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
Guest house in Clermont
4.85 out of 5 average rating, 149 reviewsDiscover Tranquility at Our Charming Guest House
26 Jun – 3 Jul
Apartment in Kissimmee
4.84 out of 5 average rating, 250 reviewsLake View Family Condo Disney Universal Orlando
4–11 Nov
Townhouse in Kissimmee
4.95 out of 5 average rating, 161 reviewsBeautiful family home near all attractions.
24–31 Oct
Apartment in Davenport
4.93 out of 5 average rating, 189 reviewsDisney Vacation Bahama Bay Resort Orlando Retreat
18–25 Aug
Apartment in Kissimmee
4.94 out of 5 average rating, 300 reviewsDisney World Condo w/ Full Kitchen, Balcony & Pool
2–9 Sep
Townhouse in Kissimmee
4.95 out of 5 average rating, 251 reviewsDisney/Universal Home Away from Home!
4–11 Sep
Apartment in Orlando
4.97 out of 5 average rating, 297 reviewsLuxurious Waterfront Resort near Disney &Universal
5–12 Feb
Townhouse in Kissimmee
4.94 out of 5 average rating, 180 reviewsNew Resort near Orlando Disney Private Hot Tub
25 Jul – 1 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)
26 Sep – 3 Oct
Place to stay in Geneva
4.94 out of 5 average rating, 929 reviewsManCave apartment
3–8 Sep
Bungalow in Mount Dora
4.91 out of 5 average rating, 267 reviewsTRENDING! Ladybug Bungalow in Downtown Mt. Dora
16–23 Jun
Guest house in Maitland
4.87 out of 5 average rating, 381 reviewsChez Bienvenu
3–10 Sep
Guest house in Orlando
4.96 out of 5 average rating, 369 reviewsThe Coach House- 2 bedroom/3 bath Orlando Getaway!
25 Mar – 1 Apr
Home in Altamonte Springs
4.97 out of 5 average rating, 277 reviewsEclectic Home Where Luxury Meets Affordability
16–23 Oct
Home in Orlando
4.83 out of 5 average rating, 176 reviewsWaterside Pet Friendly Lakefront
23–30 Jul
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
17–24 Apr
Family-friendly home rentals with a pool
Home in Clermont
4.88 out of 5 average rating, 132 reviewsDisney Pool Villa, Cranberry South,
17–24 Sep
Home in Kissimmee
4.84 out of 5 average rating, 205 reviews3 bedroom Villa in Kissimmee
21–28 Apr
Guest suite in Kissimmee
4.86 out of 5 average rating, 567 reviewsPrivate Studio in POOL home
17–24 Oct
Home in Orlando
4.95 out of 5 average rating, 314 reviews*HALF HOME* (read desc) Pool/Disney/Universal
5–12 Sep
Apartment in Kissimmee
4.92 out of 5 average rating, 264 reviewsBeautiful Beach Style Condo minutes from Disney
23–30 Oct
Flat in Sorrento
4.94 out of 5 average rating, 301 reviewsQuiet Neighborhood in the Country
14–21 Mar
Flat in Kissimmee
4.92 out of 5 average rating, 319 reviewsGreat Full Apartment. Just 5' from Disney Orlando
25 Apr – 2 May
Home in Kissimmee
4.79 out of 5 average rating, 257 reviews3 bedroom Orlando Florida pool home
17–24 Jan
Quick stats about holiday rentals that are family-friendly in Winter Garden
Total rentals
30 properties
Wifi availability
30 properties include access to wifi
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
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- Family-friendly rentals Florida
- Family-friendly rentals Kissimmee
- Rentals with pools Winter Garden
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- Monthly Rentals Winter Garden
- Rentals with a washing machine and dryer Winter Garden
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- Family-friendly rentals Orange County
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