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. ![Ibis Bay Beach Resort](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/4a09d86c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ibis Bay Beach Resort Northside Resort Save 100% on your flight $913 per person Mar 12 - Mar 16 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 8.2/10 Very Good! (2,000 reviews) Great ppl that work there! Reviewed on Feb 5, 2026 ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Oceans Edge Key West Resort, Hotel & Marina Save 100% on your flight $1,294 per person Mar 12 - Mar 16 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Key West (EYW) 9/10 Wonderful! (1,736 reviews) The room was spotless. The resort was quiet and well maintained. The staff was very helpful. Check in and check out went very smoothly. My only complaints were that I was unable to order in-room breakfast as the phone was never answered. Also, the edges of the mattress were pretty soft. Reviewed on Feb 4, 2026 ![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 $1,031 per person Apr 25 - Apr 29 found 1 day ago Roundtrip flight included Boston (BOS) to Key West (EYW) 9.6/10 Exceptional! (1,002 reviews) We stayed in a 2 bedroom villa and it was wonderful. Lots of space and had everything you needed. Right across from the ocean. The grounds were beautifully kept. Reviewed on Feb 4, 2026 ### Browse tours and tickets to explore Jackson Square ### Tours & day trips [See all 180 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 9.4/10 124 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 9.4/10 124 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 24 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 $102 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 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 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=2026-02-05&endDate=2026-02-06)[Feb 5 - Feb 6](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6249254&startDate=2026-02-05&endDate=2026-02-06) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6249254&startDate=2026-02-06&endDate=2026-02-07)[Feb 6 - Feb 7](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6249254&startDate=2026-02-06&endDate=2026-02-07) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6249254&startDate=2%2F6%2F2026&endDate=2%2F8%2F2026)[Feb 6 - Feb 8](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6249254&startDate=2%2F6%2F2026&endDate=2%2F8%2F2026) [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. Additional terms may apply. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Key West Hotels ](https://www.expedia.com/Key-West-Hotels.d1187.Travel-Guide-Hotels) - [All-inclusive Resorts in Key West ](https://www.expedia.com/Key-West-Hotels-All-Inclusive-Hotel.0-0-d1187-tAllinclusiveHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Key West ](https://www.expedia.com/Key-West-Hotels-Cheap-Hotels.0-0-d1187-tCheapHotels.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Key West ](https://www.expedia.com/Key-West-Hotels-Oceanfront-Hotels.0-0-d1187-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Hotels near Duval Street ](https://www.expedia.com/Duval-Street-Hotels.0-l6068616-0.Travel-Guide-Filter-Hotels) - [Beach Hotels in Key West ](https://www.expedia.com/Key-West-Hotels-Beach-Hotel.0-0-d1187-tBeachHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Key West ](https://www.expedia.com/Key-West-Hotels-Adults-Only-Resorts.0-0-d1187-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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