Key West Waterfront Playhouse Hotels

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Waterfront Playhouse hotels

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, (904 reviews)
"Great stay, clean room, and amazing staff!"
United States
Jennifer
The price is HK$3,150
HK$3,544 total
includes taxes & fees
4 Feb - 5 Feb
Simonton Court Historic Inn & Cottages

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)
"Fantastic location. Staff was great from check in til out. Knowledgeable and clean"
United States
Matthew
The price is HK$3,898
HK$4,824 total
includes taxes & fees
22 Feb - 23 Feb
The Marquesa 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, (1,002 reviews)
"Wonderful all around! "
United States
Elena
The price is HK$4,385
HK$4,933 total
includes taxes & fees
5 Feb - 6 Feb
The Gardens Hotel

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, (1,001 reviews)
"Clean room , friendly staff , excellent location . Would stay again ! "
United States
Kathleen
The price is HK$4,451
HK$5,007 total
includes taxes & fees
4 Feb - 5 Feb
Almond Tree Inn Hotel - 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, (1,002 reviews)
"Excellent stay"
United States
Emily Barbara
The price is HK$3,024
HK$3,402 total
includes taxes & fees
9 Feb - 10 Feb
Island City House Hotel

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, (1,005 reviews)
"Clean room and front desk very friendly."
United States
Jennifer Renee
The price is HK$5,306
HK$6,575 total
includes taxes & fees
4 Feb - 5 Feb
Ocean Key Resort - A Noble House Resort

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
4.0 star property
Old Town Key West, 0.1 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (1,039 reviews)
"Great location great staff"
United States
Lori
The price is HK$3,947
HK$4,748 total
includes taxes & fees
4 Feb - 5 Feb
Opal Key Resort & Marina, Key West

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, (152 reviews)
"Large clean room and excellent staff! Made for a great stay. "
United States
Daniel
The price is HK$3,449
HK$3,880 total
includes taxes & fees
4 Feb - 5 Feb
The Conch House Heritage Inn

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)
"Clean room, great breakfast and nice staff"
United States
Tari
The price is HK$4,336
HK$4,878 total
includes taxes & fees
10 Feb - 11 Feb
Orchid Key Inn - Adults Only

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 reviews)
"Location very good Staff friendly Pool not well maintained Breakfast and happy hour lacking compared to others"
United States
Scott
The price is HK$5,225
HK$5,879 total
includes taxes & fees
11 Feb - 12 Feb
Marrero's Guest Mansion

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 place to stay"
United States
Melody
The price is HK$3,047
HK$3,428 total
includes taxes & fees
10 Feb - 11 Feb
Ambrosia Key West

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (373 reviews)
"Nice place to stay "
United States
yulio
The price is HK$2,221
HK$2,694 total
includes taxes & fees
4 Feb - 5 Feb
Tropical Inn

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns
3.5 star property
Historic Seaport, 0.4 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (873 reviews)
"Love our stay here. The location is the best , just two blocks from the heart of Duval , but quiet and quaint. The rooms were clean , small pool in the center. Friendly staff and a lovely breakfast each morning. Will definitely be back ! "
United States
Melissa
The price is HK$3,645
HK$4,496 total
includes taxes & fees
4 Feb - 5 Feb
Ridley House - Key West Historic Inns

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, (523 reviews)
"Great location, very clean, and great staff"
United States
William
The price is HK$2,811
HK$3,592 total
includes taxes & fees
4 Feb - 5 Feb
The Key West Hotel

Pier House Resort & Spa

Pier House Resort & Spa
4.0 star property
Historic Seaport, 0.1 km from Waterfront Playhouse
9.0 out of 10, Wonderful, (1,032 reviews)
"4th time staying, great staff, location "
United States
Jeffrey
Pier House Resort & Spa

Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.9 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,005 reviews)
"Great place to stay. Walking distance to Duval St."
United States
Compton
Westwinds 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, (585 reviews)
"Great place!!"
United States
Joel
The price is HK$6,241
HK$7,548 total
includes taxes & fees
15 Feb - 16 Feb
H2O Suites - Adults Only

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, (1,001 reviews)
"Great place to stay!"
United States
Caleb
The price is HK$3,720
HK$4,677 total
includes taxes & fees
4 Feb - 5 Feb
The Marker Key West Harbor Resort

The Garden House

The Garden House
3.0 star property
Historic Seaport, 0.6 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (678 reviews)
"The room was clean. The breakfast was amazing and the Host was available tent I’ve to our needs and a fun person to be around . We slept great and we wanted to know what kind of mattress it was."
United States
Hollie
The price is HK$1,973
HK$2,388 total
includes taxes & fees
4 Feb - 5 Feb
The Garden House

Duval House

Duval House
3.0 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,002 reviews)
"Great place! "
United States
David
The price is HK$2,727
HK$3,236 total
includes taxes & fees
5 Feb - 6 Feb
Duval House
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.

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 1527 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 Ocean Key Resort - A Noble House Resort and Opal Key Resort & Marina, Key West.
How many hotels will I find near Waterfront Playhouse?
Expedia has 1527 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 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 theatre.