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Our top choices for Waterfront Playhouse hotels

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, (429 reviews)
"Really great place to stay. Nice rooms and staff. Great location for Devaul street. "
United States
Beth
The price is ฿9,357
฿10,526 total
includes taxes & fees
26 Mar - 27 Mar
Artist House Key West

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, (1,009 reviews)
"Excellent hotel in a great location just off Duval Street. The staff were very attentive, rooms clean. "
United Kingdom
Stephen
The price is ฿15,553
฿17,497 total
includes taxes & fees
16 Mar - 17 Mar
Almond Tree Inn Hotel - Adults Only

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, (917 reviews)
"Great stay, clean room, and amazing staff!"
United States
Jennifer
The price is ฿13,875
฿15,609 total
includes taxes & fees
17 Mar - 18 Mar
Simonton Court Historic Inn & Cottages

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, (290 reviews)
"Clean great staff wonderful breakfast"
United States
Kat
The Mermaid & Alligator

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, (156 reviews)
"Large clean room and excellent staff! Made for a great stay. "
United States
Daniel
The price is ฿12,220
฿13,748 total
includes taxes & fees
6 Apr - 7 Apr
The Conch House Heritage Inn

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, (142 reviews)
"We absolutely loved finding this gem to stay on our first visit to Key West. Great location, wonderful staff, and excellent room. "
United States
Sammy
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (382 reviews)
"Nice place to stay "
United States
yulio
The price is ฿11,446
฿13,667 total
includes taxes & fees
15 Mar - 16 Mar
Tropical Inn

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, (312 reviews)
"Great place with a perfect location. "
United States
Brandon
The price is ฿10,079
฿12,473 total
includes taxes & fees
22 Mar - 23 Mar
Douglas House - Adults Only

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, (588 reviews)
"Great place!!"
United States
Joel
The price is ฿20,512
฿25,210 total
includes taxes & fees
5 Apr - 6 Apr
H2O Suites - Adults Only

L'Habitation Guest House

L'Habitation Guest House
2.5 star property
Historic Seaport, 0.5 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (948 reviews)
"Great location "
United States
Scott
The price is ฿9,450
฿10,632 total
includes taxes & fees
6 Apr - 7 Apr
L'Habitation Guest House

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 place to stay"
United States
Melody
The price is ฿11,256
฿12,664 total
includes taxes & fees
23 Mar - 24 Mar
Ambrosia Key West

Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.9 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,011 reviews)
"Enjoyed our stay."
United States
Cindy
Westwinds Inn

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)
"Awesome location, comfortable, clean room. Very helpful and nice staff"
United States
Kyle
The price is ฿12,611
฿14,187 total
includes taxes & fees
22 Mar - 23 Mar
Weatherstation Inn

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)
"Great location and really nice room. Def stay here again. "
United States
Daniel
The price is ฿10,185
฿12,249 total
includes taxes & fees
15 Mar - 16 Mar
The Grand Guesthouse

Duval House

Duval House
3.0 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,013 reviews)
"Great place! "
United States
David
The price is ฿9,766
฿11,667 total
includes taxes & fees
24 Mar - 25 Mar
Duval House

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
4.0 star property
Historic Seaport, < 0.1 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (1,003 reviews)
"The staff and management were super friendly and accommodating!"
United States
burton
The price is ฿17,077
฿21,691 total
includes taxes & fees
12 Apr - 13 Apr
Ocean Key Resort - A Noble House Resort

Marrero's Guest Mansion

Marrero's Guest Mansion
3.5 star property
Downtown Key West, 0.6 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (336 reviews)
"Location very good Staff friendly Pool not well maintained Breakfast and happy hour lacking compared to others"
United States
Scott
The price is ฿14,022
฿15,775 total
includes taxes & fees
1 Apr - 2 Apr
Marrero's Guest Mansion

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, (445 reviews)
"Excellent food, location, friendly staff and pool was awesome."
United States
Karen
The price is ฿13,814
฿17,157 total
includes taxes & fees
7 Apr - 8 Apr
Ella's Cottages - Key West Historic Inns

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, (1,002 reviews)
"Great place to stay! Hope to come back!"
United States
Scott G.
The price is ฿21,048
฿25,835 total
includes taxes & fees
12 Apr - 13 Apr
Santa Maria Suites

The Garden House

The Garden House
3.0 star property
Historic Seaport, 0.6 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (686 reviews)
"Room was spotless, breakfast by the pool is a plus, host is always attentive to making everything right!"
United States
Robert
The price is ฿9,419
฿11,275 total
includes taxes & fees
15 Mar - 16 Mar
The Garden House
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.

Top Waterfront Playhouse Hotel Reviews

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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, take a look at the 1469 hotels and other accommodation options you'll find within a mile.
Where is the best place 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 traveller 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 find near Waterfront Playhouse?
Expedia has 1469 hotels and other accommodation options 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 room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might be able to still cancel and be given a refund within a 24-hour period of booking. Add your dates and click on "Search", then use the filter option "fully refundable" to view the best deals near Waterfront Playhouse.
What can I see and do near Waterfront Playhouse?
Key West Shipwreck Museum, Audubon House and Tropical Gardens and Harry S. Truman Little White House 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 Key West Burlesque Theater if you're interested in local theatre.