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.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was ￥138,880, price is now ￥96,512 per person
￥96,512
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
9.4/10 Exceptional! (1,282 reviews)
very good hotel for the price and excellent marina

Reviewed on Jul 20, 2026

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was ￥218,354, price is now ￥142,096 per person
￥142,096
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
9/10 Wonderful! (958 reviews)

Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Save 100% on your flight
Price was ￥216,033, price is now ￥149,136 per person
￥149,136
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
9/10 Wonderful! (1,199 reviews)
The beach and location was the real hit at this property. We enjoyed our stay.

Reviewed on Jul 21, 2026

Browse tours and tickets to explore Jackson Square

Tours & day trips

See all 158 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 407 reviews
Free cancellation available
Price is ￥12,387 per adult
Key West Express Day Trip from MiamiOpens in new tab

History & culture

See all 45 activities
Key West Conch Tour Train

Key West Conch Tour Train

Activity duration is 1 hour
8.8 out of 10 with 139 reviews
Free cancellation available
Price is ￥7,329 per adult
Key West Conch Tour TrainOpens in new tab

Wildlife & nature

See all 42 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 163 reviews
Free cancellation available
The previous price was ￥8,117 and current price is ￥7,306 per adult
Key West Morning Snorkel Adventure with Bottomless Mimosas & BreakfastOpens in new tab

Private & custom tours

See all 21 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 ￥2,111 per traveler*
Dry Tortugas National Park Self-Guided Audio TourOpens in new tab

Adventure & outdoor

See all 16 activities
Key West Half-Day Fishing Charter

Key West Half-Day Fishing Charter

Activity duration is 5 hours
9.4 out of 10 with 201 reviews
Free cancellation available
Price is ￥16,576 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 stop at Jackson Square. Stroll along the seaside or discover the area's beautiful sunsets.
See properties

Best Lodging Options Near Jackson Square

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
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
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
Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool

Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool

Key West FL
Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool
See all 2,633 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.