Jackson Square Tours

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.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Save 100% on your flight
Price was $1,117, price is now $758 per person
$758
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.2/10 Very Good! (2,294 reviews)
Resort was in a Great Location, all the Amenities are there although Housekeeping and Restaurant Staff not helpful Long wait for things asked for and for drinks.

Reviewed on Jul 29, 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $2,329, price is now $1,502 per person
$1,502
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (559 reviews)
This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!

Reviewed on Jul 27, 2026

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $1,113, price is now $798 per person
$798
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,302 reviews)
Wished I could have given it 5 stars but had to pay extra for parking plus resort fees. overall, a wonderful resort.

Reviewed on Jul 30, 2026

Browse tours and tickets to explore Jackson Square

Tours & day trips

See all 157 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 $76 per adult
Key West Express Day Trip from MiamiOpens in new tab

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 $39 per adult
Key West Haunted Tour : Ghosts & GravestonesOpens 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 165 reviews
Free cancellation available
The previous price was $50 and current price is $45 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 $13 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 206 reviews
Free cancellation available
Price is $102 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

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
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
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
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
Pier House Resort & 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
Marrero's Guest Mansion

Marrero's Guest Mansion

3.5 out of 5
410 Fleming Street Key West FL
Marrero's Guest Mansion
See all 2,615 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.

Explore a world of travel with Expedia