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 --- --- ## 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 $1,103 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) Said there was beach There is no beach Our initial flight was cancelled we re-rebooked for two days later The hotel would not refund the 2 nights We will reach out again to Expedia but hotel is. also very difficult to reach a live person Reviewed on Feb 5, 2026 ![The Key West Hotel](https://images.trvl-media.com/lodging/9000000/8660000/8657100/8657021/bc64cbf7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Key West Hotel Key West Historic District Save 100% on your flight $2,215 per person Apr 18 - Apr 24 found 1 day ago Roundtrip flight included Boston (BOS) to Key West (EYW) 9.2/10 Wonderful! (505 reviews) Everything was great. I couldn’t complain about anything if I wanted to. Thanks for a great stay! Reviewed on Jan 28, 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 $1,652 per person Apr 18 - Apr 24 found 1 day ago Roundtrip flight included Boston (BOS) to Key West (EYW) 8.6/10 Excellent! (2,844 reviews) I made a mistake as I did not realize this was not at main hotel it was a guest house so no amenities they did provide shuttle when asked I had three rooms. We all couldn’t shower in morning ran out of water. There was ghost ants in bathrooms Reviewed on Feb 6, 2026 ### Browse tours and tickets to explore Jackson Square ### Tours & day trips [See all 179 activities](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=ToursDayTrips) ![Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar](https://mediaim.expedia.com/localexpert/599857/aefdb7f1-206a-4531-bc6a-78614e1a0f10.jpg?impolicy=resizecrop&rw=500&rh=280) ### Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar 16h 30m 9.2/10 18 verified reviews ~~$79~~$57 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.com/things-to-do/day-trip-to-paradise-from-miami-key-west-tour-with-snorkeling-open-bar.a599857.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West Express Day Trip from Miami](https://mediaim.expedia.com/localexpert/263317/3a11b2d6-17f2-412d-af8b-373f634c42e1.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Express Day Trip from Miami 12h 15m 8.8/10 395 verified reviews Free cancellation available $76 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-west-express-day-trip-from-miami.a263317.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Miami to Key West Day Trip with Activity Options](https://mediaim.expedia.com/localexpert/1344154/fc89f93c-7834-4de4-bc12-2437ae6c1c87.jpg?impolicy=resizecrop&rw=500&rh=280) ### Miami to Key West Day Trip with Activity Options 15h 8.8/10 1,057 Viator reviews Free cancellation available $39 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/miami-to-key-west-day-trip-with-activity-options.a1344154.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar](https://mediaim.expedia.com/localexpert/2190809/50f64266-172c-47ec-a3dd-1abdcf45ef8c.jpg?impolicy=resizecrop&rw=500&rh=280) ### Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar 2h 30m 9.4/10 125 verified reviews Free cancellation available $79 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/dolphin-watch-catamaran-sunset-sail-w-tapas-and-open-bar.a2190809.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Full Day Trip in Key West from Miami](https://mediaim.expedia.com/localexpert/599608/0a5f7b52-4c57-40ec-80e7-716ee9b4b224.jpg?impolicy=resizecrop&rw=500&rh=280) ### Full Day Trip in Key West from Miami 16h 30m 6/10 6 verified reviews ~~$79~~$57 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/full-day-trip-in-key-west-from-miami.a599608.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West Day Trip from Fort Lauderdale](https://mediaim.expedia.com/localexpert/349210/0720a608-184f-4d68-81cd-14211d663799.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Day Trip from Fort Lauderdale 15h 15m 8.8/10 67 verified reviews Free cancellation available $112 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-west-day-trip-from-fort-lauderdale.a349210.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Historic Key West Old Town Trolley Hop-On Hop-Off Tour](https://mediaim.expedia.com/localexpert/191537/2dd77e4c-4c5c-4b3c-954d-bfd0d44bd289.jpg?impolicy=resizecrop&rw=500&rh=280) ### Historic Key West Old Town Trolley Hop-On Hop-Off Tour 1d+ 8.8/10 130 verified reviews Free cancellation available $58 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/historic-key-west-old-town-trolley-hop-on-hop-off-tour.a191537.