Title: Jackson Square Tours - Book Now | Expedia.com [Jackson Square Hotels](https://expedia.com/Jackson-Square-Hotels.0-l6249254-0.Travel-Guide-Filter-Hotels)[Car Rentals in Jackson Square](https://expedia.com/Car-Rentals-In-Jackson-Square.d6249254.Car-Rental-Guide)[Old Town Key West Vacations](https://expedia.com/Old-Town-Key-West.d553248635976481920.Destination-Travel-Guides) # Jackson Square Tours ![Jackson Square featuring heritage architecture and an administrative buidling](https://images.trvl-media.com/place/6249254/3cd83d52-098c-4ec4-a79e-e9a5fdfae2bf.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Jackson Square featuring heritage architecture and an administrative buidling](https://images.trvl-media.com/place/6249254/3cd83d52-098c-4ec4-a79e-e9a5fdfae2bf.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Jackson Square showing heritage architecture](https://images.trvl-media.com/place/6249254/dceb0550-7f90-49b3-a4bd-875ab95af47b.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Jackson Square featuring an administrative buidling and heritage elements](https://images.trvl-media.com/place/6249254/aa00852e-187d-472f-8733-aade873b4616.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Jackson Square showing a house and street scenes](https://images.trvl-media.com/place/6249254/4172f5c8-6097-4de4-80f7-78f165fa1af6.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Jackson Square Activities Tours & day trips [](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=ToursDayTrips) Cruises & boat tours [](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=CruisesBoatTours) Water activities [](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=Wateractivities) History & culture [](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=HistoryCulture) Wildlife & nature [](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=WildlifeNature) Private & custom tours [](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=Privatecustomtours) Food, drink & nightlife [](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=FoodDrinkNightlife) Adventure & outdoor [](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=AdventureOutdoor) Classes & workshops [](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=ClassesWorkshops) Holiday & seasonal tours [](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=HolidaySeasonalTours) Weddings & honeymoons [](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=WeddingsHoneymoons) Attractions [](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=Attractions) Transportation [](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=Transportation) Shows & concerts [](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=ShowsConcerts) --- --- ## Plan a trip to see Jackson Square Price found within the past 48 hours. Click for updated prices. ![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Vacation Club at Windward Pointe, Key West Save 100% on your flight $1,090 per person Apr 2 - Apr 6 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9.6/10 Exceptional! (1,002 reviews) I asked for a room near the elevator but I didn’t get it. The room was nice and clean. Reviewed on Feb 10, 2026 ![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pier House Resort & Spa Key West Historic District Save 100% on your flight $1,605 per person Apr 2 - Apr 6 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9/10 Wonderful! (1,006 reviews) The staff was amazing. The room was lovely and very clean. We couldn't have had a better location. Reviewed on Feb 13, 2026 ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Southernmost Beach Resort and Guesthouses Old Town Key West Save 100% on your flight $1,277 per person Apr 2 - Apr 6 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 8.6/10 Excellent! (2,844 reviews) Everything was wonderful! I highly recommend and would come again. Reviewed on Feb 12, 2026 ### Popular places to visit ![KEY WEST, FLORIDA, USA - September 2012: San Carlos institute is a historic Key West building also known as "La casa de Cuba"](https://images.trvl-media.com/place/6068607/ca50f0f1-1b80-49ca-a7a4-8a8b38bfce5d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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 beautiful beaches or experience its lively festivals. [](https://expedia.com/San-Carlos-Institute-Casa-Cuba-Old-Town-Key-West.d6068607.Vacation-Attraction) ![Duval Street featuring signage](https://images.trvl-media.com/place/6068616/5997ee0c-eca4-415b-b051-99f4d38fbc11.