Title: Summerland Key Vacation Packages & Trips 2025/2026 from CA $815 | Expedia.ca [Summerland Key Travel Guide](https://expedia.ca/Summerland-Key.dx6177802)[Hotels in Summerland Key](https://expedia.ca/Summerland-Key-Hotels.d6177802.Travel-Guide-Hotels)[Vacation Rentals in Summerland Key](https://expedia.ca/Summerland-Key-Vacation-Rentals.d6177802.Travel-Guide-VacationRentals)[Flights to Summerland Key](https://expedia.ca/Cheap-Flights-To-Summerland-Key.d6177802.Travel-Guide-Flights)[Things to do in Summerland Key](https://expedia.ca/Things-To-Do-In-Summerland-Key.d6177802.Travel-Guide-Activities)[Summerland Key Car Rentals](https://expedia.ca/Car-Rentals-In-Summerland-Key.d6177802.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6270983/d55f2489-0176-4d5a-82e3-d6afdd04d6e6.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Summerland 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 Summerland Key Vacation The hassle-free way to experience this interesting city is with a tailor-made Summerland Key vacation package. Base yourself in the neighborhood of Sugarloaf Shores, which is great for families, fishing and views or go someplace else — our package deals are all about you. [Cook Island](https://www.expedia.ca/Cook-Island-Big-Pine-Key.d553248635976197877.Vacation-Attraction), [Big Pine Key Flea Market](https://www.expedia.ca/Big-Pine-Key-Flea-Market-Big-Pine-Key.d553248621533115810.Vacation-Attraction) and [Blue Hole](https://www.expedia.ca/Blue-Hole-Big-Pine-Key.d553248621532652323.Vacation-Attraction) are just some of the sights you'll want to see during your trip to Summerland Key. Stop daydreaming and start traveling. Browse the wide range of options on Expedia today and put your Summerland Key vacation plans in motion! ## Top Summerland Key Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hawks Cay Resort CA $815 per person Jan 15 - Jan 18 found 6 hours ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8/10 Very Good! (1,011 reviews) Room was clean and spacious. Property did not have available microwave for guest. House keeping was good but did not replace soap or drinking glass. Gym not located in main hotel area and it closes at 5pm. Overall property is beautiful and good amenities. Reviewed on Nov 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-15/2026-01-18/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6068&paandie=true&dealMarker=Sr2f1ZGIa4gLxmJVmsxzBsBAfR1nEamj_23Occ_rnMpBO7ySnaTD1BmCi3V0S4Na) ![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 $1,674 per person Jan 15 - Jan 19 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) 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/2026-01-15/2026-01-19/?FromAirport=YHM&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=25451&paandie=true&dealMarker=V0g0QMdJBZkQRfZcj4bxcfA10Dj_nhMSNCXWh2Ilyn7GF_bxxOZVZiS3Tt6f_zer) ![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 $11,592 per person Jan 30 - Feb 3 found 16 hours ago Roundtrip non-stop flight included Montreal (YUL) to Miami (MIA) 8/10 Very Good! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2026-01-30/2026-02-03/?FromAirport=YUL&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&dealMarker=7kC3jKf3y2dsElbYQrze4JyqjnzbaJnoxdVeAuNFn1BfCuN0lr0McvmjPL3AmIDX) ![Park Central South Beach](https://images.trvl-media.com/lodging/1000000/10000/1200/1168/280efeed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Central South Beach South Beach CA $1,784 per person Dec 31 - Jan 7 found 1 day ago Roundtrip flight included Montreal Metropolitan Airport (YHU) to Miami (MIA) 8.6/10 Excellent! (217 reviews) Property was nice! Service at the bar needs improvement. Reviewed on Nov 8, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-31/2026-01-07/?FromAirport=YHU&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1168&paandie=true&dealMarker=zHfvOMm1PagWShKKDzcybSGZDeeW3XaruMWBaMjizsr7NYO4TuPFMw4DwrpjDXDi) ![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 $1,600 per person Dec 31 - Jan 7 found 1 day ago Roundtrip flight included