Find hotels near Waterfront Playhouse, Key West from ￥42,981

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Dec 28 - Dec 29
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Dec 29 - Dec 30
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Jan 2 - Jan 4
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Jan 9 - Jan 11

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Our top choices for Waterfront Playhouse hotels

Queen Deluxe ADA | 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, (1000)
"Great location, spotless rooms, attentive and friendly staff, great value."
United States
David
The price is ￥54,689
￥61,526 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Almond Tree Inn Hotel - Adults Only
King Room D | 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, (886)
"I loved staying here! The room was great and the staff was awesome! "
United States
Tiffany
The price is ￥42,133
￥47,399 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Simonton Court Historic Inn & Cottages
Carriage House | 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, (1002)
"Loved it. The staff were very friendly and the place was classic Key West."
United States
Ben
The price is ￥63,235
￥71,139 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Gardens Hotel
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 ￥62,471
￥79,088 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Marquesa 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, (1001)
"Staff awesome, good breakfast great location"
United States
Carin helen
The price is ￥54,142
￥60,910 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Orchid Key Inn - Adults Only
Signature Apartment, 1 Bedroom, Kitchen, Poolside (Room 17) | 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, (135)
"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
The price is ￥57,633
￥71,939 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
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, (146)
"Check in was quick, easy. "
United States
kristen
The price is ￥55,989
￥62,988 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Conch House Heritage Inn
Outdoor pool, sun loungers
The Mermaid & Alligator

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, (276)
"Great place"
United States
Carol A
The Mermaid & Alligator
Deluxe Suite, 1 King Bed, Private Pool | 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, (582)
"Great place!!"
United States
Joel
The price is ￥78,128
￥98,462 total
includes taxes & fees
Jan 4 - Jan 5, 2026
H2O Suites - Adults Only
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 ￥62,706
￥70,544 total
includes taxes & fees
Jan 11 - Jan 12, 2026
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, (470)
"The Coco Plum Inn is a wonderful place to stay. Staff is fantastic and the location is perfect. We will definitely come back and stay at the Coco Plum Inn."
United States
Brent
The price is ￥49,179
￥55,328 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Coco Plum Inn
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, (237)
"Excellent spot, I definitely recommended"
United States
Paul
The price is ￥38,264
￥47,352 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Douglas House
11 Gecko's Garden - Adults Only | 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, (364)
"Nice place to stay "
United States
yulio
The price is ￥43,232
￥52,551 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Tropical Inn
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, (1001)
"Great stay"
United States
Ginger
The Grand Guesthouse
Courtyard
Santa Maria Suites

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, (1001)
"Awesome place we loved it"
United States
Josh
The price is ￥78,100
￥98,430 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Santa Maria Suites
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, (925)
"A great no hassle stay."
United States
Gary
The price is ￥38,206
￥42,981 total
includes taxes & fees
Jan 8 - Jan 9, 2026
L'Habitation Guest House
Premium bedding, iron/ironing board, free WiFi, bed sheets
Weatherstation Inn

Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex, 0.5 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (997)
"Wonderful property safe neighborhood convenient to all activities would stay here again."
United States
William
The price is ￥55,647
￥62,603 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Weatherstation Inn
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 place to stay"
United States
Melody
The price is ￥45,115
￥50,755 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Ambrosia Key West
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, (1002)
"Great place! "
United States
David
The price is ￥38,986
￥47,225 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Duval 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, (1003)
"Enjoyed our stay."
United States
Cindy
Westwinds 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.
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Top Waterfront Playhouse Hotel Reviews

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

10/10 Excellent
"We didn't know there was breakfast until this survey! How did we miss it? The pet friendliness was great. Our dog was happy about the grass out front and the availability of ice. She loves ice."
Eric 2-night trip
Posted 3 days ago
Hyatt Centric Key West Resort and Spa

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.
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, 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.