Title: Jackson Square in Old Town Key West - Tours and Activities | Expedia.ca

[Jackson Square Hotels](https://expedia.ca/Jackson-Square-Hotels.0-l6249254-0.Travel-Guide-Filter-Hotels)[Jackson Square Car Rentals](https://expedia.ca/Car-Rentals-In-Jackson-Square.d6249254.Car-Rental-Guide)[Old Town Key West Vacations](https://expedia.ca/Old-Town-Key-West.d553248635976481920.Destination-Travel-Guides)

# Jackson Square Tours and Activities

![Jackson Square showing an administrative building and heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/64000/64075-Jackson-Square-Key-West.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Jackson Square which includes heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/64000/64076-Jackson-Square-Key-West.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Jackson Square which includes heritage elements and an administrative building](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63885-Jackson-Square-Key-West.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Jackson Square showing street scenes and a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/64000/64082-Jackson-Square-Key-West.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Jackson Square which includes art and signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/64000/64074-Jackson-Square-Key-West.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 Beach House, Key West](https://images.trvl-media.com/lodging/1000000/860000/858000/857962/fc0a2a7e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Vacation Club at Beach House, Key West

CA $1,842

per person

Jan 31 - Feb 6

found 5 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Found a roach in room

Reviewed on Dec 14, 2025

![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

CA $2,238

per person

Feb 26 - Mar 1

found 15 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (505 reviews)

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

Reviewed on Dec 12, 2025

![Ella's Cottages - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/870000/863200/863188/deb4f031_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Ella's Cottages - Key West Historic Inns

Old Town Key West

CA $2,587

per person

Jan 15 - Jan 18

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (390 reviews)

The cottage was perfect, centrally located and a wonderful place to stay!

Reviewed on Dec 13, 2025

### Tours & day trips

[See all 164 activities](https://expedia.ca/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=ToursDayTrips)

![Day trip to Paradise from Miami: Key West Tour with Snorkelling, 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 Snorkelling, Open bar

16h 30m

9/10

16 reviews

~~CA $109~~CA $79

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/day-trip-to-paradise-from-miami-key-west-tour-with-snorkelling-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

393 reviews

Free cancellation available

CA $105

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/key-west-express-day-trip-from-miami.a263317.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 reviews

~~CA $109~~CA $79

includes taxes & fees

per adult

[](https://www.expedia.ca/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 reviews

Free cancellation available

CA $155

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/key-west-day-trip-from-fort-lauderdale.a349210.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 reviews

Free cancellation available

CA $110

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/dolphin-watch-snorkelling-tour.a191577.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

122 reviews

Free cancellation available

CA $109

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/key-west-premium-dolphin-watch-sunset-sail-w-tapas-pairing.a2190809.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

134 reviews

Free cancellation available

CA $62

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/key-west-conch-tour-train.a191535.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+

8.6/10

127 reviews

Free cancellation available

CA $84

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/historic-key-west-old-town-trolley-hop-on-hop-off-tour.a191537.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

![Ultimate 90 minute Sea Doo Jet Ski Tour of Key West -Additional Rider Free!](https://mediaim.expedia.com/localexpert/444315/baabe539-1e88-497e-acfe-db8e395c2402.jpg?impolicy=resizecrop&rw=500&rh=280)

### Ultimate 90 minute Sea Doo Jet Ski Tour of Key West -Additional Rider Free!

1h 30m

9.6/10

139 reviews

Free cancellation available

CA $178

includes taxes & fees

per traveller

[](https://www.expedia.ca/things-to-do/guided-jet-ski-tour-in-key-west.a444315.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

### History & culture

[See all 54 activities](https://expedia.ca/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

134 reviews

Free cancellation available

CA $62

includes taxes & fees

per adult

[](https://www.expedia.ca/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 reviews

Free cancellation available

CA $55

includes taxes & fees

per adult

[](https://www.expedia.ca/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 reviews

Free cancellation available

CA $27

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/shipwreck-treasure-museum-tickets.a191533.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 reviews

Free cancellation available

CA $178

includes taxes & fees

per adult

[](https://www.expedia.ca/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/bbc1a777-f5eb-4976-8195-fee9056c0516.jpg?impolicy=resizecrop&rw=500&rh=280)

