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Check prices for these dates

This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

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Our top choices for Waterfront Playhouse hotels

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

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, (1,007 reviews)
"We really enjoyed our stay! The staff were amazing and the room was perfect!"
United States
Teresa
The price is SAR 935
SAR 1,051 total
includes taxes & fees
17 Nov - 18 Nov
Almond Tree Inn Hotel - Adults Only
A tropical outdoor area with palm trees, hanging plants, and string lights.

2. 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, (591 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
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.

3. The Gardens Hotel

The Gardens Hotel
4.0 star property
Downtown Key West, 0.9 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (1,000 reviews)
"Best place we have stayed. The staff was amazing location perfect and the room was perfect"
United States
Misty
The price is SAR 925
SAR 1,040 total
includes taxes & fees
30 Nov - 1 Dec
The Gardens Hotel
A modern interior with a staircase, a sofa set, a wooden table, and a television.

4. 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, (1,000 reviews)
"Staff was great rooms are older but quite charming. Would definitely stay again."
United States
William
The price is SAR 1,648
SAR 1,854 total
includes taxes & fees
25 Nov - 26 Nov
Simonton Court Historic Inn & Cottages
A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.

5. Alexander's Guesthouse - Adult Exclusive

Alexander's Guesthouse - Adult Exclusive
3.5 star property
Old Town Key West, 1.2 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (176 reviews)
"We had such a great stay, nice property, Great location , the staff was helpful, friendly and fantastic! Delicious breakfast included … we really loved this place and we are looking forward to come back!"
United States
Nestor
The price is SAR 774
SAR 1,023 total
includes taxes & fees
12 Nov - 13 Nov
Alexander's Guesthouse - Adult Exclusive
A pool area with lounge chairs and a table, surrounded by palm trees.

6. 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, (1,006 reviews)
"Fantastic property. Love staying here 💗"
United States
Jessica
The price is SAR 948
SAR 1,067 total
includes taxes & fees
1 Dec - 2 Dec
Orchid Key Inn - Adults Only
A two-story house with a covered porch, a brick pathway, and a large tree.

7. 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, (1,003 reviews)
"The property is beautiful! The staff is great!"
United States
Martha
The price is SAR 1,528
SAR 1,930 total
includes taxes & fees
29 Nov - 30 Nov
The Marquesa Hotel
A porch with a white railing, a bench, and a flag.

8. 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, (198 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 1,027
SAR 1,155 total
includes taxes & fees
15 Nov - 16 Nov
The Conch House Heritage Inn
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.

9. 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, (1,002 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 narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.

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, (1,000 reviews)
"Fun apartment style living in Key West…fun little patio with coffee and continental breakfast. Make sure you look at the check in hours :) great spot makes you feel local"
United States
Justyn
The price is SAR 685
SAR 865 total
includes taxes & fees
1 Dec - 2 Dec
The Grand Guesthouse
A pool area with lounge chairs and candles, surrounded by palm trees and a building in the background.

11. Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (457 reviews)
"Check in was easy, rooms was clean and the propery was great! Will stay again."
United States
Brandon
The price is SAR 545
SAR 707 total
includes taxes & fees
15 Nov - 16 Nov
Tropical Inn
A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.

12. Duval House

Duval House
3.0 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (1,139 reviews)
"Great stay!"
United States
Dennis
The price is SAR 634
SAR 794 total
includes taxes & fees
18 Nov - 19 Nov
Duval House
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, (1,006 reviews)
"Great place for families"
United States
Anthony
The price is SAR 1,351
SAR 1,774 total
includes taxes & fees
2 Dec - 3 Dec
Santa Maria Suites
A room with a bed, a ceiling fan, and a window with blinds.

14. 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, (331 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 1,140
SAR 1,282 total
includes taxes & fees
29 Nov - 30 Nov
The Mermaid & Alligator
A poolside area with lounge chairs and a clear blue pool surrounded by lush tropical vegetation.

15. Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.9 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,007 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 large, ornate hotel with a pool, palm trees, and a view of the ocean.

16. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
4.0 star property
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,004 reviews)
"Such a wonderful peaceful place to stay! Great food close by and Duval Street"
United States
Edward Lance
The price is SAR 635
SAR 1,189 total
includes taxes & fees
16 Nov - 17 Nov
Southernmost House - Adult Exclusive
A green house with a white porch, a flag, and a sign advertising a property for sale.

17. 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, (1,004 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 wooden deck with wicker furniture and a white railing, surrounded by lush tropical vegetation.

18. Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex, 0.5 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,000 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 747
SAR 840 total
includes taxes & fees
29 Nov - 30 Nov
Weatherstation 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, (1,002 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 swimming pool with lounge chairs, a covered deck, and a view of lush greenery.

20. 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, (580 reviews)
"Fun place, great location, pool was perfect. Breakfast was amazing too."
United States
Thomas
The price is SAR 959
SAR 1,079 total
includes taxes & fees
16 Nov - 17 Nov
Coco Plum Inn
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.
View all properties

Compare popular hotels close to Waterfront Playhouse

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A breakfast table with various food items and drinks, a pool in the background, and a tiled wall.
Almond Tree Inn Hotel - Adults Only
3.5 star property
10.0
Exceptional
1,007 reviews
View
A tropical outdoor area with palm trees, hanging plants, and string lights.
Douglas House - Adults Only
3.5 star property
9.8
Exceptional
591 reviews
View
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
The Gardens Hotel
4.0 star property
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
2.5 star property
9.8
Exceptional
1,000 reviews
View
A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.
Alexander's Guesthouse - Adult Exclusive
3.5 star property
9.8
Exceptional
176 reviews
View

Hotels recommended for families near Waterfront Playhouse

A pool area with lounge chairs and a cabana.

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

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

10/10 Excellent
"This resort is amazing. Absolutely prime location within a few minutes walking distance to Mallory square, duval street and the Truman annex. The resort is older but it is well kept. Highly recommended."
Joshua 5-night trip
Posted 15 hours ago
Hyatt Vacation Club at Sunset Harbor, Key West

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.
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.
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.