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 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

￥42,994 total

includes taxes & fees

May 27 - May 28

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

kelly

￥34,851 total

includes taxes & fees

May 28 - May 29

The Gardens Hotel

Downtown Key West, 0.9 km from Waterfront Playhouse

Markus

￥46,742 total

includes taxes & fees

Jun 11 - Jun 12

The Marquesa Hotel

Old Town Key West, 0.7 km from Waterfront Playhouse

Julian

￥60,582 total

includes taxes & fees

Jun 16 - Jun 17

Key West Villas

Downtown Key West, 0.9 km from Waterfront Playhouse

Jennifer

￥40,049 total

includes taxes & fees

May 26 - May 27

Orchid Key Inn - Adults Only

Uptown - Upper Duval, 1.3 km from Waterfront Playhouse

Vicki

￥44,619 total

includes taxes & fees

May 27 - May 28

Cigar House King Suite w/ Poolside porch | Balcony view

Island City House Hotel

Historic Seaport, 0.8 km from Waterfront Playhouse

Michael

￥39,366 total

includes taxes & fees

Jun 4 - Jun 5

The Conch House Heritage Inn

Old Town Key West, 1.3 km from Waterfront Playhouse

Lucy

￥44,605 total

includes taxes & fees

Jun 1 - Jun 2

Douglas House - Adults Only

Uptown - Upper Duval, 1.4 km from Waterfront Playhouse

Scott

￥29,386 total

includes taxes & fees

Jun 4 - Jun 5

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

Tropical Inn

Downtown Key West, 1.1 km from Waterfront Playhouse

Akhenaton

￥45,934 total

includes taxes & fees

May 26 - May 27

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

Weatherstation Inn

Truman Annex, 0.5 km from Waterfront Playhouse

A. Elise

￥35,561 total

includes taxes & fees

May 25 - May 26

Outdoor pool, free cabanas, sun loungers

Ocean Key Resort - A Noble House Resort

Historic Seaport, < 0.1 km from Waterfront Playhouse

IRENE

￥54,682 total

includes taxes & fees

Jun 9 - Jun 10

Marrero's Guest Mansion

Downtown Key West, 0.6 km from Waterfront Playhouse

Robert

￥44,499 total

includes taxes & fees

Jun 4 - Jun 5

Westwinds Inn

Historic Seaport, 0.9 km from Waterfront Playhouse

Steve

￥42,620 total

includes taxes & fees

May 25 - May 26

3 outdoor pools, a heated pool, sun loungers

Ambrosia Key West

Old Town Key West, 0.7 km from Waterfront Playhouse

Tina

￥38,048 total

includes taxes & fees

May 25 - May 26

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

H2O Suites - Adults Only

Uptown - Upper Duval, 1.6 km from Waterfront Playhouse

Barton

￥74,877 total

includes taxes & fees

Jun 7 - Jun 8

The Grand Guesthouse

Old Town Key West, 1.7 km from Waterfront Playhouse

Jacqueline

￥35,205 total

includes taxes & fees

May 28 - May 29

Coco Plum Inn

Downtown Key West, 0.8 km from Waterfront Playhouse

Brinkley

￥45,677 total

includes taxes & fees

Jun 3 - Jun 4

Duval House

Downtown Key West, 1.1 km from Waterfront Playhouse

Parmjit

￥31,830 total

includes taxes & fees

May 26 - May 27

Silver Palms Inn & Historic Homes

Old Town Key West, 1.4 km from Waterfront Playhouse

Keith

￥31,471 total

includes taxes & fees

May 26 - May 27

View all properties

Compare popular hotels close to Waterfront Playhouse

Property	Star rating	Guest rating
Almond Tree Inn Hotel - Adults Only	3.5 star property	10.0 Exceptional 1,018 reviews	View
Simonton Court Historic Inn & Cottages	2.5 star property	9.8 Exceptional 960 reviews	View
The Gardens Hotel	4.0 star property	9.8 Exceptional 1,000 reviews	View
The Marquesa Hotel	3.5 star property	9.8 Exceptional 1,005 reviews	View
Key West Villas	3.5 star property	9.8 Exceptional 261 reviews	View

Top Waterfront Playhouse Hotel Reviews

Opal Key Resort & Marina, Key West

10/10 Excellent

"Location is great, on site parking is easy, view is excellent, staff is friendly."

Southernmost Beach Resort and Guesthouses

8/10 Good

"Upon check in - I was informed I needed a CC with $1200.00 available on it - at no point was I instructed of this need - I had paid for my stay prior as I do not use CC - thank goodness some in my party had one to use. The front desk person was not friendly about this = I have read my information from Expedia and nowhere is it stated - nor is it on your resort site. The bar at the pineapple pool was on point - Annette at the front desk was very helpful also. Breakfast at the cafe was well priced and good. My room was also always cleaned - Like i previously said the only complaint would be about the credit card and how the front desk person was not kind or friendly regarding this."

Casa Marina Key West, Curio Collection by Hilton

8/10 Good

"It was centrally located. I wish the beach was more maintained for being advertised as the largest private beach in all of key west. The staff was helpful, but wasn’t extraordinary. The pools were very nice. The outdoor bar was okay. The gift shop was very nice. The rooms were mostly clean. There was a lot of dust and dirt as well as sand in corners of the room, especially in the bathroom. Room service only came when we called to request which was odd. The Florida Resort tax should’ve been made more clear, as well as the mandatory $800 card hold they charge the tax out of per night."

The Marker Key West Harbor Resort

8/10 Good

"Best part of this hotel was the location. My husband was fishing this trip and it was a 2 minute walk to the boat. Beds were comfortable and I slept well. The amenities that you pay a resort fee of $54 a night were meh. My husband did go to the pool one day but none of the other offerings were interesting. We had friends that stayed as well and they paid an additional $44 a day for parking. We got breakfast every morning and that was good but the best part was our server Nelson. Always a smile and by the second morning I didn’t even need to ask for coffee, he just had it ready. The rooms were fine and they were clean. Bring your own shampoo and conditioner. What they provide is not great. Location was the best part of our stay."

Hotels near other Waterfront Playhouse attractions

Key West Shipwreck Museum

4.3/5 (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 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 ￥29,386

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Our top choices for Waterfront Playhouse hotels

Almond Tree Inn Hotel - Adults Only

Simonton Court Historic Inn & Cottages

The Gardens Hotel

The Marquesa Hotel

Key West Villas

Orchid Key Inn - Adults Only

Island City House Hotel

The Conch House Heritage Inn

Douglas House - Adults Only

Tropical Inn

Weatherstation Inn

Ocean Key Resort - A Noble House Resort

Marrero's Guest Mansion

Westwinds Inn

Ambrosia Key West

H2O Suites - Adults Only

The Grand Guesthouse

Coco Plum Inn

Duval House

Silver Palms Inn & Historic Homes

Compare popular hotels close to Waterfront Playhouse

Top Waterfront Playhouse Hotel Reviews

Opal Key Resort & Marina, Key West

Hotels near other Waterfront Playhouse attractions

Key West Shipwreck Museum

Frequently asked questions