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Half-Day Key West's Ultimate Sandbar Adventure with Mangrove Kayak Tour](https://mediaim.expedia.com/localexpert/5210842/5976b681-8e86-4088-9b81-d36100c5f7b1.jpg?impolicy=resizecrop&rw=500&rh=280) ### Half-Day Key West's Ultimate Sandbar Adventure with Mangrove Kayak Tour 5h 9.6/10 17 verified reviews Free cancellation available ~~$140~~$126 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/half-day-key-wests-ultimate-sandbar-adventure-with-mangrove-kayak-tour.a5210842.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Miami to Key West Day Trip Adventure](https://mediaim.expedia.com/localexpert/51023091/6ddbed33-55b8-4533-a02c-03b35718b9ee.jpg?impolicy=resizecrop&rw=500&rh=280) ### Miami to Key West Day Trip Adventure 14h Free cancellation available $57 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/miami-to-key-west-adventure-in-paradise-day-trip.a51023091.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West Conch Tour Train](https://mediaim.expedia.com/localexpert/191535/9b448a2f-ece5-45c7-be77-f9172888dc8f.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Conch Tour Train 1h 8.8/10 135 verified reviews Free cancellation available $45 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-west-conch-tour-train.a191535.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ### Cruises & boat tours [See all 82 activities](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=CruisesBoatTours) ![Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar](https://mediaim.expedia.com/localexpert/599857/aefdb7f1-206a-4531-bc6a-78614e1a0f10.jpg?impolicy=resizecrop&rw=500&rh=280) ### Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar 16h 30m 9.2/10 18 verified reviews ~~$79~~$57 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.com/things-to-do/day-trip-to-paradise-from-miami-key-west-tour-with-snorkeling-open-bar.a599857.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast](https://mediaim.expedia.com/localexpert/585220/33764975-3db8-4de6-a174-18e4cf9a40c6.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast 3h 9.4/10 147 verified reviews Free cancellation available ~~$50~~$45 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-west-morning-snorkel-adventure-with-bottomless-mimosas-breakfast.a585220.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar](https://mediaim.expedia.com/localexpert/2190809/50f64266-172c-47ec-a3dd-1abdcf45ef8c.jpg?impolicy=resizecrop&rw=500&rh=280) ### Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar 2h 30m 9.4/10 125 verified reviews Free cancellation available $79 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/dolphin-watch-catamaran-sunset-sail-w-tapas-and-open-bar.a2190809.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West Sunset Sail with Live Music, Drinks and Appetizers!](https://mediaim.expedia.com/localexpert/191563/7e4be692-c00e-461c-919c-2a29890f9b88.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Sunset Sail with Live Music, Drinks and Appetizers! 2h 9.2/10 279 verified reviews Free cancellation available $80 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-west-sunset-sail-with-live-music-drinks-and-appetizers.a191563.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides](https://mediaim.expedia.com/localexpert/588901/43eed805-6849-4eda-87bf-fb57f27624fe.jpg?impolicy=resizecrop&rw=500&rh=280) ### Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides 1h 9.2/10 70 verified reviews Free cancellation available ~~$80~~$72 includes taxes & fees per traveler [](https://www.expedia.com/things-to-do/bucket-list-parasailing-in-downtown-key-west-highest-longest-rides.a588901.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West's All-Inclusive Combo With Jetski, Parasail, Snorkeling & Lunch](https://mediaim.expedia.com/localexpert/588524/809610bd-a369-477f-bc6c-dcadffbb2fa2.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West's All-Inclusive Combo With Jetski, Parasail, Snorkeling & Lunch 6h 6/10 2 verified reviews Free cancellation available ~~$179~~$161 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-wests-all-inclusive-combo-with-jetski-parasail-snorkeling-lunch.a588524.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch](https://mediaim.expedia.com/localexpert/191569/63a0da09-6295-405d-8a01-7db09d0745a6.