Title: Windley Key Kid friendly Vacations 2026 | Expedia.com ![](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 Kid friendly Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 Kid friendly vacation packages in Windley Key Price found within the past 48 hours. Click for updated prices. ![6080 Design Hotel by Eskape Collection](https://images.trvl-media.com/lodging/26000000/25060000/25053200/25053134/80814d5a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 6080 Design Hotel by Eskape Collection Mid Beach Save 100% on your flight $333 per person Apr 25 - Apr 30 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.4/10 Very Good! (1,002 reviews) Very clean and taken care of Reviewed on Jan 26, 2026 ![Bay Breeze Premium Apartments By Eskape Collection](https://images.trvl-media.com/lodging/28000000/27610000/27603500/27603405/c37fc122_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bay Breeze Premium Apartments By Eskape Collection Save 100% on your flight $435 per person Apr 25 - Apr 30 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.6/10 Excellent! (189 reviews) The staff was courteous and helpful. The apartment was equipped with basic essentials. The area was quiet. I would suggest adding oven mittens in the kitchen as there was nothing to use to take the pan out of the oven with. Reviewed on Jan 21, 2026 ![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 $818 per person Apr 25 - Apr 30 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1,120 reviews) The Florida restaurant breakfast and dinner are excellent! Reviewed on Feb 6, 2026 ![EAST Miami Residences](https://images.trvl-media.com/lodging/79000000/78580000/78570600/78570563/dca879fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### EAST Miami Residences Downtown Miami $1,172 per person Apr 25 - Apr 30 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9/10 Wonderful! (84 reviews) Es la 3 vez que me hospedo y es excelente el trato, la hubicacion y las fascilidades. Reviewed on Jan 26, 2026 ![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 Save 100% on your flight $1,518 per person Mar 26 - Apr 1 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.6/10 Excellent! (1,000 reviews) I wouldn't hesitate to book a stay here, it met all our expectations and more. For two people the room was lovely & spacious, with a seperate lounge and dining/kitchen area & a balcony that caught the morning sun. We only stayed for two nights so was hard to make the most of all the amenities. We rented bikes and cycled around the area, chilled beside the pool area with complimentary beach towels & used the free shuttle service to the sister hotels on both nights. Location was great for us as a pit stop from Key West and Miami. Lots to see and do locally. Would definitely book again. Reviewed on Feb 11, 2026 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-13/2026-03-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Kid friendly vacations in Windley Key Price found within the past 48 hours. Click for updated prices. ![EAST Miami Residences](https://images.trvl-media.com/lodging/79000000/78580000/78570600/78570563/dca879fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### EAST Miami Residences Downtown Miami $1,172 per person Apr 25 - Apr 30 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9/10 Wonderful! (84 reviews) Es la 3 vez que me hospedo y es excelente el trato, la hubicacion y las fascilidades. Reviewed on Jan 26, 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 $11,343 per person Apr 9 - Apr 14 found 1 day ago Roundtrip flight included Boston (BOS) 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 Save 100% on your flight $1,947 per person Apr 23 - Apr 27 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.4/10 Exceptional! (1,365 reviews) Room very nice but not very well designed. Bed and couch on a riser- not the floor- requiring a step up to get to each. Everytime you got up at night- a light would come on and stay on for 10 minutes. Safety so you don’t fall- but should we really have a bed on a riser? Found the light on disruptive to getting back to sleep. Very dark room- not well lit at all. No makeup mirror Slippery marble floor shower- ask for a rubber mat- which we finally got the day before our stay ended Great access to pool and beach Great service in hotel and beach Great service from the house car Very pleasant staff Mini bar beverages not cold- required ice to chill No ice machine- but they brought the ice to you if you called and requested Nice roof top pool but music was too loud to enjoy. Could not eat at Watr restaurant - roof top-due to the loud music Reserved a shower room to freshen up after check out our last day- but did not get one- had to use the gym for getting cleaned up for our flight- lot of disorganization around this entire situation. No one ever offered and explanation on what happened- did not have time to investigate- trying ti get to airport. Great location and vibe- we enjoyed our stay but would not stay here again. Reviewed on Feb 11, 2026 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-13/2026-03-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Kid friendly vacations in Windley Key Price found within the past 48 hours. Click for updated prices. ![Solé Miami, A Noble House Resort](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803820/387d2cd6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Solé Miami, A Noble House Resort Ocean Four Save 100% on your flight $358 per person May 3 - May 6 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.4/10 Very Good! (1,935 reviews) staff was awesome, room was great, elevators extremely slow Reviewed on Feb 12, 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 $5,404 per person Mar 16 - Mar 19 found 1 day ago Roundtrip flight included Boston (BOS) 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 $1,296 per person May 7 - May 10 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.4/10 