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Check prices for these dates

This weekend
Jul 24 - Jul 26
Next weekend
Jul 31 - Aug 2

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Our top choices for Waterfront Playhouse hotels

Queen Deluxe ADA | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

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, (1,006 reviews)
"Great stay! Great location and friendly, helpful staff. Loved our stay here! Would recommend."
United States
Linda
The price is ￥32,112
￥36,127 total
includes taxes & fees
Jul 27 - Jul 28
Almond Tree Inn Hotel - Adults Only
Restaurant

2. Artist House Key West

Artist House Key West
3.5 star property
Historic Seaport, 0.5 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (449 reviews)
"Great atmosphere and location."
United States
NATHAN
The price is ￥20,292
￥22,829 total
includes taxes & fees
Aug 19 - Aug 20
Artist House Key West
Queen with Pool View | Minibar, in-room safe, iron/ironing board, WiFi (free)

3. 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)
"Perfcet location and walk to everything , we very much enjoyed our stay!"
United States
Rita
The price is ￥27,464
￥30,897 total
includes taxes & fees
Jul 29 - Jul 30
Simonton Court Historic Inn & Cottages
Exterior detail

4. 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)
"Loved the hotel, Super cozy and private …"
United States
Floriza
The price is ￥32,703
￥36,791 total
includes taxes & fees
Aug 10 - Aug 11
The Gardens Hotel
Property grounds

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, (1,004 reviews)
"Wonderful place and staff!"
United States
William
The price is ￥31,056
￥34,938 total
includes taxes & fees
Jul 27 - Jul 28
Orchid Key Inn - Adults Only
Exterior

6. 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)
"Great location and beautiful property. I appreciate the parking which comes at a premium in Key West and the two swimming pools. Just enough off the beaten path to feel comfortable."
United States
Darrell
The price is ￥36,696
￥50,419 total
includes taxes & fees
Aug 11 - Aug 12
The Marquesa Hotel
Outdoor pool, open 8:00 AM to 7:00 PM, pool umbrellas, sun loungers

7. Tranquility Guest House

Tranquility Guest House
2.0 star property
Bahama Village, 0.9 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (7 reviews)
"It was a great property, very clean room and excellent price. Staff was great."
United States
Hector
The price is ￥16,234
￥32,696 total
includes taxes & fees
Jul 28 - Jul 29
Tranquility Guest House
Audubon Room - Adult Exclusive | Terrace/patio

8. The Mermaid & Alligator

The Mermaid & Alligator
3.5 star property
Old Town Key West, 1.3 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (307 reviews)
"Great location, lovely place, clean and comfortable room. Highly recommend! "
United States
Mary
The price is ￥34,713
￥39,052 total
includes taxes & fees
Jul 26 - Jul 27
The Mermaid & Alligator
Veranda Room | Terrace/patio

9. 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, (179 reviews)
"Great location "
United Kingdom
Lucy
The price is ￥30,791
￥34,640 total
includes taxes & fees
Aug 5 - Aug 6
The Conch House Heritage Inn
Superior Studio Suite, 1 King Bed with Sofa bed, Accessible, Refrigerator & Microwave | WiFi (free), bed sheets

10. Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
3.5 star property
Old Town Key West, 1.2 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (149 reviews)
"The staff and other guests were very friendly. The room was spacious and the bed was comfortable. "
United States
Annette
The price is ￥17,405
￥25,760 total
includes taxes & fees
Jul 22 - Jul 23
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Deluxe Suite, 1 King Bed, Private Pool | View from room

11. 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, (626 reviews)
"We had a wonderful stay!"
United States
Elizabeth
The price is ￥46,934
￥63,762 total
includes taxes & fees
Aug 16 - Aug 17
H2O Suites - Adults Only
Exterior

12. Douglas House - Adults Only

Douglas House - Adults Only
3.0 star property
Uptown - Upper Duval, 1.4 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (456 reviews)
"Great stay"
United States
Matthew
The price is ￥16,403
￥20,299 total
includes taxes & fees
Jul 22 - Jul 23
Douglas House - Adults Only
Cigar House King Suite w/ Poolside porch | Balcony view