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch 3h 8.6/10 131 verified reviews Free cancellation available $55 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-west-coral-reef-snorkel-with-mimosas-margaritas-or-rum-punch.a191569.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West Afternoon At The Reef Snorkeling Adventure with Open Bar!](https://mediaim.expedia.com/localexpert/587053/54666c36-0979-4755-bcfd-1df49670de5a.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Afternoon At The Reef Snorkeling Adventure with Open Bar! 3h 9.2/10 79 verified reviews Free cancellation available ~~$53~~$48 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-west-afternoon-at-the-reef-snorkeling-adventure-with-open-bar.a587053.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Lands End Sunset Cruise with Full Bar & Live Music](https://mediaim.expedia.com/localexpert/251769/cb9d1dec-662c-4e04-99eb-3ffd79b609ba.jpg?impolicy=resizecrop&rw=500&rh=280) ### Lands End Sunset Cruise with Full Bar & Live Music 2h 9/10 88 verified reviews Free cancellation available $75 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/lands-end-sunset-cruise-with-full-bar-live-music.a251769.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West's Dolphin Watch & Snorkel Tour – An Unforgettable Eco-Adventure](https://mediaim.expedia.com/localexpert/191577/ed369079-e4ef-4a29-85d1-0995f06af497.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West's Dolphin Watch & Snorkel Tour – An Unforgettable Eco-Adventure 3h 8.8/10 43 verified reviews Free cancellation available $80 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-wests-dolphin-watch-snorkel-tour-an-unforgettable-eco-adventure.a191577.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ### History & culture [See all 58 activities](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=HistoryCulture) ![Key West Conch Tour Train](https://mediaim.expedia.com/localexpert/191535/9b448a2f-ece5-45c7-be77-f9172888dc8f.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Conch Tour Train 1h 8.8/10 135 verified reviews Free cancellation available $45 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-west-conch-tour-train.a191535.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West Haunted Tour : Ghosts & Gravestones](https://mediaim.expedia.com/localexpert/329630/2026f348-b14f-4483-b492-b38853a4ef47.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Haunted Tour : Ghosts & Gravestones 1h 8.8/10 70 verified reviews Free cancellation available $40 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-west-haunted-tour-ghosts-gravestones.a329630.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Shipwreck Treasure Museum Tickets](https://mediaim.expedia.com/localexpert/191533/0194ef1a-54dc-4244-9dae-801c2ad37537.jpg?impolicy=resizecrop&rw=500&rh=280) ### Shipwreck Treasure Museum Tickets 9h 7.8/10 15 verified reviews Free cancellation available $19 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/shipwreck-treasure-museum-tickets.a191533.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West Historic Bahama Village & Hemingway Heritage](https://mediaim.expedia.com/localexpert/2599696/3edd30b6-ebb4-4d9a-8ff9-07d18d5d336f.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Historic Bahama Village & Hemingway Heritage 1h 30m 10/10 105 Viator reviews Free cancellation available $47 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-west-historic-bahama-village-hemingway-heritage.a2599696.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West Day Trip & Glass Bottom-Boat Tour from Miami](https://mediaim.expedia.com/localexpert/285065/2933e6b0-eb8a-417e-bdb5-6050489ac020.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Day Trip & Glass Bottom-Boat Tour from Miami 12h 5.4/10 27 verified reviews Free cancellation available $129 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-west-day-trip-glass-bottom-boat-tour-from-miami.a285065.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![The Dark Side of Key West Adults Only Walking Tour](https://mediaim.expedia.com/localexpert/44644109/8eef0aae-a434-4795-9a54-78642f15fb74.jpg?impolicy=resizecrop&rw=500&rh=280) ### The Dark Side of Key West Adults Only Walking Tour 1h 30m 9.4/10 11 GetYourGuide reviews Free cancellation available $35 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/the-dark-side-of-key-west-adults-only-walking-tour.a44644109.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West: Jimmy Buffet Walking Tour with Key Lime Pie](https://mediaim.expedia.com/localexpert/44635320/9b1d42e0-ed70-487c-affb-7a3c368841c6.