Title: Sugarloaf Key Vacation Packages & Trips 2025/2026 from CA $682 | Expedia.ca [Sugarloaf Key Travel Guide](https://expedia.ca/Sugarloaf-Key.dx183126)[Hotels in Sugarloaf Key](https://expedia.ca/Sugarloaf-Key-Hotels.d183126.Travel-Guide-Hotels)[Vacation Rentals in Sugarloaf Key](https://expedia.ca/Sugarloaf-Key-Vacation-Rentals.d183126.Travel-Guide-VacationRentals)[Flights to Sugarloaf Key](https://expedia.ca/Cheap-Flights-To-Sugarloaf-Key.d183126.Travel-Guide-Flights)[Things to do in Sugarloaf Key](https://expedia.ca/Things-To-Do-In-Sugarloaf-Key.d183126.Travel-Guide-Activities)[Sugarloaf Key Car Rentals](https://expedia.ca/Car-Rentals-In-Sugarloaf-Key.d183126.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6270983/d55f2489-0176-4d5a-82e3-d6afdd04d6e6.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Sugarloaf Key Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## 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 #### Your Sugarloaf Key Vacation From its highlights to its hidden gems, this city is best explored with a Sugarloaf Key vacation package. Check out hotels located in Sugarloaf Shores, which is good for families, fishing and views. Make your trip to Sugarloaf Key even more exciting by including some sightseeing. [Florida Keys Beaches](https://www.expedia.ca/Florida-Keys-Beaches-Florida.d553248635976496782.Vacation-Attraction), [Sugarloaf Beach](https://www.expedia.ca/Sugarloaf-Beach-Sugarloaf-Key.d553248635983994028.Vacation-Attraction) and [Upper Sugarloaf Sound](https://www.expedia.ca/Upper-Sugarloaf-Sound-Sugarloaf-Key.d553248635976195391.Vacation-Attraction) are among the major attractions you'll want to explore. No matter your travel plans or budget, putting together the ultimate tailored Sugarloaf Key vacation is simple with Expedia. ## Top Sugarloaf Key Vacation Deals Price found within the past 48 hours. Click for updated prices. ![The Penguin Hotel](https://images.trvl-media.com/lodging/1000000/70000/62900/62824/d4ab7ebb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Penguin Hotel South Beach CA $682 per person Jan 29 - Feb 2 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8.2/10 Very Good! (1,491 reviews) Riom, staff, beds, welcome drink...all superb. Reviewed on Nov 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-29/2026-02-02/?FromAirport=DTW&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=62824&paandie=true&dealMarker=V0g0QMdJBZkQRfZcj4bxcXNFARO4apAUVJHbkj4pHzZvKiji9hvBZ1aYh6k0IVO3) ![The Shelborne By Proper, a Member of Design Hotels](https://images.trvl-media.com/lodging/1000000/30000/25500/25451/e49031f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shelborne By Proper, a Member of Design Hotels South Beach CA $944 per person Jan 8 - Jan 11 found 13 hours ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 9.8/10 Exceptional! (39 reviews) Fantastic experience. One of the best hotels we have stayed at. Shout out to Jenny, Marta , Shane and Louis, William and Josh and all of the other wonderful staff. Definitely recommend it and will certainly go back ! Reviewed on Nov 1, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-08/2026-01-11/?FromAirport=DTW&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=25451&paandie=true&dealMarker=V0g0QMdJBZkQRfZcj4bxcUDTNHkLr081nte3ummzZArkpNnwNyDeB1POtsOv7_E6) ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach CA $7,580 per person Jan 26 - Jan 29 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 8/10 Very Good! