Hotels near Waterfront Playhouse

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
11 Jan - 12 Jan
Tomorrow
12 Jan - 13 Jan
Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Waterfront Playhouse hotels

Minibar, in-room safe, individually decorated, individually furnished
Simonton Court Historic Inn & Cottages

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, (896 reviews)
"Great location and staff. The room was clean and comfortable, nice and quiet."
United States
Jesus
The price is RM1,218
RM1,370 total
includes taxes & fees
12 Jan - 13 Jan
Simonton Court Historic Inn & Cottages
Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds
Almond Tree Inn Hotel - Adults Only

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 RM1,788
RM2,011 total
includes taxes & fees
15 Jan - 16 Jan
Almond Tree Inn Hotel - Adults Only
Exterior
The Marquesa Hotel

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, (1,001 reviews)
"Perfect place to stay. "
United States
Paulette
The price is RM1,426
RM1,833 total
includes taxes & fees
12 Jan - 13 Jan
The Marquesa Hotel
Front of property
Key West Villas

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, (248 reviews)
"Awsome staff great location "
United States
Jeffrey
Key West Villas
Property grounds
Orchid Key Inn - Adults Only

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)
"Convenient location, staff was friendly and helpful"
United States
Melissa
The price is RM1,514
RM1,703 total
includes taxes & fees
13 Jan - 14 Jan
Orchid Key Inn - Adults Only
Terrace/patio
The Mermaid & Alligator

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, (278 reviews)
"It is very quaint, clean, has a friendly atmosphere & has a great location. We love going there!"
United States
Bradley
The Mermaid & Alligator
Free WiFi, bed sheets
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

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, (138 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
Exterior
Coco Plum Inn

Coco Plum Inn

Coco Plum Inn
3.0 star property
Downtown Key West, 0.8 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (476 reviews)
"The Coco Plum Inn is a wonderful place to stay. Staff is fantastic and the location is perfect. We will definitely come back and stay at the Coco Plum Inn."
United States
Brent
The price is RM1,206
RM1,357 total
includes taxes & fees
12 Jan - 13 Jan
Coco Plum Inn
Terrace/patio
The Conch House Heritage Inn

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, (150 reviews)
"Large clean room and excellent staff! Made for a great stay. "
United States
Daniel
The price is RM1,603
RM1,804 total
includes taxes & fees
15 Jan - 16 Jan
The Conch House Heritage Inn
Balcony view
Island City House Hotel

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)
"Excellent stay"
United States
Emily Barbara
The price is RM1,490
RM1,676 total
includes taxes & fees
12 Jan - 13 Jan
Island City House Hotel
Front of property
L'Habitation Guest House

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, (930 reviews)
"Great location "
United States
Scott
The price is RM1,340
RM1,508 total
includes taxes & fees
20 Jan - 21 Jan
L'Habitation Guest House
Premium bedding, iron/ironing board, free WiFi, bed sheets
Weatherstation Inn

Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex, 0.5 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,001 reviews)
"The staff was outstanding and this location was very convenient, yet located away from the hustle and bustle of the main area."
United States
William
The price is RM1,259
RM1,416 total
includes taxes & fees
12 Jan - 13 Jan
Weatherstation Inn
Outdoor pool, pool loungers
Ocean Key Resort - A Noble House Resort

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, (1,007 reviews)
"Nice hotel but a lot of construction going on"
United States
Tobias
The price is RM1,887
RM2,439 total
includes taxes & fees
25 Jan - 26 Jan
Ocean Key Resort - A Noble House Resort
Exterior
Douglas House

Douglas House

Douglas House
3.0 star property
Uptown - Upper Duval, 1.4 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (248 reviews)
"Loved the hotel will definitely stay again "
United States
Christina
The price is RM1,060
RM1,312 total
includes taxes & fees
14 Jan - 15 Jan
Douglas House
Premium bedding, pillow-top beds, individually decorated
Tropical Inn

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (367 reviews)
"Nice place to stay "
United States
yulio
The price is RM1,495
RM1,783 total
includes taxes & fees
13 Jan - 14 Jan
Tropical Inn
3 outdoor pools, a heated pool, pool loungers
Ambrosia Key West

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 RM1,001
RM1,126 total
includes taxes & fees
12 Jan - 13 Jan
Ambrosia Key West
Lobby sitting area
Westwinds Inn

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)
"Enjoyed our stay."
United States
Cindy
Westwinds Inn
Property grounds
Duval House

Duval House

Duval House
3.0 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,018 reviews)
"Great place! "
United States
David
The price is RM851
RM1,045 total
includes taxes & fees
14 Jan - 15 Jan
Duval House
Courtyard
The Grand Guesthouse

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, (1,002 reviews)
"Great stay"
United States
Ginger
The Grand Guesthouse
Terrace/patio
Marrero's Guest Mansion

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 RM1,527
RM1,718 total
includes taxes & fees
13 Jan - 14 Jan
Marrero's Guest Mansion
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

The Key West Hotel

The Key West Hotel

10/10 Excellent
"Room was absolutely amazing!! Staff, location, and very clean. 10/10 I would give this place!!!"
Kristi 4-night trip
Posted 3 days ago
The Key West Hotel

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 1531 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 Hyatt Centric Key West Resort and Spa and Ocean Key Resort - A Noble House Resort.
How many hotels will I find near Waterfront Playhouse?
Expedia has 1531 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.