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West: Jimmy Buffet Walking Tour with Key Lime Pie 1h 30m 8.8/10 5 GetYourGuide reviews Free cancellation available $79 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-west-jimmy-buffet-walking-tour-with-key-lime-pie.a44635320.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Harry S. Truman Little White House Tour](https://mediaim.expedia.com/localexpert/246139/ffacb806-5c32-4d4b-81e6-9d29bc3903d1.jpg?impolicy=resizecrop&rw=500&rh=280) ### Harry S. Truman Little White House Tour 1h 15m 9.8/10 26 verified reviews Free cancellation available $26 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/harry-s-truman-little-white-house-tour.a246139.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Mel Fisher Maritime Museum Admission Ticket](https://mediaim.expedia.com/localexpert/690939/e5f3a695-28a4-40a4-b248-056798141443.jpg?impolicy=resizecrop&rw=500&rh=280) ### Mel Fisher Maritime Museum Admission Ticket 2h 9.2/10 9 Viator reviews Free cancellation available $18 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/mel-fisher-maritime-museum-admission-ticket.a690939.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West Ghost and Mysteries Guided Tour](https://mediaim.expedia.com/localexpert/1219258/0498384e-fe65-4c38-832e-a459a634c991.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Ghost and Mysteries Guided Tour 1h 30m 8.8/10 159 Viator reviews Free cancellation available $33 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-west-ghost-and-mysteries-guided-tour.a1219258.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ### Private & custom tours [See all 35 activities](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=Privatecustomtours) ![Dry Tortugas National Park Day Trip by Luxury Private Boat](https://mediaim.expedia.com/localexpert/47184349/0ab67fdd-10fd-4a09-964c-1c9e41e0ee10.jpg?impolicy=resizecrop&rw=500&rh=280) ### Dry Tortugas National Park Day Trip by Luxury Private Boat 8h Free cancellation available $3,864 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.com/things-to-do/dry-tortugas-national-park-day-trip-by-luxury-boat-axopar-37-xc.a47184349.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Marathon: Private Cable or Cable Kiteboarding Session](https://mediaim.expedia.com/localexpert/49206825/570dd764-a277-46ff-8f12-e8080eb09f71.jpg?impolicy=resizecrop&rw=500&rh=280) ### Marathon: Private Cable or Cable Kiteboarding Session 1h+ Free cancellation available $177 includes taxes & fees per traveler\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.com/things-to-do/marathon-private-cable-or-cable-kiteboarding-session.a49206825.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West: Private Florida Keys Sandbar Tiki Boat Cruise](https://mediaim.expedia.com/localexpert/44508897/027b6a07-e05f-4b52-a7e6-e4f8a18fd8b7.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West: Private Florida Keys Sandbar Tiki Boat Cruise 4h 10/10 1 GetYourGuide review Free cancellation available $565 includes taxes & fees per traveler\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.com/things-to-do/key-west-private-florida-keys-sandbar-tiki-boat-cruise.a44508897.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Private Sandbar Adventure in Key West Backcountry](https://mediaim.expedia.com/localexpert/47135631/383d7d0b-4397-4483-8bd0-3dfea7e87907.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Sandbar Adventure in Key West Backcountry 3h 10/10 10 Viator reviews Free cancellation available $550 includes taxes & fees per traveler\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.com/things-to-do/private-sandbar-adventure-in-key-west-backcountry.a47135631.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West: Private Sunset Cruise on an Authentic Tiki Bar Boat](https://mediaim.expedia.com/localexpert/3629519/c43ae5e9-5fd1-4a25-9574-96ffcb11acdc.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West: Private Sunset Cruise on an Authentic Tiki Bar Boat 2h 9.4/10 24 Viator reviews Free cancellation available $457 includes taxes & fees per traveler\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.com/things-to-do/2-hour-private-sunset-cruise-in-florida-keys-on-tiki-bar-boat.a3629519.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West: 4-Hour Private Sandbar Cruise on a Tiki Bar Boat](https://mediaim.expedia.com/localexpert/44635918/3d52beba-8054-4e50-9222-16b16b415ef6.