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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov

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Our top choices for Waterfront Playhouse hotels

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
3.5 star property
Downtown Key West, 1.3 km from Waterfront Playhouse
10.0 out of 10, Exceptional, (1,000 reviews)
"We really enjoyed our stay! The staff were amazing and the room was perfect!"
United States
Teresa
The price is SAR 874
SAR 984 total
includes taxes & fees
16 Nov - 17 Nov
Almond Tree Inn Hotel - Adults Only
A covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.

2. Key West Villas

Key West Villas
3.5 star property
Downtown Key West, 0.9 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (279 reviews)
"Great location and very hospitable hotel owners"
United States
Margaret
The price is SAR 841
SAR 946 total
includes taxes & fees
18 Nov - 19 Nov
Key West Villas
A wooden deck leading to a pool area with a building in the background.

3. Douglas House - Adults Only

Douglas House - Adults Only
3.5 star property
Uptown - Upper Duval, 1.4 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (596 reviews)
"Clean place, courteous staff, great location"
United States
Sandra
The price is SAR 729
SAR 1,053 total
includes taxes & fees
17 Nov - 18 Nov
Douglas House - Adults Only
An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.

4. H2O Suites - Adults Only

H2O Suites - Adults Only
3.5 star property
Uptown - Upper Duval, 1.6 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (676 reviews)
"Amazing stay! Loved the private pool!"
United States
Kimberly
The price is SAR 1,338
SAR 1,759 total
includes taxes & fees
14 Dec - 15 Dec
H2O Suites - Adults Only
A pool area with lounge chairs and a table, surrounded by palm trees.

5. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
3.5 star property
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (1,000 reviews)
"Fantastic property. Love staying here 💗"
United States
Jessica
The price is SAR 857
SAR 964 total
includes taxes & fees
29 Nov - 30 Nov
Orchid Key Inn - Adults Only
A two-story white house with green shutters, a wooden door, and a white picket fence.

6. The Conch House Heritage Inn

The Conch House Heritage Inn
3.5 star property
Old Town Key West, 1.3 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (199 reviews)
"We really enjoyed getting to know the staff. The breakfast was excellent and everything was in walking distance."
United States
Jennifer
The price is SAR 982
SAR 1,105 total
includes taxes & fees
15 Nov - 16 Nov
The Conch House Heritage Inn
A rooftop pool with clear water, surrounded by palm trees and lounge chairs.

7. Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
2.5 star property
Historic Seaport, 0.5 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (1,002 reviews)
"Staff was great rooms are older but quite charming. Would definitely stay again."
United States
William
The price is SAR 1,497
SAR 1,685 total
includes taxes & fees
17 Nov - 18 Nov
Simonton Court Historic Inn & Cottages
A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.

8. Duval House

Duval House
3.0 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (1,131 reviews)
"Great stay!"
United States
Dennis
The price is SAR 624
SAR 783 total
includes taxes & fees
16 Nov - 17 Nov
Duval House
A poolside area with a swimming pool, a staircase leading to a deck, and a building with multiple windows and balconies.

9. The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Old Town Key West, 0.7 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (1,000 reviews)
"The property is beautiful! The staff is great!"
United States
Martha
The price is SAR 1,273
SAR 1,643 total
includes taxes & fees
30 Nov - 1 Dec
The Marquesa Hotel
An outdoor patio with wooden furniture, a red umbrella, and a wooden sign with directional arrows.

10. The Grand Guesthouse

The Grand Guesthouse
2.5 star property
Old Town Key West, 1.7 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (1,003 reviews)
"Great spot for a visit to Key West, staff was very helpful and well located for a walk down Duval St."
United States
Ryan
The price is SAR 685
SAR 865 total
includes taxes & fees
1 Dec - 2 Dec
The Grand Guesthouse
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.

11. Island City House Hotel

Island City House Hotel
3.0 star property
Historic Seaport, 0.8 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (999 reviews)
"Great place with lots of character and perfect location."
United States
Elise
The price is SAR 701
SAR 788 total
includes taxes & fees
2 Dec - 3 Dec
Island City House Hotel
A covered porch with wicker furniture, potted plants, and a ceiling fan.

12. The Mermaid & Alligator

The Mermaid & Alligator
3.5 star property
Old Town Key West, 1.3 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (332 reviews)
"such a lovely location. nice and quiet for a restful stay. staff was attentive to all our needs. would definitely return"
United States
christine
The price is SAR 1,171
SAR 1,317 total
includes taxes & fees
18 Nov - 19 Nov
The Mermaid & Alligator
A pool area with lounge chairs and palm trees.

