Family-friendly holiday 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.
Holiday 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
17–24 Jul
Guesthouse in Orlando
4.94 out of 5 average rating, 388 reviewsGarden House near Orlando's cultural hub
5–12 Jun
Apartment in Orlando
4.9 out of 5 average rating, 313 reviewsBeautiful View, Newly Renovated 1 Mile to Disney
14–21 Aug
Condo in Kissimmee
4.84 out of 5 average rating, 249 reviewsLake View Family Condo Disney Universal Orlando
27 Sep – 4 Oct
Townhouse in Kissimmee
4.95 out of 5 average rating, 161 reviewsBeautiful family home near all attractions.
20–27 Jun
Condo in Orlando
4.82 out of 5 average rating, 394 reviewsModern Studio with Private Terrace near Universal
17–24 Apr
Townhouse in Kissimmee
4.95 out of 5 average rating, 251 reviewsDisney/Universal Home Away from Home!
7–14 Aug
Townhouse in Kissimmee
4.97 out of 5 average rating, 279 reviewsFind a Little Magic in a Townhouse near Disney and Universal
24–31 Aug
Family- and pet-friendly home rentals
Guest suite in Orlando
4.93 out of 5 average rating, 560 reviewsCharming Comfortable Cottage in College Park
18–25 Mar
Guest suite in Orlando
4.78 out of 5 average rating, 525 reviewsPrivate guest suite with enclosed porch
18–25 Jun
Home in Oviedo
4.92 out of 5 average rating, 259 reviews🧡Unique 6/3 ✅Pool ✔Pergola ✅Movie Room ✔UCF, 5⭐s
24–31 Mar
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
25 Mar – 1 Apr
Home in Sanford
4.95 out of 5 average rating, 157 reviewsHistoric Sanford Sunshine Cottage w/ Treetop suite
25 Mar – 1 Apr
Tiny home in Orlando
4.82 out of 5 average rating, 499 reviewsThe Ritz- Lakefront Tiny House in Orlando
16–23 Nov
Guesthouse in Windermere
4.94 out of 5 average rating, 239 reviewsSmall Guesthouse near Orlando's Theme Parks
6–13 Jan
Home in Orlando
4.85 out of 5 average rating, 124 reviewsThe Prince House w/Free Parking (Central Location)
15–22 Aug
Family-friendly home rentals with a pool
Apartment in Sorrento
4.94 out of 5 average rating, 300 reviewsQuiet Neighborhood in the Country
21–28 Feb
Home in Orlando
4.95 out of 5 average rating, 313 reviews*HALF HOME* (read desc) Pool/Disney/Universal
11–18 Jul
Guest suite in Kissimmee
4.86 out of 5 average rating, 567 reviewsPrivate Studio in POOL home
5–12 Dec
Cottage in Kissimmee
4.96 out of 5 average rating, 421 reviewsBright & Cozy Cottage Near Disney
28 Jul – 4 Aug
Cottage in Kissimmee
4.94 out of 5 average rating, 371 reviewsEntire Cottage close to Disney, Universal, Airport
4–11 Dec
Home in Kissimmee
4.79 out of 5 average rating, 256 reviews3 bedroom Orlando Florida pool home
14–21 Dec
Tiny home in Kissimmee
4.95 out of 5 average rating, 363 reviewsSunny Tiny House Cottage near all Attractions!!
6–13 Jul
Condo in Kissimmee
4.92 out of 5 average rating, 263 reviewsBeautiful Beach Style Condo minutes from Disney
14–21 Oct
Quick stats about holiday 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
$118 NZD before taxes and fees
Destinations to explore
- Orlando Holiday rentals
- Kissimmee Holiday rentals
- Tampa Holiday rentals
- Anna Maria Island Holiday rentals
- Sarasota Holiday rentals
- West Palm Beach Holiday rentals
- Boca Raton Holiday rentals
- Naples Holiday rentals
- Fort Lauderdale Holiday rentals
- Miami Beach Holiday rentals
- Miami Holiday rentals
- Key West Holiday rentals
- Family-friendly rentals United States
- Family-friendly rentals Orlando
- Family-friendly rentals Florida
- Family-friendly rentals Florida
- Family-friendly rentals Kissimmee
- House rentals Winter Springs
- Rentals with a washing machine and dryer Winter Springs
- Pet-friendly rentals Winter Springs
- Rentals with outdoor seating Winter Springs
- Rentals with pools Winter Springs
- Monthly Rentals Winter Springs
- Rentals with a patio Winter Springs
- Family-friendly rentals Seminole County
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