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West: 4-Hour Private Sandbar Cruise on a Tiki Bar Boat 4h 8.8/10 8 GetYourGuide reviews Free cancellation available $564 includes taxes & fees per traveler\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.com/things-to-do/key-west-4-hour-private-sandbar-cruise-on-a-tiki-bar-boat.a44635918.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West Private Luxury Charter Rental: Boat Tour with Captain](https://mediaim.expedia.com/localexpert/5007585/26c49cd5-6d6e-4a9b-8d78-10591ad96218.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Private Luxury Charter Rental: Boat Tour with Captain 8h 9.2/10 10 Viator reviews Free cancellation available $899 includes taxes & fees per traveler\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.com/things-to-do/private-luxury-charter-in-key-west-lower-keys-full-day.a5007585.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West’s Old Town Treasures: A Self-Guided Audio Tour](https://mediaim.expedia.com/localexpert/5153240/66c357be-7a29-4724-a1f9-cd4f27e79e57.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West’s Old Town Treasures: A Self-Guided Audio Tour 2h 9.4/10 13 Viator reviews Free cancellation available ~~$15~~$11 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-wests-old-town-treasures-a-self-guided-audio-tour.a5153240.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West: Private Tiki Bar Party Boat & Mini Sandbar](https://mediaim.expedia.com/localexpert/44647893/e37eea72-36a4-4a7b-a9c8-a9def5625c16.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West: Private Tiki Bar Party Boat & Mini Sandbar 2h 10/10 2 GetYourGuide reviews Free cancellation available $403 includes taxes & fees per traveler\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.com/things-to-do/key-west-private-tiki-bar-party-boat.a44647893.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Hemingway's Key West Self Guided outdoor Walking Audio Tour](https://mediaim.expedia.com/localexpert/50651503/1e580132-eab9-4c5b-822e-38860217dab8.jpg?impolicy=resizecrop&rw=500&rh=280) ### Hemingway's Key West Self Guided outdoor Walking Audio Tour 1h 30m Free cancellation available $8 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/hemingways-key-west-self-guided-outdoor-walking-audio-tour.a50651503.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ### Adventure & outdoor [See all 23 activities](https://expedia.com/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=AdventureOutdoor) ![Key West Half-Day Fishing Charter](https://mediaim.expedia.com/localexpert/5299343/7451f534-fa0a-4441-bee5-a3e8539ab191.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Half-Day Fishing Charter 5h 9.4/10 139 Viator reviews Free cancellation available $95 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-west-half-day-fishing-charter.a5299343.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West 6-Hour Party Boat Fishing Trip – Affordable Reef Fishing](https://mediaim.expedia.com/localexpert/689977/43568d63-40cf-4d31-8fcd-1dcd6895a753.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West 6-Hour Party Boat Fishing Trip – Affordable Reef Fishing 6h 9/10 71 Viator reviews Free cancellation available $85 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-west-deep-sea-fishing-charter-with-experienced-captains.a689977.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West Back-Country Tour with Snorkel - Drive Your Own Boat](https://mediaim.expedia.com/localexpert/587829/b428fd9d-801e-4052-a1e3-cf7bf43b3049.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Back-Country Tour with Snorkel - Drive Your Own Boat 2h 30m 10/10 5 verified reviews Free cancellation available ~~$189~~$170 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/key-west-back-country-tour-with-snorkel-drive-your-own-boat.a587829.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![6 Hour Shared Deep Sea Fishing in Key West](https://mediaim.expedia.com/localexpert/50006750/4c1b40a4-c138-4aed-a1ed-34473091ac51.jpg?impolicy=resizecrop&rw=500&rh=280) ### 6 Hour Shared Deep Sea Fishing in Key West 6h Free cancellation available $250 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/6-hour-shared-deep-sea-fishing-in-key-west.a50006750.