Montreal Metropolitan Airport (YHU) to Miami (MIA) 8.4/10 Very Good! (1,905 reviews) It was great! Breakfast & a welcome drink. Bartender and front desk person were very friendly and professional! I will stay here again! Reviewed on Nov 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-31/2026-01-07/?FromAirport=YHU&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=575859&paandie=true&dealMarker=zHfvOMm1PagWShKKDzcybSGZDeeW3XaruMWBaMjizspm2GhXoE1bDoZ4jOesWqo8) ## Where to stay in Summerland Key Find the best Summerland Key areas and neighborhoods for the activities you enjoy most. [Learn more about Summerland Key](https://expedia.ca/Summerland-Key.dx6177802) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Cutthroat Harbor Estates While Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Upper Sugarloaf Key are some notable places to visit nearby. [Find hotel + flight trips in Cutthroat Harbor Estates](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Cutthroat%20Harbor%20Estates&DestID=553248635976481702&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/498000/498222-sugarloaf-key.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Sugarloaf Shores While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby. [Find hotel + flight trips in Sugarloaf Shores](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Sugarloaf%20Shores&DestID=6270983&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Cudjoe Gardens When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Venture Out Keys, some noteworthy sights in the nearby area. [Find hotel + flight trips in Cudjoe Gardens](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Cudjoe%20Gardens&DestID=553248635976472640&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Bay Point Bay Point might not have many top sights, but Lower Sugarloaf Sound and Sugarloaf Beach are two attractions nearby that you can check out. [Find hotel + flight trips in Bay Point](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Bay%20Point&DestID=553248635976383913&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Breezeswept Beach Estates While Breezeswept Beach Estates isn't home to many top sights, Newfound Harbor Keys and Cook Island are some notable places to visit nearby. [Find hotel + flight trips in Breezeswept Beach Estates](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Breezeswept%20Beach%20Estates&DestID=553248635976468855&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Ready to book your vacation to Summerland Key? Choose your dates ## Summerland Key Hotel Deals ![Parmer's Resort](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/6492712a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Parmer's Resort 565 Barry Avenue, Summerland Key, FL Fully refundableReserve now, pay when you stay CA $154 CA $219 total Nov 19 - Nov 20 includes taxes & fees 9/10 Wonderful! (1,008 reviews) Everything was excellent 5 stars we stayed at a lot of resorts this was best by far Sue was very helpful and even talked with cleaning staff was so friendly. They ALL go above and beyond. Will be back to our private little getaway. Reviewed on Oct 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=19%2F11%2F2025&endDate=20%2F11%2F2025&selected=5561465&PinnedHotelID=5561465&HadPinnedHotel=true®ionId=6177802) ![Sugar Loaf Lodge](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/95d2903e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sugar Loaf Lodge 17001 Overseas Hwy, Summerland Key, FL Fully refundableReserve now, pay when you stay CA $139 CA $156 total Nov 30 - Dec 1 includes taxes & fees 8/10 Very Good! (1,000 reviews) This was an excellent value for the price - the room was spacious and clean, the property was quiet. There was a beautiful view with a balcony. I could not have been happier with my experience! Reviewed on Oct 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F11%2F2025&endDate=01%2F12%2F2025&selected=3918121&PinnedHotelID=3918121&HadPinnedHotel=true®ionId=6177802) ![Looe Key Reef