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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 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.

1. Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
Downtown Key West, 1.3 km from Waterfront Playhouse
United States
Teresa
CA $393
CA $442 total
includes taxes & fees
Oct 27 - Oct 28
Almond Tree Inn Hotel - Adults Only
A tropical outdoor area with palm trees, hanging plants, and string lights.
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.
An outdoor patio with a table and chairs, surrounded by lush greenery and string lights.

2. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 1.4 km from Waterfront Playhouse
United States
Maricela
CA $223
CA $275 total
includes taxes & fees
Oct 19 - Oct 20
Douglas House - Adults Only
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."

3. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
United States
ben
CA $359
CA $404 total
includes taxes & fees
Oct 27 - Oct 28
Orchid Key Inn - Adults Only
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 pool area with a clear view of a house in the background, surrounded by palm trees and greenery.
A spacious room with a large bed, a sofa, a chair, a small table, and a television.

4. Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
Historic Seaport, 0.5 km from Waterfront Playhouse
United States
William
CA $239
CA $269 total
includes taxes & fees
Oct 27 - Oct 28
Simonton Court Historic Inn & Cottages
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
A colonial-style building with a porch, surrounded by lush tropical vegetation.
A couple walking along a poolside pathway surrounded by lush greenery.
A bar area with a counter, chairs, and a clock.

5. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Gisele
CA $380
CA $428 total
includes taxes & fees
Oct 27 - Oct 28
The Gardens Hotel
A modern outdoor area with a pool, lounge chairs, and a bar area.
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.
A modern hotel with a prominent glass facade, palm trees, and a clear sky.

6. H2O Suites - Adults Only

H2O Suites - Adults Only
Uptown - Upper Duval, 1.6 km from Waterfront Playhouse
United States
Corey
CA $434
CA $584 total
includes taxes & fees
Oct 27 - Oct 28
H2O Suites - Adults Only
A gated entrance to Villas Key West with a brick pathway leading to the gate.
A house with a porch, a table, and a door with a number '6'.
A swimming pool with a hot tub, surrounded by a wooden deck and lush greenery.
A covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.

7. Key West Villas

Key West Villas
Downtown Key West, 0.9 km from Waterfront Playhouse
United States
Margaret
CA $431
CA $485 total
includes taxes & fees
Nov 18 - Nov 19
Key West Villas
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 covered porch with white wicker furniture and a blue floor, surrounded by lush tropical plants.
A restaurant with multiple tables set for dining, a wine bottle, and a glass of wine on the table.

8. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
Anna
CA $576
CA $727 total
includes taxes & fees
Nov 3 - Nov 4
The Marquesa Hotel
A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.
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.
A narrow room with a bed, a potted plant, and a window with blinds.

9. Alexander's Guesthouse - Adult Exclusive

Alexander's Guesthouse - Adult Exclusive
Old Town Key West, 1.2 km from Waterfront Playhouse
United States
Nestor
CA $342
CA $444 total
includes taxes & fees
Oct 28 - Oct 29
Alexander's Guesthouse - Adult Exclusive
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 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.

10. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 1.3 km from Waterfront Playhouse
United States
Jennifer
CA $404
CA $454 total
includes taxes & fees
Oct 25 - Oct 26
The Conch House Heritage Inn
A staircase with white balusters and blue steps leading to an exit.
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.
A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.

11. Duval House

Duval House
Downtown Key West, 1.1 km from Waterfront Playhouse
United States
Cathrine
CA $239
CA $299 total
includes taxes & fees
Oct 25 - Oct 26
Duval House
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 compact kitchen with wooden cabinets, a microwave, stove, and refrigerator. There is a dining area with a table and chairs, and a sofa.
A garden with a pond, rocks, and various plants.

12. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.8 km from Waterfront Playhouse
United States
Elise
CA $275
CA $309 total
includes taxes & fees
Oct 25 - Oct 26
Island City House Hotel
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 poolside area with lounge chairs, a covered seating area, and a small pool.
A spacious kitchen with wooden cabinets, a granite countertop, and a ceiling fan.

13. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 1.3 km from Waterfront Playhouse
United Kingdom
Adam
CA $339
CA $381 total
includes taxes & fees
Oct 19 - Oct 20
The Mermaid & Alligator
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 balcony with white railings and a table, overlooking a beach with palm trees and a clear blue sky.
A gated entrance with a blue metal gate, palm trees, and a building with a red roof in the background.

14. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
United States
Amy
CA $253
CA $464 total
includes taxes & fees
Oct 25 - Oct 26
Southernmost House - Adult Exclusive
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 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.

15. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.7 km from Waterfront Playhouse
United States
RICHARD
CA $235
CA $265 total
includes taxes & fees
Oct 25 - Oct 26
Ambrosia Key West
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.
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 wooden bench with a cushion and a small table, surrounded by bamboo plants and a wooden deck.

16. Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
Old Town Key West, 1.1 km from Waterfront Playhouse
United States
Henry
CA $283
CA $390 total
includes taxes & fees
Oct 19 - Oct 20
Ella's Cottages - Key West Historic Inns
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.

17. L'Habitation Guest House - Adults Only

L'Habitation Guest House - Adults Only
Historic Seaport, 0.5 km from Waterfront Playhouse
United States
Richard
CA $241
CA $271 total
includes taxes & fees
Oct 28 - Oct 29
L'Habitation Guest House - Adults Only
A wooden deck with wicker furniture and a white railing, surrounded by lush tropical vegetation.
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.
A breakfast tray with croissants, orange juice, and coffee on a table by a window with a view of a pool and greenery.

18. Weatherstation Inn

Weatherstation Inn
Truman Annex, 0.5 km from Waterfront Playhouse
United States
Robert
CA $366
CA $412 total
includes taxes & fees
Nov 1 - Nov 2
Weatherstation Inn
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
The entrance to Silver Palms Inn with a reception desk, a seating area, and a glass door.
A two-story yellow house with a porch, white railings, and green shutters.
A hotel with a pool, bicycles, and lush greenery.

19. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 1.4 km from Waterfront Playhouse
United States
sam
CA $126
CA $237 total
includes taxes & fees
Oct 25 - Oct 26
Silver Palms Inn & Historic Homes
A reception area with a curved marble counter, ceiling fans, large windows, and a staircase.
A bedroom with a bed, two bedside lamps, a ceiling fan, and a view of a balcony with plants.
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.

20. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.9 km from Waterfront Playhouse
United States
Anthony
CA $229
CA $258 total
includes taxes & fees
Oct 25 - Oct 26
Westwinds Inn
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Compare popular hotels close to Waterfront Playhouse

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.
Almond Tree Inn Hotel - Adults Only
10.0
Exceptional
1,002 reviews
View
A tropical outdoor area with palm trees, hanging plants, and string lights.
Douglas House - Adults Only
9.8
Exceptional
558 reviews
View
A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
9.8
Exceptional
1,000 reviews
View
A modern interior with a staircase, a sofa set, a wooden table, and a television.
Simonton Court Historic Inn & Cottages
9.8
Exceptional
1,004 reviews
View
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
The Gardens Hotel
9.8
Exceptional
1,002 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 hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.
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

Ocean Key Resort - A Noble House Resort
Key West Historic District
CA $423
CA $590 total
includes taxes & fees
Oct 19 - Oct 20
Ocean Key Resort - A Noble House Resort
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
A balcony with a view of the ocean, a sofa, and a massage table.
A view through a white-framed window with a decorative white fence, leading to a tiled patio area with a round table.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.

Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
CA $371
CA $516 total
includes taxes & fees
Nov 18 - Nov 19
Pier House Resort & Spa
A hotel with a swimming pool, balconies, and a view of the sea.
A marina with jet skis docked in front of a hotel with a dock and a boat in the background.
A balcony with a view of the ocean, a table, chairs, and a railing.
A beach wedding setup with white chairs, a wooden arch, and lanterns.

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
CA $358
CA $501 total
includes taxes & fees
Nov 2 - Nov 3
Hyatt Centric Key West Resort and Spa
A white building with green shutters and a white picket fence.
A modern kitchen with white cabinetry, a central island, and a view of the outdoors.
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

Ridley House - Key West Historic Inns
Key West Historic District
CA $283
CA $390 total
includes taxes & fees
Oct 25 - Oct 26
Ridley House - Key West Historic Inns
A large, white, two-story building with a balcony and a sign reading "The Marker Resort."
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.
A covered outdoor area with a pool, palm trees, and lounge chairs.

