Title: Cheap Vacations in Raccoon Key 2025/2026 | Expedia.ca ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Raccoon Key Cheap Vacations ## Book a Hotel + Flight or Car together to unlock savings Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place ## Flight and Cheap hotel deals in Raccoon Key Price found within the past 48 hours. Click for updated prices. ![The Perry Hotel & Marina Key West](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Perry Hotel & Marina Key West CA $3,917 per person Dec 27 - Jan 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Key West (EYW) 9.4/10 Exceptional! (1,119 reviews) I don’t have any pets Reviewed on Oct 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2026-01-03/?FromAirport=YTO&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=17313680&paandie=true&HotelClass=40&dealMarker=Z1kMevP7eAQq5xTvKgbZMZlB96TJhIwWIUYbmNYP490dLuiGYwrbbkTgrsvuCH0I) ![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Winslow's Bungalows - Key West Historic Inns Old Town Key West CA $3,922 per person Dec 27 - Jan 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Key West (EYW) 9.2/10 Wonderful! (1,021 reviews) The landscaping, grounds and pools were beautiful and kept perfectly. It all felt quiet and very safe. Easy to walk to some nice dining choices. The staff was friendly and helpful. Reviewed on Oct 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2026-01-03/?FromAirport=YTO&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=529611&paandie=true&HotelClass=40&dealMarker=qgNx3gK80nWwTZhFUtG94OXhonhtFqjGPbQ4ABnRS5U1p3ROeAqYA_4wfNDQQuqF) ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/3a4457a0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Oceans Edge Key West Resort, Hotel & Marina CA $4,051 per person Dec 27 - Jan 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Key West (EYW) 8.8/10 Excellent! (1,732 reviews) Very good stay people were very nice. Smell so good in the lobby in the rooms. The view of the room was beautiful room was very clean. There was a kitchenette area for convenience Reviewed on Oct 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2026-01-03/?FromAirport=YTO&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=16202992&paandie=true&HotelClass=40&dealMarker=qgNx3gK80nWwTZhFUtG94JZE6WpQtPdEURUueMtEKwALUjFFwpQ2tzdZTZnDTgd_) ![The Gardens Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20796/424c57d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Gardens Hotel Old Town Key West CA $4,640 per person Dec 27 - Jan 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Key West (EYW) 9.8/10 Exceptional! (1,006 reviews) Clean room and beautiful garden. Unfortunately the second morning when we were there, there's a heavy rain, we can't enjoy the garden. Reviewed on Oct 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2026-01-03/?FromAirport=YTO&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20796&paandie=true&HotelClass=40&dealMarker=Z1kMevP7eAQq5xTvKgbZMRbq385tteyPFRVnrnz5f1ihbx8JZzhzv7sH6P8LuTw2) ![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 CA $4,551 per person Dec 27 - Jan 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Key West (EYW) 8.6/10 Excellent! (2,787 reviews) Staff was so helpful, kind, and courteous especially Andrea at the reception area Reviewed on Oct 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2026-01-03/?FromAirport=YTO&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=863329&paandie=true&HotelClass=40&dealMarker=Z1kMevP7eAQq5xTvKgbZMXXPhanjqRrWfEHQrcf4gQQrDHds9nLUSm9jSanZkg1p) Don't see what you're looking for? See all available trips from Columbus to Raccoon Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-12-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Cheap holidays in Raccoon Key Price found within the past 48 hours. Click for updated prices. ![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Winslow's Bungalows - Key West Historic Inns Old Town Key West CA $1,128 per person Nov 28 - Dec 1 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Key West (EYW) 9.2/10 Wonderful! (1,021 reviews) The landscaping, grounds and pools were beautiful and kept perfectly. It all felt quiet and very safe. Easy to walk to some nice dining choices. The staff was friendly and helpful. Reviewed on Oct 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-28/2025-12-01/?FromAirport=YTO&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=529611&paandie=true&HotelClass=40&dealMarker=b5uwRSeJQQuigeUJXT0sGqylT8JuztSlAV1UH9FRsvt0CSYnWoTGn8F0pG_ZwOh2) ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/3a4457a0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Oceans Edge Key