The Best Hotels Closest to Waterfront Playhouse in Key West - 2026 Updated Prices

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

1. Almond Tree Inn Hotel - Adults Only

Downtown Key West, 1.3 km from Waterfront Playhouse

John

₹26,637

₹29,967 total

includes taxes & fees

27 Oct - 28 Oct

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

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.

A large, two-story building with a balcony, surrounded by dense tropical foliage.

2. Douglas House - Adults Only

Uptown - Upper Duval, 1.4 km from Waterfront Playhouse

Maricela

₹14,460

₹17,895 total

includes taxes & fees

14 Oct - 15 Oct

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

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

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.

3. Simonton Court Historic Inn & Cottages

Historic Seaport, 0.5 km from Waterfront Playhouse

William

₹22,892

₹25,754 total

includes taxes & fees

25 Oct - 26 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

ben

₹24,343

₹27,386 total

includes taxes & fees

27 Oct - 28 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

₹32,219

₹36,246 total

includes taxes & fees

14 Oct - 15 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 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.

6. Alexander's Guesthouse - Adult Exclusive

Old Town Key West, 1.2 km from Waterfront Playhouse

Nestor

₹21,678

₹28,384 total

includes taxes & fees

15 Oct - 16 Oct

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

A pool area with lounge chairs and a dining table, surrounded by palm trees and a house with a porch.

7. The Conch House Heritage Inn

Old Town Key West, 1.3 km from Waterfront Playhouse

John

₹27,355

₹30,775 total

includes taxes & fees

27 Oct - 28 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 covered porch with wicker furniture, a large potted plant, and a sign for Villas Key West.

A house with a porch, a table, and a door with a number '6'.

8. Key West Villas

Downtown Key West, 0.9 km from Waterfront Playhouse

₹24,913

₹28,028 total

includes taxes & fees

15 Oct - 16 Oct

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

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

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.

9. The Marquesa Hotel

Old Town Key West, 0.7 km from Waterfront Playhouse

Anna

₹34,386

₹44,072 total

includes taxes & fees

15 Oct - 16 Oct

A patio with wicker furniture, a red umbrella, and potted plants.

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

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

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

10. The Grand Guesthouse

Old Town Key West, 1.7 km from Waterfront Playhouse

Justyn

₹11,435

₹15,259 total

includes taxes & fees

14 Oct - 15 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 hallway with a white door, a wooden bench, a blue sofa, and a staircase with a white railing.

11. Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

Cliff

₹17,155

₹21,358 total

includes taxes & fees

27 Oct - 28 Oct

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

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.

A pool area with lounge chairs and a wooden building with balconies.

12. Island City House Hotel

Historic Seaport, 0.8 km from Waterfront Playhouse

Osvaldo

₹17,616

₹19,818 total

includes taxes & fees

14 Oct - 15 Oct

A pool area with lounge chairs and palm trees.

A reception area with a modern design, featuring a reception desk, a sofa, and a potted plant.

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

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

13. Santa Maria Suites

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

Anthony

₹28,639

₹38,684 total

includes taxes & fees

14 Oct - 15 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

₹22,331

₹25,123 total

includes taxes & fees

14 Oct - 15 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.

15. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

Amy

₹13,343

₹27,133 total

includes taxes & fees

28 Oct - 29 Oct

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.

16. Westwinds Inn

Historic Seaport, 0.9 km from Waterfront Playhouse

Anthony

₹15,517

₹17,456 total

includes taxes & fees

25 Oct - 26 Oct

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 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.

17. Silver Palms Inn & Historic Homes

Old Town Key West, 1.4 km from Waterfront Playhouse

sam

₹8,534

₹16,068 total

includes taxes & fees

25 Oct - 26 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 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.

A bedroom with a large bed, a sofa, a nightstand, and a painting on the wall.