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
Key West Historic District
CA $266
CA $389 total
includes taxes & fees
Oct 25 - Oct 26
The Marker Key West Harbor Resort
A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.
A cozy cabin with a wooden interior, a bed, a TV, and a kitchenette.
A spacious living area with a wooden staircase, a ceiling fan, a TV, and a view of the beach through an open door.
A pool area with lounge chairs and umbrellas, surrounded by buildings with balconies and a clear blue sky.

Eden House

Eden House
Key West Historic District
CA $216
CA $272 total
includes taxes & fees
Oct 28 - Oct 29
Eden House
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 compact kitchen with wooden cabinets, a microwave, stove, and refrigerator. There is a dining area with a table and chairs, and a sofa.
A garden with a pond, rocks, and various plants.

Island City House Hotel

Island City House Hotel
Key West Historic District
CA $275
CA $309 total
includes taxes & fees
Oct 25 - Oct 26
Island City House Hotel
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.
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 wooden bench with a cushion and a small table, surrounded by bamboo plants and a wooden deck.

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
Old Town Key West
CA $283
CA $390 total
includes taxes & fees
Oct 19 - Oct 20
Ella's Cottages - Key West Historic Inns

Top Waterfront Playhouse Hotel Reviews

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"Never stayed at an Opal resort property before..but will return! Very impressive, great location and a great restaurant!"
Claudette 2-night trip
Posted 6 hours ago
Opal Key Resort & Marina, Key West
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Staff is very friendly and helpful."
Tracy 4-night trip
Posted 11 hours ago
Pier House Resort & Spa
Weatherstation Inn

Weatherstation Inn

10/10 Excellent
"Our stay was for two nights in October 2026. This is a beautiful property in a wonderful neighborhood, the Truman Annex section of Key West. The hotel is historic, quite classic, with property filled with tropical plantings, all well maintained. The staff was so friendly, professional, polite and very helpful. Our room was spotless and nicely appointed, with extra thoughtful touches...cozy terry robes, and slippers. Bathroom was lovely, large and cheery. Additional cotton blankets and beach towels were so nice to have on hand. The self-serve breakfast included an assortment of croissant pastries and doughnuts, yogurt, fresh fruit and of course coffee, including hot chocolate and various teas. So delicious! The pool area is charming. Bicycles for rent were just inside the gate. The location couldn't be better. Quiet yet so close to everything. We love staying at historic properties. The Weatherstation Inn did not disappoint! We will definitely be back again. One more thing! Parking is included on property."
Cheryl 1-night trip
Posted 11 hours ago
Weatherstation Inn
Heron House - Adult Only

Heron House - Adult Only

10/10 Excellent
"The property was wonderfully located, clean, and beautiful. Highly recommend."
Lance 3-night trip
Posted 12 hours ago
Heron House - Adult Only
Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

10/10 Excellent
"Very good"
luis 4-night trip
Posted 15 hours ago
Ocean Key Resort - A Noble House Resort
The Marquesa Hotel

The Marquesa Hotel

10/10 Excellent
"Fantastic hotel, very clean, helpful staff, awesome Key West vibes, and great location! We were so happy with everything- breakfast at the Cafe featured friendly staff and the best bacon EVER, pool was delightful, room was great. Highly recommend if you are coming to Key West!"
Tara 3-night trip
Posted 1 day ago
The Marquesa Hotel
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Loved our stay at La Concha. Staff was excellent and constantly focused on our comfort and enjoyment. Upon arrival (kind of late), we were unsure if the bar was still serving food. Once staff became aware that we wanted food, they did everything they could think of to ensure we got what we needed. Top-notch customer service! The location of the hotel could not be beat, for our purposes. Easy to explore many different areas that we wanted to see…particularly Old Town and the seaport district. Everything is very walkable; however, if you have people in your party who cannot walk much distance, it is very easy to rent a golf cart to haul them around. An extremely enjoyable trip, made all the better by the staff and quality of La Concha."
LEE 7-night trip
Posted 1 day ago
La Concha Key West, Autograph Collection
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

10/10 Excellent
"Great location"
Joseph 4-night trip
Posted 2 days ago
Hyatt Centric Key West Resort and Spa
Ridley House - Key West Historic Inns

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."
Mary 5-night trip
Posted 4 days ago
Ridley House - Key West Historic Inns

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.
See properties
A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.

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.
See properties
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.
See properties
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.
See properties
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.
See properties
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.
See properties

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.
See properties

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 1400 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 1400 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?
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 theater.

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