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Check prices for these dates

This weekend
5 Jun - 7 Jun
Next weekend
12 Jun - 14 Jun

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Our top choices for Waterfront Playhouse hotels

Queen with Pool View | Minibar, in-room safe, individually decorated, individually furnished

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, (969 reviews)
"Great stay overall! Friendly staff, clean rooms, and a perfect location for exploring the Keys and relaxing in this little paradise 🌴"
United States
Olha
The price is 3.921.531 ₫
4.411.722 ₫ total
includes taxes & fees
4 Jun - 5 Jun
Simonton Court Historic Inn & Cottages
Queen Deluxe ADA | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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)
"Excellent accommodations"
United States
Jimmy
The price is 5.798.070 ₫
6.522.829 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Almond Tree Inn Hotel - Adults Only
Exterior

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, (1,000 reviews)
"Great accommodations and great staff"
United States
Julian
The price is 8.130.717 ₫
10.627.294 ₫ total
includes taxes & fees
3 Jun - 4 Jun
The Marquesa Hotel
Front of property

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, (262 reviews)
"This was the best place we have stayed at in Key West! It was super quiet but only a block from Duval. The owners really put a lot of care into the place and are super nice! Definitely would stay there again! "
United States
Jennifer
Key West Villas
Cigar House King Suite w/ Poolside porch | Balcony view

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, (1,000 reviews)
"Well maintained property, clean room and close to everything!!!"
United States
Troy
The price is 4.510.550 ₫
5.074.369 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Island City House Hotel
Exterior detail

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, (1,002 reviews)
"Best hotel ive ever stayed in, the hospitality was unmatched."
United States
Markus
The price is 7.076.521 ₫
7.961.086 ₫ total
includes taxes & fees
28 Jun - 29 Jun
The Gardens Hotel
Property grounds

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, (1,003 reviews)
"Great boutique hotel in the perfect location !! "
United States
Michael
The price is 5.799.392 ₫
6.524.316 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Orchid Key Inn - Adults Only
Veranda Room | Terrace/patio

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, (175 reviews)
"Great location "
United Kingdom
Lucy
The price is 6.253.394 ₫
7.035.068 ₫ total
includes taxes & fees
9 Jun - 10 Jun
The Conch House Heritage Inn
Superior Studio Suite, 1 King Bed with Sofa bed, Accessible, Refrigerator & Microwave | Free WiFi, bed sheets

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, (148 reviews)
"The staff and other guests were very friendly. The room was spacious and the bed was comfortable. "
United States
Annette
The price is 4.713.733 ₫
6.357.091 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Front of property

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, (987 reviews)
"The location and customer service were excellent. We loved our stay!"
United States
Megan
The price is 3.842.224 ₫
4.322.436 ₫ total
includes taxes & fees
10 Jun - 11 Jun
L'Habitation Guest House
Premium bedding, iron/ironing board, free WiFi, bed sheets

Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex, 0.5 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,003 reviews)
"Perfect stay!"
United States
A. Elise
The price is 4.711.101 ₫
5.299.989 ₫ total
includes taxes & fees
7 Jun - 8 Jun
Weatherstation Inn
11 Gecko's Garden - Adults Only | Premium bedding, pillow-top beds, individually decorated

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (406 reviews)
"Very friendly staff and a prime location."
United States
Akhenaton
The price is 4.444.226 ₫
5.657.532 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Tropical Inn
Outdoor pool, free pool cabanas, pool loungers

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, (1,001 reviews)
"Great location near pier, shops, restaurants, and tours in Key West! Superb staff, exceptional clean suites, and very friendly staff!"
United States
Terrie
The price is 7.963.603 ₫
11.002.197 ₫ total
includes taxes & fees
16 Jun - 17 Jun
Ocean Key Resort - A Noble House Resort
Exterior

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, (405 reviews)
"Great stay"
United States
Matthew
The price is 3.894.911 ₫
4.819.952 ₫ total
includes taxes & fees
4 Jun - 5 Jun
Douglas House - Adults Only
Deluxe Suite, 1 King Bed, Private Pool | View from room

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, (610 reviews)
"We had a wonderful stay!"
United States
Elizabeth
The price is 8.658.951 ₫
11.517.852 ₫ total
includes taxes & fees
8 Jun - 9 Jun
H2O Suites - Adults Only
Lobby sitting area

Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.9 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,004 reviews)
"Nice place to stay!"
United States
michael
The price is 5.328.382 ₫
5.994.430 ₫ total
includes taxes & fees
28 Jun - 29 Jun
Westwinds Inn
Exterior

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, (532 reviews)
"Loved the property and staff was super friendly."
United States
Brinkley
The price is 5.329.435 ₫
5.995.680 ₫ total
includes taxes & fees
10 Jun - 11 Jun
Coco Plum Inn
3 outdoor pools, a heated pool, pool loungers

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, (1,002 reviews)
"Great location and breakfast"
United States
Lori
The price is 6.501.963 ₫
7.314.708 ₫ total
includes taxes & fees
10 Jun - 11 Jun
Ambrosia Key West
Exterior

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, (1,000 reviews)
"Very nice and clean close to everything."
United States
Farid
The price is 5.935.423 ₫
8.335.069 ₫ total
includes taxes & fees
15 Jun - 16 Jun
The Marker Key West Harbor Resort
Porch

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, (1,154 reviews)
"Fantastic place, clean and great location."
United States
James
The price is 3.849.066 ₫
5.228.000 ₫ total
includes taxes & fees
4 Jun - 5 Jun
Heron House - Adult Only
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.
View all properties

Compare popular hotels close to Waterfront Playhouse

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
Queen with Pool View | Minibar, in-room safe, individually decorated, individually furnished
Simonton Court Historic Inn & Cottages
2.5 star property
9.8
Exceptional
969 reviews
View
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
1,004 reviews
View
Exterior
The Marquesa Hotel
3.5 star property
9.8
Exceptional
1,000 reviews
View
Front of property
Key West Villas
3.5 star property
9.8
Exceptional
262 reviews
View
Cigar House King Suite w/ Poolside porch | Balcony view
Island City House Hotel
3.0 star property
9.6
Exceptional
1,000 reviews
View

Top Waterfront Playhouse Hotel Reviews

Pegasus International Hotel

Pegasus International Hotel

10/10 Excellent
"We LOVED our stay at Pegasus! It was just around the corner from Duval Street and within walking distance to so many fun hot spots. The receptionist was so kind and even allowed us to check in a little early so we could park our car and explore before we started our evening adventures. The room was spacious, the pool area was clean and they had a rooftop sitting area with views of Duval. Our only complaints were that the breakfast was very minimal when we arrived at 9:30 and the room door didn't seem to close all the way. The upside to both issues was that there were so many breakfast spots within a 5 min walk and there were 3 locks on the door, so we felt safe. If we are ever in Key West again, we will definitely stay at Pegasus!"
Terri 1-night trip
Posted less than an hour ago
Pegasus International Hotel

Hotels near other Waterfront Playhouse attractions

Key West Shipwreck Museum

4.3/5 (361 reviews)
You can spend an afternoon studying the exhibits at Key West Shipwreck Museum during your trip to Key West. In the area, take in the lively festivals and beautiful sunsets.
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, take a look at the 1455 hotels and other accommodation options you'll find within a mile.
How many hotels will I find near Waterfront Playhouse?
Expedia has 1455 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?
Audubon House and Tropical Gardens, Harry S. Truman Little White House and Florida Keys Eco - Discovery Center 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 Key West Burlesque Theater, Red Barn Theater and Key West Film Society if you're interested in local theatre.