The Best Hotels Closest to Waterfront Playhouse in Key West for 2026

Q: 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 1461 hotels and other accommodations you'll find within a mile.

Q: 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 La Concha Key West, Autograph Collection and Opal Key Resort & Marina, Key West .

Q: How many hotels will I be able to find near Waterfront Playhouse?

Expedia has 1461 hotels and other accommodations within a mile from Waterfront Playhouse.

Q: 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.

Q: Where can I learn more about changing or cancelling my trip in the area near Waterfront Playhouse?

To access more information about rescheduling or cancelling your stay near Waterfront Playhouse, go to https://www.expedia.com/service/ .

Q: What can I see and do near Waterfront Playhouse?

Key West Shipwreck Museum, Audubon House and Tropical Gardens, and Mel Fisher Maritime Museum feature a variety of fascinating exhibits to see while you're in town. Sights like Harry S. Truman Little White House, 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.

Our top choices for Waterfront Playhouse hotels

Queen with Pool View | Minibar, in-room safe, individually decorated, individually furnished

Simonton Court Historic Inn & Cottages

Historic Seaport, 0.5 km from Waterfront Playhouse

Olha

AED 725 total

includes taxes & fees

28 May - 29 May

Queen Deluxe ADA | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Almond Tree Inn Hotel - Adults Only

Downtown Key West, 1.3 km from Waterfront Playhouse

Renee

AED 1,026 total

includes taxes & fees

25 May - 26 May

The Marquesa Hotel

Old Town Key West, 0.7 km from Waterfront Playhouse

Julian

AED 1,401 total

includes taxes & fees

16 Jun - 17 Jun

The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Markus

AED 848 total

includes taxes & fees

23 Jun - 24 Jun

Key West Villas

Downtown Key West, 0.9 km from Waterfront Playhouse

Jennifer

AED 815 total

includes taxes & fees

26 May - 27 May

Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

Michael

AED 969 total

includes taxes & fees

25 May - 26 May

Cigar House King Suite w/ Poolside porch | Balcony view

Island City House Hotel

Historic Seaport, 0.8 km from Waterfront Playhouse

Michael

AED 939 total

includes taxes & fees

28 May - 29 May

The Conch House Heritage Inn

Old Town Key West, 1.3 km from Waterfront Playhouse

Lucy

AED 1,031 total

includes taxes & fees

14 Jun - 15 Jun

L'Habitation Guest House

Historic Seaport, 0.5 km from Waterfront Playhouse

Michael

AED 554 total

includes taxes & fees

25 May - 26 May

Premium bedding, iron/ironing board, free WiFi, bed sheets

Weatherstation Inn

Truman Annex, 0.5 km from Waterfront Playhouse

A. Elise

AED 822 total

includes taxes & fees

25 May - 26 May

Outdoor pool, free cabanas, sun loungers

Ocean Key Resort - A Noble House Resort

Historic Seaport, < 0.1 km from Waterfront Playhouse

Terrie

AED 1,264 total

includes taxes & fees

10 Jun - 11 Jun

Douglas House - Adults Only

Uptown - Upper Duval, 1.4 km from Waterfront Playhouse

Scott

AED 673 total

includes taxes & fees

9 Jun - 10 Jun

11 Gecko's Garden - Adults Only | Premium bedding, pillowtop beds, individually decorated

Tropical Inn

Downtown Key West, 1.1 km from Waterfront Playhouse

Akhenaton

AED 1,062 total

includes taxes & fees

25 May - 26 May

Superior Studio Suite, 1 King Bed with Sofa bed, Accessible, Refrigerator & Microwave | Free WiFi, bed sheets

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Old Town Key West, 1.2 km from Waterfront Playhouse

