Browse through all of the upcoming events and savor a little culture at Waterfront Playhouse. It offers various entertaining plays catering to many tastes and interests.

You'll have sightseeing choices galore when spending time in Key West Historic District. Waterfront Playhouse is a great place to begin here, but there are numerous other fine sights to consider. Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens, and Mallory Square are not far from the arts and culture attraction and will fill in your day nicely.

Plan a trip to see Waterfront Playhouse

Price found within the past 48 hours. Click for updated prices.

The Shelborne By Proper, a Member of Design Hotels

South Beach

Save 100% on your flight

$607

per person

Nov 15 - Nov 18

found 15 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.8/10 Exceptional! (31 reviews)

Great hotel. Clearly freshly refurbished and excellent facilities. Staff were extremely attentive - everyone we bumped into in the lift, for example, even junior team members, asked how we were and whether there was anything that they could do to improve our stay. Shows a great culture! Only downsides are a bar that shuts very early (10pm) and a LOT of mosquitoes in the outdoor pool area - they give bug spray it we had to retreat late afternoon or after rain.

Reviewed on Oct 6, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$13,625

per person

Dec 3 - Dec 9

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8/10 Very Good! (1 review)

President Hotel

South Beach

$778

per person

Jan 1 - Jan 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (1,825 reviews)

Rooms were clean and front desk staff was very friendly and accommodating on check in!

Reviewed on Oct 13, 2025

Browse tours and tickets to explore Waterfront Playhouse

Tours & day trips

See all 169 activities

Key West Express Day Trip from Miami

Free cancellation available

Wildlife & nature

See all 53 activities

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

Free cancellation available

History & culture

See all 51 activities

Key West Day Trip & Glass Bottom-Boat Tour from Miami

Free cancellation available

Private & custom tours

See all 34 activities

Dry Tortugas National Park Day Trip by Luxury Private Boat

Free cancellation available

Food, drink & nightlife

See all 28 activities

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

Free cancellation available

Reviews of Waterfront Playhouse

4.2

Top Destination

5 - Excellent

3

4 - Good

1

3 - Okay

2

2 - Disappointing

0

1 - Terrible

0

3/5 - Okay

Verified traveler

Expensive

Popular places to visit

Key West Shipwreck Museum

4/5(324 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.

Mallory Square

4.5/5(3,096 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.

Mallory Dock

4.5/5(1,061 reviews)

You can search for that perfect souvenir at Mallory Dock during your visit to Key West. Wander the area's seaside or simply enjoy one of its lively bars.

Key West Aquarium

4/5(380 reviews)

Come face to face with huge sharks, feed stingrays and learn about local tropical fish at this great aquarium.

Museum of Art & History at the Custom House

4/5(15 reviews)

You can spend time exploring the galleries in Museum of Art & History at the Custom House during your trip to Key West. Discover the area's lively bars and its lively festivals.

Custom House Museum

4.5/5(29 reviews)

Visit this historic work of architecture to explore an award-winning museum, learn about the early Key West community and gaze across the Key West Harbor.