Resort](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/63d12f01_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Looe Key Reef Resort 27340 Overseas Highway, Summerland Key, FL Fully refundableReserve now, pay when you stay CA $247 CA $278 total Nov 10 - Nov 11 includes taxes & fees 7.4/10 Good! (1,001 reviews) We enjoyed our three night stay. We dived Looe Key reef every day through their dive shop. Safe shallow diving with excellent storage, easy access and excellent staff. Left the afternoon/evening open to relax or go into town. About 50 minutes from Key West. Recommend car rental for your stay Reviewed on Oct 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=10%2F11%2F2025&endDate=11%2F11%2F2025&selected=4759500&PinnedHotelID=4759500&HadPinnedHotel=true®ionId=6177802) [See all 625 properties in Summerland Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F11%2F2025&endDate=10%2F11%2F2025®ionId=6177802) 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 Summerland Key ![12 hours Day at Key West With Boat Tour and Snorkeling](https://mediaim.expedia.com/localexpert/599857/aefdb7f1-206a-4531-bc6a-78614e1a0f10.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar CA $38 per adult **80%** of travellers recommend [](https://expedia.ca/things-to-do/day-trip-to-paradise-from-miami-key-west-tour-with-snorkeling.a599857.activity-details) ![Aboard the trolley in Key West](https://mediaim.expedia.com/localexpert/191537/2dd77e4c-4c5c-4b3c-954d-bfd0d44bd289.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Historic Key West Old Town Trolley Hop-On Hop-Off Tour CA $78 per adult **86%** of travellers recommend [](https://expedia.ca/things-to-do/historic-key-west-old-town-trolley-hop-on-hop-off-tour.a191537.activity-details) ![Key West Parasailing Downtown](https://mediaim.expedia.com/localexpert/588901/43eed805-6849-4eda-87bf-fb57f27624fe.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides CA $95 per traveller **92%** of travellers recommend [](https://expedia.ca/things-to-do/bucket-list-parasailing-in-downtown-key-west-highest-longest-rides.a588901.activity-details) [See all activities in Summerland Key](https://expedia.ca/things-to-do/search?rid=6177802) ## Explore a world of travel with Expedia \* 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,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAFGUlEQVR4Xu3bTZLTOhRAYVEMPGQJWYqXZi8tS/ESGPagC73cH0nXimm4VQ+q6JwzwbmR9GXmOECpf6EyD/5EIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkVkPcydWujL7Xey/JY/Bhp32W61rfy2H7I9Waj2DZOBikg8zIQaxsngxSQeRmItY2TPyuyjVd64nBXGx62PSK+8bt8lN75LBAQEBAJRAPRQHq+Vls6stmbd5n6wr34bV9Hh/zhiI7OGyUQEBD5AwSkgIB4HyOab1/6wt3WrHJtlyAgEgiIBlJAQMr/hdT65uf17X5iKV/7Kh+BgGggFQQEBMQGv0JGvtZbDfHRt/rD532jfxQPBKSCgMxvgFggIHVGzumJvv1elu7+ZDS1jZNBLkZT2zgZ5GI0tY2TQS5GU9s4GeRiNLWNk0EuRlPbOBnkYjS1jZMDcpG6fkNf+siRGm77W9j0HAjIRSBTICAXgUx9XsRv1Y8TL7cf7efs0p+69Rfu3a5WedMu40YQPREExK5WedMuQSoIiJ746shuN/TVXh1h7d12uqv3+D7Sjfovrqu4540SCEgF0Y0gcW0/EWQE8orIu23Slqr3+NFdRrJdb+jfwsg3jk8nr/SbQA9kjEBAQFogGsgYvTSi2/utWtf683R9dku/oceNICAeSAUBAQH5HWSr/vC82Ik6qnb3Hu5uB8WR1O7xYeSBgICAgKx2BQKiPSMtH/nd291i233VItd+on66Km74dB6IBgICYiMQEJAJ8RP72io39DjqyJfu6qqO1PBReiAgIPY2yE2uQGIgIIqMfLrbq1UXN3f8Yy4Z+cYxAll1Mci4BAGRfLrbq1UXg4xLkBdFat/e797v9tQ9ndhH537IAt94DgSkgnggINM7ICDVEG0Jo/NTtyNFbvtv8k3gkOvZ1VU9EJAKAgLSAgGpHyFy4uguUzlRH571RB9p8lHGPf7Xj9gaCIjlJ4LEdjdAQDw/ESS2u/GPI+9NsLV+omyvfmJ39R6vySotrgLx7TdbCgICUkBAQPxMa0b0Vr3qO9ZW9bdrHbkrtRt6SEdFXD1rG++AgIC0QEBAbA1Ib0J6ekOPP2fHfM1e9G+meyAgFWTka/YC4oGMVyAtX7OXV0S2qr9dVzmxlFtzqz88+6o+errHr/KnLPBvAh6IjkBAKggICIh1ifx8u7qbjbRaj3airhqfTlZ5ICAgICAgEkhrRi5PbPlI7vHTiTFxCwgICAgICIj3IXKRn9jyU+SbgLaEkda/HJw/HQjIRSAgEggIiJ4Yu9ncn7q98Tx9Ri5XeSAgIBIISFzlgYC8y9rRGfEOOzEWRx05rwIZgWggICAtkNFLI/Hh+RZG/nN2vMdf/sK9yJuHXG3jZBAQEBAQEJAUIr9w64myuDjiq4r9bfJX+d9N+jv43RA/qwcCAgICAgKSRLRVFz9Gmq6Kt/29nP9z8TkQHYGAFBCQp0B0BDLyE2V7PHG0hsV7G+kq3RgC0dFobyOQuD22hsV7G4HE7bE1LN7bCCRuj61h8d5GIHF7bA2L9zYCidtja1i8t9FvIOduMpWH5/GI3Ue1P08fslS+HOg9/q0/dYdAKshkgICAeCD15ZE/F0gqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSfR7kPyPn1BKChuB1AAAAAElFTkSuQmCC)