Annette

AED 1,116 total

includes taxes & fees

22 Jun - 23 Jun

Westwinds Inn

Historic Seaport, 0.9 km from Waterfront Playhouse

michael

AED 837 total

includes taxes & fees

1 Jun - 2 Jun

3 outdoor pools, a heated pool, sun loungers

Ambrosia Key West

Old Town Key West, 0.7 km from Waterfront Playhouse

cindy

AED 880 total

includes taxes & fees

25 May - 26 May

Deluxe Suite, 1 King Bed, Private Pool | View from room

H2O Suites - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Barton

AED 1,731 total

includes taxes & fees

7 Jun - 8 Jun

Marrero's Guest Mansion

Downtown Key West, 0.6 km from Waterfront Playhouse

Robert

AED 1,318 total

includes taxes & fees

25 May - 26 May

Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

gerald

AED 695 total

includes taxes & fees

26 May - 27 May

Opal Key Resort & Marina, Key West

Old Town Key West, 0.1 km from Waterfront Playhouse

Theresa

AED 1,236 total

includes taxes & fees

11 Jun - 12 Jun

View all properties

Compare popular hotels close to Waterfront Playhouse

Property	Property class	Guest rating
Simonton Court Historic Inn & Cottages	2.5 star property	9.8 Exceptional 963 reviews	View
Almond Tree Inn Hotel - Adults Only	3.5 star property	10.0 Exceptional 1,002 reviews	View
The Marquesa Hotel	3.5 star property	9.8 Exceptional 1,000 reviews	View
The Gardens Hotel	4.0 star property	9.8 Exceptional 1,001 reviews	View
Key West Villas	3.5 star property	9.8 Exceptional 261 reviews	View

Top Waterfront Playhouse Hotel Reviews

Pier House Resort & Spa

10/10 Excellent

"The staff was very helpful, our rooms were clean. The restaurant was amazing. Would definitely recommend.!"

Pegasus International Hotel

8/10 Good

"Room was nice and clean but small. Desk is open limited hours so schedule your arrival accordingly. Parking is limited and a block away but doable. Facility overall was very nice, but be prepared: the bathrooms are rediculously small. If you're a very large person you may want to rethink a stay here. In our room, if you're sitting on the toilet, your head is hitting the wall, it's that close to the wall. And the gap between the glass shower wall and the rear wall of the shower is only 18", so if you're big you may have a hard time even getting into the shower. At least that's how it was in our room."

NYAH Key West - Adults Only

10/10 Excellent

"You'd be sharing a room with others and you get a bunk. You can store your stuff in a locker. You get towels and toiletries you need while you're here. The location is actually pretty good, especially if you're taking the ferry to Dry Tortugas. There's a pool and jacuzzi, which I liked, and also benches to grab a bite. Parking was on the street, but I'm told this is one of the safest places in the country, so it was okay. It wasn't difficult to find parking, and I got a spot right outside. I had to drive around the block a bit to look for it, though. I'd recommend checking the streets for parking instead of heading to a garage. I've always found parking around this area after a while. The only thing that didn't work out was the breakfast, which we couldn't grab because it was a bit late for us. For a place that's so convenient for the ferry, I wished they'd provide breakfast earlier. Apart from that, great experience. I'd recommend this place hands down!"

Opal Key Resort & Marina, Key West

10/10 Excellent

"Beautiful resort hotel. Location is perfect. Walking distance to just about everything. Room was clean and comfortable. The hotel restaurant Lolita's was wonderful. Great food and service. We ate breakfast, lunch and dinner over the week and were never disappointed. Shout out to Lenka at the bar. Friendly and boy did she rock a great Sangria. Highly recommend this hotel but would suggest the staff at check in take a few minutes to go over all the amenities offered."

Hotels near other Waterfront Playhouse attractions

Key West Shipwreck Museum

4.3/5 (361 reviews)

You can spend an afternoon studying the exhibits at Key West Shipwreck Museum during your trip to Key West. In the area, take in the lively festivals and beautiful sunsets.

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, check out the 1461 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 La Concha Key West, Autograph Collection and Opal Key Resort & Marina, Key West.

How many hotels will I be able to find near Waterfront Playhouse?

Expedia has 1461 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.

Where can I learn more about changing or cancelling my trip in the area near Waterfront Playhouse?

To access more information about rescheduling or cancelling your stay near Waterfront Playhouse, go to https://www.expedia.com/service/.

What can I see and do near Waterfront Playhouse?

Key West Shipwreck Museum, Audubon House and Tropical Gardens, and Mel Fisher Maritime Museum feature a variety of fascinating exhibits to see while you're in town. Sights like Harry S. Truman Little White House, 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.

Find hotels near Waterfront Playhouse, Key West from AED 554

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Our top choices for Waterfront Playhouse hotels

Simonton Court Historic Inn & Cottages

Almond Tree Inn Hotel - Adults Only

The Marquesa Hotel

The Gardens Hotel

Key West Villas

Orchid Key Inn - Adults Only

Island City House Hotel

The Conch House Heritage Inn

L'Habitation Guest House

Weatherstation Inn

Ocean Key Resort - A Noble House Resort

Douglas House - Adults Only

Tropical Inn

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Westwinds Inn

Ambrosia Key West

H2O Suites - Adults Only

Marrero's Guest Mansion

Duval House

Opal Key Resort & Marina, Key West

Compare popular hotels close to Waterfront Playhouse

Top Waterfront Playhouse Hotel Reviews

Pier House Resort & Spa

Hotels near other Waterfront Playhouse attractions

Key West Shipwreck Museum

Frequently asked questions

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