Title: Kid friendly Vacations in Windley Key 2025/2026 | 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 Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## 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. ![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 $1,433 per person Jan 10 - Jan 15 found 4 hours ago Roundtrip flight included Hamilton (YHM) to Miami (MIA) 8.6/10 Excellent! (1,273 reviews) The beach access was top tier. The amenities and service provided on the beach was immaculate. Will return Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-15/?FromAirport=YHM&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=49851&paandie=true&HotelClass=40&dealMarker=2Ibk0OHVt_n8cXiRFYK10Dyp1haoDWMVj0q9_jmQZx2EOwI8JhlmFO_UY7dT0Whs) ![The Shelborne By Proper, a Member of Design Hotels](https://images.trvl-media.com/lodging/1000000/30000/25500/25451/e49031f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shelborne By Proper, a Member of Design Hotels South Beach CA $2,302 per person Dec 28 - Jan 1 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Miami (MIA) 9.8/10 Exceptional! (39 reviews) Great hotel. Clearly freshly refurbished and excellent facilities. Staff were extremely attentive - everyone we bumped into in the lift, for example, even junior team members, asked how we were and whether there was anything that they could do to improve our stay. Shows a great culture! Only downsides are a bar that shuts very early (10pm) and a LOT of mosquitoes in the outdoor pool area - they give bug spray it we had to retreat late afternoon or after rain. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2026-01-01/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=25451&paandie=true&HotelClass=40&dealMarker=YrECUntz0aYVWoR8SqwNHUiemLvsKchLFwpCNRY3uhEbFC3tUdOG420Ikkyh2jrz) ![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 $19,679 per person Dec 29 - Jan 3 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 8/10 Very Good! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-03/?FromAirport=YMQ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&HotelClass=40&dealMarker=YrECUntz0aYVWoR8SqwNHZGjdlGGWJCQZnXSOEfLU32jRIgsO832XUhLHt037oB3) ![ANDAZ MIAMI BEACH, BY HYATT](https://images.trvl-media.com/lodging/1000000/170000/166700/166633/301bd9bb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### ANDAZ MIAMI BEACH, BY HYATT Mid Beach CA $3,067 per person Dec 4 - Dec 8 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 9.6/10 Exceptional! (80 reviews) Everything was excellent Reviewed on Oct 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-08/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=166633&paandie=true&HotelClass=40&dealMarker=ewGxJfy818B9zBgWgA_KKwjyiw9JTKrcZuiwbcguNAxljKGgNxhaaMUmYPjrkjb1) ![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 $6,149 per person Dec 29 - Jan 3 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 9.4/10 Exceptional! (1,333 reviews) The best for solo or family. Vibes were great, views were amazing, healthy food, great relaxing stay. Staff went above and beyond especially “Yasmin” was one of their BEST staff members. She made sure our stay was memorable. Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-03/?FromAirport=YMQ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1790087&paandie=true&HotelClass=40&dealMarker=74MML7436B-GsDKZYT4IfDVLwdsZynOmzTzEzjsmzYMGMdpcKmeXfnLKDcVkIdoq) 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/2025-11-19/2025-11-26/?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. ![ANDAZ MIAMI BEACH, BY HYATT](https://images.trvl-media.com/lodging/1000000/170000/166700/166633/301bd9bb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### ANDAZ MIAMI BEACH, BY HYATT Mid Beach CA $3,067 per person Dec 4 - Dec 8 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 9.6/10 Exceptional! (80 reviews) Everything was excellent Reviewed on Oct 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-04/2025-12-08/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=166633&paandie=true&HotelClass=50&dealMarker=ewGxJfy818B9zBgWgA_KKwjyiw9JTKrcZuiwbcguNAxljKGgNxhaaMUmYPjrkjb1) ![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 $19,679 per person Dec 29 - Jan 3 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 8/10 Very Good! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-03/?FromAirport=YMQ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&HotelClass=50&dealMarker=YrECUntz0aYVWoR8SqwNHZGjdlGGWJCQZnXSOEfLU32jRIgsO832XUhLHt037oB3) ![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 $6,149 per person Dec 29 - Jan 3 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 9.4/10 Exceptional! (1,333 reviews) The best for solo or family. Vibes were great, views were amazing, healthy food, great relaxing stay. Staff went above and beyond especially “Yasmin” was one of their BEST staff members. She made sure our stay was memorable. Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-03/?FromAirport=YMQ&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1790087&paandie=true&HotelClass=50&dealMarker=74MML7436B-GsDKZYT4IfDVLwdsZynOmzTzEzjsmzYMGMdpcKmeXfnLKDcVkIdoq) 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/2025-11-19/2025-11-26/?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. ![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 $1,524 per person Dec 30 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 9.4/10 Exceptional! (390 reviews) Clean Room Beach View Reviewed on Oct 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-30/2026-01-02/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=120299&paandie=true&HotelClass=40&dealMarker=onrlFngI2QN6NnkNInDwRTSnWphgI-ceB-fdIsTQV8Q0C0QqyCNm0bjmfVl3B-6P) ![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 $6,972 per person Dec 22 - Dec 25 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8/10 Very Good! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-22/2025-12-25/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&HotelClass=40&dealMarker=YrECUntz0aYVWoR8SqwNHZVViF1YT7AtnO2ShI-MVLr6vMrPzA2YTTuNaSLNQDWS) ![The Shelborne By Proper, a Member of Design Hotels](https://images.trvl-media.com/lodging/1000000/30000/25500/25451/e49031f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shelborne By Proper, a Member of Design Hotels South Beach CA $1,901 per person Dec 30 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 9.8/10 Exceptional! (39 reviews) Great hotel. Clearly freshly refurbished and excellent facilities. Staff were extremely attentive - everyone we bumped into in the lift, for example, even junior team members, asked how we were and whether there was anything that they could do to improve our stay. Shows a great culture! Only downsides are a bar that shuts very early (10pm) and a LOT of mosquitoes in the outdoor pool area - they give bug spray it we had to retreat late afternoon or after rain. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-30/2026-01-02/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=25451&paandie=true&HotelClass=40&dealMarker=YrECUntz0aYVWoR8SqwNHcaIRUZowD5xxk-ZuRA42WNVh8rso3OhMiZURmO2Ae-v) 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/2025-11-19/2025-11-26/?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. ![Nobu Hotel Miami Beach](https://images.trvl-media.com/lodging/17000000/16260000/16256600/16256597/06483b1e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Nobu Hotel Miami Beach Mid Beach CA $852 per person Nov 24 - Nov 28 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.6/10 Excellent! (1,256 reviews) 10/10 will return very soon Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-28/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=16256597&paandie=true&dealMarker=vGwP6vEw_IQ8qjurWtu0fEf4kAUAGLuIUpSlZ4dXJn1UnhwCwZ66Nfsw1oG9gWFR) ![The Shelborne By Proper, a Member of Design Hotels](https://images.trvl-media.com/lodging/1000000/30000/25500/25451/e49031f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shelborne By Proper, a Member of Design Hotels South Beach CA $2,302 per person Dec 28 - Jan 1 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Miami (MIA) 9.8/10 Exceptional! (39 reviews) Great hotel. Clearly freshly refurbished and excellent facilities. Staff were extremely attentive - everyone we bumped into in the lift, for example, even junior team members, asked how we were and whether there was anything that they could do to improve our stay. Shows a great culture! Only downsides are a bar that shuts very early (10pm) and a LOT of mosquitoes in the outdoor pool area - they give bug spray it we had to retreat late afternoon or after rain. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2026-01-01/?FromAirport=YTO&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=25451&paandie=true&dealMarker=YrECUntz0aYVWoR8SqwNHUiemLvsKchLFwpCNRY3uhEbFC3tUdOG420Ikkyh2jrz) ![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 $16,156 per person Dec 30 - Jan 3 found 22 hours ago Roundtrip non-stop flight included Montreal (YUL) to Miami (MIA) 8/10 Very Good! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-12-30/2026-01-03/?FromAirport=YUL&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12316590&paandie=true&dealMarker=YrECUntz0aYVWoR8SqwNHfb-92x-X0e9PY7kXzurJEM66idJdLo2Wx74oebSrcv5) 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/2025-11-19/2025-11-26/?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 > - 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[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. 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