10 Best Hotels & Accommodation Closest to Waterfront Playhouse in Key West from NZ$282

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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 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.

1. Almond Tree Inn Hotel - Adults Only

Downtown Key West, 1.3 km from Waterfront Playhouse

Teresa

NZ$505

includes taxes & fees

26 Oct - 27 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.

2. H2O Suites - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Kimberly

NZ$709

includes taxes & fees

28 Oct - 29 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 hotel room with a large bed, a nightstand, a desk, a bathroom with a shower, and a painting of a pier over water on the wall.

3. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

ben

NZ$505

includes taxes & fees

26 Oct - 27 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 wooden ceiling, white sofas, a patterned armchair, a glass coffee table, and a large painting on the wall.

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

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

4. Alexander's Guesthouse - Adult Exclusive

Old Town Key West, 1.2 km from Waterfront Playhouse

Nestor

NZ$551

includes taxes & fees

28 Oct - 29 Oct

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

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

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

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

5. The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Gisele

NZ$442

includes taxes & fees

27 Oct - 28 Oct

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 hotel room with a bed, a wooden floor, a seating area with a table and chairs, and a view of greenery outside.

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

6. Douglas House - Adults Only

Uptown - Upper Duval, 1.4 km from Waterfront Playhouse

Maricela

NZ$307

includes taxes & fees

26 Oct - 27 Oct

A gated entrance to Villas Key West with a brick pathway leading to the gate.

A covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.

A swimming pool with a hot tub, surrounded by a wooden deck and lush greenery.

A covered porch with wicker furniture, a large potted plant, and a sign for Villas Key West.

7. Key West Villas

Downtown Key West, 0.9 km from Waterfront Playhouse

Margaret

NZ$531

includes taxes & fees

2 Nov - 3 Nov

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.

8. Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

Cathrine

NZ$290

includes taxes & fees

26 Oct - 27 Oct

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

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

9. The Marquesa Hotel

Old Town Key West, 0.7 km from Waterfront Playhouse

Josh

NZ$986

includes taxes & fees

9 Nov - 10 Nov

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

NZ$392

includes taxes & fees

26 Oct - 27 Oct

A pool area with lounge chairs and palm trees.

A neatly made bed with patterned pillows, a bedside table with a bottle and glasses, and a window with orchids.

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.

11. Santa Maria Suites

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

Anthony

NZ$709

includes taxes & fees

26 Oct - 27 Oct

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.

12. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

Janet

NZ$504

includes taxes & fees

27 Oct - 28 Oct

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

A covered porch with wicker furniture, potted plants, and a view of the house.

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.

13. L'Habitation Guest House - Adults Only

Historic Seaport, 0.5 km from Waterfront Playhouse

Richard

NZ$286

includes taxes & fees

27 Oct - 28 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.

14. Coco Plum Inn

Downtown Key West, 0.8 km from Waterfront Playhouse

August

NZ$354

includes taxes & fees

26 Oct - 27 Oct

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

A yellow building with a door marked '7'.

A garden with a stone pathway, a wooden fence, and various tropical plants.

A room with a bed, a desk, a chair, a lamp, a painting of a boat on water, and a view of the sea.

15. Alexander Palms Court

Casa Marina, 1.8 km from Waterfront Playhouse

Brenda

NZ$282

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 wicker outdoor seating area with two chairs and a table, surrounded by lush tropical foliage.

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

16. Ambrosia Key West

Old Town Key West, 0.7 km from Waterfront Playhouse

RICHARD

NZ$354

includes taxes & fees

26 Oct - 27 Oct

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

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.

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

17. Ella's Cottages - Key West Historic Inns

Old Town Key West, 1.1 km from Waterfront Playhouse

Lisa and David

NZ$484

includes taxes & fees

26 Oct - 27 Oct

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

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.

18. Silver Palms Inn & Historic Homes

Old Town Key West, 1.4 km from Waterfront Playhouse

sam

NZ$330

includes taxes & fees

26 Oct - 27 Oct

A hotel with a covered entrance, multiple balconies, and palm trees.

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.

A covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.

19. Opal Key Resort & Marina, Key West

Old Town Key West, 0.1 km from Waterfront Playhouse

Ann

NZ$580

includes taxes & fees

26 Oct - 27 Oct

A covered porch with white railings, wooden benches, and a hanging light fixture.

A bedroom with a four-poster bed, a wicker chair, a wooden dresser, and a television.

A living room with a large mirror, a wicker chair, a television on a wooden cabinet, and a window with a view of palm trees.

A sign for Marrero's Guest Mansion in Key West, FL, by Verdigris Hotels.

20. Marrero's Guest Mansion

Downtown Key West, 0.6 km from Waterfront Playhouse

Michael

NZ$640

includes taxes & fees

26 Oct - 27 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 1,006 reviews	View
H2O Suites - Adults Only	9.8 Exceptional 669 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,003 reviews	View
Alexander's Guesthouse - Adult Exclusive	9.8 Exceptional 172 reviews	View
The Gardens Hotel	9.8 Exceptional 1,000 reviews	View

Top Waterfront Playhouse Hotel Reviews

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!"

Heart of Downtown Key West Cottage With Off-Street Parking

10/10 Excellent

"Excellent location, private parking, and great communication from host!"

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!"

Chicken Run at Custom House Inn | Unbeatable Location!

8/10 Good

"Nice basic room, convenient location, comfortable."

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)

Engage with stories of salvagers who recover cargo from sunken ships, view relics and climb this museum’s watchtower for views of the city.

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Mallory Square

9.2/10 (15,939 reviews)

Enjoy the lively crowds, energetic performers and stunning sunset that make this city square the most popular meeting place in the evenings.

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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 find the perfect gifts to bring home at Mallory Dock during your trip 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 studying the exhibits at 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 in Key West. Stroll along the area's seaside or simply savour 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, take a look at the 1400 hotels and other accommodation options you'll find within a mile.

Where is the best place 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 traveller 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 find near Waterfront Playhouse?

Expedia has 1400 hotels and other accommodation options 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 room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might be able to still cancel and be given a refund within a 24-hour period of booking. Add your dates and click on "Search", then use the filter option "fully refundable" to view the best deals near Waterfront Playhouse.

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 theatre.

Top Hotels Near Waterfront Playhouse in Key West from NZ$282

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Property class

Guest rating

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. Alexander's Guesthouse - Adult Exclusive

5. The Gardens Hotel

6. Douglas House - Adults Only

7. Key West Villas

8. Duval House

9. The Marquesa Hotel

10. Island City House Hotel

11. Santa Maria Suites

12. Southernmost House - Adult Exclusive

13. L'Habitation Guest House - Adults Only

14. Coco Plum Inn

15. Alexander Palms Court

16. Ambrosia Key West

17. Ella's Cottages - Key West Historic Inns

18. Silver Palms Inn & Historic Homes

19. Opal Key Resort & Marina, Key West

20. Marrero's Guest Mansion

Compare popular hotels close to Waterfront Playhouse

Top Waterfront Playhouse Hotel Reviews

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

Heart of Downtown Key West Cottage With Off-Street Parking

Ocean Key Resort & Spa

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