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Our top choices for Waterfront Playhouse hotels

Almond Tree Inn Hotel - Adults Only
Almond Tree Inn Hotel - Adults OnlyDowntown Key West, 1.3 km from Waterfront Playhouse
10.0 out of 10, Exceptional, (1,002 reviews)
The price is ฿9,991
฿11,239 total
includes taxes & fees
3 Jun - 4 Jun

Simonton Court Historic Inn & Cottages
Simonton Court Historic Inn & CottagesHistoric Seaport, 0.5 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (942 reviews)
The price is ฿9,358
฿10,527 total
includes taxes & fees
1 Jun - 2 Jun

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!Uptown - Upper Duval, 1.5 km from Waterfront Playhouse
10.0 out of 10, Exceptional, (6 reviews)
The price is ฿8,173
฿18,438 total
includes taxes & fees
18 May - 19 May

The Gardens Hotel
The Gardens HotelDowntown Key West, 0.9 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (1,001 reviews)
The price is ฿9,987
฿11,235 total
includes taxes & fees
24 May - 25 May

The Marquesa Hotel
The Marquesa HotelOld Town Key West, 0.7 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (1,003 reviews)
The price is ฿10,653
฿13,806 total
includes taxes & fees
31 May - 1 Jun

Key West Villas
Key West VillasDowntown Key West, 0.9 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (260 reviews)
The price is ฿10,170
฿11,442 total
includes taxes & fees
26 May - 27 May

Orchid Key Inn - Adults Only
Orchid Key Inn - Adults OnlyUptown - Upper Duval, 1.3 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (1,001 reviews)
The price is ฿9,605
฿10,806 total
includes taxes & fees
1 Jun - 2 Jun

Island City House Hotel
Island City House HotelHistoric Seaport, 0.8 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (999 reviews)
The price is ฿8,348
฿9,392 total
includes taxes & fees
5 May - 6 May

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Alexanders Guesthouse - Adult Exclusive, LGBTQ FriendlyOld Town Key West, 1.2 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (142 reviews)
The price is ฿5,799
฿7,821 total
includes taxes & fees
11 May - 12 May

The Conch House Heritage Inn
The Conch House Heritage InnOld Town Key West, 1.3 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (170 reviews)
The price is ฿10,025
฿11,278 total
includes taxes & fees
1 Jun - 2 Jun

H2O Suites - Adults Only
H2O Suites - Adults OnlyUptown - Upper Duval, 1.6 km from Waterfront Playhouse
9.8 out of 10, Exceptional, (601 reviews)
The price is ฿12,595
฿16,355 total
includes taxes & fees
1 Jun - 2 Jun

Douglas House - Adults Only
Douglas House - Adults OnlyUptown - Upper Duval, 1.4 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (372 reviews)
The price is ฿5,806
฿7,185 total
includes taxes & fees
25 May - 26 May

Tropical Inn
Tropical InnDowntown Key West, 1.1 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (398 reviews)
The price is ฿6,499
฿8,121 total
includes taxes & fees
6 May - 7 May

Weatherstation Inn
Weatherstation InnTruman Annex, 0.5 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,004 reviews)
The price is ฿7,739
฿8,706 total
includes taxes & fees
12 May - 13 May

Ambrosia Key West
Ambrosia Key WestOld Town Key West, 0.7 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,001 reviews)
The price is ฿7,613
฿8,565 total
includes taxes & fees
5 May - 6 May

Ocean Key Resort - A Noble House Resort
Ocean Key Resort - A Noble House ResortHistoric Seaport, < 0.1 km from Waterfront Playhouse
9.2 out of 10, Wonderful, (1,003 reviews)
The price is ฿10,328
฿14,133 total
includes taxes & fees
2 Jun - 3 Jun

Westwinds Inn
Westwinds InnHistoric Seaport, 0.9 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (1,007 reviews)
The price is ฿8,130
฿9,147 total
includes taxes & fees
1 Jun - 2 Jun

Coco Plum Inn
Coco Plum InnDowntown Key West, 0.8 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (521 reviews)
The price is ฿8,563
฿9,633 total
includes taxes & fees
11 May - 12 May

Marrero's Guest Mansion
Marrero's Guest MansionDowntown Key West, 0.6 km from Waterfront Playhouse
9.4 out of 10, Exceptional, (337 reviews)
The price is ฿10,005
฿11,256 total
includes taxes & fees
20 May - 21 May

The Grand Guesthouse
The Grand GuesthouseOld Town Key West, 1.7 km from Waterfront Playhouse
9.6 out of 10, Exceptional, (1,003 reviews)
The price is ฿5,849
฿7,390 total
includes taxes & fees
10 May - 11 May
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.
Compare popular hotels close to Waterfront Playhouse
Property | Property class | Guest rating | Breakfast included | Pool | Spa | Pet-friendly | WiFi included | |
|---|---|---|---|---|---|---|---|---|
![]() Almond Tree Inn Hotel - Adults Only | 10.0 Exceptional 1,002 reviews | View | ||||||
![]() Simonton Court Historic Inn & Cottages | 9.8 Exceptional 942 reviews | View | ||||||
![]() Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub! | 10.0 Exceptional 6 reviews | View | ||||||
![]() The Gardens Hotel | 9.8 Exceptional 1,001 reviews | View | ||||||
![]() The Marquesa Hotel | 9.8 Exceptional 1,003 reviews | View |
Top Waterfront Playhouse Hotel Reviews

Heron House - Adult Only
8/10 Good
















































































