Find hotels near Waterfront Playhouse, Key West from ￥41,899

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Dec 19 - Dec 20
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Dec 20 - Dec 21
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Dec 19 - Dec 21
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Dec 26 - Dec 28

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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)
"Very nice & peaceful with a wonderful staff. Our second time staying here"
United States
Sandra
The price is ￥61,104
￥68,742 total
includes taxes & fees
Jan 6 - Jan 7, 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, (882)
"Really enjoyed my stay. The staff were super friendly, and the location was amazing—close to all the Old Town activities! "
United States
Leonid
The price is ￥44,518
￥50,083 total
includes taxes & fees
Dec 21 - Dec 22
Simonton Court Historic Inn & Cottages
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 ￥82,312
￥101,355 total
includes taxes & fees
Dec 21 - Dec 22
The Marquesa Hotel
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, (1000)
"Amazing hotel, the perfect Key West vibe. Clean rooms, delicious breakfast. We will come back again"
United States
Isis
The price is ￥69,845
￥78,576 total
includes taxes & fees
Dec 20 - Dec 21
The Gardens Hotel
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, (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
Key West Villas

Key West Villas

Key West Villas
3.5 star property
Downtown Key West, 0.9 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (247)
"Awsome staff great location "
United States
Jeffrey
Key West Villas
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 ￥60,443
￥67,998 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Orchid Key Inn - 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, (1000)
"Excellent stay"
United States
Emily Barbara
The price is ￥62,318
￥70,108 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Island City House Hotel
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, (581)
"Great place!!"
United States
Joel
The price is ￥68,308
￥87,350 total
includes taxes & fees
Dec 21 - Dec 22
H2O Suites - Adults Only
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 ￥39,494
￥44,431 total
includes taxes & fees
Jan 8 - Jan 9, 2026
L'Habitation Guest 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, (363)
"The place was excellent and the service amazing "
United States
Janae
The price is ￥33,784
￥41,899 total
includes taxes & fees
Dec 24 - Dec 25
Tropical Inn
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, (995)
"Wonderful property safe neighborhood convenient to all activities would stay here again."
United States
William
The price is ￥45,594
￥51,293 total
includes taxes & fees
Dec 21 - Dec 22
Weatherstation 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, (1000)
"Great stay"
United States
Ginger
The price is ￥37,963
￥46,599 total
includes taxes & fees
Dec 21 - Dec 22
The Grand Guesthouse
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 ￥50,570
￥56,892 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Marrero's Guest Mansion
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 ￥84,827
￥107,509 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Ocean Key Resort - A Noble House Resort
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, (1000)
"Awesome place we loved it"
United States
Josh
The price is ￥78,196
￥98,474 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Santa Maria Suites
Outdoor pool
Silver Palms Inn

Silver Palms Inn

Silver Palms Inn
3.5 star property
Old Town Key West, 1.4 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1005)
"We had a wonderful stay and it was a convenient location for all the activities along Duval Street. The room was clean & comfortable with a great breakfast."
United States
Susanne
The price is ￥35,570
￥50,520 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Silver Palms Inn
Outdoor pool, open 8:00 AM to 10:00 PM, sun loungers
Ella's Cottages - Key West Historic Inns

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, (410)
"The cottage was perfect, centrally located and a wonderful place to stay!"
United States
Claudia
The price is ￥62,030
￥77,661 total
includes taxes & fees
Dec 22 - Dec 23
Ella's Cottages - Key West Historic Inns
3 outdoor pools, pool umbrellas, sun loungers
The Marker Key West Harbor Resort

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, (1000)
"Fantastic staff, great breakfast"
United States
Kelly
The price is ￥52,380
￥68,725 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Marker Key West Harbor Resort
Outdoor pool
The Key West Hotel

The Key West Hotel

The Key West Hotel
2.5 star property
Historic Seaport, 0.4 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (514)
"location was great nice bar party vibe"
United States
Robert Howard
The price is ￥47,034
￥61,471 total
includes taxes & fees
Dec 22 - Dec 23
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.
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Top Waterfront Playhouse Hotel Reviews

Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"All of the staff were nice and smiling and helped me out when I checked in. "
Dustin 1-night trip
Posted 7 hours ago
Pier House Resort & 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 1532 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 Ocean Key Resort - A Noble House Resort and Opal Key Resort & Marina, Key West.
How many hotels will I be able to find near Waterfront Playhouse?
Expedia has 1532 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.