Title: Luxury Florida Keys Vacation Packages 2026/2026 | Expedia.ca ![](https://images.trvl-media.com/place/6246822/f00ad239-b8ad-4f0c-b162-acc6426db1e2.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Top Luxury Florida Keys 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 ## Flight and Luxury hotel deals in Florida Keys Price found within the past 48 hours. Click for updated prices. ![Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton](https://images.trvl-media.com/lodging/2000000/1170000/1169600/1169583/16bbce87_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton CA $1,582 per person Jan 14 - Jan 21 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 8.8/10 Excellent! (1,275 reviews) Excellent experience. Excellent staff Ultra clean All in all, great location, ambiance and value. Reviewed on Dec 7, 2025 ![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 $1,789 per person Jan 14 - Jan 21 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 8/10 Very Good! (1,003 reviews) Beautiful balcony and porch views. Reviewed on Dec 8, 2025 ![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/2efaf74f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Tranquility Bay Beachfront Hotel and Resort CA $2,479 per person Jan 14 - Jan 21 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 8.8/10 Excellent! (1,003 reviews) I was overcharged for my room Reviewed on Dec 7, 2025 ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort CA $1,767 per person Jan 21 - Jan 27 found 5 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Miami (MIA) 9/10 Wonderful! (108 reviews) Beautiful room, stunning views Reviewed on Nov 19, 2025 ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cheeca Lodge & Spa Matecumbe CA $3,666 per person Jan 14 - Jan 21 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) Everything was awsome Reviewed on Dec 7, 2025 Don't see what you're looking for? See all available trips from Columbus to Florida Keys [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-09/2026-01-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury holidays in Florida Keys Price found within the past 48 hours. Click for updated prices. ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cheeca Lodge & Spa Matecumbe CA $3,666 per person Jan 14 - Jan 21 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) Everything was awsome Reviewed on Dec 7, 2025 Don't see what you're looking for? See all available trips from Columbus to Florida Keys [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-09/2026-01-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury holidays in Florida Keys Price found within the past 48 hours. Click for updated prices. ![Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton](https://images.trvl-media.com/lodging/2000000/1170000/1169600/1169583/16bbce87_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton CA $975 per person Feb 23 - Feb 26 found 21 hours ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 8.8/10 Excellent! (1,275 reviews) Excellent experience. Excellent staff Ultra clean All in all, great location, ambiance and value. Reviewed on Dec 7, 2025 ![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 $1,722 per person Feb 12 - Feb 15 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Miami (MIA) 8/10 Very Good! (1,003 reviews) Beautiful balcony and porch views. Reviewed on Dec 8, 2025 ![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/2efaf74f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Tranquility Bay Beachfront Hotel and Resort CA $1,837 per person Feb 15 - Feb 18 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.8/10 Excellent! (1,003 reviews) I was overcharged for my room Reviewed on Dec 7, 2025 Don't see what you're looking for? See all available trips from Columbus to Florida Keys [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-09/2026-01-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury holidays in Florida Keys 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 $1,680 per person Feb 15 - Feb 19 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8/10 Very Good! (1,003 reviews) Beautiful balcony and porch views. Reviewed on Dec 8, 2025 ![Tranquility Bay Beachfront Hotel and Resort](https://images.trvl-media.com/lodging/1000000/120000/117100/117099/2efaf74f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Tranquility Bay Beachfront Hotel and Resort CA $2,216 per person Feb 15 - Feb 19 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.8/10 Excellent! (1,003 reviews) I was overcharged for my room Reviewed on Dec 7, 2025 ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cheeca Lodge & Spa Matecumbe CA $3,235 per person Feb 15 - Feb 19 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) Everything was awsome Reviewed on Dec 7, 2025 Don't see what you're looking for? See all available trips from Columbus to Florida Keys [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-09/2026-01-16/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the perfect luxury Florida Keys vacation with Expedia #### What are some benefits when booking luxury Florida Keys vacations? When you book a luxury Florida Keys vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax. #### How can I find all-inclusive luxury vacations in Florida Keys? If you're looking for something luxurious in Florida Keys, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together. #### Can I book a cheap luxury vacation? While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $975, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 36\. