Hotels near Waterfront Playhouse

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Dec 21 - Dec 22
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Dec 22 - Dec 23
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Dec 26 - Dec 28
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Jan 2 - Jan 4

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Our top choices for Waterfront Playhouse hotels

Balcony
Simonton Court Historic Inn & Cottages

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, (882)
"The staff was really nice"
United States
doug
The price is P19,320
P21,734 total
includes taxes & fees
Dec 22 - Dec 23
Simonton Court Historic Inn & Cottages
Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Almond Tree Inn Hotel - Adults Only

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, (1002)
"Great location, spotless rooms, attentive and friendly staff, great value."
United States
David
The price is P21,128
P23,769 total
includes taxes & fees
Dec 22 - Dec 23
Almond Tree Inn Hotel - Adults Only
Exterior
The Marquesa Hotel

The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Historic Seaport, 0.7 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (1000)
"Perfect place to stay. "
United States
Paulette
The price is P31,064
P38,250 total
includes taxes & fees
Dec 22 - Dec 23
The Marquesa Hotel
Terrace/patio
The Gardens Hotel

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, (1001)
"Amazing hotel, the perfect Key West vibe. Clean rooms, delicious breakfast. We will come back again"
United States
Isis
The price is P26,359
P29,654 total
includes taxes & fees
Dec 22 - Dec 23
The Gardens Hotel
Exterior
Orchid Key Inn - 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, (1000)
"Staff awesome, good breakfast great location"
United States
Carin helen
The price is P21,128
P23,769 total
includes taxes & fees
Dec 22 - Dec 23
Orchid Key Inn - Adults Only
Outdoor pool, sun loungers
The Conch House Heritage Inn

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, (145)
"Fantastic location "
United States
ANDREW
The price is P20,167
P22,688 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Conch House Heritage Inn
Front of property
L'Habitation Guest House

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, (924)
"A great no hassle stay."
United States
Gary
The price is P10,301
P11,589 total
includes taxes & fees
Dec 23 - Dec 24
L'Habitation Guest House
Fountain
Island City House Hotel

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, (1001)
"Excellent stay"
United States
Emily Barbara
The price is P20,083
P22,593 total
includes taxes & fees
Dec 23 - Dec 24
Island City House Hotel
Exterior
Coco Plum Inn

Coco Plum Inn

Coco Plum Inn
3.0 star property
Downtown Key West, 0.8 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (467)
"Love the place convenient, clean and really nice"
United States
Matthew
The price is P17,916
P20,156 total
includes taxes & fees
Dec 22 - Dec 23
Coco Plum Inn
Terrace/patio
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

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, (134)
"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
Front of property - evening/night
Opal Key Resort & Marina, Key West

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, (1025)
"Our stay was great!"
United States
Richard
The price is P23,430
P28,672 total
includes taxes & fees
Dec 22 - Dec 23
Opal Key Resort & Marina, Key West
Premium bedding, pillowtop beds, individually decorated
Tropical Inn

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (363)
"The place was excellent and the service amazing "
United States
Janae
The price is P14,413
P17,682 total
includes taxes & fees
Dec 23 - Dec 24
Tropical Inn
Outdoor pool, sun loungers
Ocean Key Resort - A Noble House Resort

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, (1006)
"Clean and spacious room, staff "
United States
Parikshit
The price is P30,533
P38,908 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Ocean Key Resort - A Noble House Resort
3 outdoor pools, a heated pool, sun loungers
Ambrosia Key West

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, (1001)
"Great location and clean room. Pool was relaxing; breakfast was good!"
United States
Jennifer
The price is P16,422
P18,474 total
includes taxes & fees
Dec 23 - Dec 24
Ambrosia Key West
View from room
H2O Suites - 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, (581)
"Great place!!"
United States
Joel
The price is P25,779
P32,965 total
includes taxes & fees
Dec 23 - Dec 24
H2O Suites - Adults Only
Outdoor pool, pool umbrellas, sun loungers
Marrero's Guest Mansion

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, (335)
"Location very good Staff friendly Pool not well maintained Breakfast and happy hour lacking compared to others"
United States
Scott
The price is P19,085
P21,471 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Marrero's Guest Mansion
Garden
Douglas House

Douglas House

Douglas House
3.0 star property
Uptown - Upper Duval, 1.4 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (229)
"We were very pleased with everything and great location."
United States
Lynn
The price is P12,983
P16,066 total
includes taxes & fees
Dec 23 - Dec 24
Douglas House
Lobby sitting area
Westwinds Inn

Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.9 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1001)
"Great location and loved the heated pool!"
United States
Tammy
Westwinds Inn
View from property
Duval House

Duval House

Duval House
3.0 star property
Downtown Key West, 1 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1001)
"I loved this place the location was absolutely perfect "
United States
Frank
The price is P11,652
P14,371 total
includes taxes & fees
Dec 23 - Dec 24
Duval House
Exterior
The Grand Guesthouse

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, (1000)
"Great stay"
United States
Ginger
The price is P10,883
P13,712 total
includes taxes & fees
Dec 22 - Dec 23
The Grand Guesthouse
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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Top Waterfront Playhouse Hotel Reviews

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"Good stay. Initially the room had an issue with the window blinds but the hotel corrected the issue immediately. All was great after that. "
Mark 3-night trip
Posted 3 days ago
Opal Key Resort & Marina, Key West

Hotels near other Waterfront Playhouse attractions

Exploring the view from Key West Shipwreck Museum in Key West, Florida on a sunny day with vibrant skies and coastal charm

Key West Shipwreck Museum

4.2/5 (358 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
Sunset sailing at Mallory Square in Key West, Florida, featuring multiple sailboats against an orange sky

Mallory Square

4.5/5 (7,700 reviews)
Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.
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 1527 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 1527 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 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 theater.