10 Best Hotels & Accommodation Closest to Waterfront Playhouse in Key West from AU$191

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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 breakfast table with various food items and drinks, a pool in the background, and a tiled wall.

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

AU$283

includes taxes & fees

30 Sept - 1 Oct

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 room with a bed, sofa, coffee table, and artwork.

A modern hotel with a prominent glass facade, palm trees, and a clear sky.

2. H2O Suites - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Corey

AU$543

includes taxes & fees

30 Sept - 1 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 colonial-style building with a porch, surrounded by lush tropical vegetation.

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

3. The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Forrest

AU$419

includes taxes & fees

1 Oct - 2 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 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.

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

4. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

Nicholas

AU$295

includes taxes & fees

30 Sept - 1 Oct

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

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

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.

5. The Conch House Heritage Inn

Old Town Key West, 1.3 km from Waterfront Playhouse

John

AU$304

includes taxes & fees

30 Sept - 1 Oct

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 spacious room with a large bed, a sofa, a chair, a small table, and a television.

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

6. Simonton Court Historic Inn & Cottages

Historic Seaport, 0.5 km from Waterfront Playhouse

William

AU$271

includes taxes & fees

30 Sept - 1 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 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.

7. Alexander's Guesthouse - Adult Exclusive

Old Town Key West, 1.2 km from Waterfront Playhouse

Nestor

AU$406

includes taxes & fees

4 Oct - 5 Oct

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

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 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.

8. The Marquesa Hotel

Old Town Key West, 0.7 km from Waterfront Playhouse

Darrell

AU$511

includes taxes & fees

30 Sept - 1 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 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

Christopher

AU$200

includes taxes & fees

5 Oct - 6 Oct

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

AU$236

includes taxes & fees

30 Sept - 1 Oct

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

A covered outdoor area with a wooden staircase, seating, and potted plants.

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.

11. The Grand Guesthouse

Old Town Key West, 1.7 km from Waterfront Playhouse

Alissa

AU$216

includes taxes & fees

30 Sept - 1 Oct

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.

12. Island City House Hotel

Historic Seaport, 0.8 km from Waterfront Playhouse

Osvaldo

AU$247

includes taxes & fees

30 Sept - 1 Oct

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

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

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.

13. Tropical Inn

Downtown Key West, 1.1 km from Waterfront Playhouse

Natalie

AU$233

includes taxes & fees

1 Oct - 2 Oct

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

Adam

AU$289

includes taxes & fees

30 Sept - 1 Oct

A pool area with lounge chairs and palm trees.

A sign for Santa Maria Resort surrounded by lush greenery 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.

15. Santa Maria Suites

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

Anthony

AU$495

includes taxes & fees

30 Sept - 1 Oct

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 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.

16. Alexander Palms Court

Casa Marina, 1.8 km from Waterfront Playhouse

Andrew

AU$191

includes taxes & fees

30 Sept - 1 Oct

A rectangular pool with a white deck, surrounded by lush greenery and a gazebo.

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

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

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.

17. Ambrosia Key West

Old Town Key West, 0.7 km from Waterfront Playhouse

Tricia

AU$215

includes taxes & fees

30 Sept - 1 Oct

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

A breakfast tray with croissants, orange juice, and coffee on a table by a window with a view of a pool and greenery.

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

AU$287

includes taxes & fees

5 Oct - 6 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.

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

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.

19. Silver Palms Inn & Historic Homes

Old Town Key West, 1.4 km from Waterfront Playhouse

sam

AU$239

includes taxes & fees

30 Sept - 1 Oct

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

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.

A grand staircase with ornate railings and a chandelier.

20. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

yessy

AU$403

includes taxes & fees

13 Oct - 14 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 1,007 reviews	View
H2O Suites - Adults Only	9.8 Exceptional 659 reviews	View
The Gardens Hotel	9.8 Exceptional 1,005 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,005 reviews	View
The Conch House Heritage Inn	9.8 Exceptional 190 reviews	View

Top Waterfront Playhouse Hotel Reviews

Hyatt Centric Key West Resort and Spa

10/10 Excellent

"We had a wonderful stay at Hyatt Centric Key West Resort & Spa! The pool was a perfect place to relax, and we especially loved seeing the rescued turtles - such a unique and memorable part of the property. The location could not be better: everything we wanted to explore in Key West was within easy walking distance. It was incredibly convenient to enjoy the sights, restaurants, and lively atmosphere without needing a car. We would gladly stay here again!"

La Concha Key West, Autograph Collection

10/10 Excellent

"Hotel is very conveniently located to old town Key West. The renovations that have been made to the hotel really make it a very fun place to stay."

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"A+"

Ridley House - Key West Historic Inns

10/10 Excellent

"Exceptional resort! Beautiful room and extra friendly staff! Best place ever!"

Ocean Key Resort - A Noble House Resort

10/10 Excellent

"Loved the decor! The lobby, lobby bar and deck were so cute! I specially picked this resort and the room fur the decor-very tropical and fabulous! But honestly, the staff is what made this resort so great! From the front desk, to concierge, to the staff at Hot Tin Roof, to the pool bartender/ they all went above and beyond!"

Pier House Resort & Spa

10/10 Excellent

"Great location and superb private beach"

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."

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)

Costumed actors performing re-enactments and treasures from sunken ships give an insight into Key West’s history of salvaging and the lives of “wreckers”.

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Mallory Square

9.2/10 (15,939 reviews)

Enjoy the Sunset Celebration, a nightly festival with street performers and market stalls, as you watch the sun sink into the Gulf of Mexico from this town square.

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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 AU$191

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. The Gardens Hotel

4. Orchid Key Inn - Adults Only

5. The Conch House Heritage Inn

6. Simonton Court Historic Inn & Cottages

7. Alexander's Guesthouse - Adult Exclusive

8. The Marquesa Hotel

9. Duval House

10. Douglas House - Adults Only

11. The Grand Guesthouse

12. Island City House Hotel

13. Tropical Inn

14. The Mermaid & Alligator

15. Santa Maria Suites

16. Alexander Palms Court

17. Ambrosia Key West

18. Weatherstation Inn

19. Silver Palms Inn & Historic Homes

20. Southernmost House - Adult Exclusive

Compare popular hotels close to Waterfront Playhouse

Top Waterfront Playhouse Hotel Reviews

Hyatt Centric Key West Resort and Spa

La Concha Key West, Autograph Collection

Southernmost Beach Resort and Guesthouses

Ridley House - Key West Historic Inns

Ocean Key Resort - A Noble House Resort

Pier House Resort & Spa

Simonton Court Historic Inn & Cottages

The Penthouse at Custom House Inn | New!

Heart of Downtown Key West Cottage With Off-Street Parking

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