### The Dark Side of Key West Adults Only Walking Tour

1h 30m

8/10

3 reviews

Free cancellation available

CA $48

includes taxes & fees

per adult

[](https://www.expedia.ca/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 Craft Cocktail Crawl](https://mediaim.expedia.com/localexpert/1343979/c4ad3835-0ee8-4e91-b822-6e281ebcf542.jpg?impolicy=resizecrop&rw=500&rh=280)

### Key West Craft Cocktail Crawl

3h

9.6/10

8 reviews

Free cancellation available

CA $129

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/key-west-craft-cocktail-crawl.a1343979.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

Free cancellation available

CA $65

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/key-west-historic-district-small-group-walking-tour.a2599696.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

10/10

1 review

Free cancellation available

CA $109

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/key-west-jimmy-buffet-walking-tour-with-key-lime-pie.a44635320.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

8.6/10

7 reviews

Free cancellation available

CA $45

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/key-west-ghost-and-mysteries-guided-tour.a1219258.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 reviews

Free cancellation available

CA $35

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/harry-s-truman-little-white-house-tour.a246139.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

### Wildlife & nature

[See all 44 activities](https://expedia.ca/things-to-do/search?&rid=6249254&location=Jackson+Square&filter.categories=WildlifeNature)

![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

142 reviews

Free cancellation available

~~CA $69~~CA $62

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/morning-reef-snorkel-with-unlimited-mimosas-breakfast.a585220.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 reviews

Free cancellation available

CA $110

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/dolphin-watch-snorkelling-tour.a191577.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

15 reviews

Free cancellation available

~~CA $193~~CA $173

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/half-day-key-wests-ultimate-sandbar-adventure-with-mangrove-kayak-eco-tour.a5210842.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

![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

9/10

18 reviews

Free cancellation available

CA $131

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/half-day-fishing-tour-in-key-west.a5299343.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

![Key West Afternoon At The Reef Snorkelling 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 Snorkelling Adventure with Open Bar!

3h

9/10

78 reviews

Free cancellation available

~~CA $73~~CA $66

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/key-west-afternoon-snorkel-with-open-well-bar.a587053.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

![Dolphin and Snorkel](https://mediaim.expedia.com/localexpert/44991362/0af7b5ef-8c18-4f45-a635-e6b2b31df2d6.jpg?impolicy=resizecrop&rw=500&rh=280)

### Dolphin and Snorkel

3h 30m

Free cancellation available

CA $186

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/dolphin-watching-snorkelling.a44991362.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

![Afternoon Key West Reef Snorkel & Catamaran Sail w/ Open Bar](https://mediaim.expedia.com/localexpert/509396/5395da13-64fe-47ec-a21b-47cb58b7b791.jpg?impolicy=resizecrop&rw=500&rh=280)

### Afternoon Key West Reef Snorkel & Catamaran Sail w/ Open Bar

3h

9/10

11 reviews

Free cancellation available

CA $94

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/afternoon-key-west-reef-snorkel-catamaran-sail.a509396.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

![Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour](https://mediaim.expedia.com/localexpert/871719/a6166402-5f03-40af-8190-7e15d45b8798.jpg?impolicy=resizecrop&rw=500&rh=280)

### Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour

3h 30m

9.8/10

26 reviews

Free cancellation available

CA $165

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/island-adventure-eco-tour.a871719.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

![Key West Morning Catamaran Snorkel with Mimosa's and Gourmet Breakfast](https://mediaim.expedia.com/localexpert/191553/589a2db9-41a0-4672-9843-7cf955834d32.jpg?impolicy=resizecrop&rw=500&rh=280)

### Key West Morning Catamaran Snorkel with Mimosa's and Gourmet Breakfast

3h

8.8/10

107 reviews

Free cancellation available

CA $62

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/morning-key-west-reef-snorkel-catamaran-sail.a191553.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

![Key West Dolphin Watch & Snorkel Combo With Unlimited Beer & Wine](https://mediaim.expedia.com/localexpert/588436/5accaab1-e6ca-48f8-a46b-01d1f2701e97.jpg?impolicy=resizecrop&rw=500&rh=280)

