Family-friendly vacation rentals in Winter Springs
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Winter Springs
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Springs family-friendly rentals
Family-friendly home rentals with a hot tub
Apartment in Orlando
4.92 out of 5 average rating, 131 reviewsLuxury & Modern Apartment
Guesthouse in Orlando
4.94 out of 5 average rating, 388 reviewsGarden House near Orlando's cultural hub
Apartment in Kissimmee
4.88 out of 5 average rating, 267 reviewsKing Bed Family Condo Orlando Disney Universal
Condo in Orlando
4.87 out of 5 average rating, 396 reviewsDELUXE STUDIO NEAR UNIVERSAL/DISNEY/CONVEN. CENTER
Condo in Orlando
4.83 out of 5 average rating, 305 reviewsLakefront Studio apt~ 5 min from Universal Studios
Townhouse in Kissimmee
4.95 out of 5 average rating, 251 reviewsDisney/Universal Home Away from Home!
Condo in Davenport
4.92 out of 5 average rating, 377 reviewsMediterranean Resort! 2+2 Condo. 10 mins to Disney
Townhouse in Kissimmee
4.97 out of 5 average rating, 280 reviewsFind a Little Magic in a Townhouse near Disney and Universal
Family- and pet-friendly home rentals
Guest suite in Orlando
4.93 out of 5 average rating, 562 reviewsCharming Comfortable Cottage in College Park
Home in Oviedo
4.92 out of 5 average rating, 260 reviews🧡Unique 6/3 ✅Pool ✔Pergola ✅Movie Room ✔UCF, 5⭐s
Guesthouse in Windermere
4.94 out of 5 average rating, 240 reviewsSmall Guesthouse near Orlando's Theme Parks
Home in Sanford
4.95 out of 5 average rating, 157 reviewsHistoric Sanford Sunshine Cottage w/ Treetop suite
Guest suite in Orlando
4.78 out of 5 average rating, 525 reviewsPrivate guest suite with enclosed porch
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
Home in Orlando
4.85 out of 5 average rating, 124 reviewsThe Prince House w/Free Parking (Central Location)
Guesthouse in Orlando
4.96 out of 5 average rating, 367 reviewsThe Coach House- 2 bedroom/3 bath Orlando Getaway!
Family-friendly home rentals with a pool
Apartment in Sorrento
4.94 out of 5 average rating, 301 reviewsQuiet Neighborhood in the Country
Home in Kissimmee
4.84 out of 5 average rating, 205 reviews3 bedroom Villa in Kissimmee
Cottage in Kissimmee
4.96 out of 5 average rating, 421 reviewsBright & Cozy Cottage Near Disney
Home in Orlando
4.95 out of 5 average rating, 313 reviews*HALF HOME* (read desc) Pool/Disney/Universal
Guest suite in Kissimmee
4.86 out of 5 average rating, 567 reviewsPrivate Studio in POOL home
Cottage in Kissimmee
4.94 out of 5 average rating, 404 reviewsEntire cottage for 5, close to Disney, Universal!
Tiny home in Kissimmee
4.95 out of 5 average rating, 365 reviewsSunny Tiny House Cottage near all Attractions!!
Condo in Kissimmee
4.92 out of 5 average rating, 264 reviewsBeautiful Beach Style Condo minutes from Disney
Quick stats about vacation rentals that are family-friendly in Winter Springs
Total rentals
30 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Total number of reviews
1.6K reviews
Nightly prices starting at
$70 before taxes and fees
Destinations to explore
- Orlando Vacation rentals
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- Tampa Vacation rentals
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- Family-friendly rentals United States
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