18. L'Habitation Guest House - Adults Only

Historic Seaport, 0.5 km from Waterfront Playhouse

Richard

₹16,293

₹18,330 total

includes taxes & fees

28 Oct - 29 Oct

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

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

A living room with a spiral staircase, a sofa, a chair, a coffee table, and a view of an outdoor seating area.

A wooden bench with a cushion and a small table, surrounded by bamboo plants and a wooden deck.

19. Ella's Cottages - Key West Historic Inns

Old Town Key West, 1.1 km from Waterfront Playhouse

Henry

₹21,072

₹28,556 total

includes taxes & fees

14 Oct - 15 Oct

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

A white colonial-style building with a balcony, surrounded by palm trees and a white picket fence.

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.

20. Coco Plum Inn

Downtown Key West, 0.8 km from Waterfront Playhouse

Riley

₹17,198

₹19,347 total

includes taxes & fees

14 Oct - 15 Oct

View all properties

Compare popular hotels close to Waterfront Playhouse

Property	Property class	Guest rating
Almond Tree Inn Hotel - Adults Only	10.0 Exceptional 1,004 reviews	View
Douglas House - Adults Only	9.8 Exceptional 555 reviews	View
Simonton Court Historic Inn & Cottages	9.8 Exceptional 1,006 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,002 reviews	View
The Gardens Hotel	9.8 Exceptional 1,008 reviews	View

Hotels recommended for families near Waterfront Playhouse

A pool area with lounge chairs and a cabana.

A balcony with a table set for breakfast, overlooking the sea.

A waterfront hotel with a long pier, multiple balconies, and a view of the ocean.

A dining area with a glass table, clear glass bottles, a bowl of fruit, and a wicker chair.

Ocean Key Resort - A Noble House Resort

Key West Historic District

₹30,042

₹41,556 total

includes taxes & fees

27 Oct - 28 Oct

A beachfront hotel with a covered patio, palm trees, and a boat on the sand.

A view through a white-framed window with a decorative white fence, leading to a tiled patio area with a round table.

A balcony with a view of the ocean, a sofa, and a massage table.

A resort with a beach, a dock, and a water view.

Pier House Resort & Spa

Key West Historic District

₹32,167

₹42,869 total

includes taxes & fees

26 Oct - 27 Oct

A hotel with a swimming pool, balconies, and a view of the sea.

A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.

A balcony with a view of the ocean, a table, chairs, and a railing.

A marina with jet skis docked in front of a hotel with a dock and a boat in the background.

Hyatt Centric Key West Resort and Spa

Key West Historic District

₹23,275

₹32,865 total

includes taxes & fees

14 Oct - 15 Oct

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 brick pathway leading to a green door, surrounded by lush tropical plants and a white fence.

Ridley House - Key West Historic Inns

Key West Historic District

₹21,072

₹28,556 total

includes taxes & fees

15 Oct - 16 Oct

A large, white, two-story building with a balcony and a sign reading "The Marker Resort."

A covered outdoor area with a pool, palm trees, and lounge chairs.

A tropical setting with palm trees and a building with a white facade and dark roof.

A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.

The Marker Key West Harbor Resort

Key West Historic District

₹18,036

₹26,325 total

includes taxes & fees

25 Oct - 26 Oct

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 gray sofa, wooden staircase, and a kitchen in the background.

A pool area with lounge chairs and umbrellas, surrounded by buildings with balconies and a clear blue sky.

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

Eden House

Key West Historic District

₹12,515

₹15,769 total

includes taxes & fees

14 Oct - 15 Oct

Island City House Hotel

Key West Historic District

₹17,616

₹19,818 total

includes taxes & fees

14 Oct - 15 Oct

Ella's Cottages - Key West Historic Inns

Old Town Key West

₹21,072

₹28,556 total

includes taxes & fees

14 Oct - 15 Oct

Top Waterfront Playhouse Hotel Reviews

Simonton Court Historic Inn & Cottages

10/10 Excellent

"We loved this place! On of the most charming cottages we have ever stayed at. Very nice pool and beautiful grounds. Within walking distance of great restaurants, shopping and historical sites. Rooms were very pretty and comfortable with one exception. We like sleeping in dark rooms and outside lights left the room a little light if this bothers you. Blackout shades or curtains are the only thing I would change but we were still very happy with our stay"

