Search Hotels Near Waterfront Playhouse, Key West

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
5 Jun - 7 Jun
In two weeks
12 Jun - 14 Jun

Filter by

Guest rating
Guest rating
Star rating

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, (966 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 ₹16,580
₹18,653 total
includes taxes & fees
1 Jun - 2 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, (1,000 reviews)
"Excellent accommodations"
United States
Jimmy
The price is ₹21,366
₹24,037 total
includes taxes & fees
7 Jun - 8 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 ₹29,356
₹38,370 total
includes taxes & fees
1 Jun - 2 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, (261 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
The price is ₹18,725
₹21,067 total
includes taxes & fees
4 Jun - 5 Jun
Key West Villas
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 ₹27,681
₹31,142 total
includes taxes & fees
23 Jun - 24 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, (1,002 reviews)
"Great boutique hotel in the perfect location !! "
United States
Michael
The price is ₹21,366
₹24,037 total
includes taxes & fees
7 Jun - 8 Jun
Orchid Key Inn - Adults Only
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 ₹16,096
₹18,108 total
includes taxes & fees
2 Jun - 3 Jun
Island City House Hotel
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 ₹23,713
₹26,677 total
includes taxes & fees
7 Jun - 8 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, (147 reviews)
"The staff and other guests were very friendly. The room was spacious and the bed was comfortable. "
United States
Annette
The price is ₹17,015
₹22,947 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, (985 reviews)
"The location and customer service were excellent. We loved our stay!"
United States
Megan
The price is ₹11,885
₹13,372 total
includes taxes & fees
2 Jun - 3 Jun
L'Habitation Guest House
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 ₹16,042
₹20,422 total
includes taxes & fees
7 Jun - 8 Jun
Tropical Inn
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 ₹31,256
₹41,575 total
includes taxes & fees
2 Jun - 3 Jun
H2O Suites - Adults Only
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, (399 reviews)
"Great stay"
United States
Matthew
The price is ₹15,547
₹19,239 total
includes taxes & fees
1 Jun - 2 Jun
Douglas House - 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, (1,001 reviews)
"Nice place to stay!"
United States
michael
The price is ₹16,673
₹18,757 total
includes taxes & fees
1 Jun - 2 Jun
Westwinds 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, (1,000 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 ₹23,293
₹33,579 total
includes taxes & fees
29 Jun - 30 Jun
Ocean Key Resort - A Noble House Resort
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, (1,000 reviews)
"Great location and breakfast"
United States
Lori
The price is ₹23,475
₹26,410 total
includes taxes & fees
1 Jun - 2 Jun
Ambrosia Key West
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 ₹19,242
₹21,647 total
includes taxes & fees
8 Jun - 9 Jun
Coco Plum Inn
Terrace/patio

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 ₹23,656
₹26,613 total
includes taxes & fees
4 Jun - 5 Jun
Marrero's Guest Mansion
Property grounds

Duval House

Duval House
3.0 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,033 reviews)
"Great location and staff"
United States
gerald
The price is ₹18,906
₹23,311 total
includes taxes & fees
17 Jun - 18 Jun
Duval House
Courtyard

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, (1,000 reviews)
"This is a great place to stay, quiet and nice accommodations. Awesome little courtyard for breakfast."
United States
Jacqueline
The price is ₹15,221
₹19,499 total
includes taxes & fees
1 Jun - 2 Jun
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.
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
966 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
1,000 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
261 reviews
View
Exterior detail
The Gardens Hotel
4.0 star property
9.8
Exceptional
1,002 reviews
View

Top Waterfront Playhouse Hotel Reviews

Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Loved everything about this hotel, will be staying again on next vacation."
Viscencio 3-night trip
Posted 4 hours ago
Pier House Resort & Spa

Hotels near other Waterfront Playhouse attractions

Key West Shipwreck Museum

4.3/5 (361 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

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.
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 La Concha Key West, Autograph Collection.
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.