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2026-01-26/2026-01-29/?FromAirport=YYZ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&dealMarker=hqrzlFyS8DwRVlr4irIrHsdf3lqLBIxov210FHgtXNVA_bFAfLak6jwVk0d3uSzz) ![Bentley Hotel South Beach](https://images.trvl-media.com/lodging/1000000/130000/120300/120299/8ae6370c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bentley Hotel South Beach South Beach CA $1,096 per person Jan 29 - Feb 2 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 9.4/10 Exceptional! (390 reviews) Beautifully renovated with great additional touches like Continental breakfast and champagne at 5:00 Reviewed on Nov 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-29/2026-02-02/?FromAirport=DTW&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=120299&paandie=true&dealMarker=V0g0QMdJBZkQRfZcj4bxcXNFARO4apAUVJHbkj4pHzbyOVPhX3pqNx9XQWdu8Y3w) ![President Hotel](https://images.trvl-media.com/lodging/1000000/580000/575900/575859/5a013cab_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### President Hotel South Beach CA $702 per person Jan 29 - Feb 2 found 1 day ago Roundtrip flight included Detroit (DTW) to Miami (MIA) 8.4/10 Very Good! (1,905 reviews) Everything was great Reviewed on Nov 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-29/2026-02-02/?FromAirport=DTW&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=575859&paandie=true&dealMarker=V0g0QMdJBZkQRfZcj4bxcXNFARO4apAUVJHbkj4pHzZi_yJAphvXLAN137wU3wYD) ## Ready to book your vacation to Sugarloaf Key? Choose your dates ## Sugarloaf Key Hotel Deals ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/3a4457a0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Oceans Edge Key West Resort, Hotel & Marina 5950 Peninsular Avenue, Key West, FL Fully refundableReserve now, pay when you stay CA $215 CA $327 total Nov 16 - Nov 17 includes taxes & fees 8.8/10 Excellent! (1,727 reviews) We’ve stayed here twice now. Staff is great, the shuttle into town is super convenient (hi Jeffrey!). We love that you can use the kayaks or paddleboards every day. The tiki hut crew is the best! The place is clean and I feel safe walking around there. It’s well lit and easy to navigate. Reviewed on Nov 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=16202992&PinnedHotelID=16202992&HadPinnedHotel=true®ionId=183126) ![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/cb0a4c1e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Blue Flamingo Resort Key West 3820 North Roosevelt Boulevard, Key West, FL Fully refundableReserve now, pay when you stay CA $143 CA $240 total Nov 18 - Nov 19 includes taxes & fees 7.8/10 Good! (1,647 reviews) Very nice friendly service and fun atmosphere. Reviewed on Nov 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=18%2F11%2F2025&endDate=19%2F11%2F2025&selected=12599231&PinnedHotelID=12599231&HadPinnedHotel=true®ionId=183126) ![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Beachside Resort & Residences 3841 N Roosevelt Blvd, Key West, FL Fully refundableReserve now, pay when you stay CA $179 CA $273 total Nov 30 - Dec 1 includes taxes & fees 8.6/10 Excellent! (1,653 reviews) Loved the atmosphere. Beautiful & clean room. Heated pool well maintained and open 24 hours. Plan on staying again. future Reviewed on Nov 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F11%2F2025&endDate=01%2F12%2F2025&selected=25865&PinnedHotelID=25865&HadPinnedHotel=true®ionId=183126) [See all 3,534 properties in Sugarloaf Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F11%2F2025&endDate=09%2F11%2F2025®ionId=183126) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ![](https://forever.travel-assets.com/flex/flexmanager/images/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) ### What to do in Sugarloaf Key ![Education with one of our top rated guides! ](https://mediaim.expedia.com/localexpert/2599656/2f145c89-cd67-4ef5-92ed-497b3499b5d5.