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
Townhouse in Kissimmee
4.83 out of 5 average rating, 287 reviewsResort Living 4 Bed 3.5 Bath Townhome
Home in Kissimmee
4.89 out of 5 average rating, 193 reviewsPrivate Jacuzzi-Heated ResortPool-BBQ-7 mls Disney
Home in Davenport
4.91 out of 5 average rating, 122 reviewsThe Shire -Private Pool & Hot Tub, Close to parks!
Home in Kissimmee
4.89 out of 5 average rating, 168 reviewsLuxurious Private Retreat w/Spa & Saltwater Pool
Townhouse in Kissimmee
4.88 out of 5 average rating, 180 reviewsAdorable 2 bdr lakefront w/jacuzzi 5 min *Disney*
Villa in Kissimmee
4.96 out of 5 average rating, 104 reviewsBeautiful Home, 6Bdrm,5Bath, near Disney, Pool&Spa
Home in Clermont
4.68 out of 5 average rating, 237 reviews4br/3ba Disney Area Luxury Resort with pool/spa
Townhouse in Kissimmee
4.94 out of 5 average rating, 192 reviewsNew Resort near Orlando Disney Private Hot Tub
Family- and pet-friendly home rentals
Townhouse in Kissimmee
4.8 out of 5 average rating, 135 reviewsCompass Bay 5164 AD - Beautiful and Near Disney
Home in Kissimmee
4.83 out of 5 average rating, 106 reviews5 Stars Vacation Home with Private Pool/Jacuzzi
Guesthouse in Windermere
4.94 out of 5 average rating, 251 reviewsParadise nook near Orlando's theme parks
Rental unit in Kissimmee
4.79 out of 5 average rating, 209 reviewsFantastic Award Winning Renovated 2+2 Near Disney
Farm stay in Oviedo
4.9 out of 5 average rating, 105 reviewsThe Guest House in Oviedo countryside
Home in Orlando
4.84 out of 5 average rating, 197 reviewsWaterside Pet Friendly Lakefront
Home in Sanford
4.95 out of 5 average rating, 178 reviewsHistoric Sanford Sunshine Cottage w/ Treetop suite
Guesthouse in Maitland
4.87 out of 5 average rating, 386 reviewsChez Bienvenu
Family-friendly home rentals with a pool
Villa in Kissimmee
4.96 out of 5 average rating, 170 reviews4 bed villa w/private pool near Disney, sleeps 6+
Home in Kissimmee
4.92 out of 5 average rating, 101 reviewsHidden Treasure -Beautiful Pool Home - Sleeps 6
Home in Davenport
4.81 out of 5 average rating, 142 reviewsWelcoming fully equipped villa in Davenport
Townhouse in Kissimmee
4.83 out of 5 average rating, 105 reviewsMajorca Paradise: Townhome Near Magic Disney
Home in Kissimmee
4.89 out of 5 average rating, 128 reviewsRemy's Refuge: Stylish 4BR - 10 min to Disney!
Townhouse in Kissimmee
4.79 out of 5 average rating, 167 reviewsAmazing family home with pool near Disney
Home in Davenport
4.79 out of 5 average rating, 135 reviewsBeautiful 4 bed home, south-facing pool,games room
Bungalow in Davenport
4.74 out of 5 average rating, 305 reviewsFlorida Palm's near Disney where dreams come true
Quick stats about vacation rentals that are family-friendly in Winter Park
Total rentals
190 properties
Total number of reviews
7.4K reviews
Pet-friendly rentals
90 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Wifi availability
190 properties include access to wifi
Destinations to explore
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