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Hotels near Waterfront Playhouse

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Check prices for these dates

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

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Our top choices for Waterfront Playhouse hotels

A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.

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, (1,010 reviews)
"We really enjoyed our stay! The staff were amazing and the room was perfect!"
United States
Teresa
The price is RM978
RM1,101 total
includes taxes & fees
1 Nov - 2 Nov
Almond Tree Inn Hotel - Adults Only
A tropical outdoor area with palm trees, hanging plants, and string lights.

2. Douglas House - Adults Only

Douglas House - Adults Only
3.0 star property
Uptown - Upper Duval, 1.4 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (571 reviews)
"Loved our stay! I would definitely stay there again."
United States
Maricela
The price is RM579
RM716 total
includes taxes & fees
29 Oct - 30 Oct
Douglas House - Adults Only
A modern outdoor area with a pool, lounge chairs, and a bar area.

3. H2O Suites - Adults Only

H2O Suites - Adults Only
3.5 star property
Uptown - Upper Duval, 1.6 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (670 reviews)
"Amazing stay! Loved the private pool!"
United States
Kimberly
The price is RM1,297
RM1,735 total
includes taxes & fees
1 Nov - 2 Nov
H2O Suites - Adults Only
A pool area with lounge chairs and a table, surrounded by palm trees.

4. 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, (1,003 reviews)
"Stayed there for a week for our honeymoon, could not have had a better stay."
United States
ben
The price is RM978
RM1,100 total
includes taxes & fees
1 Nov - 2 Nov
Orchid Key Inn - Adults Only
A two-story house with a covered porch, a brick pathway, and a large tree.

5. The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Old Town Key West, 0.7 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (1,006 reviews)
"This is my favorite hotel in the world, and Key West"
United States
Josh
The price is RM1,839
RM2,299 total
includes taxes & fees
11 Nov - 12 Nov
The Marquesa Hotel
A porch with a white railing, a bench, and a flag.

6. The Conch House Heritage Inn

The Conch House Heritage Inn
3.5 star property
Old Town Key West, 1.3 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (196 reviews)
"We really enjoyed getting to know the staff. The breakfast was excellent and everything was in walking distance."
United States
Jennifer
The price is RM1,265
RM1,424 total
includes taxes & fees
29 Oct - 30 Oct
The Conch House Heritage Inn
A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.

7. Duval House

Duval House
3.0 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (1,128 reviews)
"Great stay!"
United States
Emily
The price is RM687
RM860 total
includes taxes & fees
3 Nov - 4 Nov
Duval House
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.

8. 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, (1,002 reviews)
"Great place with lots of character and perfect location."
United States
Elise
The price is RM845
RM950 total
includes taxes & fees
3 Nov - 4 Nov
Island City House Hotel
A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.

9. The Grand Guesthouse

The Grand Guesthouse
2.5 star property
Old Town Key West, 1.7 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (1,004 reviews)
"Fun apartment style living in Key West…fun little patio with coffee and continental breakfast. Make sure you look at the check in hours :) great spot makes you feel local"
United States
Justyn
The price is RM635
RM817 total
includes taxes & fees
29 Oct - 30 Oct
The Grand Guesthouse
A pool area with lounge chairs and palm trees.

10. Santa Maria Suites

Santa Maria Suites
4.0 star property
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (1,005 reviews)
"Great place for families"
United States
Anthony
The price is RM1,304
RM1,743 total
includes taxes & fees
29 Oct - 30 Oct
Santa Maria Suites
A reception area with a curved marble counter, ceiling fans, large windows, and a staircase.

11. Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.9 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,008 reviews)
"Breakfast was great . Pools were great and easy walk or bike ride to Duval street"
United States
Shari
The price is RM736
RM828 total
includes taxes & fees
29 Oct - 30 Oct
Westwinds Inn
A rectangular pool with a white deck, surrounded by lush greenery and a gazebo.

