Search Hotels Near Waterfront Playhouse, Key West

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Waterfront Playhouse hotels

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, 0.8 mi from Waterfront Playhouse
10.0 out of 10, Exceptional, (1,004 reviews)
"Loved this hotel & staff!"
United States
Renee
The price is £200
includes taxes & fees
22 Jun - 23 Jun
Almond Tree Inn Hotel - Adults Only
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, 0.3 mi from Waterfront Playhouse
9.8 out of 10, Exceptional, (964 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 £122
includes taxes & fees
3 Jun - 4 Jun
Simonton Court Historic Inn & Cottages
Exterior

The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Old Town Key West, 0.4 mi from Waterfront Playhouse
9.8 out of 10, Exceptional, (1,000 reviews)
"Great accommodations and great staff"
United States
Julian
The price is £282
includes taxes & fees
17 Jun - 18 Jun
The Marquesa Hotel
Exterior detail

The Gardens Hotel

The Gardens Hotel
4.0 star property
Downtown Key West, 0.6 mi from Waterfront Playhouse
9.8 out of 10, Exceptional, (1,003 reviews)
"Best hotel ive ever stayed in, the hospitality was unmatched."
United States
Markus
The price is £199
includes taxes & fees
15 Jun - 16 Jun
The Gardens Hotel
Front of property

Key West Villas

Key West Villas
3.5 star property
Downtown Key West, 0.6 mi 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 £164
includes taxes & fees
3 Jun - 4 Jun
Key West Villas
Property grounds

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
3.5 star property
Uptown - Upper Duval, 0.8 mi from Waterfront Playhouse
9.8 out of 10, Exceptional, (1,003 reviews)
"Great boutique hotel in the perfect location !! "
United States
Michael
The price is £179
includes taxes & fees
1 Jun - 2 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, 0.5 mi from Waterfront Playhouse
9.6 out of 10, Exceptional, (1,000 reviews)
"Nice location "
United States
Michael
The price is £171
includes taxes & fees
9 Jun - 10 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, 0.8 mi from Waterfront Playhouse
9.8 out of 10, Exceptional, (175 reviews)
"Great location "
United Kingdom
Lucy
The price is £178
includes taxes & fees
28 May - 29 May
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, 0.8 mi 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 £225
includes taxes & fees
22 Jun - 23 Jun
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Exterior

Douglas House - Adults Only

Douglas House - Adults Only
3.0 star property
Uptown - Upper Duval, 0.9 mi from Waterfront Playhouse
9.6 out of 10, Exceptional, (391 reviews)
"Great location, helpful staff and fun people. Would stay here again…the pool and room were fantastic"
United States
Scott
The price is £120
includes taxes & fees
2 Jun - 3 Jun
Douglas House - Adults Only
11 Gecko's Garden - Adults Only | Premium bedding, pillow-top beds, individually decorated

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 0.7 mi from Waterfront Playhouse
9.6 out of 10, Exceptional, (406 reviews)
"Very friendly staff and a prime location."
United States
Akhenaton
The price is £165
includes taxes & fees
27 May - 28 May
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 mi from Waterfront Playhouse
9.8 out of 10, Exceptional, (609 reviews)
"This resort was in the perfect location for exploring Key West. Highly recommend!"
United States
Barton
The price is £349
includes taxes & fees
7 Jun - 8 Jun
H2O Suites - Adults Only
Front of property

L'Habitation Guest House

L'Habitation Guest House
2.5 star property
Historic Seaport, 0.3 mi from Waterfront Playhouse
9.4 out of 10, Exceptional, (984 reviews)
"Quaint B&B. One block from Duval street so very close to everything. Great breakfast every morning. Staff very friendly and helpful."
United States
Michael
The price is £104
includes taxes & fees
28 May - 29 May
L'Habitation Guest House
Premium bedding, iron/ironing board, free WiFi, bed sheets

Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex, 0.3 mi from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,002 reviews)
"Perfect stay!"
United States
A. Elise
The price is £149
includes taxes & fees
28 May - 29 May
Weatherstation Inn
Lobby sitting area

Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.6 mi from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,001 reviews)
"Nice place to stay!"
United States
michael
The price is £161
includes taxes & fees
3 Jun - 4 Jun
Westwinds Inn
3 outdoor pools, a heated pool, pool loungers

Ambrosia Key West

Ambrosia Key West
3.5 star property
Old Town Key West, 0.4 mi from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,001 reviews)
"Breakfast was very nice."
United States
cindy
The price is £194
includes taxes & fees
1 Jun - 2 Jun
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 mi from Waterfront Playhouse
9.2 out of 10, Wonderful, (1,005 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 £255
includes taxes & fees
10 Jun - 11 Jun
Ocean Key Resort - A Noble House Resort
Exterior

Coco Plum Inn

Coco Plum Inn
3.0 star property
Downtown Key West, 0.5 mi 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 £204
includes taxes & fees
3 Jun - 4 Jun
Coco Plum Inn
Property grounds

Duval House

Duval House
3.0 star property
Downtown Key West, 0.7 mi from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,036 reviews)
"Great location and staff"
United States
gerald
The price is £182
includes taxes & fees
7 Jun - 8 Jun
Duval House
2 outdoor pools, pool loungers

Santa Maria Suites

Santa Maria Suites
4.0 star property
Uptown - Upper Duval, 1.1 mi from Waterfront Playhouse
9.6 out of 10, Exceptional, (1,001 reviews)
"Great hotel and room. Very clean, great location."
United States
Cindy
The price is £307
includes taxes & fees
21 Jun - 22 Jun
Santa Maria Suites
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 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
1,004 reviews
View
Queen with Pool View | Minibar, in-room safe, individually decorated, individually furnished
Simonton Court Historic Inn & Cottages
2.5 star property
9.8
Exceptional
964 reviews
View
Exterior
The Marquesa Hotel
3.5 star property
9.8
Exceptional
1,000 reviews
View
Exterior detail
The Gardens Hotel
4.0 star property
9.8
Exceptional
1,003 reviews
View
Front of property
Key West Villas
3.5 star property
9.8
Exceptional
261 reviews
View

Top Waterfront Playhouse Hotel Reviews

The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

10/10 Excellent
"The location of this hotel is more than excellent- and for its age is maintained well! With a breakfast and a happy hour and and a pool and hot tub - awesome! Parking is always an issue in this area of key west (30 dollars for overnight at the hotel and 37 for overnight in city lot parking practically next door if needed.) Pricy but somehow seems reasonable. Just being here makes it worth it for me."
Thomas 1-night trip
Posted 7 hours ago
The Cabana Inn Key West - Adults Only

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 1459 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 La Concha Key West, Autograph Collection and Opal Key Resort & Marina, Key West.
How many hotels will I find near Waterfront Playhouse?
Expedia has 1459 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, Mel Fisher Maritime Museum 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.