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Guided Bike Tour of Old Town Key West](https://mediaim.expedia.com/localexpert/1343820/41e37625-1a25-4a87-b217-575e752918da.jpg?impolicy=resizecrop&rw=500&rh=280) ### Guided Bike Tour of Old Town Key West 2h 9.8/10 304 Viator reviews Free cancellation available $59 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/guided-bicycle-tour-of-old-town-key-west.a1343820.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![4 Hour Shared Deep Sea Fishing in Key West](https://mediaim.expedia.com/localexpert/49951843/dc6da1bd-6845-4dd1-8e46-fd431fd441ed.jpg?impolicy=resizecrop&rw=500&rh=280) ### 4 Hour Shared Deep Sea Fishing in Key West 4h 10/10 1 Viator review Free cancellation available $200 includes taxes & fees per adult [](https://www.expedia.com/things-to-do/4-hour-shared-deep-sea-fishing-in-key-west.a49951843.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West Conch Republic Tiki Pedicab Experience by Kokomo Cabs](https://mediaim.expedia.com/localexpert/2599693/b6702a3e-e02b-4446-b5c0-8fafe69095a5.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Conch Republic Tiki Pedicab Experience by Kokomo Cabs 2h 30m 10/10 29 Viator reviews Free cancellation available $180 includes taxes & fees per traveler\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.com/things-to-do/private-key-west-conch-republic-tiki-bike-experience-by-kokomo-cabs-key-west.a2599693.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Six Fins Private Bachelorette Charter–Key West Yacht Party Cruise](https://mediaim.expedia.com/localexpert/49230665/1a95f75e-c63e-4a97-bb27-b67923c5bd50.jpg?impolicy=resizecrop&rw=500&rh=280) ### Six Fins Private Bachelorette Charter–Key West Yacht Party Cruise 6h $1,670 includes taxes & fees per traveler\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.com/things-to-do/private-key-west-wedding-charter.a49230665.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Key West Deep Sea Fishing: Big Fish](https://mediaim.expedia.com/localexpert/1280332/9381ff42-e7c5-4208-acbe-92146c3ea898.jpg?impolicy=resizecrop&rw=500&rh=280) ### Key West Deep Sea Fishing: Big Fish 4h 9.8/10 18 Viator reviews $950 includes taxes & fees per traveler\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.com/things-to-do/corsair-2-sportfishing-key-west.a1280332.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ![Fishing Charters in Key West Florida](https://mediaim.expedia.com/localexpert/45754110/db14ebb1-5f80-41c2-b17d-e0d945e20a3b.jpg?impolicy=resizecrop&rw=500&rh=280) ### Fishing Charters in Key West Florida 4h 8.4/10 5 Viator reviews Free cancellation available $900 includes taxes & fees per traveler\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.com/things-to-do/fishing-charters-in-key-west-florida.a45754110.activity-details?&rid=6249254&location=Jackson+Square&swp=off) ### 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 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 seaside 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 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. [](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 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 [](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 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. [](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 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. [](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 4.5/5(47 reviews) 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=2026-02-07&endDate=2026-02-08)[Feb 7 - Feb 8](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6249254&startDate=2026-02-07&endDate=2026-02-08) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6249254&startDate=2026-02-08&endDate=2026-02-09)[Feb 8 - Feb 9](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6249254&startDate=2026-02-08&endDate=2026-02-09) [Next 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) ![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) ![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) ![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) ![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) ![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) ![Opal Key Resort & Marina, Key West](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/f2c5f58d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Opal Key Resort & Marina, Key West 245 Front Street Key West FL [](https://expedia.com/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) [See all 2,751 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. 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