Title: Kid friendly Vacations in Florida Keys 2026 | Expedia.ca ![](https://images.trvl-media.com/place/6246822/f00ad239-b8ad-4f0c-b162-acc6426db1e2.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Florida Keys Kid friendly Vacations ## 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 Kid friendly hotel deals in Florida Keys Price found within the past 48 hours. Click for updated prices. ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Siesta Resort & Villas Matecumbe CA $1,240 per person Jan 25 - Jan 30 found 9 hours ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 8.6/10 Excellent! (1,000 reviews) Clean, spacious room. Property was beautiful. Staff friendly. Nice to be able to go to the sister resorts as well. Reviewed on Dec 15, 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 $1,298 per person Feb 18 - Feb 21 found 1 day ago Roundtrip non-stop flight included Hartford (BDL) to Miami (MIA) 8/10 Very Good! (1,006 reviews) Outstanding in every wat Reviewed on Dec 15, 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 $1,740 per person Jan 18 - Jan 25 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9/10 Wonderful! (108 reviews) Overall it was a nice stay. They didn’t have elevators so it was rough carrying up full suitcases and we did find a couple of fish hooks in our rooms as those the maids only did what they must did. It wasn’t a thorough cleaning of the room. The staff was nice and very friendly. Food was good We would probably stay again Reviewed on Dec 15, 2025 ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Oceans Edge Key West Resort, Hotel & Marina CA $1,635 per person Feb 18 - Feb 21 found 1 day ago Roundtrip non-stop flight included Hartford (BDL) to Key West (EYW) 9/10 Wonderful! (1,736 reviews) I was only given a room upgrade after making a complaint before the stay (a link to a website did not work). Silly me but I was also unaware of the $52 per day “resort fee”. I probably could have parked on the street and avoided the $30 daily parking fee. The little fridge took some figuring to lower the temp but after a couple of days it eventually went back up to 70 degrees all its own, so some food went bad and my cold drinks became close to room temp. The toilet was a wrestling match but that’s on me as I did not complain about it. The service in the restaurant was indifferent but the food was very good. I only ate there once. It’s not a bad place by any stretch but I doubt I’d return! Who knows? Reviewed on Dec 17, 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 $2,340 per person Feb 18 - Feb 21 found 1 day ago Roundtrip non-stop flight included Hartford (BDL) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) Ate dinner at the Asian restaurant Nikki- the Chilean Seabass was delicious andmelted with every bite. And service was good Reviewed on Dec 18, 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/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Kid friendly 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 $2,340 per person Feb 18 - Feb 21 found 1 day ago Roundtrip non-stop flight included Hartford (BDL) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) Ate dinner at the Asian restaurant Nikki- the Chilean Seabass was delicious andmelted with every bite. And service was good Reviewed on Dec 18, 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/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Kid friendly 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 $1,298 per person Feb 18 - Feb 21 found 1 day ago Roundtrip non-stop flight included Hartford (BDL) to Miami (MIA) 8/10 Very Good! (1,006 reviews) Outstanding in every wat Reviewed on Dec 15, 2025 ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Oceans Edge Key West Resort, Hotel & Marina CA $1,635 per person Feb 18 - Feb 21 found 1 day ago Roundtrip non-stop flight included Hartford (BDL) to Key West (EYW) 9/10 Wonderful! (1,736 reviews) I was only given a room upgrade after making a complaint before the stay (a link to a website did not work). Silly me but I was also unaware of the $52 per day “resort fee”. I probably could have parked on the street and avoided the $30 daily parking fee. The little fridge took some figuring to lower the temp but after a couple of days it eventually went back up to 70 degrees all its own, so some food went bad and my cold drinks became close to room temp. The toilet was a wrestling match but that’s on me as I did not complain about it. The service in the restaurant was indifferent but the food was very good. I only ate there once. It’s not a bad place by any stretch but I doubt I’d return! Who knows? Reviewed on Dec 17, 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 $2,340 per person Feb 18 - Feb 21 found 1 day ago Roundtrip non-stop flight included Hartford (BDL) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) Ate dinner at the Asian restaurant Nikki- the Chilean Seabass was delicious andmelted with every bite. And service was good Reviewed on Dec 18, 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/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Kid friendly 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 $1,477 per person Feb 19 - Feb 23 found 2 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Miami (MIA) 8/10 Very Good! (1,006 reviews) Outstanding in every wat Reviewed on Dec 15, 2025 ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Oceans Edge Key West Resort, Hotel & Marina CA $2,045 per person Feb 19 - Feb 23 found 2 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Key West (EYW) 9/10 Wonderful! (1,736 reviews) I was only given a room upgrade after making a complaint before the stay (a link to a website did not work). Silly me but I was also unaware of the $52 per day “resort fee”. I probably could have parked on the street and avoided the $30 daily parking fee. The little fridge took some figuring to lower the temp but after a couple of days it eventually went back up to 70 degrees all its own, so some food went bad and my cold drinks became close to room temp. The toilet was a wrestling match but that’s on me as I did not complain about it. The service in the restaurant was indifferent but the food was very good. I only ate there once. It’s not a bad place by any stretch but I doubt I’d return! Who knows? Reviewed on Dec 17, 2025 ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Southernmost Beach Resort and Guesthouses Old Town Key West CA $2,003 per person Feb 19 - Feb 23 found 2 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Key West (EYW) 8.6/10 Excellent! (2,844 reviews) Great experience. Will definitely go back! Reviewed on Dec 16, 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/2026-01-18/2026-01-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the perfect family-friendly vacation in Florida Keys with Expedia #### What are some benefits of booking a family-friendly vacation? Whether it's luxurious or cheap, family vacations in Florida Keys are among the most memorable experiences you'll ever have with your family. It can be a great way to bond and explore new destinations with the people you love most. Plus, it's