Jackson Square

The Monroe County Courthouse with a clock tower, surrounded by trees and a clear blue sky.
A historic courthouse with white columns and a red brick facade, surrounded by lush greenery and palm trees.
Monroe County Court House with a clock tower, surrounded by palm trees and a clear blue sky.
A street lined with colorful historic buildings, a clear blue sky, and a motorcyclist riding down the road.
A mural with the word "BAR" and two green parrots.

Stay near popular Jackson Square attractions

Jackson Square

8.8/10 (110 reviews)
You can learn about the history of Key West with a trip to Jackson Square. Stroll along the seaside or discover the area's beautiful sunsets.
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Top 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
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
601 Front St Key West FL
Hyatt Centric Key West Resort and Spa
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
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
Pier House Resort & Spa
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
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St Key West FL
Heron House - Adult Only
Pegasus International Hotel

Pegasus International Hotel

2.5 out of 5
501 Southard Street Key West FL
Pegasus International 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
Marrero's Guest Mansion

Marrero's Guest Mansion

3.5 out of 5
410 Fleming Street Key West FL
Marrero's Guest Mansion
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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.