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.
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,416, price is now $1,286 per person
$1,286
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (390 reviews)
Everything was great. Staff were all super helpful. Location fantastic. Breakfast served outside the room on the verander we loved (the health shots were a lovely touch). We had a great stay. Would definitely recommend.

Reviewed on Nov 22, 2025

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was $2,389, price is now $1,293 per person
$1,293
per person
Feb 24 - Mar 2
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
The staff was courteous. The room was beautiful n spotless. But the refrigerators weren't working correctly n my food that I brought was spoiled. Ms. Gwendolyn, provided excellent service and Ms. Sophia, provided discount for my stayed. Also the showers needs to be repaired, it leaked when taking showers. Water was all over the floors, so we put towels on the floor to soak up the water. *At the restaurant Alex was an awesome server, highly recommend him*.

Reviewed on Dec 3, 2025

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was $4,640, price is now $2,649 per person
$2,649
per person
Feb 24 - Mar 2
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Beautiful private oasis

Reviewed on Nov 25, 2025

Browse tours and tickets to explore Jackson Square

Tours & day trips

See all 174 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
9.0 out of 10 with 16 reviews
The previous price was $79 and current price is $57 per adult
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History & culture

See all 59 activities
Key West Conch Tour Train

Key West Conch Tour Train

Activity duration is 1 hour
8.8 out of 10 with 134 reviews
Free cancellation available
Price is $45 per adult
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Wildlife & nature

See all 49 activities
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

Activity duration is 3 hours
9.4 out of 10 with 140 reviews
Free cancellation available
The previous price was $50 and current price is $45 per adult
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Private & custom tours

See all 35 activities
Dry Tortugas National Park Day Trip by Luxury Private Boat

Dry Tortugas National Park Day Trip by Luxury Private Boat

Activity duration is 8 hours
Free cancellation available
Price is $3,864 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
9.0 out of 10 with 18 reviews
Free cancellation available
The previous price was $95 and current price is $86 per adult
Key West Half-Day Fishing CharterOpens in new tab

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

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
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
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St Key West FL
Heron House - Adult Only
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
Pegasus International Hotel

Pegasus International Hotel

2.5 out of 5
501 Southard Street Key West FL
Pegasus International Hotel
Marrero's Guest Mansion

Marrero's Guest Mansion

3.5 out of 5
410 Fleming Street Key West FL
Marrero's Guest Mansion
Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool

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

Key West FL
Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool
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
See all 2,677 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.

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