Jackson Square Tours

Jackson Square featuring heritage architecture and an administrative buidling
Jackson Square showing heritage architecture
Jackson Square featuring an administrative buidling and heritage elements
Jackson Square showing a house and street scenes
Jackson Square showing signage and art

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

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (1,668 reviews)
Everything was great loved the property

Reviewed on Jul 18, 2025

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
10/10 Exceptional! (1,002 reviews)
I would highly recommend staying there. It’s quiet and within walking distance of restaurants and shops.

Reviewed on Jul 18, 2025

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
Very clean, relaxing, and the staff went above and beyond. Highly recommend!

Reviewed on Jul 13, 2025

Browse tours and tickets to explore Jackson Square

Tours & day trips

See all 158 activities
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

Activity duration is 16 hours and 30 minutes
7.8 out of 10 with 15 reviews
The previous price was $49 and current price is $27 per adult
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History & culture

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Key West Day Trip & Glass Bottom-Boat Tour from Miami

Key West Day Trip & Glass Bottom-Boat Tour from Miami

Activity duration is 12 hours
5.0 out of 10 with 27 reviews
Free cancellation available
Price is $129 per traveler
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Wildlife & nature

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Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

Activity duration is 3 hours
9.2 out of 10 with 125 reviews
Free cancellation available
Price is $50 per adult
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Private & custom tours

See all 35 activities
Dry Tortugas National Park Day Trip by Luxury Boat: Axopar 37 XC

Dry Tortugas National Park Day Trip by Luxury Boat: Axopar 37 XC

Activity duration is 8 hours
Free cancellation available
Price is $2,999 per adult*
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Adventure & outdoor

See all 19 activities
Key West Half-Day Fishing Charter

Key West Half-Day Fishing Charter

Activity duration is 5 hours
9.2 out of 10 with 14 reviews
Free cancellation available
Price is $95 per adult
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Popular places to visit

San Carlos Institute - Casa Cuba

San Carlos Institute - Casa Cuba

4.5/5(22 reviews)

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.

San Carlos Institute - Casa Cuba
Duval Street featuring signage

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
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
Harry S. Truman Little White House showing a 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
22 room mansion all decked out for Valentine’s Day. Home to Florida’s 1st millionaire.

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
Audubon House and Tropical Gardens showing a house

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 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
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
Duval House

Duval House

3 out of 5
815 Duval St, Key West, FL
Duval House
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 Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
200 William Street, Key West, FL
The Marker Key West Harbor Resort
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street, Key West, FL
Casa Marina Key West, Curio Collection by Hilton
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
See all 2,706 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.