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

Tonight
25 Jan - 26 Jan
Tomorrow
26 Jan - 27 Jan
Next weekend
30 Jan - 1 Feb
In two weeks
6 Feb - 8 Feb

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, (900 reviews)
"Wonderful and welcoming staff. The grounds are beautiful. Proximity to Duval Street was perfect. We will definitely stay here again."
United States
Jonathan Van
The price is ฿15,503
฿17,441 total
includes taxes & fees
1 Feb - 2 Feb
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, (1,005 reviews)
"Clean room , friendly staff , excellent location . Would stay again ! "
United States
Kathleen
The price is ฿14,245
฿16,026 total
includes taxes & fees
1 Feb - 2 Feb
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, (1,002 reviews)
"Perfect place to stay. "
United States
Paulette
The price is ฿13,548
฿16,989 total
includes taxes & fees
26 Jan - 27 Jan
The Marquesa Hotel
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, (140 reviews)
"We absolutely loved finding this gem to stay on our first visit to Key West. Great location, wonderful staff, and excellent room. "
United States
Sammy
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Audubon Room - Adult Exclusive | Terrace/patio

The Mermaid & Alligator

The Mermaid & Alligator
3.5 star property
Old Town Key West, 1.3 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (281 reviews)
"Lovely place"
United States
Nikhil
The Mermaid & Alligator
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, (1,002 reviews)
"Excellent stay"
United States
Emily Barbara
The price is ฿12,249
฿13,780 total
includes taxes & fees
27 Jan - 28 Jan
Island City House 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, (1,004 reviews)
"Room was great along with the staff. The hotel is in a great location "
United States
James
The price is ฿14,136
฿15,903 total
includes taxes & fees
1 Feb - 2 Feb
Orchid Key Inn - Adults Only
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, (934 reviews)
"Great location "
United States
Scott
The price is ฿10,017
฿11,270 total
includes taxes & fees
1 Feb - 2 Feb
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, (371 reviews)
"Nice place to stay "
United States
yulio
The price is ฿14,628
฿17,233 total
includes taxes & fees
3 Feb - 4 Feb
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, (583 reviews)
"Great place!!"
United States
Joel
The price is ฿22,649
฿27,578 total
includes taxes & fees
26 Jan - 27 Jan
H2O Suites - Adults Only
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, (1,005 reviews)
"Great place to stay"
United States
Melody
The price is ฿11,329
฿12,745 total
includes taxes & fees
16 Feb - 17 Feb
Ambrosia Key West
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, (1,005 reviews)
"Clean room and front desk very friendly."
United States
Jennifer Renee
The price is ฿19,542
฿24,397 total
includes taxes & fees
26 Jan - 27 Jan
Ocean Key Resort - A Noble House Resort
Exterior

Douglas House

Douglas House
3.0 star property
Uptown - Upper Duval, 1.4 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (264 reviews)
"Loved the hotel will definitely stay again "
United States
Christina
The price is ฿11,033
฿13,653 total
includes taxes & fees
28 Jan - 29 Jan
Douglas House
Front of property – evening/night

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 ฿13,120
฿15,983 total
includes taxes & fees
26 Jan - 27 Jan
Opal Key Resort & Marina, Key West
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, (1,009 reviews)
"Great place to stay. Walking distance to Duval St."
United States
Compton
Westwinds Inn
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, (1,005 reviews)
"Great location and really nice room. Def stay here again. "
United States
Daniel
The Grand Guesthouse
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, (1,006 reviews)
"Great place! "
United States
David
The price is ฿10,799
฿12,817 total
includes taxes & fees
26 Jan - 27 Jan
Duval House
Outdoor pool

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, (519 reviews)
"Great location, very clean, and great staff"
United States
William
The price is ฿11,937
฿15,138 total
includes taxes & fees
26 Jan - 27 Jan
The Key West Hotel
Exterior

The Garden House

The Garden House
3.0 star property
Historic Seaport, 0.6 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (677 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 ฿9,010
฿10,804 total
includes taxes & fees
27 Jan - 28 Jan
The Garden House
Outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

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, (427 reviews)
"Excellent food, location, friendly staff and pool was awesome."
United States
Karen
The price is ฿14,366
฿17,734 total
includes taxes & fees
26 Jan - 27 Jan
Ella's Cottages - Key West Historic Inns
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

Top Waterfront Playhouse Hotel Reviews

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

10/10 Excellent
"Room had a great view. Clean and comfortable. Staff was very accommodating and courteous. This was our 3rd stay at Ocean Key and we will definitely be back. "
Christina 5-night trip
Posted 23 hours ago
Ocean Key Resort - A Noble House Resort

Hotels near other Waterfront Playhouse attractions

Exploring the view from Key West Shipwreck Museum in Key West, Florida on a sunny day with vibrant skies and coastal charm

Key West Shipwreck Museum

4.2/5 (358 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
Sunset sailing at Mallory Square in Key West, Florida, featuring multiple sailboats against an orange sky

Mallory Square

4.5/5 (7,700 reviews)
Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.
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 1532 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 1532 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 Ernest Hemingway Home and Museum, Key West Lighthouse and Keeper's Quarters Museum and Fort Zachary Taylor Historic State Park 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.