Top Hotels Near Waterfront Playhouse in Key West from AU$281

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Check prices for these dates

Tonight
13 Nov - 14 Nov
Tomorrow
14 Nov - 15 Nov
This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

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Our top choices for Waterfront Playhouse hotels

A swimming pool with lounge chairs, surrounded by palm trees and greenery.

1. Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
3.5 star property
Downtown Key West, 1.3 km from Waterfront Playhouse
10.0 out of 10, Exceptional, (1,000 reviews)
"We really enjoyed our stay! The staff were amazing and the room was perfect!"
United States
Teresa
The price is AU$309
includes taxes & fees
18 Nov - 19 Nov
Almond Tree Inn Hotel - Adults Only
A wooden deck leading to a pool area with a building in the background.

2. Douglas House - Adults Only

Douglas House - Adults Only
3.5 star property
Uptown - Upper Duval, 1.4 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (593 reviews)
"Clean place, courteous staff, great location"
United States
Sandra
The price is AU$410
includes taxes & fees
18 Nov - 19 Nov
Douglas House - Adults Only
A pool area with lounge chairs and a table, surrounded by palm trees.

3. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
3.5 star property
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (1,000 reviews)
"Fantastic property. Love staying here 💗"
United States
Jessica
The price is AU$415
includes taxes & fees
1 Dec - 2 Dec
Orchid Key Inn - Adults Only
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.

4. Island City House Hotel

Island City House Hotel
3.0 star property
Historic Seaport, 0.8 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (999 reviews)
"Great place with lots of character and perfect location."
United States
Elise
The price is AU$309
includes taxes & fees
2 Dec - 3 Dec
Island City House Hotel
A rectangular pool with a white deck, surrounded by lush greenery and a gazebo.

5. Ambrosia Key West

Ambrosia Key West
3.5 star property
Old Town Key West, 0.7 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,000 reviews)
"Great location beautiful property we enjoyed our stay !"
United States
daniela
The price is AU$342
includes taxes & fees
29 Nov - 30 Nov
Ambrosia Key West
A garden pathway leading to a building with a door, surrounded by lush greenery and a palm tree.

6. Alexander Palms Court

Alexander Palms Court
2.5 star property
Casa Marina, 1.8 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,007 reviews)
"We love staying at Alexander’s!!!"
United States
Brenda
The price is AU$281
includes taxes & fees
1 Dec - 2 Dec
Alexander Palms Court
A swimming pool with water splashing, surrounded by palm trees and a building in the background.

7. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
3.5 star property
Old Town Key West, 1.4 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,040 reviews)
"Very central location"
United States
TODD
The price is AU$349
includes taxes & fees
2 Dec - 3 Dec
Silver Palms Inn & Historic Homes
A covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.

8. Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
5.0 star property
Old Town Key West, 0.1 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (1,225 reviews)
"have stayed here many times. nice location in old Town."
United States
A
The price is AU$486
includes taxes & fees
29 Nov - 30 Nov
Opal Key Resort & Marina, Key West
A large, white, two-story building with a balcony and a sign reading "The Marker Resort."

9. The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
4.0 star property
Historic Seaport, 0.6 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (1,051 reviews)
"Great location!"
United States
Katherine
The price is AU$493
includes taxes & fees
29 Nov - 30 Nov
The Marker Key West Harbor Resort
A hotel with a swimming pool, balconies, and a view of the sea.

10. Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
4.0 star property
Historic Seaport, 0.4 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (1,005 reviews)
"Wonderful property with wonderful staff"
United States
Michael Joseph
The price is AU$506
includes taxes & fees
29 Nov - 30 Nov
Hyatt Centric Key West Resort and Spa
A building with a sign reading "HERON HOUSE OFFICE" at the entrance, surrounded by lush greenery and palm trees.

11. Heron House - Adult Only

Heron House - Adult Only
3.5 star property
Downtown Key West, 0.7 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (1,144 reviews)
"Great staff and clean rooms"
United States
Dan
The price is AU$306
includes taxes & fees
17 Nov - 18 Nov
Heron House - Adult Only
A two-story building with a white picket fence, palm trees, and a sign that reads 'DUVAL GARDENS.'

12. Duval Gardens - Adults Only

Duval Gardens - Adults Only
4.0 star property
Uptown - Upper Duval, 1.3 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (926 reviews)
"Great rooms and staff, the breakfast is amazing "
United States
JoAnn
The price is AU$295
includes taxes & fees
8 Dec - 9 Dec
Duval Gardens - Adults Only
A narrow brick pathway flanked by large potted plants and a pink wall.

13. The Key West Hotel

The Key West Hotel
3.0 star property
Historic Seaport, 0.4 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (565 reviews)
"Great place to stay - highly recommend."
United States
Preston
The price is AU$658
includes taxes & fees
30 Nov - 1 Dec
The Key West Hotel
A pool area with lounge chairs, a hot tub, and a deck with a railing.

14. Seascape Tropical Inn - Adult Exclusive

Seascape Tropical Inn - Adult Exclusive
3.0 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.0 out of 10, Wonderful, (490 reviews)
"Nice and quiet."
United States
Carl
The price is AU$343
includes taxes & fees
18 Nov - 19 Nov
Seascape Tropical Inn - Adult Exclusive
A porch with white railings, a rocking chair, and a covered area with a teal awning.

