Title: Cutthroat Harbor Estates Vacation Packages & Trips 2025 from $470 | Expedia.ca [Hotels in Cutthroat Harbor Estates](https://expedia.ca/Cutthroat-Harbor-Estates-Summerland-Key-Hotels.0-n553248635976481702-0.Travel-Guide-Filter-Hotels)[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)[Cutthroat Harbor Estates Car Rentals](https://expedia.ca/Car-Rentals-In-Cutthroat-Harbor-Estates.d553248635976481702.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Cutthroat Harbor Estates 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 ## Top Holiday Package Deals in Cutthroat Harbor Estates Price found within the past 48 hours. Click for updated prices. ![Pelican Grand Beach Resort - A Noble House Resort](https://images.trvl-media.com/lodging/1000000/50000/49900/49851/12ee1484_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pelican Grand Beach Resort - A Noble House Resort East Fort Lauderdale CA $971 per person Oct 22 - Oct 27 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Miami (MIA) 8.8/10 Excellent! (1,224 reviews) The outdated exterior made me nervous initially, but as soon as I walked in I was pleasantly surprised by how beautiful the property was - it even smelled great. Staff was very nice throughout my stay, the rooms were beautiful, Reviewed on Sep 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-10-22/2025-10-27/?FromAirport=YHM&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=49851&paandie=true&dealMarker=2DiU_P4-nLNyF9F3ne5-o9G2h9JTjhsrojuFvhfX4yxFbmF2z8NqoNrUVhQi22au) ![Cavalier Hotel South Beach](https://images.trvl-media.com/lodging/1000000/20000/13600/13579/a4231273_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cavalier Hotel South Beach South Beach CA $1,250 per person Dec 4 - Dec 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.4/10 Very Good! (1,001 reviews) Great staff. Nice rooms close to beach Reviewed on Sep 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-09/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=13579&paandie=true&dealMarker=zaGoH4BVnK1VySrLKPUQYFBxmb2qKE2UksHKkyd0VFlvw0Yjrt4FC4TP9Ftaz9L8) ![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 $1,778 per person Dec 4 - Dec 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 9.2/10 Wonderful! (311 reviews) Clean room, staff, Beach View Reviewed on Sep 9, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-09/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=120299&paandie=true&dealMarker=zaGoH4BVnK1VySrLKPUQYFBxmb2qKE2UksHKkyd0VFlB7LF8IAA8O9n7olKwfam1) ![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 $1,162 per person Dec 4 - Dec 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.4/10 Very Good! (1,794 reviews) The staff excellent very accommodation Henry excellent guest services Reviewed on Sep 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-09/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=575859&paandie=true&dealMarker=9DAksQPwR4dwRZ5oJ36EtkOu5t7zlP_cpBC_M3hzEgvqbsQwF0USr5-rYVLH9-5d) ![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 $1,088 per person Dec 4 - Dec 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.2/10 Very Good! (1,432 reviews) This was so nice to stay here. I would stay there again anytime Reviewed on Sep 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-09/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=62824&paandie=true&dealMarker=9DAksQPwR4dwRZ5oJ36EtpPiqap-oEajdOq77A2bzzdPGAzb4GLvgFARq0zVBZpc) ## Where to stay in Cutthroat Harbor Estates Find the best Cutthroat Harbor Estates areas and neighborhoods for the activities you enjoy most. [Learn more about Cutthroat Harbor Estates](https://expedia.ca/Summerland-Key-Cutthroat-Harbor-Estates.dx553248635976481702) ![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) ### Breezeswept Beach Estates While Breezeswept Beach Estates isn't home to many top sights, Cook Island and Crab Key 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) ## Cutthroat Harbor Estates 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 $232 CA $342 total Sep 18 - Sep 19 includes taxes & fees [](https://expedia.ca/Hotel-Search?startDate=18%2F09%2F2025&endDate=19%2F09%2F2025&selected=16202992&PinnedHotelID=16202992&HadPinnedHotel=true®ionId=553248635976481702) ![Hilton Garden Inn Key West / The Keys Collection](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/5c83029c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Garden Inn Key West / The Keys Collection 3850 N Roosevelt Blvd, Key West, FL Fully refundableReserve now, pay when you stay CA $152 CA $210 total Sep 21 - Sep 22 includes taxes & fees [](https://expedia.ca/Hotel-Search?startDate=21%2F09%2F2025&endDate=22%2F09%2F2025&selected=1376&PinnedHotelID=1376&HadPinnedHotel=true®ionId=553248635976481702) ![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 $191 CA $285 total Sep 14 - Sep 15 includes taxes & fees [](https://expedia.ca/Hotel-Search?startDate=14%2F09%2F2025&endDate=15%2F09%2F2025&selected=25865&PinnedHotelID=25865&HadPinnedHotel=true®ionId=553248635976481702) [See all 1,387 properties in Cutthroat Harbor Estates](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F09%2F2025&endDate=13%2F09%2F2025®ionId=553248635976481702) 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) ## Frequently asked