Hotels near Waterfront Playhouse

  • 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

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)
"Excellent hotel in a great location just off Duval Street. The staff were very attentive, rooms clean. "
United Kingdom
Stephen
The price is P37,479
P42,164 total
includes taxes & fees
Feb 10 - Feb 11
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, (905 reviews)
"Great stay, clean room, and amazing staff!"
United States
Jennifer
The price is P25,275
P28,434 total
includes taxes & fees
Feb 24 - Feb 25
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)
"Great accommodations and great staff"
United States
Julian
The price is P29,392
P36,379 total
includes taxes & fees
Feb 22 - Feb 23
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, (1,000 reviews)
"Wonderful all around! "
United States
Elena
The price is P33,073
P37,208 total
includes taxes & fees
Feb 9 - Feb 10
The Gardens 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, (251 reviews)
"Awsome staff great location "
United States
Jeffrey
Key West Villas

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 P28,845
P32,450 total
includes taxes & fees
Feb 8 - Feb 9
The Conch House Heritage Inn

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, (938 reviews)
"Great location "
United States
Scott
The price is P21,300
P23,962 total
includes taxes & fees
Feb 9 - Feb 10
L'Habitation Guest House

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, (1,036 reviews)
"Great location great staff"
United States
Lori
The price is P32,467
P38,845 total
includes taxes & fees
Feb 5 - Feb 6
Opal Key Resort & Marina, 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, (1,004 reviews)
"Clean room and front desk very friendly."
United States
Jennifer Renee
The price is P39,414
P48,914 total
includes taxes & fees
Feb 8 - Feb 9
Ocean Key Resort - A Noble House Resort

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)
"Great location and really nice room. Def stay here again. "
United States
Daniel
The Grand Guesthouse

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 P17,616
P21,084 total
includes taxes & fees
Feb 5 - Feb 6
Duval House

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 P29,442
P36,834 total
includes taxes & fees
Mar 3 - Mar 4
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 P17,121
P20,528 total
includes taxes & fees
Feb 8 - Feb 9
The Garden House

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 P25,049
P31,421 total
includes taxes & fees
Feb 8 - Feb 9
The Key West Hotel

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, (430 reviews)
"Excellent food, location, friendly staff and pool was awesome."
United States
Karen
The price is P35,302
P42,697 total
includes taxes & fees
Feb 24 - Feb 25
Ella's Cottages - Key West Historic Inns

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, (1,001 reviews)
"Room was clean, staff was helpful "
United States
Barbara
The price is P34,112
P42,353 total
includes taxes & fees
Feb 10 - Feb 11
Santa Maria Suites

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 P35,305
P42,701 total
includes taxes & fees
Feb 5 - Feb 6
Ridley House - Key West Historic Inns

Caribbean House

Caribbean House
3.0 star property
Bahama Village, 1 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (312 reviews)
"Great place to stay in the middle of key west"
United States
jerry
The price is P17,853
P21,558 total
includes taxes & fees
Feb 8 - Feb 9
Caribbean House

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection
4.0 star property
Historic Seaport, 0.5 km from Waterfront Playhouse
9.0 out of 10, Wonderful, (328 reviews)
"Nice rooms and the staff was amazing way beyond what i expected, i will definitely be back again "
United States
Joshua
The price is P34,701
P41,027 total
includes taxes & fees
Feb 5 - Feb 6
La Concha Key West, Autograph Collection

The Saint Hotel Key West, Autograph Collection, Adult Only

The Saint Hotel Key West, Autograph Collection, Adult Only
3.5 star property
Historic Seaport, 0.5 km from Waterfront Playhouse
9.0 out of 10, Wonderful, (350 reviews)
"Fantastic spot, close to everything, but just far enough away. "
United States
Ruth
The price is P27,042
P30,422 total
includes taxes & fees
Feb 9 - Feb 10
The Saint Hotel Key West, Autograph Collection, 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.

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, check out the 1527 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 1527 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.
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.