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Duval-Street-Key-West-Historic-District.d6068616.Vacation-Attraction) ![Oldest House Museum and Garden](https://images.trvl-media.com/place/553248621533115800/70a0f34e-7380-4b3c-a674-576bd0702110.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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 [](https://expedia.com/Oldest-House-Museum-And-Garden-Key-West-Historic-District.d553248621533115800.Vacation-Attraction) ![Harry S. Truman Little White House showing a house](https://images.trvl-media.com/place/6068605/4f5f7570-d796-4d5a-9a98-d925004bc7d6.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Harry-S-Truman-Little-White-House-Old-Town-Key-West.d6068605.Vacation-Attraction) ![Audubon House and Tropical Gardens showing a house](https://images.trvl-media.com/place/6068599/1247082a-f056-4999-8b19-9cbb1174b48f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Audubon-House-And-Tropical-Gardens-Key-West-Historic-District.d6068599.Vacation-Attraction) ![St Maarten and St Martin](https://images.trvl-media.com/place/6163799/e86a432d-0e24-416d-b029-e5045c466cdf.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Mel-Fisher-Maritime-Museum-Old-Town-Key-West.d6163799.Vacation-Attraction) --- ## Best Lodging Options Near Jackson Square ## Check availability on hotels close to Jackson Square [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6249254&startDate=2026-02-13&endDate=2026-02-14)[Feb 13 - Feb 14](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6249254&startDate=2026-02-13&endDate=2026-02-14) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6249254&startDate=2026-02-14&endDate=2026-02-15)[Feb 14 - Feb 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6249254&startDate=2026-02-14&endDate=2026-02-15) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6249254&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026)[Feb 13 - Feb 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6249254&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026) ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Southernmost Beach Resort and Guesthouses 1319 Duval Street Key West FL [](https://expedia.com/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![La Concha Key West, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/3900/3853/aebf156d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Concha Key West, Autograph Collection 430 Duval St Key West FL [](https://expedia.com/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.Hotel-Information) ![Hyatt Centric Key West Resort and Spa](https://images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Centric Key West Resort and Spa 601 Front St Key West FL [](https://expedia.com/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) ![The Cabana Inn Key West - Adults Only](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/98bddc65_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Cabana Inn Key West - Adults Only 413 Applerouth Lane Key West FL [](https://expedia.com/Key-West-Hotels-The-Cabana-Inn-Key-West-Adults-Only.h6576609.Hotel-Information) ![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pier House Resort & Spa 1 Duval St Key West FL [](https://expedia.com/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![Duval House](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/d8706fe9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Duval House 815 Duval St Key West FL [](https://expedia.com/Key-West-Hotels-Duval-House.h900423.Hotel-Information) ![NYAH Key West - Adults Only](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/77f11bb4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### NYAH Key West - Adults Only 420 Margaret Street Key West FL [](https://expedia.com/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) ![Pegasus International Hotel](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/81c4c567_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pegasus International Hotel 501 Southard Street Key West FL [](https://expedia.com/Key-West-Hotels-Pegasus-International-Hotel.h977303.Hotel-Information) ![Heron House - Adult Only](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/04396af1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Heron House - Adult Only 512 Simonton St Key West FL [](https://expedia.com/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information) [See all 2,679 properties in Jackson