Family-friendly holiday rentals in Winter Park
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Winter Park
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 Park 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
Apartment in Orlando
4.9 out of 5 average rating, 313 reviewsBeautiful View, Newly Renovated 1 Mile to Disney
13–20 Sep
Condo in Kissimmee
4.84 out of 5 average rating, 249 reviewsLake View Family Condo Disney Universal Orlando
13–20 May
Condo in Orlando
4.82 out of 5 average rating, 395 reviewsModern Studio with Private Terrace near Universal
27 Nov – 4 Dec
Condo in Orlando
4.87 out of 5 average rating, 394 reviewsDELUXE STUDIO NEAR UNIVERSAL/DISNEY/CONVEN. CENTER
25 Jan – 1 Feb
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
Townhouse in Kissimmee
4.97 out of 5 average rating, 279 reviewsFind a Little Magic in a Townhouse near Disney and Universal
11–18 Apr
Family- and pet-friendly home rentals
Tiny home in Orlando
4.8 out of 5 average rating, 482 reviewsOrlando Venice- A Lakefront Tiny House
13–20 Mar
Guesthouse in Mount Dora
4.9 out of 5 average rating, 705 reviewsKey West cottage of Mt Dora
13–20 Jul
Place to stay in Geneva
4.94 out of 5 average rating, 927 reviewsManCave apartment
15–20 Jul
Guesthouse in Windermere
4.94 out of 5 average rating, 239 reviewsSmall Guesthouse near Orlando's Theme Parks
21–28 Mar
Home in Orlando
4.85 out of 5 average rating, 124 reviewsThe Prince House w/Free Parking (Central Location)
21–28 Jul
Townhouse in Kissimmee
4.92 out of 5 average rating, 226 reviewsBeautiful Farm House Decor near Disney, Sleeps 6
18–23 Sep
Bungalow in Mount Dora
4.91 out of 5 average rating, 266 reviewsTRENDING! Ladybug Bungalow in Downtown Mt. Dora
23–30 Aug
Home in Orlando
4.83 out of 5 average rating, 175 reviewsWaterside Pet Friendly Lakefront
26 Nov – 3 Dec
Family-friendly home rentals with a pool
Home in Orlando
4.95 out of 5 average rating, 313 reviews*HALF HOME* (read desc) Pool/Disney/Universal
16–23 Jun
Cottage in Kissimmee
4.94 out of 5 average rating, 371 reviewsEntire Cottage close to Disney, Universal, Airport
4–11 Dec
Apartment in Sorrento
4.94 out of 5 average rating, 300 reviewsQuiet Neighborhood in the Country
19–26 Apr
Cottage in Kissimmee
4.96 out of 5 average rating, 421 reviewsBright & Cozy Cottage Near Disney
28 Feb – 7 Mar
Guest suite in Kissimmee
4.86 out of 5 average rating, 567 reviewsPrivate Studio in POOL home
5–12 Dec
Houseboat in Sanford
4.98 out of 5 average rating, 177 reviewsFloating Cottage - Sweet River Retreat in Florida
6–13 Mar
Tiny home in Kissimmee
4.94 out of 5 average rating, 328 reviewsBlue Bungalow Tiny House near all Attractions!!
1–8 Apr
Home in Kissimmee
4.84 out of 5 average rating, 205 reviews3 bedroom Villa in Kissimmee
28 Jun – 5 Jul
Quick stats about holiday rentals that are family-friendly in Winter Park
Total rentals
200 properties
Wi-Fi availability
200 properties include access to Wi-Fi
Rentals with dedicated workspaces
140 properties have a dedicated workspace
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
90 properties allow pets
Total number of reviews
7.3K 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
- 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
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- Monthly Rentals Winter Park
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