13. 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)
"We loved our time here! This was a child friendly space in a beautiful setting. The staff was very kind, the space was clean and comfortable. We will definitely be back!"
United States
Brittany
The price is ￥30,221
￥33,999 total
includes taxes & fees
Jul 26 - Jul 27
Island City House Hotel
11 Gecko's Garden - Adults Only | Premium bedding, pillowtop beds, iron/ironing board, WiFi (free)

14. Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (424 reviews)
"It’s a super unique property and has a ton of character . Pool and garden area are fantastic . Right in the heart of Duval st. and all the action. Would stay again"
United States
Brandon Colby
The price is ￥26,655
￥34,049 total
includes taxes & fees
Jul 22 - Jul 23
Tropical Inn
Outdoor pool

15. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
3.5 star property
Old Town Key West, 1.4 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,035 reviews)
"Nice staff and close to everything. I would stay there again"
United States
Alex
The price is ￥11,823
￥24,263 total
includes taxes & fees
Aug 5 - Aug 6
Silver Palms Inn & Historic Homes
Courtyard

16. 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, (1,001 reviews)
"The room was clean and quaint, the staff was very friendly, the property was beautiful and the location was excellent. Would love to stay again!"
United States
Jason
The price is ￥25,308
￥32,534 total
includes taxes & fees
Jul 26 - Jul 27
The Grand Guesthouse
Property grounds

17. Duval House

Duval House
3.0 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,054 reviews)
"The hotel has a perfect location. We enjoyed the breakfast. It was clean and the staff was amazing."
United States
david
The price is ￥17,200
￥22,842 total
includes taxes & fees
Aug 11 - Aug 12
Duval House
Lobby sitting area

18. Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.9 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,002 reviews)
"Nice place to stay!"
United States
michael
The price is ￥27,040
￥30,420 total
includes taxes & fees
Jul 22 - Jul 23
Westwinds Inn
Exterior

19. 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, (1,003 reviews)
"The room was amazing with a great kitchen, and very clean. The staff was very professional and friendly and the breakfast delicious."
United States
Alina
The price is ￥22,623
￥46,005 total
includes taxes & fees
Aug 10 - Aug 11
Southernmost House - Adult Exclusive
Exterior

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, (547 reviews)
"Perfect stay, we will be back!"
United States
Jake
The price is ￥28,602
￥32,177 total
includes taxes & fees
Jul 28 - Jul 29
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
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
Queen Deluxe ADA | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Almond Tree Inn Hotel - Adults Only
3.5 star property
10.0
Exceptional
1,006 reviews
View
Restaurant
Artist House Key West
3.5 star property
9.8
Exceptional
449 reviews
View
Queen with Pool View | Minibar, in-room safe, iron/ironing board, WiFi (free)
Simonton Court Historic Inn & Cottages
2.5 star property
9.8
Exceptional
1,002 reviews
View
Exterior detail
The Gardens Hotel
4.0 star property
9.8
Exceptional
1,000 reviews
View
Property grounds
Orchid Key Inn - Adults Only
3.5 star property
9.8
Exceptional
1,004 reviews
View

Top Waterfront Playhouse Hotel Reviews

Pier House Resort & Spa

Pier House Resort & Spa

8/10 Good
"The beach and location was the real hit at this property. We enjoyed our stay."
Lyndsay 3-night trip
Posted 2 hours ago
Pier House Resort & Spa

Hotels near other Waterfront Playhouse attractions

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

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 1438 hotels and other accommodations you'll find within a mile.
What's the best hotel to stay near Waterfront Playhouse?
Adjacent to Waterfront Playhouse, Hyatt Centric Key West Resort and Spa is one of the top choices for your stay based on our traveler data, and this resort offers a marina and a full-service spa. Other good options within a short distance include Pier House Resort & Spa and Opal Key Resort & Marina, Key West.
How many hotels will I be able to find near Waterfront Playhouse?
Expedia has 1438 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?
Key West Shipwreck Museum, Harry S. Truman Little White House, and Florida Keys Eco - Discovery Center feature a variety of fascinating exhibits to see while you're in town. Sights like Key West Historic Seaport, Ernest Hemingway Home and Museum, and Key West Lighthouse and Keeper's Quarters Museum 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.