Jackson Square Tours
Visit Jackson Square
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Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,966, price is now $1,089 per person
$1,089
per person
Mar 5 - Mar 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Had a wonderful view from our room. Shuttle is super convenient to Key West! Pools are very clean and live music was fantastic. Already booked for next year 😊
Reviewed on Jan 20, 2026
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $2,001, price is now $1,182 per person
$1,182
per person
Apr 2 - Apr 7
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
Definitely recommend for anyone interested in exploring the Keys: good location, well appointed kitchen, comfortable beds and beautiful pool area. Started our days with breakfast on the screened-in balcony, then explored a new beach or downtown area, and ended with relaxing in the hot tub. Would stay here again without hesitation.
Reviewed on Jan 19, 2026
The Key West Hotel
Key West Historic District
Price was $2,266, price is now $1,348 per person
$1,348
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Great location, very clean, and great staff
Reviewed on Jan 18, 2026
Browse tours and tickets to explore Jackson Square
Tours & day trips
See all 178 activities
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Activity duration is 16 hours and 30 minutes
9.2 out of 10 with 18 reviews
Cruises & boat tours
See all 85 activitiesDay trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Activity duration is 16 hours and 30 minutes
9.2 out of 10 with 18 reviews
History & culture
See all 58 activities
Key West Conch Tour Train
Activity duration is 1 hour
8.8 out of 10 with 135 reviews
Free cancellation available
Private & custom tours
See all 35 activities
Dry Tortugas National Park Day Trip by Luxury Private Boat
Activity duration is 8 hours
Free cancellation available
Adventure & outdoor
See all 23 activities
Key West Half-Day Fishing Charter
Activity duration is 5 hours
9.0 out of 10 with 19 reviews
Free cancellation available
Popular places to visit
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 seaside 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
La Concha Key West, Autograph Collection
430 Duval St Key West FL
Duval House
815 Duval St Key West FL
The Cabana Inn Key West - Adults Only
413 Applerouth Lane Key West FL
Heron House - Adult Only
512 Simonton St Key West FL
Pegasus International Hotel
501 Southard Street Key West FL
Pier House Resort & Spa
1 Duval St Key West FL
Opal Key Resort & Marina, Key West
245 Front Street Key West FL
NYAH Key West - Adults Only
420 Margaret Street Key West FL
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.
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- Ernest Hemingway Home and Museum
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- San Carlos Institute - Casa Cuba
- Fort Zachary Taylor Historic State Park
- Harry S. Truman Little White House
- Oldest House Museum and Garden
- Red Barn Theater
- Curry Mansion Museum
- Donkey Milk House
- Key West Lighthouse and Keeper's Quarters Museum
- Mel Fisher Maritime Museum
- Audubon House and Tropical Gardens
- Roy John-Karl Gallery
- Custom House Museum
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- Florida Keys Eco - Discovery Center
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- Mallory Dock
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- Schooner Western Union
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- City Zoo Gallery
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- Sails To Rails Museum at Flagler Station
- Visit Downtown Key West
- Southernmost Point