Plan a trip to see Jackson Square

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

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight

$891

per person

Mar 16 - Mar 20

found 2 days ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Beautiful grounds, a lot of activities to do

Reviewed on Dec 19, 2025

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,262

per person

Mar 16 - Mar 20

found 2 days ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (505 reviews)

Being right on Duval Street if city noise bothers you you might want to stay a block or two off Duval. But if you want all the action then this place is fantastic. Staff is great and the room was nicely appointed and very comfortable.

Reviewed on Dec 12, 2025

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$1,028

per person

Feb 1 - Feb 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.6/10 Exceptional! (1,002 reviews)

Room was just right - met our needs and allowed us to do the things we wanted. Perhaps adding more towel bars or hooks in the bathroom would be nice, but really, it is a very nice condo. Location worked well, pool and hot tub great, all amenities fun. Staff was kind and helpful and very responsive. Thank y'all - Enjoy a Merry Christmas!

Reviewed on Dec 19, 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

History & culture

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Key West Conch Tour Train

Free cancellation available

Wildlife & nature

See all 50 activities

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

Free cancellation available

Private & custom tours

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Dry Tortugas National Park Day Trip by Luxury Private Boat

Free cancellation available

Classes & workshops

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Florida: Sunset Champagne Cruise on the Marathon Mermaid

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.

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 beautiful beaches or experience its lively festivals.