
Family-friendly vacation rentals in Windsor Hills
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Windsor Hills
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Magical Adv 5 Star Villa Movie Room Arcade Pool an
Experience enchantment at Magical Adventure Villa, a top-rated 6-bedroom and 4-bath home for 12 guests. Conveniently located in Windsor Hills Resort, just 2 miles from Disney WorldĀ®. Experience the highly acclaimed getaway that has garnered rave reviews. Enjoy a private pool, home theater, and a thrilling arcade. Unleash your inner Jedi at the state-of-the-art Star Wars gaming center with a movie theater, Xbox One, Nintendo Switch, and immersive 3D designs. *Work vehicles are not permitted to b

Game & Theater Room, Castle Bunks, Pool & Spa
Vacation at Windsorās Best located in Windsor Hills Resort just 2 miles from Walt Disney World. This one-story 4 bed, 4 bath vacation villa has everything you need for a wonderful getaway with family or friends. Situated on an elevated corner lot, this spacious villa with it's private pool and spillover spa offers a beautiful view overlooking the resort community. Plus, guests have access to the family-friendly Windsor Hills Resort amenities, including the water park, playgrounds, gym and more.

Poolside 3Br~Windsor Hills~Waterpark~2mi to Disney
Your Windsor Hills Getaway starts here! This top-rated condo overlooks the resort pool & waterpark and is just minutes from Disney World! New appliances and updated furnishings, this 3rd floor condo sleeps 8, with plenty of parking. The screened-in balcony canāt be beat, overlooking the pool, hot tub, and waterpark with waterslides! The clubhouse is just steps away, with a store, food, drinks, game room, and fitness center. No resort, parking, or hidden fees. Full access to all amenities!

*Brand New!* Minutes to Disney + Free Resort!
Closest FREE resort to Disney Parks! Hibiscus Hideaway is a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in October 2022! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting & ROCK CLIMBING WALL! * New Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW BBQ grill & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

Mickey's Dream: Free Waterpark, 10min to Disney!
This Mickey-themed 3-bedroom, 3-bath townhouse is located just 10minutes from the Disney gate in the popular & secure Windsor Hills Resort. Amenities include: FREE WATER PARK and SPLASH PAD, pool, playgrounds, fitness center, arcade and more! Screened in back patio complete with private splash pool. Open concept main floor includes space for enjoying a movie night or eating dinner as a family. Living room and 3 bedrooms come with Smart TVs for streaming. Hi-speed WiFi, cable TV. Washer/Dryer

Beautiful 2/2 Gem, 2 mi to Disney with Water Park!
Brand new flooring, mattresses, AC, water heater and more! Disney SO close! Our Property Manager will see to any needs during your stay, a rental registration is required. Beautiful, clean and comfy condo in Windsor Hills Resort with a new WATER PARK and tons of amenities. Stainless appliances and granite, free wifi/cable, desk/charging station and PS 3 with games, Pack N play, stroller, high chair, wash/dryer, a starter kit of supplies. No hidden fees, free parking. Perfect for families!

Mr. Clean's Cozy Disney Home w/ Luxury Finishes
⢠Newest house in the #1 resort community in the Disney Area, Windsor Hills ⢠ALL Mattresses & Pillows are encased in waterproof SANITIZED covers. ⢠2 FUN children themed rooms (Star Wars, & Frozen) ⢠Onsite, driveway parking for 3 vehicles ⢠FREE pool heat + BBQ with ALL rentals ⢠Fully equipped + stocked kitchen; including Keurig machine ⢠Self check-in with digital lock ⢠Super FAST Wi-Fi wireless internet speed at +1,000 Mbps!! ⢠Property is managed directly by owner

Windsor Orlando Private Arcades,Theater,Pool-Spa
Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.

DISNEY, WATER park, Private POOL, Comfort by A3G
Your dream getaway, starts In this 3beds 3 baths vacation home away from home! With private pool, Located in the amazing 5 stars resort at WINDSOR HILLS, only 3 miles away from all the wonders and magic of Disney. For Endless entertainment just walk to the Clubhouse and encounter the beautiful typhoon style pool, jacuzzi, brand new water park, arcade, fitness center, volleyball and basquetbol courts, kids playground and much more

One in a Minion condo your kids will love +450Mbps
Enjoy of sophisticated and modern accommodations on your next visit to Orlando. This One in a Minion themed two bedroom condo boasts 1082 SQ FT of living space and it's fully equipped for 6 guests. Conveniently located on the ground floor and a short stroll to the clubhouse, pool and dueling water slides. It features a smart lock, High-speed WIFI Internet +450Mbps, cable TV, telephone line, linens & towels and washer/dryer.