West Resort, Hotel & Marina CA $1,880 per person Dec 31 - Jan 3 found 16 hours ago Roundtrip flight included Toronto (YYZ) to Key West (EYW) 8.8/10 Excellent! (1,732 reviews) Very good stay people were very nice. Smell so good in the lobby in the rooms. The view of the room was beautiful room was very clean. There was a kitchenette area for convenience Reviewed on Oct 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-31/2026-01-03/?FromAirport=YYZ&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=16202992&paandie=true&HotelClass=40&dealMarker=B5efonpnkDbUO5UEb9kmECJpfEUdlIECeN6rN5rZrMpG0p0OXmdbf0cpx8OONFjw) ![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/ed076ab9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pier House Resort & Spa Key West Historic District CA $1,938 per person Jan 8 - Jan 11 found 16 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Key West (EYW) 9/10 Wonderful! (1,017 reviews) Great location , very walkable to so much. Staff was very friendly. I felt very safe venturing out by myself . We will definitely be back Reviewed on Oct 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-08/2026-01-11/?FromAirport=YYZ&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19307&paandie=true&HotelClass=40&dealMarker=B5efonpnkDbUO5UEb9kmEEhF6EL_oL_oWgeulfX7BTXDuWi4ZH_eKV9UzQ8t-or6) Don't see what you're looking for? See all available trips from Columbus to Raccoon Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-12-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Cheap holidays in Raccoon Key Price found within the past 48 hours. Click for updated prices. ![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Winslow's Bungalows - Key West Historic Inns Old Town Key West CA $2,672 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Montreal (YUL) to Key West (EYW) 9.2/10 Wonderful! (1,021 reviews) The landscaping, grounds and pools were beautiful and kept perfectly. It all felt quiet and very safe. Easy to walk to some nice dining choices. The staff was friendly and helpful. Reviewed on Oct 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YUL&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=529611&paandie=true&dealMarker=i7rXaTNLcePxpL7sId40Hng8qqKgoSpyF4s48tuDBS8bcbJYGENWbyTK5zIgKMib) ![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 $4,335 per person Dec 26 - Dec 30 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Key West (EYW) 9.2/10 Wonderful! (498 reviews) Great location and friendly staff. They have remodeled a lot and are doing a super job. Nice decorations and LOVE the tiki bar and pool area. Key West Aloe products were a nice touch as well as the key lime cookies. The porch deck and handrail outside the Envy/Lust room needs a little attention. Overall, very comfortable and accommodating. I would definitely stay here again. Reviewed on Oct 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2025-12-30/?FromAirport=YYZ&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=8657021&paandie=true&dealMarker=lDTH6YKwALsfVcTMdz6RtIObCmub8kc2sFX0a1bKcHtVsmU64nbeDoH64mbpPWcY) ![Lighthouse Hotel - Key West Historic Inns](https://images.trvl-media.com/lodging/2000000/1180000/1171100/1171079/2155599f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lighthouse Hotel - Key West Historic Inns Old Town Key West CA $2,739 per person Dec 26 - Dec 30 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Key West (EYW) 9/10 Wonderful! (803 reviews) Easy access to Duvall and Hemingway house. Very comfortable bed and room over all. Reviewed on Oct 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2025-12-30/?FromAirport=YYZ&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1171079&paandie=true&dealMarker=lDTH6YKwALsfVcTMdz6RtAbdoVzzQdfByguZxGl7rRm4p-i-Aa4yCcHknAolNel4) Don't see what you're looking for? See all available trips from Columbus to Raccoon Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-12-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=EYW&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## More Vacations Ideas [Flights to Raccoon Key](https://expedia.ca/Cheap-Flights-To-Raccoon-Key.d180164.Travel-Guide-Flights)[Raccoon Key Hotels](https://expedia.ca/Raccoon-Key-Hotels.d180164.Travel-Guide-Hotels)[Raccoon Key Vacation Rentals](https://expedia.ca/Raccoon-Key-Vacation-Rentals.d180164.Travel-Guide-VacationRentals)[Raccoon Key Car Rentals](https://expedia.ca/Car-Rentals-In-Raccoon-Key.d180164.Car-Rental-Guide)[Raccoon Key Vacations](https://expedia.ca/Raccoon-Key.d180164.Destination-Travel-Guides)[Things to do in Raccoon Key](https://expedia.ca/Things-To-Do-In-Raccoon-Key.d180164.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)