Jackson Square Tours and Activities

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Activities

Tours & day trips

Cruises & boat tours

Water activities

Plan a trip to see Jackson Square

Price found within the past 48 hours. Click for updated prices.

Oceans Edge Key West Resort, Hotel & Marina

CA $1,475

per person

Jun 6 - Jun 13

found 16 hours ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

9/10 Wonderful! (1,848 reviews)

Amazing location, the room and property were spotless. Staff were very friendly. Would stay here again!

Reviewed on Apr 2, 2026

Hyatt Vacation Club at Windward Pointe, Key West

CA $2,013

per person

Jun 6 - Jun 13

found 16 hours ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,011 reviews)

Rooms were clean and neat and everything we expected. Thank you so much for a wonderful honeymoon.

Reviewed on Apr 3, 2026

Hyatt Vacation Club at Beach House, Key West

CA $2,168

per person

Jun 6 - Jun 13

found 16 hours ago

Roundtrip flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,004 reviews)

These are recently renovated “condos” with 2 beds/2 baths, full kitchen, dining, and living area. Master bath is very nicely done with a giant shower for two. Very large deck/porch off each unit. The A/C went out but the friendly front desk and maintenance crew repaired it quickly. Resort has a large pool and large sand beach area with plenty of chairs and cabanas. New gas grills are near the pool area. There is a tiki bar on site with food. No complaints about this property whatsoever. There is a kayak tour guide right next door and I highly recommend their night kayak tour. The property is at the opposite end of the island to Old town/Duvall street. It’s about a 20 min bike ride to Duvall, and a 9 minute bike ride to Publix.

Reviewed on Apr 1, 2026

Popular places to visit

KEY WEST, FLORIDA, USA - September 2012: San Carlos institute is a historic Key West building also known as "La casa de Cuba"

San Carlos Institute - Casa Cuba

You can spend an afternoon exploring the galleries in San Carlos Institute - Casa Cuba during your trip to Key West. Stroll along the area's beautiful beaches or experience its lively festivals.

Duval Street

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.

Oldest House Museum and Garden

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

Harry S. Truman Little White House

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

Audubon House and Tropical Gardens

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

Mel Fisher Maritime Museum

Key West’s definitive maritime museum is an important attraction for anyone wanting to learn about early life in the Keys. Hear stories of slavery, pirates and fishermen.

Best Lodging Options Near Jackson Square

Check availability on hotels close to Jackson Square

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Opal Key Resort & Marina, Key West

245 Front Street Key West FL

The Cabana Inn Key West - Adults Only

413 Applerouth Lane Key West FL

Pier House Resort & Spa

1 Duval St Key West FL

La Concha Key West, Autograph Collection

430 Duval St Key West FL

Pegasus International Hotel

501 Southard Street Key West FL

Heron House - Adult Only

512 Simonton St Key West FL

Duval House

815 Duval St Key West FL

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

Key West FL

See all 2,579 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.