### Key West Dolphin Watch & Snorkel Combo With Unlimited Beer & Wine

3h

9/10

28 reviews

Free cancellation available

~~CA $90~~CA $80

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/key-west-dolphin-watch-snorkel-combo.a588436.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

### Private & custom tours

[See all 33 activities](https://expedia.ca/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

CA $5,320

includes taxes & fees

per adult\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/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)

![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

Free cancellation available

CA $778

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/key-west-private-florida-keys-sandbar-tiki-boat-cruise.a44508897.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

![Hemingway's Key West Self Guided 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 Walking Audio Tour

1h 30m

Free cancellation available

CA $11

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/hemingways-key-west-self-guided-walking-audio-tour.a50651503.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

CA $244

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/marathon-private-cable-or-cable-kiteboarding-session.a49206825.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

Free cancellation available

CA $21

includes taxes & fees

per adult

[](https://www.expedia.ca/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 Charter Rental: Luxury Boat with Captain](https://mediaim.expedia.com/localexpert/5007585/26c49cd5-6d6e-4a9b-8d78-10591ad96218.jpg?impolicy=resizecrop&rw=500&rh=280)

### Key West Private Charter Rental: Luxury Boat with Captain

8h

Free cancellation available

CA $1,238

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/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 Smartphone guided Ghost Walking Tour App/GPS/EMF Reader](https://mediaim.expedia.com/localexpert/4867509/0e929ca4-9623-48ee-bf33-e2ebdced8ed0.jpg?impolicy=resizecrop&rw=500&rh=280)

### Key West Smartphone guided Ghost Walking Tour App/GPS/EMF Reader

55m

Free cancellation available

CA $13

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/key-wests-self-guided-ghost-walking-tours-smartphone-navigated-on-walkntours.a4867509.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

Free cancellation available

CA $757

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/private-sandbar-adventure-in-key-west-backcountry.a47135631.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

Free cancellation available

CA $248

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/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)

![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

Free cancellation available

CA $629

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/2-hour-private-sunset-cruise-on-tiki-bar-boat-in-key-west.a3629519.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

### Adventure & outdoor

[See all 15 activities](https://expedia.ca/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

9/10

18 reviews

Free cancellation available

CA $131

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/half-day-fishing-tour-in-key-west.a5299343.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

![Key West Fishing Party Boat Charter with Experienced Captains](https://mediaim.expedia.com/localexpert/689977/43568d63-40cf-4d31-8fcd-1dcd6895a753.jpg?impolicy=resizecrop&rw=500&rh=280)

### Key West Fishing Party Boat Charter with Experienced Captains

6h

8.4/10

7 reviews

Free cancellation available

CA $117

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/key-west-fishing-day-trip.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 reviews

Free cancellation available

~~CA $261~~CA $234

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/key-west-back-country-eco-tour-with-snorkel-for-2.a587829.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

![FALL SALE!-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)

### FALL SALE!-Guided Bike Tour of Old Town Key West

2h

9.8/10

9 reviews

Free cancellation available

CA $74

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/guided-bicycle-tour-of-old-town-key-west.a1343820.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

8/10

1 review

CA $1,308

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/corsair-2-sportfishing.a1280332.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

Free cancellation available

CA $248

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/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)

![Private Fishing Charter Florida Keys](https://mediaim.expedia.com/localexpert/49744985/fe597b6e-5afe-4887-b4d2-ef90fc467528.jpg?impolicy=resizecrop&rw=500&rh=280)

### Private Fishing Charter Florida Keys

4h

Free cancellation available

CA $1,102

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/private-fishing-charter-florida-keys.a49744985.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

![Travel the Florida Keys Private Adventure](https://mediaim.expedia.com/localexpert/48970854/d8ae64d0-46a9-4b14-944c-5bd8d7e46b8b.jpg?impolicy=resizecrop&rw=500&rh=280)

### Travel the Florida Keys Private Adventure

4d

CA $6,196

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/travel-the-florida-keys-private-adventure.a48970854.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

