Family-friendly vacation rentals in Windsor Hills

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Top-rated family-friendly rentals in Windsor Hills

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
A vibrant pool area is depicted, featuring colorful water slides and various water play structures. Nearby, a spacious balcony can be seen with outdoor furniture, offering views of the resort. Inside, a cozy living area includes a children's play table, while a bright theme room showcases colorful wall art inspired by Disney.
Condo in Kissimmee
4.81 out of 5 average rating, 135 reviews

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

Top guest favorite
The spacious living area features comfortable seating arrangements, large windows, and a decorative area rug. The view leads to the private screened-in pool, providing a seamless indoor-outdoor experience. The room is illuminated by natural light and complemented by a modern ceiling fan.
Home in Kissimmee
4.99 out of 5 average rating, 142 reviews

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.

Top guest favorite
An outdoor dining area features a large, custom-built wooden table surrounded by black chairs. Blue plates and glassware are meticulously arranged for an inviting meal. A bright blue pool glimmers in the background, enclosed by a mesh screen to ensure privacy.
Villa in Kissimmee
4.97 out of 5 average rating, 144 reviews

*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!

Guest favorite
An inviting living space features a modern gray sofa centered around a round coffee table, set on a plush area rug adorned with a playful pattern. A wall-mounted fan circulates air beneath a vibrant Mickey Mouse artwork, while a dining table for four is positioned nearby.
Condo in Kissimmee
4.94 out of 5 average rating, 171 reviews

🏖 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.

Top guest favorite
The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.
Apartment in Kissimmee
4.99 out of 5 average rating, 128 reviews

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!

Top guest favorite
A recreational game room is presented, featuring an air hockey table and a pool table centered in the space. Two gaming chairs are positioned near flat-screen monitors on the wall. Colorful LED lighting creates an engaging atmosphere in the room.
Villa in Kissimmee
4.96 out of 5 average rating, 149 reviews

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

Top guest favorite
A vibrant games room is equipped with various arcade machines, including SpongeBob Racing. A massage chair is positioned nearby, while a theater room features plush seating. An outdoor space highlights a screened-in pool area surrounded by palm trees, visible through large windows.
Home in Kissimmee
5 out of 5 average rating, 242 reviews

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.

Top guest favorite
Home in Kissimmee
4.97 out of 5 average rating, 150 reviews

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!

Guest favorite
A private pool area is enclosed by a protective screen, providing a serene oasis. The pool is surrounded by tiled flooring, with a table and chairs nearby for relaxation. Bright curtains frame the entrance to the living space, enhancing the overall inviting atmosphere.
Townhouse in Kissimmee
4.91 out of 5 average rating, 245 reviews

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

Guest favorite
An overhead view reveals the expansive pool area of the resort, featuring a large heated pool surrounded by lounge chairs. A vibrant water park with slides and play areas is visible, set among lush greenery and palm trees, providing ample recreation options.
Condo in Kissimmee
4.87 out of 5 average rating, 216 reviews

@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!

Top guest favorite
Home in Kissimmee
4.97 out of 5 average rating, 125 reviews

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

Top guest favorite
A spacious living area features a large leather sofa and wall art, creating an inviting space. The open-concept layout connects to the kitchen and dining area, while large windows allow natural light to fill the room. A vibrant resort-style pool area and water slides are visible outside.
Condo in Kissimmee
4.96 out of 5 average rating, 151 reviews

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

When is the best time to visit Windsor Hills?

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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