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 1455 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 Opal Key Resort & Marina, Key West and La Concha Key West, Autograph Collection .

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

Expedia has 1455 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?

Audubon House and Tropical Gardens, Harry S. Truman Little White House, and Florida Keys Eco - Discovery Center 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 Key West Burlesque Theater, Red Barn Theater, and Key West Film Society 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 613 total

includes taxes & fees

7 Jun - 8 Jun

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

Jimmy

AED 1,015 total

includes taxes & fees

9 Jun - 10 Jun

The Marquesa Hotel

Old Town Key West, 0.7 km from Waterfront Playhouse

Julian

AED 1,483 total

includes taxes & fees

8 Jun - 9 Jun

Cigar House King Suite w/ Poolside porch | Balcony view

Island City House Hotel

Historic Seaport, 0.8 km from Waterfront Playhouse

Troy

AED 708 total

includes taxes & fees

10 Jun - 11 Jun

The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Markus

AED 988 total

includes taxes & fees

28 Jun - 29 Jun

The Conch House Heritage Inn

Old Town Key West, 1.3 km from Waterfront Playhouse

Lucy

AED 883 total

includes taxes & fees

9 Jun - 10 Jun

Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

Michael

AED 1,042 total

includes taxes & fees

9 Jun - 10 Jun

L'Habitation Guest House

Historic Seaport, 0.5 km from Waterfront Playhouse

Megan

AED 574 total

includes taxes & fees

8 Jun - 9 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 790 total

includes taxes & fees

8 Jun - 9 Jun

Douglas House - Adults Only

Uptown - Upper Duval, 1.4 km from Waterfront Playhouse

Matthew

AED 495 total

includes taxes & fees

9 Jun - 10 Jun

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

H2O Suites - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Elizabeth

AED 1,607 total

includes taxes & fees

8 Jun - 9 Jun

Westwinds Inn

Historic Seaport, 0.9 km from Waterfront Playhouse

michael

AED 762 total

includes taxes & fees

9 Jun - 10 Jun

The Grand Guesthouse

Old Town Key West, 1.7 km from Waterfront Playhouse

Kim

AED 635 total

includes taxes & fees

9 Jun - 10 Jun

3 outdoor pools, a heated pool, sun loungers

Ambrosia Key West

Old Town Key West, 0.7 km from Waterfront Playhouse

Lori

AED 809 total

includes taxes & fees

7 Jun - 8 Jun

Opal Key Resort & Marina, Key West

Old Town Key West, 0.1 km from Waterfront Playhouse

Margarita

AED 1,215 total

includes taxes & fees

23 Jun - 24 Jun

Marrero's Guest Mansion

Downtown Key West, 0.6 km from Waterfront Playhouse

Robert

AED 1,012 total

includes taxes & fees

23 Jun - 24 Jun

Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

gerald

AED 695 total

includes taxes & fees

8 Jun - 9 Jun

Outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

Ella's Cottages - Key West Historic Inns

Old Town Key West, 1.1 km from Waterfront Playhouse

Nanci

AED 818 total

includes taxes & fees

29 Jun - 30 Jun

Outdoor pool, free cabanas, sun loungers

Ocean Key Resort - A Noble House Resort

Historic Seaport, < 0.1 km from Waterfront Playhouse

Terrie

AED 1,535 total

includes taxes & fees

23 Jun - 24 Jun

Santa Maria Suites

Uptown - Upper Duval, 1.8 km from Waterfront Playhouse

Jill

AED 1,525 total

includes taxes & fees

21 Jun - 22 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 973 reviews	View
Almond Tree Inn Hotel - Adults Only	3.5 star property	10.0 Exceptional 1,005 reviews	View
The Marquesa Hotel	3.5 star property	9.8 Exceptional 1,000 reviews	View
Island City House Hotel	3.0 star property	9.6 Exceptional 1,001 reviews	View
The Gardens Hotel	4.0 star property	9.8 Exceptional 1,001 reviews	View

Top Waterfront Playhouse Hotel Reviews

Ridley House - Key West Historic Inns

10/10 Excellent

"The staff were AMAZING. Our room was beautifully decorated and clean with great air conditioning. The historic aspect of this house was architecturally stunning and was among others that lined to streets in Old Town, Key West. It was in walking distance to great restaurants, Mallory Square and an amazing sunset. My favorite part was the breakfast that was served each morning. It had five star quality buffet with several options to choose from. I would highly recommend staying at the Ridley House."

Pier House Resort & Spa

10/10 Excellent

"My wife and I went down there for a four night stay and had a wonderful experience! We stayed in an ocean view room, which was absolutely beautiful. The staff was very friendly and helpful. The location could not have been better, and it is in walking distance to pretty much everything. The resort has its own private pool and beach, which was such a unique bonus. We were also very impressed by how intentional the resort is about wheelchair accessibility. My mother-in-law has ALS and is in a wheelchair, so we are already planning a trip to bringing her to this resort. We give it five stars!"

Hyatt Vacation Club at Sunset Harbor, Key West

8/10 Good

"Like almost everywhere in the Keys, you start off by paying to park. Pool was great with a nice hot tub and swings and barbecue grills to use. We were asked to do the vacation club tour and at first I agree but then the $200 visa gift card turned into vouchers, etc. Since we only stayed a few days, it wasn’t worth our while, and we had already done all the tours. I mainly didn’t like that. I kept hearing anywhere from 100, 150 and 200 at different times from different people and it went from a Visa gift card to vouchers, less legitimate when you’re not on the same page. Why would I trust to join a vacation club when they can’t even be upfront about what they’re offering to just show up The one bedroom unit we stayed in, was great with plenty of seating and an amazing balcony overlooking the pool and the Gulf of America. I would stay again and it’s a great location to all the main attractions"

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 1455 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 Opal Key Resort & Marina, Key West and La Concha Key West, Autograph Collection.

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

Expedia has 1455 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?

Audubon House and Tropical Gardens, Harry S. Truman Little White House, and Florida Keys Eco - Discovery Center 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 Key West Burlesque Theater, Red Barn Theater, and Key West Film Society if you're interested in local theater.

Find hotels near Waterfront Playhouse, Key West from AED 495

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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

Island City House Hotel

The Gardens Hotel

The Conch House Heritage Inn

Orchid Key Inn - Adults Only

L'Habitation Guest House

Tropical Inn

Douglas House - Adults Only

H2O Suites - Adults Only

Westwinds Inn

The Grand Guesthouse

Ambrosia Key West

Opal Key Resort & Marina, Key West

Marrero's Guest Mansion

Duval House

Ella's Cottages - Key West Historic Inns

Ocean Key Resort - A Noble House Resort

Santa Maria Suites

Compare popular hotels close to Waterfront Playhouse

Top Waterfront Playhouse Hotel Reviews

Ridley House - Key West Historic Inns

Hotels near other Waterfront Playhouse attractions

Key West Shipwreck Museum

Frequently asked questions

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Hotels near popular Key West Attractions

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