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
Flat in Orlando
4.92 out of 5 average rating, 132 reviewsLuxury & Modern Apartment
3–10 Sep
Apartment in Orlando
4.82 out of 5 average rating, 397 reviewsModern Studio with Private Terrace near Universal
4–11 Sep
Apartment in Orlando
4.87 out of 5 average rating, 396 reviewsDELUXE STUDIO NEAR UNIVERSAL/DISNEY/CONVEN. CENTER
11–18 Mar
Flat in Kissimmee
4.87 out of 5 average rating, 268 reviewsKing Bed Family Condo Orlando Disney Universal
22–29 Sep
Apartment in Orlando
4.91 out of 5 average rating, 409 reviewsCozy Cay Condo Convn Ctr Vista Cay 2BR 2Ba 4 bds
24–31 Aug
Townhouse in Kissimmee
4.95 out of 5 average rating, 251 reviewsDisney/Universal Home Away from Home!
5–12 Sep
Townhouse in Kissimmee
4.97 out of 5 average rating, 280 reviewsFind a Little Magic in a Townhouse near Disney and Universal
28 Jul – 4 Aug
Home in Davenport
4.95 out of 5 average rating, 161 reviewsDOLPHIN COVE NEAR DISNEY
23–30 Apr
Family- and pet-friendly home rentals
Home in Orlando
4.83 out of 5 average rating, 176 reviewsWaterside Pet Friendly Lakefront
16–23 Apr
Home in Orlando
4.85 out of 5 average rating, 124 reviewsThe Prince House w/Free Parking (Central Location)
8–15 Sep
Tiny home in Orlando
4.8 out of 5 average rating, 482 reviewsOrlando Venice- A Lakefront Tiny House
15–22 Jan
Guest house in Mount Dora
4.9 out of 5 average rating, 707 reviewsKey West cottage of Mt Dora
4–11 Mar
Place to stay in Geneva
4.94 out of 5 average rating, 929 reviewsManCave apartment
5–10 Feb
Guest house in Windermere
4.94 out of 5 average rating, 240 reviewsSmall Guesthouse near Orlando's Theme Parks
12–19 Dec
Bungalow in Mount Dora
4.91 out of 5 average rating, 267 reviewsTRENDING! Ladybug Bungalow in Downtown Mt. Dora
15–22 Oct
Townhouse in Kissimmee
4.92 out of 5 average rating, 227 reviewsBeautiful Farm House Decor near Disney, Sleeps 6
18–23 Sep
Family-friendly home rentals with a pool
Home in Kissimmee
4.84 out of 5 average rating, 205 reviews3 bedroom Villa in Kissimmee
22–29 Apr
Cottage in Kissimmee
4.96 out of 5 average rating, 421 reviewsBright & Cozy Cottage Near Disney
28 Jul – 4 Aug
Home in Orlando
4.95 out of 5 average rating, 313 reviews*HALF HOME* (read desc) Pool/Disney/Universal
4–11 Sep
Flat in Sorrento
4.94 out of 5 average rating, 301 reviewsQuiet Neighborhood in the Country
30 Sep – 7 Oct
Guest suite in Kissimmee
4.86 out of 5 average rating, 567 reviewsPrivate Studio in POOL home
25 Jan – 1 Feb
Cottage in Kissimmee
4.94 out of 5 average rating, 371 reviewsEntire Cottage close to Disney, Universal, Airport
19–26 Jul
Tiny home in Kissimmee
4.94 out of 5 average rating, 328 reviewsBlue Bungalow Tiny House near all Attractions!!
5–12 Aug
Home in Kissimmee
4.79 out of 5 average rating, 257 reviews3 bedroom Orlando Florida pool home
9–16 Dec
Quick stats about holiday rentals that are family-friendly in Winter Park
Total rentals
200 properties
Wifi availability
200 properties include access to wifi
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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- Family-friendly rentals Kissimmee
- Flat rentals Winter Park
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