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Guided Clear Kayak Eco-Tour Near Key West CA $110 per adult [](https://expedia.ca/things-to-do/guided-clear-kayak-eco-tour-near-key-west.a2599656.activity-details) ![Photograph endangered Key Deer](https://mediaim.expedia.com/localexpert/1344852/ff138428-01c2-46a6-aa85-98dad5815158.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West CA $236 per adult [](https://expedia.ca/things-to-do/full-day-tour-of-florida-keys-including-aquarium-encounters-from-key-west.a1344852.activity-details) ![Private Sandbar Adventure in Key West Backcountry](https://mediaim.expedia.com/localexpert/47135631/383d7d0b-4397-4483-8bd0-3dfea7e87907.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Private Sandbar Adventure in Key West Backcountry CA $767 per traveller [](https://expedia.ca/things-to-do/private-sandbar-adventure-in-key-west-backcountry.a47135631.activity-details) [See all activities in Sugarloaf Key](https://expedia.ca/things-to-do/search?rid=183126) ## Explore a world of travel with Expedia - 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Higgs Memorial Beach Park](https://www.expedia.ca/Clarence-S-Higgs-Memorial-Beach-Park-Old-Town-Key-West.d6246822.Vacation-Attraction) - [Cudjoe Key Vacations](https://www.expedia.ca/Cudjoe-Key.d3000430966.Destination-Travel-Guides) - [Visit Cudjoe Key](https://www.expedia.ca/Cudjoe-Key.dx3000430966) - [Dredgers Key Vacations](https://www.expedia.ca/Dredgers-Key.d180165.Destination-Travel-Guides) - [Dry Tortugas National Park](https://www.expedia.ca/Dry-Tortugas-National-Park-Key-West.d6091118.Vacation-Attraction) - [Duval Street](https://www.expedia.ca/Duval-Street-Key-West-Historic-District.d6068616.Vacation-Attraction) - [Fleming Key Vacations](https://www.expedia.ca/Fleming-Key.d180162.Destination-Travel-Guides) - [Florida Keys Eco - Discovery Center](https://www.expedia.ca/Florida-Keys-Eco-Discovery-Center-Old-Town-Key-West.d6069247.Vacation-Attraction) - [Fort East Martello Museum and Gallery](https://www.expedia.ca/Fort-East-Martello-Museum-And-Gallery-Key-West.d6069253.Vacation-Attraction) - [Harry S. Truman Little White House](https://www.expedia.ca/Harry-S-Truman-Little-White-House-Old-Town-Key-West.d6068605.Vacation-Attraction) - [Key West Historic District Vacations](https://www.expedia.ca/Key-West-Historic-District.d6281809.Destination-Travel-Guides) - [Key West Lighthouse and Keeper's Quarters Museum](https://www.expedia.ca/Key-West-Lighthouse-And-Keepers-Quarters-Museum-Old-Town-Key-West.d501383.Vacation-Attraction) - [Key West Shipwreck Museum](https://www.expedia.ca/Key-West-Shipwreck-Museum-Key-West-Historic-District.d6063545.Vacation-Attraction) - [Key West Vacations](https://www.expedia.ca/Key-West.d1187.Destination-Travel-Guides) - [Lower Florida Keys Vacations](https://www.expedia.ca/Lower-Florida-Keys.d553248635975748710.Destination-Travel-Guides) - [Visit Lower Florida Keys](https://www.expedia.ca/Lower-Florida-Keys.dx553248635975748710) - [Lower Keys Vacations](https://www.expedia.ca/Lower-Keys.d553248621593965863.Destination-Travel-Guides) - [Mallory Square](https://www.expedia.ca/Mallory-Square-Key-West-Historic-District.d501385.Vacation-Attraction) - [Mel Fisher Maritime Museum](https://www.expedia.ca/Mel-Fisher-Maritime-Museum-Old-Town-Key-West.d6163799.Vacation-Attraction) - [National Key Deer Refuge Visitor Center](https://www.expedia.ca/National-Key-Deer-Refuge-Visitor-Center-Big-Pine-Key.d553248635974766232.Vacation-Attraction) - [No Name Key