Family-friendly holiday rentals in Winter Garden
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Winter Garden
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 Garden family-friendly rentals
Family-friendly home rentals with a hot tub
Condo in Kissimmee
4.84 out of 5 average rating, 249 reviewsLake View Family Condo Disney Universal Orlando
13–20 May
Guesthouse in Clermont
4.85 out of 5 average rating, 149 reviewsDiscover Tranquility at Our Charming Guest House
19–26 Jun
Townhouse in Kissimmee
4.95 out of 5 average rating, 161 reviewsBeautiful family home near all attractions.
20–27 Jun
Apartment in Orlando
4.9 out of 5 average rating, 313 reviewsBeautiful View, Newly Renovated 1 Mile to Disney
13–20 Sep
Condo in Orlando
4.97 out of 5 average rating, 296 reviewsLuxurious Waterfront Resort near Disney &Universal
31 Aug – 7 Sep
Apartment in Orlando
4.92 out of 5 average rating, 131 reviewsLuxury & Modern Apartment
17–24 Jul
Condo in Orlando
4.91 out of 5 average rating, 406 reviewsCozy Cay Condo Convn Ctr Vista Cay 2BR 2Ba 4 bds
24 Sep – 1 Oct
Townhouse in Kissimmee
4.95 out of 5 average rating, 251 reviewsDisney/Universal Home Away from Home!
7–14 Aug
Family- and pet-friendly home rentals
Home in Orlando
4.85 out of 5 average rating, 124 reviewsThe Prince House w/Free Parking (Central Location)
21–28 Jul
Guesthouse in Maitland
4.87 out of 5 average rating, 381 reviewsChez Bienvenu
23–30 Mar
Home in Clermont
4.86 out of 5 average rating, 117 reviewsCozy Family Home near Disney
29 Jul – 5 Aug
Tiny home in Orlando
4.8 out of 5 average rating, 482 reviewsOrlando Venice- A Lakefront Tiny House
13–20 Mar
Home in Altamonte Springs
4.97 out of 5 average rating, 274 reviewsEclectic Home Where Luxury Meets Affordability
30 Aug – 6 Sep
Guesthouse in Orlando
4.96 out of 5 average rating, 366 reviewsThe Coach House- 2 bedroom/3 bath Orlando Getaway!
31 Dec – 7 Jan
Condo in Champions Gate
4.85 out of 5 average rating, 262 reviewsMagical Champions Gate 3/2 Tuscan Penthouse
10–17 Aug
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
20–27 Dec
Family-friendly home rentals with a pool
Guest suite in Kissimmee
4.86 out of 5 average rating, 567 reviewsPrivate Studio in POOL home
5–12 Dec
Cottage in Kissimmee
4.94 out of 5 average rating, 371 reviewsEntire Cottage close to Disney, Universal, Airport
4–11 Dec
Condo in Kissimmee
4.92 out of 5 average rating, 263 reviewsBeautiful Beach Style Condo minutes from Disney
6–13 Oct
Home in Kissimmee
4.79 out of 5 average rating, 256 reviews3 bedroom Orlando Florida pool home
10–17 Dec
Apartment in Kissimmee
4.92 out of 5 average rating, 319 reviewsGreat Full Apartment. Just 5' from Disney Orlando
8–15 Oct
Apartment in Kissimmee
4.92 out of 5 average rating, 119 reviews14-206 Modern, Lake View, heated Pool near Disney
18–25 Aug
Home in Clermont
4.88 out of 5 average rating, 132 reviewsDisney Pool Villa, Cranberry South,
28 Nov – 5 Dec
Cottage in Kissimmee
4.9 out of 5 average rating, 210 reviewsBe Our Guest Sandcastle Cottage 81
16–23 Sep
Quick stats about holiday rentals that are family-friendly in Winter Garden
Total rentals
30 properties
Wi-Fi availability
30 properties include access to Wi-Fi
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
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
- Naples Holiday rentals
- Boca Raton 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
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- Family-friendly rentals Florida
- Family-friendly rentals Kissimmee
- Rentals with a patio Winter Garden
- Pet-friendly rentals Winter Garden
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- Monthly Rentals Winter Garden
- Rentals with pools Winter Garden
- Rentals with a washing machine and dryer Winter Garden
- Rentals with outdoor seating Winter Garden
- Family-friendly rentals Orange County
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