The Best Hotels Closest to Waterfront Playhouse in Key West for 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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 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

Teresa

SAR 923

SAR 1,039 total

includes taxes & fees

25 Oct - 26 Oct

A pool area with lounge chairs and a table, surrounded by 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."

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.

2. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

ben

SAR 934

SAR 1,051 total

includes taxes & fees

26 Oct - 27 Oct

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.

3. Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

Cathrine

SAR 480

SAR 621 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 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 bathroom with a vanity, a mirror, and a window with blinds.

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

4. L'Habitation Guest House - Adults Only

Historic Seaport, 0.5 km from Waterfront Playhouse

Richard

SAR 533

SAR 600 total

includes taxes & fees

27 Oct - 28 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 large, two-story house with a prominent tower and a covered porch.

A gated entrance with a blue metal gate, palm trees, and a building with a red roof in the background.

5. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

Janet

SAR 672

SAR 1,231 total

includes taxes & fees

25 Oct - 26 Oct

A two-story building with a white picket fence, palm trees, and a sign that reads 'DUVAL GARDENS.'

A porch with wicker chairs and a table, white railings, and a window with a view of a palm tree.

A kitchen counter with a coffee maker, a bottle of champagne, and various fruits and pastries.

6. Duval Gardens - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

JoAnn

SAR 691

SAR 925 total

includes taxes & fees

25 Oct - 26 Oct

A pool area with a brick patio, potted plants, and a covered seating area.

A porch with a white chair, a wooden door, and a small indoor dining area visible through the door.

A view through a glass door with a metal handle, leading to a white fence and a blue car parked outside.

A white picket fence, a palm tree, and a sign reading "Garden House Key West".

7. The Garden House

Historic Seaport, 0.6 km from Waterfront Playhouse

Brad

SAR 371

SAR 498 total

includes taxes & fees

26 Oct - 27 Oct

A covered porch with wicker furniture, potted plants, and a sign for the "Office" at the Palm Hotel.

A compact kitchen with white cabinets, a microwave, and a small dining area with two wicker chairs.

A hotel with a white facade, multiple balconies, and lush tropical landscaping.

A row of bicycles parked in front of a building with a white balcony and a palm tree.

8. The Palms Hotel

The Meadows, 1.5 km from Waterfront Playhouse

Jerry

SAR 657

SAR 824 total

includes taxes & fees

25 Oct - 26 Oct

A swimming pool with clear water, surrounded by lush greenery and palm trees.

A bathroom with a shower, sink, and toilet.

A yellow building with a blue door and shutters, a number '302' on the wall, and a small porch area.

A covered porch with white columns and wicker furniture.

9. Tranquility Guest House

Bahama Village, 0.9 km from Waterfront Playhouse

Sandra

SAR 439

SAR 827 total

includes taxes & fees

27 Oct - 28 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 spacious living area with a wooden staircase, a ceiling fan, a TV, and a view of the beach through an open door.

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

10. Eden House

Historic Seaport, 1.1 km from Waterfront Playhouse

Michelle

SAR 572

SAR 721 total

includes taxes & fees

27 Oct - 28 Oct

A breakfast setup with wine bottles, fruits, and pastries on a tray by a door with a view of a staircase and greenery.

A white building with a grey roof, surrounded by potted plants and a blue umbrella.

A patio with sun loungers, a table with an umbrella, and potted plants.

A spacious kitchen with wooden cabinets and a dining area with a round table and chairs.

11. The Cabana Inn Key West - Adults Only

Downtown Key West, 0.7 km from Waterfront Playhouse

Donna

SAR 604

SAR 849 total

includes taxes & fees

25 Oct - 26 Oct

A deck with sun loungers and a railing overlooking the sea.

A poolside area with lounge chairs and umbrellas, palm trees, and a view of the sea.

A beach scene with two people relaxing under a white umbrella, a palm tree, and a clear blue sky.

A room with a view of the beach and ocean, a bed with a white and blue blanket, and a small table with a potted plant.

12. Southernmost Beach Resort and Guesthouses

Uptown - Upper Duval, 1.7 km from Waterfront Playhouse

Jacob Stuart

SAR 444

SAR 787 total

includes taxes & fees

26 Oct - 27 Oct

A beach with a wooden pier, palm trees, and beach umbrellas.

A modern bar area with a central island, white bar stools, and a view of the ocean.

An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.

A resort with a pool, lounge chairs, umbrellas, palm trees, and a view of the ocean.

13. The Reach Key West, Curio Collection by Hilton

Uptown - Upper Duval, 1.9 km from Waterfront Playhouse

Brett

SAR 672

SAR 1,009 total

includes taxes & fees

26 Oct - 27 Oct

A wooden deck with wicker furniture and a glass balustrade overlooking a beach.

A beachside spa with two massage tables under a canopy, overlooking the sea and a pier.

A beach with white lounge chairs and umbrellas, a sandy shore, and a calm sea under a partly cloudy sky.

A resort with a pool leading to a beach, surrounded by palm trees and white buildings.

