
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.

Charming Windsor Hills Condo Near Disney Parks
Experience the magic of Disney and create memories for a lifetime at your very own “Avengers Retreat" Conveniently situated less than 2 miles from the Walt Disney Resort, you can bring home the fantasy and adventure to this family-friendly condo in the highly sought-after resort of Windsor Hills. The floor plan boasts 3 Bedroom and 2 bathrooms and the entire design is inspired by your favorite Disney films FULL ACCESS to the resort Clubhouse (Pools/Water Park/Gym) NO resort fees; Free Parking

Game & Theater Room, Castle Bunks, Pool & Spa
Vacation at Windsor’s 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.

*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!

🏖 Resort Condo | 🎢 2mi -> Disney | 💦 Waterpark Fun
Welcome to Mickasita @ Windsor Hill's! Our condo is the ideal family vacation spot, conveniently located just minutes away from Disney World and all your desired attractions. During your stay, our whole-condo dehumidifier will maintain a comfortable and healthy level of humidity. Recently upgraded, our condo is sparkling clean and offers many resort amenities with the convenience of a home. You'll find new beds with fresh linens, flat-screen TVs, high-speed internet, a gym, and more.

Chic Vibes Comfy King Bed Next to Parks/Food/shops
Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

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.

Winter Special - 6 Mi to Disney - 4 Master Suites
📍 Amazing Location Near Disney • 6 miles to Walt Disney World • 15 miles to Universal Orlando Resort • 13 miles to SeaWorld Orlando • 30 miles to LEGOLAND Florida • 25 miles to Orlando International Airport • 1 mile to Walmart, Target, Publix & dining 🏡 4 bedrooms, each with a private bath. Smart TVs in every room. Private free heated plunge pool, plus resort pool access and free parking. One of the closest communities to Disney!

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

@Look@ ~ 3bed/2bath/1st floor! ~ Sleeps 7!
1ST FLOOR! 3 Bedroom/2 Bathroom Condo with 2 Master Suites! Main Master Suite has a King bed, TV and DVD player, walk in closet and a walk in shower. Second Master Suite has a King bed, TV and DVD player, and a door with direct access to the second bathroom. Guest Bedroom 3 has two Twin beds and a TV and DVD player. The living room features a TV over a beautiful electric fireplace and leather sofas - one is a sofa sleeper!

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

Disney Oasis
Enjoy Disney Oasis, our 3-bedroom, 2-bath condo, ideal for families! Nestled in a gated community with 24/7 security, we're just 3 miles from Walt Disney World® and close to other theme parks. Indulge in our resort-style amenities: a double Olympic-sized pool, thrilling waterslides, and a fun splash pad. Enjoy the convenience of nearby shopping, dining, and entertainment.
Popular amenities for Windsor Hills family-friendly rentals
Family-friendly home rentals with a hot tub

Magic Stay at Windsor Hills! 2 bedroom apartment!

No Airbnb fees! Home Theater! Pvt Pool/ Spa 278291

3 Miles 2 Disney | DisneyThemed | Fully Renovated

ReDesigned | Windsor Hills | Location | Water Park

Disney Escape at Windsor Hills

Resort Home 3.5 miles to Disney with home theater

Disney Retreat Princess Dress-Up + Pool

Westgate Vacation Villas - 1 Bedroom
Family- and pet-friendly home rentals

Cinderella’s, 4 miles Disney, Pool • Spa • Games

1BD Cottage "Limoncello" in Margaritaville

Waterfront Condo minutes to Disney & Universal

Orlando Home with Private Pool & Game Room !

Disney R US! Universal Escape! 3BDR 3Bath

Fantasy World Jurassic Park Villa, Free Water Park

*New*Peaceful and Cozy 4br 10 mins to Disney

Disney Themed Townhome- 5 miles to Disney Property
Family-friendly home rentals with a pool

Windsor Hills Resort| 8 min to Disney| Priv Pool

Windsor Hills Home w/Arcade Game Room|Near Disney

Mickey Train Bed, Free Waterpark, 10 min to Disney

Harry Potter 3BR• Windsor Hills+ Pool• Near Disney

Private Pool~BabyReady~Princess Playroom~Waterpark

The Eights House by Disney. Themed Island Dream

Pvt Pool~2 King Suites~Disney 4mi~Free H2O Slides

Family Disney Home | Pool | Game Room | Hot Tub
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ852 | ﺩ.ﺇ859 | ﺩ.ﺇ922 | ﺩ.ﺇ936 | ﺩ.ﺇ826 | ﺩ.ﺇ852 | ﺩ.ﺇ907 | ﺩ.ﺇ823 | ﺩ.ﺇ749 | ﺩ.ﺇ841 | ﺩ.ﺇ863 | ﺩ.ﺇ955 |
| 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 590 vacation rentals in Windsor Hills

Nightly prices starting at
Windsor Hills vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

Verified guest reviews
Over 13,180 verified reviews to help you choose

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
580 properties feature pools

Rentals with dedicated workspaces
350 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
- Serviced apartment rentals Windsor Hills
- Rentals with a hot tub Windsor Hills
- Condo rentals Windsor Hills
- Rentals with a washer and dryer Windsor Hills
- Rentals with pools Windsor Hills
- House rentals Windsor Hills
- Rentals with a patio Windsor Hills
- Rentals with an EV charger Windsor Hills
- Apartment rentals Windsor Hills
- Fitness-friendly rentals Windsor Hills
- Villa rentals Windsor Hills
- Pet-friendly rentals Windsor Hills
- Rentals with outdoor seating Windsor Hills
- Rentals with a home theater Windsor Hills
- Family-friendly rentals Four Corners
- Family-friendly rentals Osceola County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Give Kids the World Village
- Disney Springs
- Walt Disney World Resort Golf
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- ESPN Wide World of Sports
- Disney's Animal Kingdom Theme Park
- Epcot
- Old Town
- Kia Center
- Reunion Resort Golf Courses - Palmer & Watson
- Universal's Volcano Bay
- Discovery Cove
- Aquatica
- Bluegreen Vacations Fountains, Ascend Resort Collection
- Disney's Hollywood Studios
- Island H2O Live!
- ICON Park
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club