12. 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, (1,005 reviews)
"Great location beautiful property we enjoyed our stay !"
United States
daniela
The price is RM765
RM861 total
includes taxes & fees
29 Oct - 30 Oct
Ambrosia Key West
A wooden deck with wicker furniture and a white railing, surrounded by lush tropical vegetation.

13. Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex, 0.5 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,005 reviews)
"This was the perfect location for access to Key West by foot!!!! We loved the community the resort is in!"
United States
Jane
The price is RM1,059
RM1,191 total
includes taxes & fees
18 Nov - 19 Nov
Weatherstation Inn
A gated entrance with lush green foliage and a white picket fence.

14. Coco Plum Inn

Coco Plum Inn
3.0 star property
Downtown Key West, 0.8 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (574 reviews)
"Location was perfect"
United States
August
The price is RM990
RM1,114 total
includes taxes & fees
4 Nov - 5 Nov
Coco Plum Inn
A swimming pool with water splashing, surrounded by palm trees and a building in the background.

15. 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, (1,036 reviews)
"Great location Beautiful property very clean and quiet. Great omelet station w breakfast."
United States
Carleen
The price is RM511
RM851 total
includes taxes & fees
2 Nov - 3 Nov
Silver Palms Inn & Historic Homes
A large, ornate hotel with a pool, palm trees, and a view of the ocean.

16. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
4.0 star property
Uptown - Upper Duval, 1.8 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,003 reviews)
"staff was super friendly and accomodating"
United States
Janet
The price is RM856
RM1,480 total
includes taxes & fees
15 Nov - 16 Nov
Southernmost House - Adult Exclusive
A room with a door featuring horizontal blinds, a visible outdoor view through the window, and a patterned carpet.

17. Alexander Palms Court

Alexander Palms Court
2.5 star property
Casa Marina, 1.8 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,009 reviews)
"We love staying at Alexander’s!!!"
United States
Brenda
The price is RM585
RM658 total
includes taxes & fees
29 Oct - 30 Oct
Alexander Palms Court
A poolside area with lounge chairs, umbrellas, and a pergola.

18. Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
3.5 star property
Old Town Key West, 1.1 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (517 reviews)
"Clean room, comfortable bed, friendly staff, good amenities!"
United States
Lisa and David
The price is RM940
RM1,265 total
includes taxes & fees
29 Oct - 30 Oct
Ella's Cottages - Key West Historic Inns
A covered porch with white railings, wooden benches, and a hanging light fixture.

19. Marrero's Guest Mansion

Marrero's Guest Mansion
3.5 star property
Downtown Key West, 0.6 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (345 reviews)
"Awesome place to stay!"
United States
Michael
The price is RM1,406
RM1,582 total
includes taxes & fees
29 Oct - 30 Oct
Marrero's Guest Mansion
A bedroom with a four-poster bed, a wooden desk, wicker chairs, and a view of the outdoors.

20. Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 1.1 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (450 reviews)
"We will definitely stay here again!"
United States
Natalie
The price is RM471
RM632 total
includes taxes & fees
29 Oct - 30 Oct
Tropical Inn
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 modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.
Almond Tree Inn Hotel - Adults Only
3.5 star property
10.0
Exceptional
1,010 reviews
View
A tropical outdoor area with palm trees, hanging plants, and string lights.
Douglas House - Adults Only
3.0 star property
9.8
Exceptional
571 reviews
View
A modern outdoor area with a pool, lounge chairs, and a bar area.
H2O Suites - Adults Only
3.5 star property
9.8
Exceptional
670 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
1,003 reviews
View
A two-story house with a covered porch, a brick pathway, and a large tree.
The Marquesa Hotel
3.5 star property
9.8
Exceptional
1,006 reviews
View

Hotels recommended for families near Waterfront Playhouse

A pool area with lounge chairs and a cabana.

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
4.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (1,004)
The price is RM1,143
RM1,617 total
includes taxes & fees
23 Nov - 24 Nov
Ocean Key Resort - A Noble House Resort

Top Waterfront Playhouse Hotel Reviews

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Fun"
Brian 2-night trip
Posted 1 hour ago
La Concha Key West, Autograph Collection

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)
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, 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.