Exceptional! (1,365 reviews) Room very nice but not very well designed. Bed and couch on a riser- not the floor- requiring a step up to get to each. Everytime you got up at night- a light would come on and stay on for 10 minutes. Safety so you don’t fall- but should we really have a bed on a riser? Found the light on disruptive to getting back to sleep. Very dark room- not well lit at all. No makeup mirror Slippery marble floor shower- ask for a rubber mat- which we finally got the day before our stay ended Great access to pool and beach Great service in hotel and beach Great service from the house car Very pleasant staff Mini bar beverages not cold- required ice to chill No ice machine- but they brought the ice to you if you called and requested Nice roof top pool but music was too loud to enjoy. Could not eat at Watr restaurant - roof top-due to the loud music Reserved a shower room to freshen up after check out our last day- but did not get one- had to use the gym for getting cleaned up for our flight- lot of disorganization around this entire situation. No one ever offered and explanation on what happened- did not have time to investigate- trying ti get to airport. Great location and vibe- we enjoyed our stay but would not stay here again. Reviewed on Feb 11, 2026 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-13/2026-03-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Kid friendly vacations in Windley Key Price found within the past 48 hours. Click for updated prices. ![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 Save 100% on your flight $558 per person Apr 23 - Apr 27 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.4/10 Very Good! (1,775 reviews) Room service could be better. Did not clean even after asked to clean. Breakfast options were same for all days. Staff was very good. Excellent location. Reviewed on Feb 11, 2026 ![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 Save 100% on your flight $700 per person Mar 19 - Mar 23 found 1 day ago Roundtrip flight included Boston (BOS) 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 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 Save 100% on your flight $560 per person Apr 23 - Apr 27 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.2/10 Very Good! (1,491 reviews) Good staff, good room. Missing coffee in room and microwave Reviewed on Feb 13, 2026 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-13/2026-03-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## FAQs: family vacation packages in Windley Key #### How can I find the best family vacation packages in Windley Key? For fam-tastic vacation packages in Windley Key, check the family-friendly filter and add child-charming amenities, like water parks and pools. Read reviews written by other broods to be sure your chosen stay packs plenty of rest and play. #### How can I book family-friendly vacations in Windley Key on a budget? For family- and wallet-friendly trips, filter your search results by budget. You can also sort by price. When bringing the whole brigade on a budget, consider staying in low season or outside the city or. To save more coin, accommodation with a kitchen can be your friend—a bowl of pasta at home is always cheaper than feeding the team at a restaurant. #### What does a family trip to Windley Key cost? You could book your amazing family trip to Windley Key just $333\. But with so many brilliant breaks on offer, there’s something for every wallet. Prices and availability are subject to change. Additional terms may apply. #### Can I book an all-inclusive Windley Key family vacation package? Check the all-inclusive filter for an all-you-could-ever-wish-for family vacay. Click more of your favorite filters for even more extravagance. Perhaps an ocean view, spa, or hot tub. Maybe a water park, epic kids club, or activities galore. #### How can I plan a fun family vacation in Windley Key? Search for stays with kid-satisfying extras, like water parks, and teenage-friendly free Wi-Fi, so they can post about all their vacation adventures for all their buddies back home. Book up local attractions, excursions, and experiences—and they might even put their phone down for a few minutes. #### How can I find Windley Key family vacation deals? Delightful deals often dwell outside high season, so move your travel dates around for top deals. You can also book up a little away from the major Windley Key landmarks to save cash. Whenever you wish to travel, sort your search results by deals for the most brilliant bargains. #### Can I book a Windley Key family vacation package with free cancellation and/or flexible dates? Free cancellation makes for a hassle-free family vacation. Filter by payment option to find fully flexible trips, including buy now, pay later options. #### Why should I book my Windley Key family trip with Expedia? You can easily find fun for all the family with the super-handy filters. It’s easy to build your dream kid-friendly vacation in just a few clicks. And you can bundle your accommodation, airfare, and car rental in just a few more. ## 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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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Vacation Ideas [Flights to Windley Key ](https://expedia.com/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[ Windley Key Hotels ](https://expedia.com/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[ Vacation Rentals in Windley Key ](https://expedia.com/Windley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[ Car Rentals in Windley Key ](https://expedia.com/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)[ Windley Key Vacations ](https://expedia.com/Windley-Key.d553248635976197663.Destination-Travel-Guides)[ Things to do in Windley Key ](https://expedia.com/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 even more - get up to 20% on select hotels 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