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

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 588 total

includes taxes & fees

18 Jun - 19 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 827 total

includes taxes & fees

16 Jun - 17 Jun

The Marquesa Hotel

Old Town Key West, 0.7 km from Waterfront Playhouse

Julian

AED 1,359 total

includes taxes & fees

24 Jun - 25 Jun

Key West Villas

Downtown Key West, 0.9 km from Waterfront Playhouse

Jennifer

AED 852 total

includes taxes & fees

16 Jun - 17 Jun

The Conch House Heritage Inn

Old Town Key West, 1.3 km from Waterfront Playhouse

Lucy

AED 982 total

includes taxes & fees

14 Jun - 15 Jun

The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Joseph

AED 988 total

includes taxes & fees

28 Jun - 29 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

15 Jun - 16 Jun

Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

Michael

AED 784 total

includes taxes & fees

15 Jun - 16 Jun

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 887 total

includes taxes & fees

14 Jun - 15 Jun

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

Weatherstation Inn

Truman Annex, 0.5 km from Waterfront Playhouse

Bret

AED 740 total

includes taxes & fees

14 Jun - 15 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 721 total

includes taxes & fees

15 Jun - 16 Jun

L'Habitation Guest House

Historic Seaport, 0.5 km from Waterfront Playhouse

Richard

AED 533 total

includes taxes & fees

16 Jun - 17 Jun

Westwinds Inn

Historic Seaport, 0.9 km from Waterfront Playhouse

michael

AED 762 total

includes taxes & fees

14 Jun - 15 Jun

Douglas House - Adults Only

Uptown - Upper Duval, 1.4 km from Waterfront Playhouse

Matthew

AED 566 total

includes taxes & fees

15 Jun - 16 Jun

Coco Plum Inn

Downtown Key West, 0.8 km from Waterfront Playhouse

Brinkley

AED 742 total

includes taxes & fees

12 Jul - 13 Jul

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

6 Jul - 7 Jul

Marrero's Guest Mansion

Downtown Key West, 0.6 km from Waterfront Playhouse

Robert

AED 946 total

includes taxes & fees

13 Jul - 14 Jul

3 outdoor pools, a heated pool, sun loungers

Ambrosia Key West

Old Town Key West, 0.7 km from Waterfront Playhouse

Lori

AED 738 total

includes taxes & fees

14 Jun - 15 Jun

Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

Wendy S

AED 518 total

includes taxes & fees

17 Jun - 18 Jun

The Grand Guesthouse

Old Town Key West, 1.7 km from Waterfront Playhouse

Duncan

AED 615 total

includes taxes & fees

14 Jun - 15 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 981 reviews	View
Almond Tree Inn Hotel - Adults Only	3.5 star property	10.0 Exceptional 1,013 reviews	View
The Marquesa Hotel	3.5 star property	9.8 Exceptional 1,001 reviews	View
Key West Villas	3.5 star property	9.8 Exceptional 262 reviews	View
The Conch House Heritage Inn	3.5 star property	9.8 Exceptional 176 reviews	View

Top Waterfront Playhouse Hotel Reviews

Southernmost Beach Resort and Guesthouses

6/10 Okay

"The property is dated. The rooms were small and old. The so-called balconies were not in the rooms, they were common for all. The pool bar closed at 7, the main bar closed at 9. Sometimes there were no towels at the pool and the number of chairs were limited."

Opal Key Resort & Marina, Key West

8/10 Good

"The Opal Key Resort was close to the heart of Key West. The grounds were well kept and everything was clean and in order. The staff was friendly and very accommodating. Our room was immaculate. We ate at Lolita’s restaurant and the food and prices were good. The only issues I had were minor maintenance issues that included a blackout shade in the room that didn’t go down (the window had blinds which we closed) and the sliding curtain’s track was not allowing the room darkening curtain to be closed easily. There was also a significant crack in the wall up by the top of the window. The bathtub also needed something to minimize the slipperiness since we’re older and falling on slippery surfaces can be hazardous. These issues did not affect our stay, but they need attention."

Ridley House - Key West Historic Inns

8/10 Good

"We really enjoyed our stay here. Things were very clean. We stayed in Room 6 that had a front balcony. Our first 30 minutes there we actually locked ourselves out on the balcony. 😜 Help was there swiftly. Be sure to use the lock latch to catch the door behind you. Otherwise it will lock you out. Bring ear plugs so the roosters don’t wake you at 4AM. Easy walk to anywhere on the island. We loved Fort Zachary Beach. Breakfast was served every morning as well."

La Concha Key West, Autograph Collection

6/10 Okay

"The hotel is in a great location. There were a few issues: I booked a king room But they gave us 2 queen beds plus the internet never worked so no streaming Netflix, prime or tv. They sent engineers to our room several times but never got it to work. I wish there was a hot tub but there isn’t and there are no ice machines, you have to ask front desk for ice whenever needed."

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.

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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 1450 hotels and other accommodations you'll find within a mile.

What's the best hotel to stay near Waterfront Playhouse?

Adjacent to Waterfront Playhouse, Hyatt Centric Key West Resort and Spa is one of the top choices for your stay based on our traveler data, and this resort offers a marina and a full-service spa. Other good options within a short distance include Pier House Resort & Spa and Opal Key Resort & Marina, Key West.

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

Expedia has 1450 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 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 518

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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

Key West Villas

The Conch House Heritage Inn

The Gardens Hotel

Island City House Hotel

Orchid Key Inn - Adults Only

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Weatherstation Inn

Tropical Inn

L'Habitation Guest House

Westwinds Inn

Douglas House - Adults Only

Coco Plum Inn

H2O Suites - Adults Only

Marrero's Guest Mansion

Ambrosia Key West

Duval House

The Grand Guesthouse

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

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Hotels near popular Key West Attractions

Other Hotels near Waterfront Playhouse, Key West Historic District

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