easy to keep an eye on your little ones without having to worry about how they are with a sitter back home. You may even meet some other families and establish long-lasting friendships. #### How can I find the best family-friendly vacations? Using search filters makes finding the perfect family-friendly vacation easy. You can implement the search filter for family-friendly accommodations specifically, but that's just the beginning. You'll also find search filters for price range along with the desired number of bedrooms, so you can ensure you have enough space for everyone you want to bring to Florida Keys. #### Are there cheap family vacations to Florida Keys? Price varies quite a bit, ranging from to . The price you'll be paying depends on a variety of factors, and you can filter for them all. You can implement a filter for your budget limitations and also remove any 4- and 5-star stays from your search. You can even filter by accommodation type, which can present you with cheap alternatives to what is typically considered standard. #### When should I book family-friendly vacation packages? The right time to book family-friendly vacation packages in Florida Keys depends on what you're looking for. If you're looking to save, booking during least popular month tends to be cheaper compared to the rest of the year, though that's not always a guarantee. Keep in mind that the off-season and the busy season differ from place to place, with family-friendly vacations in Canada being very different compared to options in France and Spain, for example. #### Can I book an all-inclusive family vacation in Florida Keys? Yes, you'll find plenty of all-inclusive family vacation packages for Florida Keys. To see what's available, just select the all-inclusive filter on your search. #### How can I book the best family activity vacation? If you're looking to make the most out of the available activities in Florida Keys, you'll need to consider what your family likes to do. Cater your itinerary to your family's interests, and you'll create memories that you and your kids will hold on to for the rest of your lives whether it's family ski vacations in Florida Keys or something a bit more relaxed. #### Can I find luxury family vacations in Florida Keys? If you're looking for a luxury family vacation to Florida Keys, you can use search filters to find the best options available. Activate the filter for 5-star packages to only see the best of the best. Plus, you'll find a range of first-class flights available to make even the journey there top-of-the-line. #### How can I search for family vacation deals? Finding deals is easy when you take advantage of the array of available search filters. You can set budget limitations and remove 4- and 5-star options from your search. If you don't want to miss out on your favourite amenities, however, you can consider travelling during , which often have lower prices because of the off-season in Florida Keys. #### Can I book a family vacation package that is fully refundable? If you're looking for a fully refundable reservation, you won't have to look far on Expedia. Quite a few properties in Florida Keys are fully refundable. You can search for this feature, but always make sure to check the specific property's policies and requirements before booking. #### Why should I book my family trip with Expedia? When you book with Expedia, you can book your accommodation and your flight together, with some discounts available for doing both at once. Additionally, you may be able to enjoy special discounts with Expedia Rewards that will earn you points you can then put toward discounts for subsequent bookings. ## Kid friendly Hotels in Florida Keys ![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hawks Cay Resort 61 Hawks Cay Blvd Marathon FL - 2 hours drive from Duval Street Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ... 8/10 Very Good! (1,002 reviews) The resort was beautiful, the room was nice and clean although the day after we arrived housekeeping did not come to our room to empty garbages and give us fresh towels and had to ask at front desk. But after that it was not a problem. Also 1 morning we woke up to no water in our room and had to ... Reviewed on Dec 14, 2025 [](https://expedia.ca/Marathon-Hotels-Hawks-Cay-Resort.h6068.Hotel-Information) ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Southernmost Beach Resort and Guesthouses 1319 Duval Street Key West FL - 11 min walk from Duval Street Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ... 8.6/10 Excellent! (2,933 reviews) Beach and pool - bar, music and great staff Reviewed on Dec 14, 2025 [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Islander Resort 82100 Overseas Highway Islamorada FL - 3 hours drive from Duval Street Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ... 9.2/10 Wonderful! (1,006 reviews) The resort was perfect Everyone from checking in and during our stay could not have been nicer and helpful Reviewed on Dec 17, 2025 [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) [See all 8,415 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 Kid friendly Vacation Destinations > - [Family vacations in the United Kingdom ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/190/United-Kingdom) > - [Family vacations in Bali ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/602651/Bali) > - [Family vacations in Ontario ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/2680/Ontario) > - [Family vacations in France ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/59/France) > - [Family vacations in Spain ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/166/Spain) > - [Family vacations in Paris ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/179898/Paris) > - [Family vacations in Switzerland ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/174/Switzerland) > - [Family vacations in Italy ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/86/Italy) > - [Family vacations in South Africa ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/165/South-Africa) > - [Family vacations in Victoria ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/1418/Victoria) > - [Family vacations in Scotland ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/11219/Scotland) > - [Family vacations in Alaska ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/203/Alaska) > - [Family vacations in Bournemouth ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/654/Bournemouth) > - [Family vacations in Philippines ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/145/Philippines) > - [Family vacations in Tenerife ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/6047194/Tenerife) > - [Family vacations in Australia ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/10/Australia) > - [Family vacations in Egypt ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/52/Egypt) > - [Family vacations in Tuscany ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/601686/Tuscany) > - [Family vacations in Panama ](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/142/Panama) ## 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