questions ### How much does a Cutthroat Harbor Estates vacation package cost? > From as low as CA $971. Yes, you read that right. Our Cutthroat Harbor Estates packages are an easy way to make your budget go further. Bundle your hotels, flights and car rentals and get to know this wonderful destination. ### How do I get a cheap travel package to Cutthroat Harbor Estates? > Lock in flights that fit in with your schedule, add a hotel to your booking and watch the savings pile up with a Cutthroat Harbor Estates vacation package. It's as easy as that! From hotels and flights to tours and rental cars, Expedia makes traveling cheaply a cinch. And with over 550 airlines and 1,000,000 hotels throughout the world to select from, you won't be short of choice. ### What are the top hotels in Cutthroat Harbor Estates? > Get your vacation off to a fantastic start by booking a stay at [Oceanfront Home With Large Private Deck With Boat Dockage](https://www.expedia.ca/Cudjoe-Key-Hotels-Oceanfront-Home-With-Large-Private-Deck-With-Boat-Dockage.h65464375.Hotel-Information). It's one of most popular properties in Cutthroat Harbor Estates. Another option is [Dazzling Bayfront Home With 2 Boat Docks](https://www.expedia.ca/Cudjoe-Key-Hotels-Dazzling-Bayfront-Home-W-2-Boat-Docks.h69746699.Hotel-Information). ### How far in advance should I book my Cutthroat Harbor Estates vacation? > Browse Expedia to compare international flights as soon as you know your travel dates. You can usually purchase a seat up to 12 months before departure. If you don't see your preferred carrier, or you've left things to the last moment, don't despair. Cheap tickets to Cutthroat Harbor Estates sometimes emerge just weeks before the date of departure. ### What does an Expedia Cutthroat Harbor Estates travel package include? > Expedia has all you need to organize your Cutthroat Harbor Estates trip, but how you structure your package is your choice. Pick from a combination of rental cars, flights and hotels. Searching for some tours or activities to keep you busy? Once you've made your booking, you can add them on too. Whatever your budget or style, there's a package deal to meet your needs. ### What should I know before booking a Cutthroat Harbor Estates travel package? > Find deals that fit your budget with an Expedia package. Flights, hotels, rental cars — we have them all. You'll save big dollars just for combining your bookings. Whether you're taking off on a ski adventure or sipping cocktails on a beach, your dream vacation is only a few clicks away. ### Can I choose my airline with a Cutthroat Harbor Estates Expedia vacation package? > Yes, the choice is yours. Expedia has access to more than 550 partner airlines around the world, so you can tailor your Cutthroat Harbor Estates adventure according to your needs and budget. ### If I'm not able to travel, can I cancel my Cutthroat Harbor Estates vacation package? > Your situation can change in a flash, so yes, you can. You may be able to cancel or alter your Cutthroat Harbor Estates vacation package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, hotel or airline may charge additional fees. Want more information? Take a look at our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105). We're here to help make sure your getaway goes off without a hitch. ## Other vacations you might like - Vacations and trips to popular cities - Best vacation destinations by month - [Las Vegas Vacations](https://expedia.ca/Las-Vegas.d178276.Destination-Travel-Guides) - [New York Vacations](https://expedia.ca/New-York.d178293.Destination-Travel-Guides) - [Orlando Vacations](https://expedia.ca/Orlando.d178294.Destination-Travel-Guides) - [Los Angeles Vacations](https://expedia.ca/Los-Angeles.d178280.Destination-Travel-Guides) - [Miami Vacations](https://expedia.ca/Miami.d178286.Destination-Travel-Guides) - [San Francisco Vacations](https://expedia.ca/San-Francisco.d178305.Destination-Travel-Guides) - [New Orleans Vacations](https://expedia.ca/New-Orleans.d178292.Destination-Travel-Guides) - [Chicago Vacations](https://expedia.ca/Chicago.d178248.Destination-Travel-Guides) - [Fort Lauderdale Vacations](https://expedia.ca/Fort-Lauderdale.d601750.Destination-Travel-Guides) - [Boston Vacations](https://expedia.ca/Boston.d178239.Destination-Travel-Guides) - [January Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-january) - [February Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-february) - [March Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-march) - [April Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-april) - [May Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-may) - [June Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-june) - [July Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-july) - [August Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-august) - [September Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-september) - [October Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-october) - [November Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-november) - [December Vacations and Deals](https://www.expedia.ca/lp/b/where-to-go/vacations-december) \* 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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)