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Our top choices for Waterfront Playhouse hotels

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, (1,002 reviews)
"Great staff, breakfast and happy hour. "
United States
Tina
The price is ฿9,991
฿11,239 total
includes taxes & fees
3 Jun - 4 Jun
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, (942 reviews)
"Very unique, great staff, and great location"
United States
Jason
The price is ฿9,358
฿10,527 total
includes taxes & fees
1 Jun - 2 Jun
Simonton Court Historic Inn & Cottages

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
3.0 star property
Uptown - Upper Duval, 1.5 km from Waterfront Playhouse
10.0 out of 10, Exceptional, (6 reviews)
"Property was clean and quiet nice amenities "
United States
Bradley
The price is ฿8,173
฿18,438 total
includes taxes & fees
18 May - 19 May
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

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, (1,001 reviews)
"Breakfasts were great and they had a very good selection of drinks at the bar."
United States
Dennis
The price is ฿9,987
฿11,235 total
includes taxes & fees
24 May - 25 May
The Gardens Hotel

The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Old Town Key West, 0.7 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (1,003 reviews)
"Great accommodations and great staff"
United States
Julian
The price is ฿10,653
฿13,806 total
includes taxes & fees
31 May - 1 Jun
The Marquesa Hotel

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, (260 reviews)
"Fabulous staff, our villa had everything we needed, perfect location off Duval with a peaceful vibe at the swimming pool and patio, and the happy hour cocktails were the best! "
United States
Sarah
The price is ฿10,170
฿11,442 total
includes taxes & fees
26 May - 27 May
Key West Villas

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 ฿9,605
฿10,806 total
includes taxes & fees
1 Jun - 2 Jun
Orchid Key Inn - Adults Only

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, (999 reviews)
"We absolutely loved staying here!"
United States
Victoria E
The price is ฿8,348
฿9,392 total
includes taxes & fees
5 May - 6 May
Island City House Hotel

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)
"Staff very courteous and friendly, public spaces lovely."
United States
Paul
The price is ฿5,799
฿7,821 total
includes taxes & fees
11 May - 12 May
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

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, (170 reviews)
"The breakfast was fantastic! Located close enough to Duval for convenience but far enough to be quiet. "
United States
Bob
The price is ฿10,025
฿11,278 total
includes taxes & fees
1 Jun - 2 Jun
The Conch House Heritage Inn

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, (601 reviews)
"This resort was in the perfect location for exploring Key West. Highly recommend!"
United States
Barton
The price is ฿12,595
฿16,355 total
includes taxes & fees
1 Jun - 2 Jun
H2O Suites - Adults Only

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, (372 reviews)
"Wonderful location and very clean with amazing staff. "
United States
Sherry
The price is ฿5,806
฿7,185 total
includes taxes & fees
25 May - 26 May
Douglas House - Adults Only

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (398 reviews)
"We stayed for three nights and it was a great place. The room was lovely with a balcony overlooking the pool. It’s a great location, within walking distance of everything. Brandy was very helpful and accommodating, making sure everything went well with our stay. Would definitely come back again."
Canada
Lisa
The price is ฿6,499
฿8,121 total
includes taxes & fees
6 May - 7 May
Tropical Inn

Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex, 0.5 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,004 reviews)
"Perfect stay!"
United States
A. Elise
The price is ฿7,739
฿8,706 total
includes taxes & fees
12 May - 13 May
Weatherstation Inn

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, (1,001 reviews)
"Breakfast by the pool was excellent! Pools were nice, with plenty of areas for privacy. We especially enjoyed the private patios and courtyards. Fantastic location!"
United States
Tina
The price is ฿7,613
฿8,565 total
includes taxes & fees
5 May - 6 May
Ambrosia Key West

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 ฿10,328
฿14,133 total
includes taxes & fees
2 Jun - 3 Jun
Ocean Key Resort - A Noble House Resort

Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.9 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,007 reviews)
"Quant little bungalow in great location - heated pool and outside breakfast were very welcoming. "
United States
Peter
The price is ฿8,130
฿9,147 total
includes taxes & fees
1 Jun - 2 Jun
Westwinds Inn

Coco Plum Inn

Coco Plum Inn
3.0 star property
Downtown Key West, 0.8 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (521 reviews)
"Great location, pleasant staff & cute pool. "
United States
julie
The price is ฿8,563
฿9,633 total
includes taxes & fees
11 May - 12 May
Coco Plum 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 ฿10,005
฿11,256 total
includes taxes & fees
20 May - 21 May
Marrero's Guest Mansion

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 ฿5,849
฿7,390 total
includes taxes & fees
10 May - 11 May
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.

Compare popular hotels close to Waterfront Playhouse

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
Queen Deluxe ADA | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds
Almond Tree Inn Hotel - Adults Only
3.5 star property
10.0
Exceptional
1,002 reviews
View
Queen with Pool View | Minibar, in-room safe, individually decorated, individually furnished
Simonton Court Historic Inn & Cottages
2.5 star property
9.8
Exceptional
942 reviews
View
House (1 Bedroom) | Interior
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
3.0 star property
10.0
Exceptional
6 reviews
View
Exterior detail
The Gardens Hotel
4.0 star property
9.8
Exceptional
1,001 reviews
View
Exterior
The Marquesa Hotel
3.5 star property
9.8
Exceptional
1,003 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, 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, Pier House Resort & Spa is one of the top choices for your stay based on our traveller 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 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 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 theatre.