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 1450 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, 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 .

Q: 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.

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 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 613 total

includes taxes & fees

9 Jun - 10 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

The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Markus

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

10 Jun - 11 Jun

Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

Michael

AED 1,045 total

includes taxes & fees

10 Jun - 11 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

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

Weatherstation Inn

Truman Annex, 0.5 km from Waterfront Playhouse

A. Elise

AED 703 total

includes taxes & fees

10 Jun - 11 Jun

L'Habitation Guest House

Historic Seaport, 0.5 km from Waterfront Playhouse

Amy

AED 517 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

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 620 total

includes taxes & fees

9 Jun - 10 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

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

14 Jun - 15 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

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

8 Jun - 9 Jun

Marrero's Guest Mansion

Downtown Key West, 0.6 km from Waterfront Playhouse

Robert

AED 988 total

includes taxes & fees

8 Jun - 9 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

11 Jun - 12 Jun

Coco Plum Inn

Downtown Key West, 0.8 km from Waterfront Playhouse

Brinkley

AED 764 total

includes taxes & fees

9 Jun - 10 Jun

Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

gerald

AED 571 total

includes taxes & fees

8 Jun - 9 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 975 reviews	View
Almond Tree Inn Hotel - Adults Only	3.5 star property	10.0 Exceptional 1,008 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 1,003 reviews	View
Island City House Hotel	3.0 star property	9.6 Exceptional 1,002 reviews	View

Top Waterfront Playhouse Hotel Reviews

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"Comfortable room, friendly staff, great location, well maintained property"

The Marker Key West Harbor Resort

10/10 Excellent

"Just a heads-up for families: the restaurant and bar close early (around 5:00 or 5:30 PM). While this might not bother guests who plan to hit the town at night, it’s frustrating for families who want to return from a day of excursions, swim, and relax poolside with food and drinks. It definitely limits your ability to unwind on-site in the evening."

Pier House Resort & Spa

8/10 Good

"Great location lovely room rainforest balcony. Overall great I'm just listing they're not so great things: the bad mattress gave me lower back pain what I didn't have for 10 years, but we told the front desk and they will tell that to management. The gym is nice but one machine is out of order. Spa was not hot enough and the Spa and gym attendant lady was hovering in both places, making us uncomfortable enough to leave from both places. She started to change linen on the already occupied by us lounge chair, almost breaking my expensive glasses. Otherwise, especially this time of the year is relaxing cute little beach. You are definitely paying for the location more than anything."

Simonton Court Historic Inn & Cottages

10/10 Excellent

"This place is a gem! This place is beautiful! They treat you as their personal guest, even a hand written welcome card. The staff, rooms, service from employees there was the best and better than any hotel. Kudos to Violet and the the front desk Gentleman and Karmala. Thank you for a wonderful stay."

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."

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 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 434

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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

Island City House Hotel

Orchid Key Inn - Adults Only

The Conch House Heritage Inn

Weatherstation Inn

L'Habitation Guest House

Tropical Inn

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Douglas House - Adults Only

Ambrosia Key West

Ocean Key Resort - A Noble House Resort

H2O Suites - Adults Only

Westwinds Inn

Marrero's Guest Mansion

Opal Key Resort & Marina, Key West

Coco Plum Inn

Duval House

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

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