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. ![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 $523 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 ![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 $8,019 per person Apr 25 - Apr 30 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 $1,943 per person Apr 25 - Apr 30 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 ![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 Save 100% on your flight $921 per person Apr 2 - Apr 5 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1,120 reviews) Staff are great but the bed and pillows were uncomfortable. Especially the pillows they are horrible. I had to use a towel as my pillow. Other hotels have feather pillows that are far more comfortable. It would be nice to have a choice. For this reason we won’t return. It’s too bad because everything else was nice. Reviewed on Feb 19, 2026 ![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 Save 100% on your flight $945 per person Apr 25 - Apr 30 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.2/10 Wonderful! (466 reviews) Room was clean and nice but dark‼️ The platform bed was larger than the mattress and was the same color as the floor. No night lights. Used the restroom during the night, tripped on the platform bed. I dislocated my shoulder and fractured my arm at 1:00AM and there was no drinking involved. I was taken by ambulance to Mt Sinai hospital to reset my dislocation which took until 7:30 AM in the morning. Staff was very pleasant and professional at the hospital. Reviewed on Feb 18, 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/2026-03-20/2026-03-27/?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. ![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 Save 100% on your flight $1,113 per person May 7 - May 12 found 16 hours ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.2/10 Wonderful! (1,262 reviews) Room was very nice and plenty of room. First time visitor. Tub on the balcony was unexpected bonus Reviewed on Feb 17, 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 $8,019 per person Apr 25 - Apr 30 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 $1,943 per person Apr 25 - Apr 30 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/2026-03-20/2026-03-27/?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. ![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 Save 100% on your flight $704 per person Apr 27 - Apr 30 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 9.4/10 Exceptional! (56 reviews) Clean room, excellent staff at the front desk, dining room, pool staff, and beach staff. Sergiy was especially helpful telling us all about the hotel. Reviewed on Feb 13, 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 $9,624 per person Apr 29 - May 2 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![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 Save 100% on your flight $921 per person Apr 2 - Apr 5 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1,120 reviews) Staff are great but the bed and pillows were uncomfortable. Especially the pillows they are horrible. I had to use a towel as my pillow. Other hotels have feather pillows that are far more comfortable. It would be nice to have a choice. For this reason we won’t return. It’s too bad because everything else was nice. Reviewed on Feb 19, 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/2026-03-20/2026-03-27/?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. ![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 $559 per person Apr 26 - Apr 30 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1,004 reviews) Great little hotel! In a really nice location Reviewed on Feb 17, 2026 ![Cavalier Hotel South Beach](https://images.trvl-media.com/lodging/1000000/20000/13600/13579/c0c3faa8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cavalier Hotel South Beach South Beach Save 100% on your flight $975 per person Mar 25 - Mar 29 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.4/10 Very Good! (1,001 reviews) Great location, clean room and beautiful. Reviewed on Feb 19, 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 $10,676 per person Mar 25 - Mar 29 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) 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/2026-03-20/2026-03-27/?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 $523\. 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