Top 10 Hotels Near 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 1453 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 Hyatt Centric Key West Resort and Spa and Opal Key Resort & Marina, Key West .

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

Expedia has 1453 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: 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 theater.

Our top choices for Waterfront Playhouse hotels

Minibar, in-room safe, individually decorated, individually furnished

Simonton Court Historic Inn & Cottages

Historic Seaport, 0.5 km from Waterfront Playhouse

Rita

P12,924 total

includes taxes & fees

Jul 7 - Jul 8

Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Almond Tree Inn Hotel - Adults Only

Downtown Key West, 1.3 km from Waterfront Playhouse

Jimmy

P10,668 total

includes taxes & fees

Jun 29 - Jun 30

The Marquesa Hotel

Old Town Key West, 0.7 km from Waterfront Playhouse

Helia

P17,381 total

includes taxes & fees

Jul 7 - Jul 8

The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Joseph

P13,608 total

includes taxes & fees

Jun 23 - Jun 24

Key West Villas

Downtown Key West, 0.9 km from Waterfront Playhouse

Jennifer

P14,094 total

includes taxes & fees

Jun 29 - Jun 30

Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

Michael

P12,890 total

includes taxes & fees

Jun 24 - Jun 25

Island City House Hotel

Historic Seaport, 0.8 km from Waterfront Playhouse

Paul

P12,652 total

includes taxes & fees

Jun 25 - Jun 26

L'Habitation Guest House

Historic Seaport, 0.5 km from Waterfront Playhouse

Richard

P8,555 total

includes taxes & fees

Jun 28 - Jun 29

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Old Town Key West, 1.2 km from Waterfront Playhouse

Annette

P18,467 total

includes taxes & fees

Jun 23 - Jun 24

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

Weatherstation Inn

Truman Annex, 0.5 km from Waterfront Playhouse

Bret

P12,241 total

includes taxes & fees

Jun 28 - Jun 29

The Conch House Heritage Inn

Old Town Key West, 1.3 km from Waterfront Playhouse

Lucy

P16,248 total

includes taxes & fees

Jun 24 - Jun 25

Premium bedding, pillowtop beds, individually decorated

Tropical Inn

Downtown Key West, 1.1 km from Waterfront Playhouse

Akhenaton

P11,928 total

includes taxes & fees

Jun 23 - Jun 24

Douglas House - Adults Only

Uptown - Upper Duval, 1.4 km from Waterfront Playhouse

Matthew

P8,776 total

includes taxes & fees

Jul 7 - Jul 8

3 outdoor pools, a heated pool, sun loungers

Ambrosia Key West

Old Town Key West, 0.7 km from Waterfront Playhouse

Lori

P11,051 total

includes taxes & fees

Jun 29 - Jun 30

Westwinds Inn

Historic Seaport, 0.9 km from Waterfront Playhouse

Kelly

P11,386 total

includes taxes & fees

Jun 29 - Jun 30

H2O Suites - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Rosa

P26,601 total

includes taxes & fees

Jul 6 - Jul 7

Marrero's Guest Mansion

Downtown Key West, 0.6 km from Waterfront Playhouse

Robert

P13,609 total

includes taxes & fees

Jun 29 - Jun 30

Outdoor pool, free cabanas, sun loungers

Ocean Key Resort - A Noble House Resort

Historic Seaport, < 0.1 km from Waterfront Playhouse

Joseph

P29,952 total

includes taxes & fees

Jun 30 - Jul 1

Coco Plum Inn

Downtown Key West, 0.8 km from Waterfront Playhouse

Brinkley

P12,278 total

includes taxes & fees

Jul 12 - Jul 13

Opal Key Resort & Marina, Key West

Old Town Key West, 0.1 km from Waterfront Playhouse

Margarita

P20,105 total

includes taxes & fees

Jun 28 - Jun 29

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 988 reviews	View
Almond Tree Inn Hotel - Adults Only	3.5 star property	10.0 Exceptional 1,001 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 1,000 reviews	View
Key West Villas	3.5 star property	9.8 Exceptional 262 reviews	View

Top Waterfront Playhouse Hotel Reviews

Southernmost Beach Resort and Guesthouses

8/10 Good

"Rooms were clean. Not enough seating at the pools. You have to get a chair by 9:30 am or you can’t get one. The umbrellas at the pool are worn and have mildew. The pier with the loungers has broken umbrellas. The lawn area is worn and looks nothing like the pictures online. The seaweed at this time of year is so bad that you can’t go in the water and it smells very horrible. Only stay here if the seaweed is gone ."

Ocean Key Resort - A Noble House Resort

10/10 Excellent

"First.. Pros.. greeted at valet parking with welcome glass of champagne..from that moment on customer service was excellent. Grounds were kept spotless at all times, especially the pool area with amazing attendants. Location could not be better. Room 323 was amazing. Only cons were shower had no door or curtain and water ran all the way out to hall. Also, yes room states partial ocean view, but due to trees the potential for nice views was almost no view."

NYAH Key West - Adults Only

8/10 Good

"It’s not bad for budget. Nothing crazy bad just a bit loud and typical Key West construction so everything is heard when you talk and walk through the walls. So good thing was AC was perfectly cold, pool was decent, and the staff helped me out. I booked a dorm style room so I won’t comment on the single rooms. Anyways good enough for my quick weekend to visit the Dry Tortuga’s."

Simonton Court Historic Inn & Cottages

10/10 Excellent

"I rarely review places but when I do they deserve it! Simonton Court was top notch. We got a good price for the stay. We arrived to find an inviting flower covered, palm lined inviting walkway. They upgraded us to a king size bed, but that was 3rd floor so we chose to stay in our queen on the first floor. The little houses would have been perfect to stay in. Pools were nice, place clean, breakfast nice, hoped for omelets. Located 1 block from Duval St in the center of everything but far enough for it to be quiet. But all in all I rate our Stay a 9 out of 10,"

Hotels near other Waterfront Playhouse attractions

Key West Shipwreck Museum

8.6/5 (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, check out the 1453 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 Hyatt Centric Key West Resort and Spa and Opal Key Resort & Marina, Key West.

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

Expedia has 1453 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.

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 theater.

Hotels near Waterfront Playhouse

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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

L'Habitation Guest House

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Weatherstation Inn

The Conch House Heritage Inn

Tropical Inn

Douglas House - Adults Only

Ambrosia Key West

Westwinds Inn

H2O Suites - Adults Only

Marrero's Guest Mansion

Ocean Key Resort - A Noble House Resort

Coco Plum Inn

Opal Key Resort & Marina, Key West

Compare popular hotels close to Waterfront Playhouse

Top Waterfront Playhouse Hotel Reviews

Southernmost Beach Resort and Guesthouses

Hotels near other Waterfront Playhouse attractions

Key West Shipwreck Museum

Frequently asked questions