Square](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6249254) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 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[Harry S. Truman Little White House ](https://www.expedia.com/Harry-S-Truman-Little-White-House-Old-Town-Key-West.d6068605.Vacation-Attraction) - [Oldest House Museum and Garden ](https://www.expedia.com/Oldest-House-Museum-And-Garden-Key-West-Historic-District.d553248621533115800.Vacation-Attraction) - [Red Barn Theater ](https://www.expedia.com/Red-Barn-Theater-Key-West-Historic-District.d6069271.Vacation-Attraction) - [Curry Mansion Museum ](https://www.expedia.com/Curry-Mansion-Museum-Key-West-Historic-District.d553248621532652631.Vacation-Attraction) - [Donkey Milk House ](https://www.expedia.com/Donkey-Milk-House-Key-West-Historic-District.d6249268.Vacation-Attraction) - [Key West Lighthouse and Keeper's Quarters Museum ](https://www.expedia.com/Key-West-Lighthouse-And-Keepers-Quarters-Museum-Old-Town-Key-West.d501383.Vacation-Attraction) - [Mel Fisher Maritime Museum ](https://www.expedia.com/Mel-Fisher-Maritime-Museum-Old-Town-Key-West.d6163799.Vacation-Attraction) - [Audubon House and Tropical Gardens ](https://www.expedia.com/Audubon-House-And-Tropical-Gardens-Key-West-Historic-District.d6068599.Vacation-Attraction) - [Roy John-Karl Gallery ](https://www.expedia.com/Roy-John-Karl-Gallery-Key-West-Historic-District.d553248621532652462.Vacation-Attraction) - [Custom House Museum ](https://www.expedia.com/Custom-House-Museum-Old-Town-Key-West.d6069265.Vacation-Attraction) - [Key West Museum of Art and History ](https://www.expedia.com/Key-West-Museum-Of-Art-And-History-Old-Town-Key-West.d6069279.Vacation-Attraction) - [Florida Keys Eco - Discovery Center ](https://www.expedia.com/Florida-Keys-Eco-Discovery-Center-Old-Town-Key-West.d6069247.Vacation-Attraction) - [Bahama Village Vacations ](https://www.expedia.com/Bahama-Village.d553248621533115696.Destination-Travel-Guides) - [Key West Historic District Vacations ](https://www.expedia.com/Key-West-Historic-District.d6281809.Destination-Travel-Guides) - [The Kite House ](https://www.expedia.com/The-Kite-House-Old-Town-Key-West.d553248621532652628.Vacation-Attraction) - [Tennessee Williams Key West Exhibit ](https://www.expedia.com/Tennessee-Williams-Key-West-Exhibit-Old-Town-Key-West.d553248621561885356.Vacation-Attraction) - [Romantic Vacation Packages Key West ](https://www.expedia.com/lp/theme-vacations/romantic-vacations/1187/Key-West) - [Mallory Dock ](https://www.expedia.com/Mallory-Dock-Key-West-Historic-District.d553248621563220296.Vacation-Attraction) - [Key West Cemetery ](https://www.expedia.com/Key-West-Cemetery-Old-Town-Key-West.d6068615.Vacation-Attraction) - [Florida Keys National Marine Sanctuary ](https://www.expedia.com/Florida-Keys-National-Marine-Sanctuary-Key-West.d6163838.Vacation-Attraction) - [Saint Mary Star of the Sea ](https://www.expedia.com/Saint-Mary-Star-Of-The-Sea-Old-Town-Key-West.d553248621532652618.Vacation-Attraction) - [Schooner Western Union ](https://www.expedia.com/Schooner-Western-Union-Key-West-Historic-District.d6069261.Vacation-Attraction) - [South Beach ](https://www.expedia.com/South-Beach-Old-Town-Key-West.d6246827.Vacation-Attraction) - [City Zoo Gallery ](https://www.expedia.com/City-Zoo-Gallery-Old-Town-Key-West.d553248621532652613.Vacation-Attraction) - [Old Town Key West Vacations ](https://www.expedia.com/Old-Town-Key-West.d553248635976481920.Destination-Travel-Guides) - [Sails To Rails Museum at Flagler Station ](https://www.expedia.com/Sails-To-Rails-Museum-At-Flagler-Station-Key-West-Historic-District.d553248621532652635.Vacation-Attraction) - [Visit Downtown Key West ](https://www.expedia.com/Key-West-Downtown-Key-West.dx553248635976470405) - [Southernmost Point ](https://www.expedia.com/Southernmost-Point-Old-Town-Key-West.d501380.Vacation-Attraction) - [Car rentals near Key West ](https://www.expedia.com/Car-Rentals-In-Key-West.d1187.Car-Rental-Guide) - [Hertz Rental Cars in Key West ](https://www.expedia.com/Hertz-Car-Rentals-In-Key-West.d1187-c40.Car-Rental-Guide-Suppliers) - [Budget Rental Cars in Key West ](https://www.expedia.com/Budget-Car-Rentals-In-Key-West.d1187-c39.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in Key West ](https://www.expedia.com/Enterprise-Car-Rentals-In-Key-West.d1187-c15.Car-Rental-Guide-Suppliers) - [Mini Car Rentals in Key West ](https://www.expedia.com/Mini-Car-Rentals-In-Key-West.d1187-tMini.Car-Rental-Guide-Class) - 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