14. Casa Marina Key West, Curio Collection by Hilton

Casa Marina, 2.2 km from Waterfront Playhouse

Jaime

SAR 922

SAR 1,290 total

includes taxes & fees

3 Nov - 4 Nov

A poolside area with lounge chairs, a staircase leading to a balcony, and a pool.

A Southernmost Inn with a porch, a sign indicating vacancy, and a staircase leading to the entrance.

An outdoor patio with tables and chairs, surrounded by trees and a house.

A dining area with round tables and wicker chairs, a ceiling fan, and a bar area in the background.

15. The Southernmost Inn - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Craig

SAR 409

SAR 629 total

includes taxes & fees

25 Oct - 26 Oct

A neatly made bed with white linens and a blue throw blanket, a bedside table with a lamp, and an air conditioning unit mounted on the wall.

A youth hostel with a white exterior, a blue awning, and a white picket fence.

A room with a wooden floor, a white door with horizontal slats, a wooden wall, and a small shelf with a black object.

A motel sign, parked bicycles, and a building with a covered porch.

16. Seashell Motel

Casa Marina, 1.8 km from Waterfront Playhouse

Yuliya

SAR 510

SAR 573 total

includes taxes & fees

25 Oct - 26 Oct

A two-story Victorian-style house with a prominent tower, a balcony, and a front porch.

A staircase with wooden balusters and a white console table with two lamps and decorative items.

A wooden deck with lounge chairs and a small pool, surrounded by lush greenery and a brick building.

A corner seating area with a marble countertop, a chandelier, and a view of greenery outside.

17. Grand Maloney Hotel

Historic Seaport, 0.4 km from Waterfront Playhouse

James

SAR 784

SAR 1,525 total

includes taxes & fees

27 Oct - 28 Oct

A pool area with lounge chairs and palm trees, overlooking the ocean.

A beach view with palm trees and lounge chairs.

A beachfront hotel with multiple buildings, palm trees, and a clear view of the ocean.

18. Coconut Beach Resort Timeshare

Casa Marina, 2 km from Waterfront Playhouse

Wayne

SAR 5,623

SAR 6,326 total

includes taxes & fees

24 Oct - 25 Oct

A modern kitchen with white cabinets, stainless steel appliances, and a wooden door.

A narrow brick pathway leading to a gated entrance with a sign reading "533 Caroline The Bartlum".

A compact hotel room with a bed, a desk with two chairs, a kitchenette, and a TV.

A modern kitchen with white cabinets, a stainless steel refrigerator, and a dishwasher.

19. The Bartlum Luxury Studio In Prime Location

Historic Seaport, 0.4 km from Waterfront Playhouse

SAR 1,107

SAR 2,120 total

includes taxes & fees

27 Oct - 28 Oct

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

A hotel room with a large bed, a desk, a chair, a television, and a ceiling fan.

A marina with boats docked, a swimming pool, and palm trees.

A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

20. The Perry Hotel & Marina Key West

Stock Island, 6.9 km from Waterfront Playhouse

Jade

SAR 391

SAR 660 total

includes taxes & fees

26 Oct - 27 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 1,005 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,003 reviews	View
Duval House	9.6 Exceptional 1,125 reviews	View
L'Habitation Guest House - Adults Only	9.4 Exceptional 1,000 reviews	View
Southernmost House - Adult Exclusive	9.4 Exceptional 1,001 reviews	View

Hotels recommended for families near Waterfront Playhouse

A pool area with lounge chairs and a cabana.

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.

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

Ocean Key Resort - A Noble House Resort

Key West Historic District

SAR 1,050

SAR 1,485 total

includes taxes & fees

23 Nov - 24 Nov

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

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.

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

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

Pier House Resort & Spa

Key West Historic District

SAR 651

SAR 994 total

includes taxes & fees

26 Oct - 27 Oct

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 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.

Ridley House - Key West Historic Inns

Key West Historic District

SAR 751

SAR 1,035 total

includes taxes & fees

26 Oct - 27 Oct

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

Key West Historic District

SAR 866

SAR 1,249 total

includes taxes & fees

25 Oct - 26 Oct

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

A marina with various boats docked, including a green and white boat named 'Jolly Roger'.

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

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

The Marker Key West Harbor Resort

Key West Historic District

SAR 680

SAR 1,010 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

Ella's Cottages - Key West Historic Inns

Old Town Key West

SAR 751

SAR 1,035 total

includes taxes & fees

25 Oct - 26 Oct

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with a white facade.

A modern kitchen with a wooden counter, two stools, a wicker chair, and a hanging light fixture.

A table with chairs in a lush indoor garden setting.

A bedroom with a sloped ceiling, a bed, two chairs, a hanging light fixture, and a window with a view of greenery.

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

SAR 751

SAR 1,035 total

includes taxes & fees

25 Oct - 26 Oct

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

A garden with a pond, rocks, and various plants.

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.

Island City House Hotel

Key West Historic District

SAR 743

SAR 835 total

includes taxes & fees

26 Oct - 27 Oct