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.

Plan a trip to see Jackson Square

Price found within the past 48 hours. Click for updated prices.
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Price was £1,460, price is now £1,043 per person
£1,043
per person
1 Nov - 4 Nov
found 1 day ago
Return flight included
Miami (MIA) to Key West (EYW)
9.4/10 Exceptional! (1,004 reviews)

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was £4,302, price is now £2,563 per person
£2,563
per person
4 Dec - 11 Dec
found 20 hours ago
Return flight included
London (LON) to Key West (EYW)
9.2/10 Wonderful! (562 reviews)

The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Save 100% on your flight
Price was £2,958, price is now £2,017 per person
£2,017
per person
4 Dec - 11 Dec
found 20 hours ago
Return flight included
London (LON) to Key West (EYW)
9.8/10 Exceptional! (1,003 reviews)
Excellent Hotel, staff very helpful and room was excellent. Breakfast was included which was delicious. Beautiful surrounding gardens. Highly recommend

Reviewed on 26 Sept 2026

Tours & day trips

See all 169 activities
Key West Express Day Trip from Miami

Key West Express Day Trip from Miami

Activity duration is 12 hours and 15 minutes
8.8 out of 10 with 410 reviews
Free cancellation available
Price is £58 per adult
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History & culture

See all 48 activities
Key West Haunted Tour : Ghosts & Gravestones

Key West Haunted Tour : Ghosts & Gravestones

Activity duration is 1 hour
8.8 out of 10 with 78 reviews
Free cancellation available
Price is £31 per adult
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Wildlife & nature

See all 48 activities
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

Activity duration is 3 hours
9.4 out of 10 with 168 reviews
Free cancellation available
The previous price was £38 and current price is £32 per adult
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Private & custom tours

See all 25 activities
Dry Tortugas National Park Self-Guided Audio Tour

Dry Tortugas National Park Self-Guided Audio Tour

Activity duration is 8 hours
Free cancellation available
Price is £10 per traveller*
Dry Tortugas National Park Self-Guided Audio TourOpens in new tab

Adventure & outdoor

See all 21 activities
Key West Half-Day Fishing Charter

Key West Half-Day Fishing Charter

Activity duration is 5 hours
9.4 out of 10 with 221 reviews
Free cancellation available
Price is £77 per adult
Key West Half-Day Fishing CharterOpens in new tab

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.
See properties

Top Hotel Deals

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
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
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
Pier House Resort & Spa
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
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
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
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
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
Duval House
Pegasus International Hotel

Pegasus International Hotel

2.5 out of 5
501 Southard Street Key West FL
Pegasus International Hotel
See all 2,599 properties in Jackson Square
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.