Title: Kid friendly Vacations in Windley Key 2026 | Expedia.ca ![](https://images.trvl-media.com/place/553248635997958830/30b22f53-286f-436b-ae7a-d035c9062e6c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windley Key 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 Windley Key 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 $1,223 per person Apr 10 - Apr 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.6/10 Excellent! (1,000 reviews) excellent location very nice simple breakfast close to liz’s of activities great poool Reviewed on Feb 2, 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 $19,508 per person Mar 14 - Mar 21 found 9 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Miami (MIA) 8/10 Very Good! (1 review) ![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 $2,545 per person Apr 4 - Apr 7 found 1 day ago Roundtrip flight included Hamilton (YHM) 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 ![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 $2,216 per person Apr 10 - Apr 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) We stayed in Premiere ocean front king. The weather was unusually cold and windy so we didn't get to experience the resort as we had hoped. The staff at restaurants were very courteous and service prompt. Beach is lovely -- although not a natural sand beach. Gym could have been larger. We found spa unimpressive for a 5 star resort and its pricing. Golf course was poorly maintained and clubs ancient. We found quality of room more 4 star than 5 star. Only irritation was they put us in an accessible room without asking us and we had to request to be moved. There were plenty of rooms available and we were staying 4 nights. I found that disrespectful as though Expedia bookings get the less desirable rooms. Beaware of this potential practice. Not sure if Premiere room is worth the extra price given overall resort. Reviewed on Feb 4, 2026 ![Isla Bella Beach Resort & Spa](https://images.trvl-media.com/lodging/25000000/24110000/24101800/24101706/f4f56036_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Isla Bella Beach Resort & Spa CA $2,382 per person Apr 10 - Apr 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 9.2/10 Wonderful! (1,055 reviews) Watch out for hidden fees! More than $30 a night for parking! Other add on expenses that should be included at a resort in this price range. The rooms are nice but a bit dated. Reviewed on Jan 31, 2026 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Kid friendly holidays in Windley Key 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 $2,216 per person Apr 10 - Apr 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) We stayed in Premiere ocean front king. The weather was unusually cold and windy so we didn't get to experience the resort as we had hoped. The staff at restaurants were very courteous and service prompt. Beach is lovely -- although not a natural sand beach. Gym could have been larger. We found spa unimpressive for a 5 star resort and its pricing. Golf course was poorly maintained and clubs ancient. We found quality of room more 4 star than 5 star. Only irritation was they put us in an accessible room without asking us and we had to request to be moved. There were plenty of rooms available and we were staying 4 nights. I found that disrespectful as though Expedia bookings get the less desirable rooms. Beaware of this potential practice. Not sure if Premiere room is worth the extra price given overall resort. Reviewed on Feb 4, 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 $19,508 per person Mar 14 - Mar 21 found 9 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Miami (MIA) 8/10 Very Good! (1 review) ![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 $2,545 per person Apr 4 - Apr 7 found 1 day ago Roundtrip flight included Hamilton (YHM) 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 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Kid friendly holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Miami Beach](https://images.trvl-media.com/lodging/1000000/80000/74600/74574/7ff98ba1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Miami Beach Mid Beach CA $977 per person Apr 8 - Apr 11 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8/10 Very Good! (1,120 reviews) Clean and friendly and close to the beach Reviewed on Feb 2, 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 $10,754 per person Mar 7 - Mar 10 found 1 day ago Roundtrip flight included Montreal (YMQ) to Miami (MIA) 8/10 Very Good! (1 review) ![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 $2,545 per person Apr 4 - Apr 7 found 1 day ago Roundtrip flight included Hamilton (YHM) 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 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Kid friendly holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![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 $767 per person Apr 12 - Apr 16 found 6 hours ago Roundtrip flight included Toronto (YYZ) 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 $12,917 per person Apr 22 - Apr 26 found 2 hours ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8/10 Very Good! (1 review) ![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 $1,122 per person Apr 9 - Apr 13 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 8.4/10 Very Good! (1,775 reviews) Hotel is on a great location and the breakfast is great. It’s a bit dated, but well maintained. Reviewed on Feb 4, 2026 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the perfect family-friendly vacation in Windley Key with Expedia #### What are some benefits of booking a family-friendly vacation? Whether it's luxurious or cheap, family vacations in Windley Key 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 Windley Key. #### Are there cheap family vacations to Windley Key? 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 Windley Key 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 Windley Key? Yes, you'll find plenty of all-inclusive family vacation packages for Windley Key. 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 Windley Key, 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 Windley Key or something a bit more relaxed. #### Can I find luxury family vacations in Windley Key? If you're looking for a luxury family vacation to Windley Key, 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 Windley Key. #### 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 Windley Key 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. ## 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 Windley Key ](https://expedia.ca/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[ Windley Key Hotels ](https://expedia.ca/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[ Windley Key Vacation Rentals ](https://expedia.ca/Windley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[ Windley Key Car Rentals ](https://expedia.ca/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)[ Windley Key Vacations ](https://expedia.ca/Windley-Key.d553248635976197663.Destination-Travel-Guides)[ Things to do in Windley Key ](https://expedia.ca/Things-To-Do-In-Windley-Key.d553248635976197663.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