![Full Day Charter Snorkelling Sandbar and Eco Safari Adventure](https://mediaim.expedia.com/localexpert/45711560/3d94553b-babf-45a4-ba06-15d9bde3ee6d.jpg?impolicy=resizecrop&rw=500&rh=280)

### Full Day Charter Snorkelling Sandbar and Eco Safari Adventure

6h

Free cancellation available

CA $1,239

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/full-day-charter-snorkelling-sandbar-and-eco-safari-adventure.a45711560.activity-details?&rid=6249254&location=Jackson+Square&swp=off)

### Popular places to visit

![San Carlos Institute - Casa Cuba](https://mediaim.expedia.com/destination/9/f7afdd341a025549202e7a7d034556b6.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### San Carlos Institute - Casa Cuba

5/5(1 review)

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.ca/San-Carlos-Institute-Casa-Cuba-Florida.d6068607.Vacation-Attraction)

![Duval Street](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/497000/497443-duval-street-key-west.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Duval Street

4.5/5(161 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.ca/Duval-Street-Key-West-Historic-District.d6068616.Vacation-Attraction)

![Oldest House Museum and Garden](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/340000/340381-Oldest-House-Museum-And-Garden.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.ca/Oldest-House-Museum-And-Garden-Florida.d553248621533115800.Vacation-Attraction)

![Harry S. Truman Little White House showing a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63938-Harry-S-Truman-Little-White-House.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Harry S. Truman Little White House

4/5(28 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.ca/Harry-S-Truman-Little-White-House-Old-Town-Key-West.d6068605.Vacation-Attraction)

![Curry Mansion Museum](https://mediaim.expedia.com/destination/2/fa65eb6bc194e3ed5cd35d722e95df05.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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. 

[](https://expedia.ca/Curry-Mansion-Museum-Florida.d553248621532652631.Vacation-Attraction)

![Audubon House and Tropical Gardens](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/339000/339918-Audubon-House-And-Tropical-Gardens.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Audubon House and Tropical Gardens

4/5(14 reviews)

Visit a house named after famed naturalist John James Audubon. Learn the history of why the house came to be here.

[](https://expedia.ca/Audubon-House-And-Tropical-Gardens-Florida.d6068599.Vacation-Attraction)

---

## Best Lodging Options Near Jackson Square

## Check availability on hotels close to Jackson Square

[Tonight

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6249254&startDate=2025-12-16&endDate=2025-12-17)[Dec 16 - Dec 17](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6249254&startDate=2025-12-16&endDate=2025-12-17)

[Tomorrow night

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6249254&startDate=2025-12-17&endDate=2025-12-18)[Dec 17 - Dec 18](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6249254&startDate=2025-12-17&endDate=2025-12-18)

[This weekend

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6249254&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025)[Dec 19 - Dec 21](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6249254&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025)

[Next weekend

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6249254&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025)[Dec 26 - Dec 28](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6249254&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025)

![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.ca/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.ca/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.ca/Key-West-Hotels-The-Cabana-Inn-Key-West-Adults-Only.h6576609.Hotel-Information)

![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.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.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.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information)

![Amsterdam's Curry Mansion Inn](https://images.trvl-media.com/lodging/1000000/10000/300/217/c6778dc1_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Amsterdam's Curry Mansion Inn

511 Caroline St Key West FL

[](https://expedia.ca/Key-West-Hotels-Amsterdams-Curry-Mansion-Inn.h217.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.ca/Key-West-Hotels-Pegasus-International-Hotel.h977303.Hotel-Information)

![Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool](https://images.trvl-media.com/lodging/35000000/34090000/34083800/34083792/8044f411_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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

 Key West FL

[](https://expedia.ca/Key-West-Hotels-Heavenly-Hideout-At-Rainbows-End-Key-West-Steps-From-Duval-W-Private-Pool.h34083792.Hotel-Information)

![Marrero's Guest Mansion](https://images.trvl-media.com/lodging/22000000/21530000/21529500/21529421/6273e943_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Marrero's Guest Mansion

410 Fleming Street Key West FL

[](https://expedia.ca/Key-West-Hotels-Marreros-Guest-Mansion.h21529421.Hotel-Information)

[See all 2,752 properties in Jackson Square](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=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.