Title: Summerland Key Vacation Packages & Trips 2026 from CA $826 | 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/6177802/bda449a1-0506-4d80-94a6-fb19766bc7f4.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. ![Casablanca Miami Beach](https://images.trvl-media.com/lodging/32000000/31660000/31652200/31652150/628e521a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Casablanca Miami Beach North Beach CA $826 per person Apr 10 - Apr 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 5.8/10 (311 reviews) I stood in the multiple bed 1 bedroom everything was good beach right there pool and security where very friendly Reviewed on Nov 12, 2025 ![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Creekside Inn CA $904 per person Apr 10 - Apr 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8/10 Very Good! (1,004 reviews) Room was clean, spacious with a wonderful canal view. Reviewed on Jan 27, 2026 ![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 $19,627 per person Mar 14 - Mar 21 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Miami (MIA) 8/10 Very Good! (1 review) ![W South Beach](https://images.trvl-media.com/lodging/1000000/20000/11900/11881/f8e7300f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### W South Beach South Beach CA $7,698 per person Apr 29 - May 6 found 1 day ago Roundtrip flight included Montreal (YMQ) to Miami (MIA) 9.2/10 Wonderful! (1,002 reviews) Clean rooms great service Reviewed on Jan 29, 2026 ![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/w4800h3297x0y3-ab24f575_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel South Beach South Beach CA $11,095 per person Apr 29 - May 6 found 1 day ago Roundtrip flight included Montreal (YMQ) to Miami (MIA) 9.4/10 Exceptional! (1,365 reviews) Amazing hotel. Beyond our expectations. Rooms are huge. Modern and stylish Lobby is fabulous as is the bars and restaurants You must stay here !!! Total wow Reviewed on Jan 21, 2026 ## 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) ![Bird refuge wildlife background panorama banner of nature landscape ocean birds in Key West, Florida. Animals of the USA.](https://images.trvl-media.com/place/553248635976481702/7efc6f73-bf7b-4c19-9424-6ca3071f1ffe.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) ![Sugarloaf Shores featuring a bay or harbor](https://images.trvl-media.com/place/6270983/44cc35b6-7c5a-4d30-8d33-616900dbf0d6.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 Upper Sugarloaf Sound, 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) ![Bahia Honda State Park - Calusa Beach, Florida Keys - tropical beach - USA.](https://images.trvl-media.com/place/553248635976468855/342969f8-bf72-47fd-9555-c44c22f7719e.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Breezeswept Beach Estates While Breezeswept Beach Estates isn't home to many top sights, Cook Island and Newfound Harbor Keys 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 ![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 7.4/10 Good! (1,006 reviews) Very helpful staff Reviewed on Feb 3, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=4759500&PinnedHotelID=4759500&HadPinnedHotel=true®ionId=6177802) [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=4759500&PinnedHotelID=4759500&HadPinnedHotel=true®ionId=6177802) ![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 $405 CA $500 total Feb 10 - Feb 11 includes taxes & fees 8.8/10 Excellent! (1,003 reviews) The rooms were very clean! Views were beautiful. Pool was heated the cool days we were there. The breakfast was good and fresh. Loved the afternoon tea, hot chocolate, and coffee selections. Staff were very welcoming! Reviewed on Feb 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=10%2F02%2F2026&endDate=11%2F02%2F2026&selected=5561465&PinnedHotelID=5561465&HadPinnedHotel=true®ionId=6177802) ![Sugarloaf Key Hotel at KOA Resort](https://images.trvl-media.com/lodging/102000000/101140000/101135800/101135765/3a7e709a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sugarloaf Key Hotel at KOA Resort 251 Co Rd 939 Summerland Key FL 9.6/10 Exceptional! (481 reviews) The staff were wonderful, seam-less check. Immaculate and spacious rooms! I would just add a multi use counter top toaster oven seeing as there is no oven. Reviewed on Feb 4, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=101135765&PinnedHotelID=101135765&HadPinnedHotel=true®ionId=6177802) [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=101135765&PinnedHotelID=101135765&HadPinnedHotel=true®ionId=6177802) [See all 607 properties in Summerland Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®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 ![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 $85 per adult **88%** of travellers recommend [](https://expedia.ca/things-to-do/historic-key-west-old-town-trolley-hop-on-hop-off-tour.a191537.activity-details) ![12-Hours Day Trip in Key West from Miami](https://mediaim.expedia.com/localexpert/599608/0a5f7b52-4c57-40ec-80e7-716ee9b4b224.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Full Day Trip in Key West from Miami CA $37 per adult [](https://expedia.ca/things-to-do/full-day-trip-in-key-west-from-miami.a599608.activity-details) ![Passengers enjoying the shade on the Conch Tour Train in Key West](https://mediaim.expedia.com/localexpert/191535/9b448a2f-ece5-45c7-be77-f9172888dc8f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Key West Conch Tour Train CA $63 per adult **88%** of travellers recommend [](https://expedia.ca/things-to-do/key-west-conch-tour-train.a191535.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