
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

Mills Cottage

3,000 Sqft Historic Home With Pool Near Everything

Villa with Guest House & Pool-Patio

Spacious Home with Pool & Hot Tub near Downtown

Cheerful, updated 4 BR 3B w/ large, lush back yard

Stunning Orlando Getaway w/Spa & Heated Pool

Garden House near Orlando's cultural hub

Jungle in Orlando: Glamp Life the Experience
Family- and pet-friendly home rentals

Modern 3/2 in Ivanhoe Village

Mirror House

Grey House near Orlando Universal Parks

Private guest suite - Studio Retreat

Private pool home near Downtown

Renovated!Charming private suite with Kitchenette

The Orlando Retreat.

The Cottage A Pet Friendly Guesthouse
Family-friendly home rentals with a pool

Oviedo Oasis:2/1 attached Guest Suite;Private Pool

Orlando Oasis in the heart of Thornton Park

DT Orlando High-Rise Sunset View - Free Parking!

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

Kyle's Place - Private Unit, Pool + Laundry Room

Charming Retreat In Winter Park

Modern Tropical House Heated Salt Pool

"Winnie's Place" A Peaceful Guesthouse with Pool.
Quick stats about vacation rentals that are family-friendly in Winter Park
Total rentals
190 properties
Total number of reviews
8.6K reviews
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Wifi availability
180 properties include access to wifi
Destinations to explore
- Seminole Vacation rentals
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- Rentals with a hot tub Winter Park
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- Guesthouse rentals Winter Park
- Family-friendly rentals Orange County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Old Town Kissimmee
- Discovery Cove
- Disney Springs
- Disney's Animal Kingdom Theme Park
- Magic Kingdom Park
- ESPN Wide World of Sports
- Epcot
- Amway Center
- Playalinda Beach
- Daytona International Speedway
- Walt Disney World Resort Golf
- Aquatica
- Titusville Beach
- Island H2O Water Park
- Apollo Beach
- Disney's Hollywood Studios
- Universal CityWalk
- ChampionsGate Golf Club
- ICON Park
- Things to do Winter Park
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- Things to do United States
- Entertainment United States
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- Nature and outdoors United States
- Art and culture United States
- Wellness United States
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- Sightseeing United States
- Sports activities United States