Jackson Square

Jackson Square which includes heritage architecture and an administrative building
Jackson Square which includes heritage architecture
Jackson Square showing heritage elements and an administrative building
Jackson Square which includes street scenes and a house
Jackson Square featuring art and signage


Tours & day trips

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History & culture

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Wildlife & nature

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Private & custom tours

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Adventure & outdoor

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Popular places to visit


Top Jackson Square Hotel Deals

Southernmost Beach Resort and Guesthouses
Southernmost Beach Resort and Guesthouses
4 out of 5
1319 Duval Street, Key West, FL
Southernmost Beach Resort and Guesthouses
La Concha Key West, Autograph Collection
La Concha Key West, Autograph Collection
4 out of 5
430 Duval St, Key West, FL
La Concha Key West, Autograph Collection
The Cabana Inn Key West - Adults Only
The Cabana Inn Key West - Adults Only
3 out of 5
413 Applerouth Lane, Key West, FL
The Cabana Inn Key West - Adults Only
Pier House Resort & Spa
Pier House Resort & Spa
4 out of 5
1 Duval St, Key West, FL
Pier House Resort & Spa
Duval House
Duval House
3 out of 5
815 Duval St, Key West, FL
Duval House
Winslow's Bungalows - Key West Historic Inns
Winslow's Bungalows - Key West Historic Inns
4 out of 5
725 Truman Avenue, Key West, FL
Winslow's Bungalows - Key West Historic Inns
Island City House Hotel
Island City House Hotel
3 out of 5
411 William Street, Key West, FL
Island City House Hotel
Opal Key Resort & Marina, Key West
Opal Key Resort & Marina, Key West
4 out of 5
245 Front Street, Key West, FL
Opal Key Resort & Marina, Key West
NYAH Key West - Adults Only
NYAH Key West - Adults Only
3 out of 5
420 Margaret Street, Key West, FL
NYAH Key West - Adults Only
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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.