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 12 - Aug 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (1,669 reviews)
Everything was great with the exception of the breakfast pre purchase. The description says “full breakfast” but it doesn’t say that the egg breakfast is the only item that you can get.

Reviewed on Jul 4, 2025

Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
New Town
Save 100% on your flight
per person
Aug 12 - Aug 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (1,739 reviews)
Nice and clean hotel, very Cuban Many amenities available in the hotel like drink and delicious food. A lot of free drinks at the pool area I will definitely be repeating the experience Love it!

Reviewed on Jun 30, 2025

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Save 100% on your flight
per person
Aug 12 - Aug 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,555 reviews)
It wasn’t as nice as pictures made out to be on internet Beachside had this terrible smelling seaweed, that you couldn’t even sit on the beach due to the smell being so bad!!

Reviewed on Jul 6, 2025

Browse tours and tickets to explore Jackson Square

Tours & day trips

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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 26 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 117 reviews
Free cancellation available
Price is $50 per adult
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Private & custom tours

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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

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Key West Half-Day Fishing Charter

Key West Half-Day Fishing Charter

Activity duration is 5 hours
9.4 out of 10 with 13 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
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
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
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
Amsterdam's Curry Mansion Inn
Amsterdam's Curry Mansion Inn
3 out of 5
511 Caroline St, Key West, FL
Amsterdam's Curry Mansion Inn
See all 2,722 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.