Jackson Square Tours

Jackson Square showing heritage architecture
Choose one or more items to build your trip:

Plan a trip to see Jackson Square

Prices and availability subject to change. Additional terms may apply.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Jun 27 - Jul 1
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
Jun 9 - Jun 12
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (1,012 reviews)
Staff is wonderful and the food and drinks were great. Highly recommend.

Reviewed on Apr 24, 2024

Ocean Villas of Deerfield

Ocean Villas of Deerfield

2.5 out of 5
Save 100% on your flight
per person
May 25 - Jun 1
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,007 reviews)
Ms. Debbie keeps this place in great condition! Our villa was extremely clean and efficient for our 5 day stay! Close and walkable to beach, shops, and restaurants!!! We had a relaxing and enjoyable stay in Deerfield! Ms. Debbie is all about her business, so if she comes across a little too forward, just remember what it takes to run a tight ship and keep it that way! This place gets 5 ⭐️. I can't brag enough about the cleanliness of the rooms!!! We will be back!!

Reviewed on Apr 24, 2024

Browse tours and tickets to explore Jackson Square

Tours & day trips

See all 170 activitiesOpens in new tab
Key West Express Day Trip from Miami

Key West Express Day Trip from Miami

Activity duration is 12 hours and 15 minutes
4.3 out of 5 with 346 reviews
Free cancellation available
Price is $79 per adult
Key West Express Day Trip from Miami

History & culture

See all 58 activitiesOpens in new tab
Key West Haunted Tour : Ghosts & Gravestones

Key West Haunted Tour : Ghosts & Gravestones

Activity duration is 1 hour
4.3 out of 5 with 65 reviews
Free cancellation available
Price is $40 per adult
Key West Haunted Tour : Ghosts & Gravestones

Private & custom tours

See all 44 activitiesOpens in new tab
Florida Key West Self-Driving Tour (Overseas Highway, 7 Mile Bridge)

Florida Key West Self-Driving Tour (Overseas Highway, 7 Mile Bridge)

Activity duration is 2 hours
3.7 out of 5 with 3 reviews
Free cancellation available
Price is $17 per traveler*
Florida Key West Self-Driving Tour (Overseas Highway, 7 Mile Bridge)

Wildlife & nature

See all 40 activitiesOpens in new tab
Morning Reef Snorkel With Unlimited Mimosas & Breakfast

Morning Reef Snorkel With Unlimited Mimosas & Breakfast

Activity duration is 3 hours
4.5 out of 5 with 87 reviews
Free cancellation available
Price is $46 per adult
Morning Reef Snorkel With Unlimited Mimosas & Breakfast

Holiday & seasonal tours

See all 7 activitiesOpens in new tab
Key West: Private Tiki Boat Sunset Cruise

Key West: Private Tiki Boat Sunset Cruise

Activity duration is 2 hours
Free cancellation available
Price is $457 per traveler*
Key West: Private Tiki Boat Sunset Cruise

Popular places to visit

Image for San Carlos Institute - Casa Cuba

San Carlos Institute - Casa Cuba

4.5/5(22 reviews)

You can enjoy some culture when you stop by San Carlos Institute - Casa Cuba in Key West. Stroll along the beautiful beaches or seek out the biking trails.

San Carlos Institute - Casa Cuba
Image for Duval Street

Duval Street

4.5/5(3,475 reviews)

Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.

Duval Street
Image for Oldest House Museum and Garden

Oldest House Museum and Garden

4.5/5(8 reviews)

With its period décor and vintage documents, South Florida’s oldest house provides an impression of life in the Florida Keys archipelago in the 19th century

Oldest House Museum and Garden
Image for Harry S. Truman Little White House

Harry S. Truman Little White House

4.5/5(834 reviews)

Visit the winter home of President Harry S. Truman to see where some of America’s most important post-war decisions were made.

Harry S. Truman Little White House
Image for Curry Mansion Museum

Curry Mansion Museum

You can spend time studying the exhibits at Curry Mansion Museum during your trip to Key West. Stroll along the area's seaside or experience its lively festivals.

Curry Mansion Museum
Image for Audubon House and Tropical Gardens

Audubon House and Tropical Gardens

4.5/5(291 reviews)

Visit a house named after famed naturalist John James Audubon. Learn the history of why the house came to be here.

Audubon House and Tropical Gardens

Best Lodging Options Near Jackson Square

Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Southernmost Beach Resort
Heron House - Adult Only
Heron House - Adult Only
3.5 out of 5
512 Simonton St, Key West, FL
Heron House - Adult Only
La Concha Key West
La Concha Key West
4 out of 5
430 Duval St, Key West, FL
La Concha Key West
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
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
Eden House
Eden House
3.5 out of 5
1015 Fleming St, Key West, FL
Eden House
NYAH Key West - Adults Only
NYAH Key West - Adults Only
3 out of 5
420 Margaret Street, Key West, FL
NYAH Key West - Adults Only
Lighthouse Hotel - Key West Historic Inns
Lighthouse Hotel - Key West Historic Inns
3.5 out of 5
902 Whitehead St, Key West, FL
Lighthouse Hotel - Key West Historic Inns
Heron House Court - Adult Only
Heron House Court - Adult Only
3 out of 5
412 Frances St, Key West, FL
Heron House Court - Adult Only
See all 2,573 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.