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first. #### Are there luxury spa vacations? Yes, luxury spa vacations are available and quite popular in Florida Keys. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search. #### What should I look for in a luxury family vacation in Florida Keys? When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Florida Keys. #### Can I book last-minute luxury vacations? Yes, last-minute bookings are often available in Florida Keys. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces. #### What can help me find the best luxury vacation deals in Florida Keys? You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Florida Keys or travelling to more obscure destinations altogether can often lead to lower prices. #### Can I book a luxury vacation that is fully refundable? Yes, fully refundable reservations are sometimes available on luxury vacation packages in Florida Keys. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking. #### Why should I book my luxury vacation with Expedia? When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings. ## Luxury Hotels in Florida Keys ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Oceans Edge Key West Resort, Hotel & Marina 5950 Peninsular Avenue Key West FL - 10 min drive from Duval Street Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ... 8.8/10 Excellent! (1,747 reviews) Very nice clean and big room. Great view over the pools and harbor. Reviewed on Dec 4, 2025 [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![The Marker Key West Harbor Resort](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/15d13ee3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Marker Key West Harbor Resort 200 William Street Key West FL - 10 min walk from Duval Street Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful ... 9/10 Wonderful! (1,000 reviews) Loved this hotel. Staff was very friendly, rooms were clean and property is very nice. Location and parking for hotel guests. Can say enough will definitely return. Reviewed on Dec 3, 2025 [](https://expedia.ca/Key-West-Hotels-The-Marker-Key-West-Harbor-Resort.h9148379.Hotel-Information) ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cheeca Lodge & Spa 81801 Overseas Highway, Mile Marker 82 Islamorada FL - 3 hours drive from Duval Street Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ... 9/10 Wonderful! (1,278 reviews) Property is beautiful with tons of amenities. The room was very nice and overall we were very happy. Here are a few of the issues we had though for full transparency. The beach is sand, but it's hard in a way that's a bit unnatural and doesn't flow into the water. There were weddings on two nights ... Reviewed on Dec 3, 2025 [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) [See all 8,448 properties in Florida Keys](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6023765) 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. ## 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) ### Top Luxury Vacation Destinations > - [Luxury vacations in India ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/80/India) > - [Luxury vacations in France ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/59/France) > - [Luxury vacations in Switzerland ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/174/Switzerland) > - [Luxury vacations in Canada ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/31/Canada) > - [Luxury vacations in Jamaica ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/88/Jamaica) > - [Luxury vacations in Italy ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/86/Italy) > - [Luxury vacations in New Zealand ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/133/New-Zealand) > - [Luxury vacations in the Maldives ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/109/Maldives) > - [Luxury vacations in Costa Rica ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/42/Costa-Rica) > - [Luxury vacations in Florida Keys ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6023765/Florida-Keys) > - [Luxury vacations in Mexico ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/117/Mexico) > - [Luxury vacations in the Caribbean ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6022969/Caribbean) > - [Luxury vacations in Zanzibar ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/4186/Zanzibar) > - [Luxury vacations in Cancun ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/179995/Cancun) > - [Luxury vacations in Kerala ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/602187/Kerala) > - [Luxury vacations in Australia ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/10/Australia) > - [Luxury vacations in Puglia ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6048562/Puglia) > - [Luxury vacations in Cuba ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/44/Cuba) > - [Luxury vacations in Cyprus ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/45/Cyprus) ## More Vacations Ideas [Flights to Florida Keys ](https://expedia.ca/Cheap-Flights-To-Florida-Keys.d6023765.Travel-Guide-Flights)[ Florida Keys Hotels ](https://expedia.ca/Florida-Keys-Hotels.d6023765.Travel-Guide-Hotels)[ Florida Keys Vacation Rentals ](https://expedia.ca/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)[ Florida Keys Car Rentals ](https://expedia.ca/Car-Rentals-In-Florida-Keys.d6023765.Car-Rental-Guide)[ Florida Keys Vacations ](https://expedia.ca/Florida-Keys.d6023765.Destination-Travel-Guides)[ Things to do in Florida Keys ](https://expedia.ca/Things-To-Do-In-Florida-Keys.d6023765.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