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
Jul. 17 – 24
Guesthouse in Orlando
4.94 out of 5 average rating, 388 reviewsGarden House near Orlando's cultural hub
Jun. 5 – 12
Apartment in Orlando
4.9 out of 5 average rating, 313 reviewsBeautiful View, Newly Renovated 1 Mile to Disney
Aug. 14 – 21
Condo in Kissimmee
4.84 out of 5 average rating, 249 reviewsLake View Family Condo Disney Universal Orlando
Sep. 27 – Oct. 4
Townhouse in Kissimmee
4.95 out of 5 average rating, 161 reviewsBeautiful family home near all attractions.
Jun. 20 – 27
Condo in Orlando
4.82 out of 5 average rating, 395 reviewsModern Studio with Private Terrace near Universal
Apr. 17 – 24
Townhouse in Kissimmee
4.95 out of 5 average rating, 251 reviewsDisney/Universal Home Away from Home!
Aug. 7 – 14
Townhouse in Kissimmee
4.97 out of 5 average rating, 279 reviewsFind a Little Magic in a Townhouse near Disney and Universal
Aug. 24 – 31
Family- and pet-friendly home rentals
Guest suite in Orlando
4.93 out of 5 average rating, 560 reviewsCharming Comfortable Cottage in College Park
Mar. 18 – 25
Guest suite in Orlando
4.78 out of 5 average rating, 525 reviewsPrivate guest suite with enclosed porch
Jun. 18 – 25
Home in Oviedo
4.92 out of 5 average rating, 259 reviews🧡Unique 6/3 ✅Pool ✔Pergola ✅Movie Room ✔UCF, 5⭐s
Mar. 24 – 31
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
Mar. 25 – Apr. 1
Home in Sanford
4.95 out of 5 average rating, 157 reviewsHistoric Sanford Sunshine Cottage w/ Treetop suite
Mar. 25 – Apr. 1
Tiny homes in Orlando
4.82 out of 5 average rating, 499 reviewsThe Ritz- Lakefront Tiny House in Orlando
Nov. 16 – 23
Guesthouse in Windermere
4.94 out of 5 average rating, 239 reviewsSmall Guesthouse near Orlando's Theme Parks
Jan. 6 – 13
Home in Orlando
4.85 out of 5 average rating, 124 reviewsThe Prince House w/Free Parking (Central Location)
Aug. 15 – 22
Family-friendly home rentals with a pool
Apartment in Sorrento
4.94 out of 5 average rating, 300 reviewsQuiet Neighborhood in the Country
Feb. 21 – 28
Home in Orlando
4.95 out of 5 average rating, 313 reviews*HALF HOME* (read desc) Pool/Disney/Universal
Jul. 11 – 18
Guest suite in Kissimmee
4.86 out of 5 average rating, 567 reviewsPrivate Studio in POOL home
Dec. 5 – 12
Cottage in Kissimmee
4.96 out of 5 average rating, 421 reviewsBright & Cozy Cottage Near Disney
Jul. 28 – Aug. 4
Cottage in Kissimmee
4.94 out of 5 average rating, 371 reviewsEntire Cottage close to Disney, Universal, Airport
Dec. 4 – 11
Home in Kissimmee
4.79 out of 5 average rating, 256 reviews3 bedroom Orlando Florida pool home
Dec. 14 – 21
Tiny homes in Kissimmee
4.95 out of 5 average rating, 364 reviewsSunny Tiny House Cottage near all Attractions!!
Jul. 6 – 13
Condo in Kissimmee
4.92 out of 5 average rating, 263 reviewsBeautiful Beach Style Condo minutes from Disney
Oct. 14 – 21
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
$96 CAD before taxes and fees
Destinations to explore
- Orlando Vacation rentals
- Kissimmee Vacation rentals
- Tampa Vacation rentals
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- Family-friendly rentals United States
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- Family-friendly rentals Florida
- Family-friendly rentals Kissimmee
- House rentals Winter Springs
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- Pet-friendly rentals Winter Springs
- Rentals with outdoor seating Winter Springs
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- Monthly Rentals Winter Springs
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