3BD/3BA Themed House Near Disney
Welcome to our charming 3-bedroom, 3-bathroom house, thoughtfully created to create magical moments for your entire family! Immerse yourself in our themed rooms, each capturing the magic of beloved stories like Happy Potter and Mickey Mouse. Accommodating up to 10 guests, your Disney adventure starts here! The following extra services include additional costs: Grill Early Check-in Late Check-out

7754 Windsor Hills 6B Luxury Pool Home Near Disney
Welcome to Your Ultimate Windsor Hills Vacation Escape! This newly renovated 6-bedroom beauty is the perfect blend of luxury and fun, designed for families looking to unwind and create unforgettable memories. Just a stoneās throw from Disney World and surrounded by world-class dining, top-notch shopping, and Orlandoās hottest attractions, youāll have everything you need for an amazing getaway.
Popular amenities for Windsor Hills family-friendly rentals
Family-friendly home rentals with a hot tub

Free Arcade! All Rooms Themed! South Facing Pool!

Dumbo House

Fully Themed Harry Potter Magical Experience!

4 minutes to Disney - Sleeps 14, Arcade, Pool

4 bed/ 4 bath Windsor Hills

Themed Windsor Hills 6BR Private Pool Gameroom

Once upon a galaxy: Star Wars/fairytale retreat

Luxury Home | Pool, Spa | Game Room | Golf View
Family- and pet-friendly home rentals

Modern 3BR w/ Private Pool ā 10 Min to Disney

Cinderellaās Castle Pool ⢠Spa ⢠Games ⢠Pets OK

Renovated First Floor Disney Family Condo

Superb Townhouse Newly Renovated 1 mile to Disney

Orlando Home with Private Pool & Game Room !

Disneyās Home Away From Home (5 miles from Disney)

Westgate Vacation Villas - 1 Bedroom

Luxury Encore Pool Spa Pets Game Rm Theater Gym
Family-friendly home rentals with a pool

Themed villa w Pvt Pool near Disney|Gameroom, BBQ

Luxury Mickey Themed Townhome in Windsor Hills Res

Harry Potter 3BR | Windsor Hills ⢠Pool + Resort

Hot Deals! Free Waterpark, Close to Disney

New 2025! 2 miles to Disney 3 Ensuites 3.5 Baths

Cozy Themed Villa 6 BR | Close to Disney

Single-Level Comfortable Home, POOL, By Disney

Lovely Themed Home w/Private Pool -3m from Disney!
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R3,974Ā ZAR | R4,008Ā ZAR | R4,299Ā ZAR | R4,367Ā ZAR | R3,854Ā ZAR | R3,974Ā ZAR | R4,230Ā ZAR | R3,837Ā ZAR | R3,494Ā ZAR | R3,922Ā ZAR | R4,025Ā ZAR | R4,453Ā ZAR |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about vacation rentals that are family-friendly in Windsor Hills

Total vacation rentals
Explore 620 vacation rentals in Windsor Hills

Nightly prices starting at
Windsor Hills vacation rentals start at R1,199Ā ZAR per night before taxes and fees

Verified guest reviews
Over 12,680 verified reviews to help you choose

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
610 properties feature pools

Rentals with dedicated workspaces
360 properties have a dedicated workspace

Wi-Fi availability
590 of Windsor Hills vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Windsor Hills rentals

4.7 Average rating
Windsor Hills stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Rentals with an EV chargerĀ Windsor Hills
- Rentals with a washer and dryerĀ Windsor Hills
- Rentals with a patioĀ Windsor Hills
- Pet-friendly rentalsĀ Windsor Hills
- Apartment rentalsĀ Windsor Hills
- Serviced apartment rentalsĀ Windsor Hills
- Rentals with poolsĀ Windsor Hills
- Rentals with a hot tubĀ Windsor Hills
- Fitness-friendly rentalsĀ Windsor Hills
- Condo rentalsĀ Windsor Hills
- Villa rentalsĀ Windsor Hills
- House rentalsĀ Windsor Hills
- Rentals with outdoor seatingĀ Windsor Hills
- Rentals with a home theaterĀ Windsor Hills
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- Family-friendly rentalsĀ United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- Disney Springs
- SeaWorld Orlando
- Disney's Animal Kingdom Theme Park
- Magic Kingdom Park
- Old Town Kissimmee
- Walt Disney World Resort Golf
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Universal's Islands of Adventure
- Ventura Country Club
- Kissimmee Lakefront Park




