Family-friendly vacation 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.
Vacation 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, 132 reviewsLuxury & Modern Apartment
Oct 4 – 11
Condo in Orlando
4.82 out of 5 average rating, 397 reviewsModern Studio with Private Terrace near Universal
Feb 24 – Mar 3
Townhouse in Kissimmee
4.94 out of 5 average rating, 181 reviewsNew Resort near Orlando Disney Private Hot Tub
May 15 – 22
Condo in Orlando
4.82 out of 5 average rating, 223 reviewsGated Condo minutes to Parks 2/2 with amenities
Jul 9 – 16
Apartment in Kissimmee
4.87 out of 5 average rating, 268 reviewsKing Bed Family Condo Orlando Disney Universal
Jan 21 – 28
Condo in Kissimmee
4.8 out of 5 average rating, 117 reviewsStunning view, near Disney. 2 pools
Jul 28 – Aug 4
Condo in Orlando
4.9 out of 5 average rating, 314 reviewsConvention Center Classic in Luxury Resort wlk2mkt
Sep 22 – 29
Townhouse in Kissimmee
4.95 out of 5 average rating, 252 reviewsDisney/Universal Home Away from Home!
Sep 19 – 26
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)
Aug 18 – 25
Tiny home in Orlando
4.8 out of 5 average rating, 482 reviewsOrlando Venice- A Lakefront Tiny House
Jul 16 – 23
Place to stay in Geneva
4.94 out of 5 average rating, 929 reviewsManCave apartment
Oct 5 – 10
Guesthouse in Windermere
4.94 out of 5 average rating, 240 reviewsSmall Guesthouse near Orlando's Theme Parks
Jun 25 – Jul 2
Guesthouse in Mount Dora
4.9 out of 5 average rating, 708 reviewsKey West cottage of Mt Dora
Oct 4 – 11
Home in Orlando
4.83 out of 5 average rating, 177 reviewsWaterside Pet Friendly Lakefront
Dec 13 – 20
Bungalow in Mount Dora
4.91 out of 5 average rating, 268 reviewsTRENDING! Ladybug Bungalow in Downtown Mt. Dora
May 22 – 29
Townhouse in Kissimmee
4.88 out of 5 average rating, 247 reviewsDisney fireworks new house - 5 minutes to Disney
Nov 17 – 22
Family-friendly home rentals with a pool
Home in Kissimmee
4.84 out of 5 average rating, 206 reviews3 bedroom Villa in Kissimmee
Apr 25 – May 2
Apartment in Sorrento
4.94 out of 5 average rating, 302 reviewsQuiet Neighborhood in the Country
Sep 30 – Oct 7
Cottage in Kissimmee
4.96 out of 5 average rating, 423 reviewsBright & Cozy Cottage Near Disney
Apr 12 – 19
Home in Orlando
4.95 out of 5 average rating, 314 reviews*HALF HOME* (read desc) Pool/Disney/Universal
Aug 22 – 29
Guest suite in Kissimmee
4.86 out of 5 average rating, 568 reviewsPrivate Studio in POOL home
Jan 12 – 19
Houseboat in Sanford
4.98 out of 5 average rating, 177 reviewsFloating Cottage - Sweet River Retreat in Florida
Jan 8 – 15
Cottage in Kissimmee
4.94 out of 5 average rating, 372 reviewsEntire Cottage close to Disney, Universal, Airport
Jul 19 – 26
Tiny home in Kissimmee
4.95 out of 5 average rating, 365 reviewsSunny Tiny House Cottage near all Attractions!!
Nov 4 – 11
Quick stats about vacation 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
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