Jackson Square Tours and Activities

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.
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
Old Town Key West
Price was CA $2,334, price is now CA $1,678 per person
CA $1,678
per person
Oct 26 - Oct 30
found 15 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Key West (EYW)
9.2/10 Wonderful! (1,158 reviews)

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was CA $3,412, price is now CA $2,359 per person
CA $2,359
per person
Nov 19 - Nov 23
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (562 reviews)
Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Price was CA $3,069, price is now CA $2,232 per person
CA $2,232
per person
Nov 19 - Nov 23
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.8/10 Exceptional! (1,003 reviews)
Wonderful property and staff! Annette, Luna and George, our pool bartenders and breakfast staff were outstanding. Front desk staff very helpful and pleasant as well. Beautiful gardens and grounds, clean rooms, love that the pool is open all night for swimming. Live music every afternoon. Great location centrally located in old town, convenient to everything! Will definitely book here again!

Reviewed on Sep 12, 2026

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 410 reviews
Free cancellation available
Price is CA $106 per adult
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History & culture

See all 46 activities
Key West Haunted Tour : Ghosts & Gravestones

Key West Haunted Tour : Ghosts & Gravestones

Activity duration is 1 hour
8.8 out of 10 with 76 reviews
Free cancellation available
Price is CA $57 per adult
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Wildlife & nature

See all 45 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 CA $70 and current price is CA $59 per adult
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Private & custom tours

See all 24 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 CA $18 per traveller*
Dry Tortugas National Park Self-Guided Audio TourOpens in new tab

Adventure & outdoor

See all 20 activities
Key West Half-Day Fishing Charter

Key West Half-Day Fishing Charter

Activity duration is 5 hours
9.4 out of 10 with 219 reviews
Free cancellation available
Price is CA $141 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
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
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
Pegasus International Hotel

Pegasus International Hotel

2.5 out of 5
501 Southard Street Key West FL
Pegasus International Hotel
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St Key West FL
Heron House - Adult Only
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
Duval House
See all 2,618 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.