13. Santa Maria Suites

Santa Maria Suites
4.0 star property
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (1,000 reviews)
"Great place for families"
United States
Anthony
The price is SAR 1,351
SAR 1,774 total
includes taxes & fees
29 Nov - 30 Nov
Santa Maria Suites
A green house with a white porch, a flag, and a sign advertising a property for sale.

14. L'Habitation Guest House - Adults Only

L'Habitation Guest House - Adults Only
2.5 star property
Historic Seaport, 0.5 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,000 reviews)
"A very cute, cozy and comfortable place to stay especially for old Key West charm. Will definitely stay here again."
United States
Callie
The price is SAR 638
SAR 718 total
includes taxes & fees
1 Dec - 2 Dec
L'Habitation Guest House - Adults Only
A pathway leading to a building with a white facade, surrounded by lush greenery and palm trees.

15. Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex, 0.5 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,001 reviews)
"This was the perfect location for access to Key West by foot!!!! We loved the community the resort is in!"
United States
Jane
The price is SAR 672
SAR 756 total
includes taxes & fees
1 Dec - 2 Dec
Weatherstation Inn
A pool surrounded by tropical plants and palm trees, with lounge chairs and a small building in the background.

16. Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.9 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,003 reviews)
"Breakfast was great . Pools were great and easy walk or bike ride to Duval street"
United States
Shari
The price is SAR 811
SAR 912 total
includes taxes & fees
29 Nov - 30 Nov
Westwinds Inn
A poolside area with lounge chairs, umbrellas, and a pergola.

17. Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
3.5 star property
Old Town Key West, 1.1 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (521 reviews)
"Staff was friendly and helpful. The grounds were clean and very beautiful."
United States
JENNIFER L
The price is SAR 826
SAR 1,119 total
includes taxes & fees
29 Nov - 30 Nov
Ella's Cottages - Key West Historic Inns
A white colonial-style building with a balcony, surrounded by palm trees and a white picket fence.

18. Coco Plum Inn

Coco Plum Inn
3.0 star property
Downtown Key West, 0.8 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (582 reviews)
"Fun place, great location, pool was perfect. Breakfast was amazing too."
United States
Thomas
The price is SAR 846
SAR 952 total
includes taxes & fees
29 Nov - 30 Nov
Coco Plum Inn
A rectangular pool with a white deck, surrounded by lush greenery and a gazebo.

19. Ambrosia Key West

Ambrosia Key West
3.5 star property
Old Town Key West, 0.7 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,000 reviews)
"Great location beautiful property we enjoyed our stay !"
United States
daniela
The price is SAR 781
SAR 878 total
includes taxes & fees
29 Nov - 30 Nov
Ambrosia Key West
A garden pathway leading to a building with a door, surrounded by lush greenery and a palm tree.

20. Alexander Palms Court

Alexander Palms Court
2.5 star property
Casa Marina, 1.8 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,001 reviews)
"We love staying at Alexander’s!!!"
United States
Brenda
The price is SAR 638
SAR 718 total
includes taxes & fees
1 Dec - 2 Dec
Alexander Palms Court
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Compare popular hotels close to Waterfront Playhouse

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A swimming pool with lounge chairs, surrounded by palm trees and greenery.
Almond Tree Inn Hotel - Adults Only
3.5 star property
10.0
Exceptional
1,000 reviews
View
A covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.
Key West Villas
3.5 star property
9.8
Exceptional
279 reviews
View
A wooden deck leading to a pool area with a building in the background.
Douglas House - Adults Only
3.5 star property
9.8
Exceptional
596 reviews
View
An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.
H2O Suites - Adults Only
3.5 star property
9.8
Exceptional
676 reviews
View
A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
3.5 star property
9.8
Exceptional
1,000 reviews
View

Hotels recommended for families near Waterfront Playhouse

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

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
4.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (1,000)
The price is SAR 954
SAR 1,377 total
includes taxes & fees
29 Nov - 30 Nov
Ocean Key Resort - A Noble House Resort

Top Waterfront Playhouse Hotel Reviews

Heron House - Adult Only

Heron House - Adult Only

10/10 Excellent
"Excellent location,"
Ezequiel 1-night trip
Posted 1 day ago
Heron House - Adult Only

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)
You can spend an afternoon studying the exhibits at Key West Shipwreck Museum during your trip to Key West. In the area, take in the lively festivals and beautiful sunsets.
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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, 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.
Where can I learn more about changing or cancelling my trip in the area near Waterfront Playhouse?
To access more information about rescheduling or cancelling your stay near Waterfront Playhouse, go to https://www.expedia.com/service/.
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.