Ridley House - Key West Historic Inns

10/10 Excellent

"My husband and I loved our stay at Ridley house. The property is beautiful and well maintained and our room was a nice size with a comfortable bed. We were served a breakfast spread every morning with plenty of food choices. The manager Angel was so helpful and knowledgeable, and he asked us every time he saw us if we needed anything. I don't remember the person's name who filled in for him, but she helped us set up rentals and a sandbar sunset cruise. We used the pool every day, to soak up some sun before heading out for the day. Duval street was an easy two blocks away."

Amsterdam's Curry Mansion Inn

8/10 Good

"Great location. Large rooms. Pool area is nice. Only gripes are the limited parking, and the fact that you can’t ever check in before 4pm, even though you can see the room sitting there empty. Also, the 10am checkout in an area known for nightlife is downright criminal."

Ocean Key Resort - A Noble House Resort

10/10 Excellent

"The property is located in an excellent location, walking all restaurants, boats, nightlife. The vibe is island, great pool, good food and the staff is wonderful. Could use some maintenance in the rooms, but it’s pretty good. Overall, it’s a fun place!"

The Marquesa Hotel

10/10 Excellent

"The staff was friendly and my room was clean , and the hotel was very nice!"

The Marker Key West Harbor Resort

10/10 Excellent

"Nice clean room and close to all the attractions"

Opal Key Resort & Marina, Key West

10/10 Excellent

"Great location. Walking distance to Anything you’d want to do in Key West. Housekeeping staff very attentive. Valets very friendly and quick to attend. Room was clean spacious and bed comfortable. Restaurant was just OK. Staff there not as friendly and attentive. Pool was ok."

Ambrosia Key West

10/10 Excellent

"My wife and I were at Ambrosia for three days and found it excellent in every way--everything as advertised or better. Our lovely two-room suite was in walking distance of food and entertainment, and the staff was unfailingly friendly, efficient, and eager to help. Not a glitch while we were there."

Weatherstation Inn

10/10 Excellent

"We liked how close the Inn was to everything we wanted to do. Very walkable and in a quiet area. Staff was friendly, the breakfast bake goods were great."

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 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.

Search Hotels Near Waterfront Playhouse, Key West

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. Douglas House - Adults Only

3. Simonton Court Historic Inn & Cottages

4. Orchid Key Inn - Adults Only

5. The Gardens Hotel

6. Alexander's Guesthouse - Adult Exclusive

7. The Conch House Heritage Inn

8. Key West Villas

9. The Marquesa Hotel

10. The Grand Guesthouse

11. Duval House

12. Island City House Hotel

13. Santa Maria Suites

14. The Mermaid & Alligator

15. Southernmost House - Adult Exclusive

16. Westwinds Inn

17. Silver Palms Inn & Historic Homes

18. L'Habitation Guest House - Adults Only

19. Ella's Cottages - Key West Historic Inns

20. Coco Plum Inn

Compare popular hotels close to Waterfront Playhouse

Hotels recommended for families near Waterfront Playhouse

Ocean Key Resort - A Noble House Resort

Pier House Resort & Spa

Hyatt Centric Key West Resort and Spa

Ridley House - Key West Historic Inns

The Marker Key West Harbor Resort

Eden House

Island City House Hotel

Ella's Cottages - Key West Historic Inns

Top Waterfront Playhouse Hotel Reviews

Simonton Court Historic Inn & Cottages

Ridley House - Key West Historic Inns

Amsterdam's Curry Mansion Inn

Ocean Key Resort - A Noble House Resort

The Marquesa Hotel

The Marker Key West Harbor Resort

Opal Key Resort & Marina, Key West

Ambrosia Key West

Weatherstation Inn

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