Vacations](https://www.expedia.ca/No-Name-Key.d553248635976193734.Destination-Travel-Guides) - [Raccoon Key Vacations](https://www.expedia.ca/Raccoon-Key.d180164.Destination-Travel-Guides) - [Rockland Key Vacations](https://www.expedia.ca/Rockland-Key.d553248635976197596.Destination-Travel-Guides) - [Smathers Beach](https://www.expedia.ca/Smathers-Beach-Beachside.d6069255.Vacation-Attraction) - [South Beach](https://www.expedia.ca/South-Beach-Old-Town-Key-West.d6246827.Vacation-Attraction) - [Southernmost Point](https://www.expedia.ca/Southernmost-Point-Old-Town-Key-West.d501380.Vacation-Attraction) - [Stock Island Vacations](https://www.expedia.ca/Stock-Island.d180166.Destination-Travel-Guides) - [Sugarloaf Shores Vacations](https://www.expedia.ca/Sugarloaf-Shores.d6270983.Destination-Travel-Guides) ### Cars - [Car rentals near Cudjoe Key](https://www.expedia.ca/Car-Rentals-In-Cudjoe-Key.d3000430966.Car-Rental-Guide) - [Car rentals near Lower Sugarloaf Key](https://www.expedia.ca/Car-Rentals-In-Lower-Sugarloaf-Key.d553248635976195908.Car-Rental-Guide) - [Enterprise Rental Cars in Lower Florida Keys](https://www.expedia.ca/Enterprise-Car-Rentals-In-Lower-Florida-Keys.d553248635975748710-c15.Car-Rental-Guide-Suppliers) - [Express Travel Group Rental Cars in Lower Sugarloaf Key](https://www.expedia.ca/Express-Travel-Group-Car-Rentals-In-Lower-Sugarloaf-Key.d553248635976195908-c1124.Car-Rental-Guide-Suppliers) - [First-Car Rental Cars in Lower Florida Keys](https://www.expedia.ca/First-Car-Car-Rentals-In-Lower-Florida-Keys.d553248635975748710-c1019.Car-Rental-Guide-Suppliers) - [Get Your Car Rental Cars in Lower Florida Keys](https://www.expedia.ca/Get-Your-Car-Car-Rentals-In-Lower-Florida-Keys.d553248635975748710-c1120.Car-Rental-Guide-Suppliers) - [Global Rent a Car Rental Cars in Lower Sugarloaf Key](https://www.expedia.ca/Global-Rent-A-Car-Car-Rentals-In-Lower-Sugarloaf-Key.d553248635976195908-c1062.Car-Rental-Guide-Suppliers) - [Goldcar Key’n Go Rental Cars in Lower Florida Keys](https://www.expedia.ca/Goldcar-Keyn-Go-Car-Rentals-In-Lower-Florida-Keys.d553248635975748710-c1044.Car-Rental-Guide-Suppliers) - [Hawk Rental Cars in Lower Sugarloaf Key](https://www.expedia.ca/Hawk-Car-Rentals-In-Lower-Sugarloaf-Key.d553248635976195908-c1076.Car-Rental-Guide-Suppliers) - [Luxury Car Rentals in Lower Florida Keys](https://www.expedia.ca/Luxury-Car-Rentals-In-Lower-Florida-Keys.d553248635975748710-tLuxury.Car-Rental-Guide-Class) - [Ok Mobility Rental Cars in Lower Florida Keys](https://www.expedia.ca/OK-Mobility-Car-Rentals-In-Lower-Florida-Keys.d553248635975748710-c1057.Car-Rental-Guide-Suppliers) - [Sicily By Car Rental Cars in Lower Florida Keys](https://www.expedia.ca/Sicily-By-Car-Car-Rentals-In-Lower-Florida-Keys.d553248635975748710-c1048.Car-Rental-Guide-Suppliers) - [Standard Car Rentals in Lower Florida Keys](https://www.expedia.ca/Standard-Car-Rentals-In-Lower-Florida-Keys.d553248635975748710-tStandard.Car-Rental-Guide-Class) - [Top Rent a Car Rental Cars in Lower Florida Keys](https://www.expedia.ca/Top-Rent-A-Car-Car-Rentals-In-Lower-Florida-Keys.d553248635975748710-c1028.Car-Rental-Guide-Suppliers) ### Vacation Rental - [Cudjoe Key Vacation Rentals](https://www.expedia.ca/Cudjoe-Key-Vacation-Rentals.d3000430966.Travel-Guide-VacationRentals) ### Other - [Things to do in Cudjoe Key](https://www.expedia.ca/Things-To-Do-In-Cudjoe-Key.d3000430966.Travel-Guide-Activities) - [Things to do in Lower Florida Keys](https://www.expedia.ca/Things-To-Do-In-Lower-Florida-Keys.d553248635975748710.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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