.

A two-story building with a white picket fence, palm trees, and a clear blue sky.

A swimming pool with a white picket fence, surrounded by lounge chairs and potted plants.

A pathway leading to a building with a white facade, surrounded by lush greenery and palm trees.

18. Weatherstation Inn

Truman Annex, 0.5 km from Waterfront Playhouse

Svetlana

CA $235

CA $265 total

includes taxes & fees

Sep 21 - Sep 22

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

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

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.

19. Westwinds Inn

Historic Seaport, 0.9 km from Waterfront Playhouse

Tricia

CA $162

CA $182 total

includes taxes & fees

Sep 23 - Sep 24

A room with a door featuring horizontal blinds, a visible outdoor view through the window, and a patterned carpet.

A pool area with a covered seating area, palm trees, and a small pavilion.

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 yellow building with a door marked '7'.

20. Alexander Palms Court

Casa Marina, 1.8 km from Waterfront Playhouse

Andrew

CA $166

CA $187 total

includes taxes & fees

Sep 23 - Sep 24

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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 1,004 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,003 reviews	View
The Marquesa Hotel	9.8 Exceptional 1,002 reviews	View
Simonton Court Historic Inn & Cottages	9.8 Exceptional 1,000 reviews	View
The Gardens Hotel	9.8 Exceptional 1,000 reviews	View

Top Waterfront Playhouse Hotel Reviews

Amsterdam's Curry Mansion Inn

8/10 Good

"We loved our stay at the James House. We stayed 3 nights in room 305, upstairs. We had a private balcony with a cute table and chairs. We had privacy. There is no staff on site but, there is plenty of what you need. An ice machine. Filtered water, coffee pods, garbage bags, cups. Plenty of towels and a change of bedding in the closet. We stayed in the off season (September) so we always had a parking space. Everything we did was within walking distance. Location location location. This was worth the money. Reason I gave a four star review is because the floor could be cleaner. I had to keep my sandals on. There needs some over due details on the window seals and base boards, blinds. They should put a broom and dust pan/swiffer in the room. I surly would have swept up after myself. Over all I would stay again because of privacy and location. Plus I slept like a baby every night."

Hyatt Vacation Club at Sunset Harbor, Key West

10/10 Excellent

"Hyatt Vacation Club at Sunset Harbor is an absolutely beautiful resort. We had a fantastic view of the marina and the pool. We were on third floor and our well appointed room had vaulted ceilings, a small kitchen, and a super comfortable bed with the best pillows. This resort is so close to Duval Street, Truman Waterfront Park, and one of the main trolley stops. We booked for one night but expanded our stay to 2 nights because we didn't want to leave. Special shout out to the Surly Siren Saloon for one the best burgers! Highly recommend!"

Opal Key Resort & Marina, Key West

10/10 Excellent

"This place had everything we needed. Can’t wait to come back!"

Southernmost Beach Resort and Guesthouses

8/10 Good

"The check in staff was not friendly. The elevator in our building wasn’t working, the pool was closed and the beach was closed because of Scargasim. Also there was a $50.00 per night parking fee and none of these points were discussed with us beforehand and no discounts were offered. Two other couples that checked in after us were traveling together and their rooms were far apart and they asked to be moved closer and the staff at check in made no effort to accommodate them. The other pools were fine and the breakfast was great. The rooms were very nice and the resort is in a quiet peaceful area about a mile from lower Duval where the action is. I would be hesitant to stay there again."

Ridley House - Key West Historic Inns

8/10 Good

"The Ridley House is beautiful and full of old world charm. Large bedrooms and great location. Breakfast each day was fabulous. Not your typical continental breakfast! We stayed in room 6 with a front balcony on Caroline St. Within the first 5 minutes of us being there, we locked ourselves out of the room, on the balcony b/c the door locks automatically when it shuts! Luckily some passersby were able to get the front desk to help us and it was just a funny story after that. We noticed the ear plugs on the side tables due to the roosters crowing and they weren't kidding. We discovered some of them roost high up in the trees, level with the balcony, and sing their "little" songs all night long! Also, another funny story to tell about one of our trips to KW. I would stay at the Ridley House again, but perhaps a room farther away from the road. Ha"

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!"

The Penthouse at Custom House Inn | New!

10/10 Excellent

"This place was in the perfect location. It is located above The Smallest Bar on Duval Street. We walked out of the gate on to Duval. It was very clean, spacious, and wonderful hosts! They went above and beyond to make us comfortable. If you book this property, you won't be sorry!"

Heart of Downtown Key West Cottage With Off-Street Parking

10/10 Excellent

"The whole place was spotlessly clean. The host was very easy to contact at all times. Parking was a dream, with off road parking right in the centre of things, but with easy access in and out. The air conditioning was easily adjustable, if a little noisy. With a lot of the attractions within a 15 minute walk we were ideally located. Internet and tv access were great. A two minute walk to the Route 1 marker post, we must now try and get to the other end!Would I go back, in a heart beat. Thank you for allowing us to share your little piece of heaven."

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

10/10 Excellent

"Beautiful property in a great location . We loved the convenience to everything. The pool was just too big a tease though during our stay in July during 100 degree days. Every thing else perfect"

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 1412 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 1412 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?

Key West Shipwreck 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 $136

Change your mind

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. Orchid Key Inn - Adults Only

3. The Marquesa Hotel

4. Simonton Court Historic Inn & Cottages

5. The Gardens Hotel

6. The Conch House Heritage Inn

7. H2O Suites - Adults Only

8. Alexander's Guesthouse - Adult Exclusive

9. Duval House

10. Douglas House - Adults Only

11. Tropical Inn

12. The Grand Guesthouse

13. Island City House Hotel

14. The Mermaid & Alligator

15. Santa Maria Suites

16. Silver Palms Inn & Historic Homes

17. Southernmost House - Adult Exclusive

18. Weatherstation Inn

19. Westwinds Inn

20. Alexander Palms Court

Compare popular hotels close to Waterfront Playhouse

Top Waterfront Playhouse Hotel Reviews

Amsterdam's Curry Mansion Inn

Hyatt Vacation Club at Sunset Harbor, Key West

Opal Key Resort & Marina, Key West

Southernmost Beach Resort and Guesthouses

Ridley House - Key West Historic Inns

Ocean Key Resort & Spa

The Penthouse at Custom House Inn | New!

Heart of Downtown Key West Cottage With Off-Street Parking

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

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

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