Hotels near Waterfront Playhouse

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Our top choices for Waterfront Playhouse hotels

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, (945 reviews)
"Very unique, great staff, and great location"
United States
Jason
The price is P13,433
P15,112 total
includes taxes & fees
May 10 - May 11
Simonton Court Historic Inn & Cottages

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, (1,004 reviews)
"Great staff, breakfast and happy hour. "
United States
Tina
The price is P17,716
P19,930 total
includes taxes & fees
May 25 - May 26
Almond Tree Inn Hotel - Adults Only

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, (1,001 reviews)
"Breakfast menu was fresh, rooms were cleaned every day, staff couldn’t have been nicer."
United States
Thomas L
The price is P17,716
P19,930 total
includes taxes & fees
May 25 - May 26
Orchid Key Inn - Adults Only

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, (143 reviews)
"The staff and other guests were very friendly. The room was spacious and the bed was comfortable. "
United States
Annette
The price is P10,820
P14,592 total
includes taxes & fees
May 11 - May 12
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

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, (1,001 reviews)
"We absolutely loved staying here!"
United States
Victoria E
The price is P15,462
P17,394 total
includes taxes & fees
May 10 - May 11
Island City House Hotel

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, (978 reviews)
"This was a lovely well stocked, and comfortable stay."
United States
Pat
The price is P10,433
P11,738 total
includes taxes & fees
May 10 - May 11
L'Habitation Guest House

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, (377 reviews)
"Great location, helpful staff and fun people. Would stay here again…the pool and room were fantastic"
United States
Scott
The price is P10,942
P13,540 total
includes taxes & fees
May 25 - May 26
Douglas House - Adults Only

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
4.0 star property
Old Town Key West, 0.1 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (1,099 reviews)
"Loved the location and the prximity to so many things we wanted to visit. The pool and services there were great!"
United States
Pamela
The price is P15,886
P20,287 total
includes taxes & fees
May 25 - May 26
Opal Key Resort & Marina, Key West

Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.9 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,009 reviews)
"Quant little bungalow in great location - heated pool and outside breakfast were very welcoming. "
United States
Peter
The price is P14,408
P16,209 total
includes taxes & fees
Jun 3 - Jun 4
Westwinds Inn

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, (337 reviews)
"It was nice. Get a smart tv 😂"
United States
Robert
The price is P18,667
P21,001 total
includes taxes & fees
May 20 - May 21
Marrero's Guest Mansion

Duval House

Duval House
3.0 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,033 reviews)
"Very clean and convenient staff was very nice will stay again "
United States
Brian
The price is P11,593
P14,360 total
includes taxes & fees
May 12 - May 13
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)
"Room was neat, very friendly and kind staff, beautiful place, great view, breakfast was delicious, we will definitely come back "
United States
IRENE
The price is P17,153
P24,058 total
includes taxes & fees
May 25 - May 26
Ocean Key Resort - A Noble House Resort

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)
"This is a great place to stay, quiet and nice accommodations. Awesome little courtyard for breakfast."
United States
Jacqueline
The price is P10,914
P13,788 total
includes taxes & fees
May 14 - May 15
The Grand Guesthouse

Heron House - Adult Only

Heron House - Adult Only
3.5 star property
Downtown Key West, 0.7 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (1,152 reviews)
"Good fresh breakfast, great location and a nice pool. "
United States
Joseph
The price is P9,130
P12,368 total
includes taxes & fees
May 10 - May 11
Heron House - Adult Only

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)
"Nice suites , staff very friendly. Conveniently located. Check your room bills carefully. "
United States
Kristine
The price is P20,480
P27,117 total
includes taxes & fees
Jun 1 - Jun 2
Santa Maria Suites

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, (1,028 reviews)
"Excellent place and convenience was perfect"
United States
Bonnie
The price is P7,829
P12,886 total
includes taxes & fees
May 10 - May 11
Silver Palms Inn & Historic Homes

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, (471 reviews)
"Cute place. Great location to everything on Duval. Service was great and friendly."
United States
DJS Darren Jay
The price is P15,886
P20,977 total
includes taxes & fees
Jun 1 - Jun 2
Ella's Cottages - Key West Historic Inns

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns
3.5 star property
Historic Seaport, 0.4 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (908 reviews)
"Staff was amazing from check in to check out. Located in a great location, close to everything but far enough its not loud while sleeping."
United States
Brennan
The price is P14,034
P18,893 total
includes taxes & fees
May 26 - May 27
Ridley House - Key West Historic Inns

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
4.0 star property
Historic Seaport, 0.6 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (1,004 reviews)
"Great place to stay. Friendly staff well kept property. Great food as well"
United States
Bradley
The price is P14,283
P19,933 total
includes taxes & fees
May 26 - May 27
The Marker Key West Harbor Resort

The Key West Hotel

The Key West Hotel
3.0 star property
Historic Seaport, 0.4 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (552 reviews)
"Great location"
United States
David
The price is P20,245
P26,150 total
includes taxes & fees
May 10 - May 11
The Key West Hotel
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.

Compare popular hotels close to Waterfront Playhouse

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
Minibar, in-room safe, individually decorated, individually furnished
Simonton Court Historic Inn & Cottages
2.5 star property
9.8
Exceptional
945 reviews
View
Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Almond Tree Inn Hotel - Adults Only
3.5 star property
10.0
Exceptional
1,004 reviews
View
Property grounds
Orchid Key Inn - Adults Only
3.5 star property
9.8
Exceptional
1,001 reviews
View
Free WiFi, bed sheets
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
3.5 star property
9.8
Exceptional
143 reviews
View
Balcony view
Island City House Hotel
3.0 star property
9.6
Exceptional
1,001 reviews
View

Top Waterfront Playhouse Hotel Reviews

Hotels near other Waterfront Playhouse attractions

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 1469 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 Opal Key Resort & Marina, Key West and Ocean Key Resort - A Noble House Resort.
How many hotels will I be able to find near Waterfront Playhouse?
Expedia has 1469 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.
What can I see and do near Waterfront Playhouse?
Key West Shipwreck Museum, Audubon House and Tropical Gardens, and Mel Fisher Maritime Museum feature a variety of fascinating exhibits to see while you're in town. Sights like Harry S. Truman Little White House, 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 theater.