15. Eden House

Eden House
4.0 star property
Historic Seaport, 1.1 km from Waterfront Playhouse
9.0 out of 10, Wonderful, (1,001 reviews)
"Staff is very friendly. The location is excellent! We were going to Dry Tortugas National Park and Eden House was a short 7 min walk to the port. The rooms had everything we needed for our stay and it was very clean."
United States
Telma
The price is AU$283
includes taxes & fees
30 Nov - 1 Dec
Eden House
A swimming pool with clear water, surrounded by lush greenery and palm trees.

16. Tranquility Guest House

Tranquility Guest House
2.0 star property
Bahama Village, 0.9 km from Waterfront Playhouse
9.0 out of 10, Wonderful, (40 reviews)
"The room was clean and the location was perfect."
United States
Sandra
The price is AU$345
includes taxes & fees
18 Nov - 19 Nov
Tranquility Guest House
Room

17. The Independent Inn

The Independent Inn
3.0 star property
Historic Seaport, 1.1 km from Waterfront Playhouse
9.0 out of 10, Wonderful, (73 reviews)
"Dan and Emma own the property and they go out of their way to give you the best experience you can receive. They are continuously on the property, working trying to maintain and make improvements. Thoroughly enjoyed the stay."
United States
Malcolm
The price is AU$299
includes taxes & fees
24 Nov - 25 Nov
The Independent Inn
A pool area with lounge chairs and a staircase leading to a balcony.

18. The Saint Hotel Key West, Autograph Collection, Adult Only

The Saint Hotel Key West, Autograph Collection, Adult Only
3.5 star property
Historic Seaport, 0.5 km from Waterfront Playhouse
9.0 out of 10, Wonderful, (378 reviews)
"Great place for couples!"
United States
R Frederick
The price is AU$350
includes taxes & fees
8 Dec - 9 Dec
The Saint Hotel Key West, Autograph Collection, Adult Only
A gated entrance with a gazebo, palm trees, and a brick pathway leading to a building with a red roof.

19. Duval Inn

Duval Inn
3.0 star property
Downtown Key West, 0.9 km from Waterfront Playhouse
8.8 out of 10, Excellent, (853 reviews)
"Bed was very comfortable, and the location was a quick walk to anything."
United States
April
The price is AU$387
includes taxes & fees
13 Dec - 14 Dec
Duval Inn
A pool area with palm trees, lounge chairs, and umbrellas.

20. Coconut Beach Resort

Coconut Beach Resort
2.5 star property
Casa Marina, 2 km from Waterfront Playhouse
8.8 out of 10, Excellent, (230 reviews)
"Clean room,comfortable bed. Beautiful beach view and lovely pool area."
United States
Angela
The price is AU$722
includes taxes & fees
16 Nov - 17 Nov
Coconut Beach Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Compare popular hotels close to Waterfront Playhouse

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A swimming pool with lounge chairs, surrounded by palm trees and greenery.
Almond Tree Inn Hotel - Adults Only
3.5 star property
10.0
Exceptional
1,000 reviews
View
A wooden deck leading to a pool area with a building in the background.
Douglas House - Adults Only
3.5 star property
9.8
Exceptional
593 reviews
View
A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
3.5 star property
9.8
Exceptional
1,000 reviews
View
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.
Island City House Hotel
3.0 star property
9.6
Exceptional
999 reviews
View
A rectangular pool with a white deck, surrounded by lush greenery and a gazebo.
Ambrosia Key West
3.5 star property
9.4
Exceptional
1,000 reviews
View

Other attractions near Waterfront Playhouse

A historic building with a tall tower, palm trees, and a vintage trolley.

Key West Shipwreck Museum

8.6/10 (361 reviews)
Costumed actors performing re-enactments and treasures from sunken ships give an insight into Key West’s history of salvaging and the lives of “wreckers”.
See properties

Top Waterfront Playhouse Hotel Reviews

A swimming pool with lounge chairs, surrounded by palm trees and greenery.
Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
Old Town Key West

10/10 Excellent

there was nothing at all to dislike. The staff were very cheerful very helpful. The location was excellent. The room was clean and spacious. If I ever returned to Key West, I would have no hesitation at all booking this hotel again.
Australia
Robyn
Reviewed August 6, 2026
Almond Tree Inn Hotel - Adults Only

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, take a look at the 1400 hotels and other accommodation options you'll find within a mile.

Where is the best place 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 traveller 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 find near Waterfront Playhouse?

Expedia has 1400 hotels and other accommodation options 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 room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might be able to still cancel and be given a refund within a 24-hour period of booking. Add your dates and click on "Search", then use the filter option "fully refundable" to view the best deals near Waterfront Playhouse.

What can I see and do near Waterfront Playhouse?

Harry S. Truman Little White House, Florida Keys Eco - Discovery Center and Ernest Hemingway Home and Museum feature a variety of fascinating exhibits to see while you're in town. Sights like Key West Lighthouse and Keeper's Quarters Museum, Fort Zachary Taylor Historic State Park and Fort East Martello Museum and Gallery are landmarks to visit in the area. You can watch performances at Red Barn Theater, Key West Film Society and The Key West Theater if you're interested in local theatre.