Top Family-Friendly Vacation Rentals Near Disney World With Pools
Planning your dream vacation to Disney World? Choosing the right place to stay can make or break your family getaway. While hotels have their perks, an increasing number of travelers are opting for vacation rental communities, which offer space, privacy, and value for money. If you’re seeking resorts near Disney World with pools, you’re in for a treat! We’ve rounded up the top five family-friendly Orlando rental communities that offer comfort, convenience, and splash-worthy amenities to cool off after your theme park adventures.
1. Windsor Hills Resort, FL
Windsor Hills Resort is a favorite among families—and for good reason. Located just two miles from the gates of Disney World, this gated community combines proximity with premium amenities.
- Short-term rentals near Magic Kingdom: Choose from condos, townhomes, and spacious pool homes.
- Gated community near Disney: Enjoy peace of mind with 24/7 security.
- Amenities include a lagoon-style pool, water slides, splash pad, game room, fitness center, and movie theater.
- Family-friendly vibe: With playgrounds and sports courts, it’s perfect for kids.
If you’re looking for the best places to stay in Kissimmee that feel like a resort but offer the flexibility of a home, Windsor Hills Resort FL is your go-to. With 24/7 gated security and plenty of kid-friendly activities, Windsor Hills offers peace of mind and fun for the whole family.
For a complete guide on what to pack for your Disney World trip, check out our What to Pack for Disney World in Orlando blog.
2. Windsor at Westside
Windsor at Westside is another standout option just minutes from Disney World. This newer gated community is known for its stunning clubhouse and robust amenities.
- Orlando resort comparisons: Guests often rank this high for luxury and location.
- Resort-style features: Lazy river, water slides, full-service restaurant, and fitness center.
- Accommodations: Townhomes and villas, many with private pools.
This community is an excellent fit for those looking for a more resort-like feel with a private rental space.
3. Encore Resort at Reunion
Encore Resort offers one of the most unique experiences among Kissimmee vacation communities. With its own water park and upscale homes, it’s ideal for multi-family gatherings or large groups.
- Gated community near Disney with luxury services like in-home chefs and a concierge.
- Vacation homes: Larger properties with 5 to 13 bedrooms.
- Attractions: Water park, sports facilities, and dining options on-site.
Although it’s a bit pricier, the level of service and amenities make it worth it for families looking for something special.
4. Storey Lake Resort
Storey Lake Resort is centrally located near shopping, dining, and attractions, making it one of the best vacation rental communities in the area.
- Short-term rentals near Magic Kingdom and Disney Springs.
- Modern homes: Stylish townhomes and villas with private pools and themed rooms.
- Amenities: Resort-style pool, lazy river, mini-golf, and kayaking.
It’s a top choice for those who want a newer, modern aesthetic.
5. Solara Resort
Solara Resort stands out with its surf simulator and vibrant atmosphere, which appeal to active families and groups.
- Family-friendly Orlando rentals with diverse amenities.
- Community features: Heated pool, splash pad, basketball courts, and a clubhouse.
- Close to Disney: Just 15 minutes away.
Solara brings a high-energy, social environment ideal for families with older kids and teens.
What You Need to Know Before Booking a Windsor Hills Rental
Windsor Hills isn’t just another resort near Disney—it’s a vacation community built with families in mind. Here’s everything you need to know before booking:
Why Windsor Hills Resort FL Stands Out
- Close to Disney Parks: Just 2 miles away, making your commute a breeze.
- Windsor Hills gated community: Offers round-the-clock security.
- Amenities: Includes a massive pool, splash zone, and an on-site market.
- Value for money: Windsor Hills offers excellent pricing compared to similar Orlando resort communities.
Types of Rentals Available
- Condos: Great for small families or couples.
- Townhomes: Offer more space and often include a private splash pool.
- Pool Homes are typically 4-6 bedrooms with private pools and game rooms. Perfect for large families or groups.
Guest Reviews and Trust
With thousands of 5-star reviews, Windsor Hills remains a trusted name in family vacations. From cleanliness to customer service, the resort consistently exceeds expectations.
Discover why families love Chillax Inn and what differentiates us from other Windsor Hills vacation home rentals.
Pro Tip: For families visiting Windsor Hills Resort, consider timing your pool visits early in the morning or late afternoon to avoid crowds and enjoy a more relaxing swim. Also, check the community calendar for special events or kids’ activities during your stay.
Inside Chillax Inn: The Perfect Windsor Hills Retreat for Families
Looking for a place that combines comfort, convenience, and Disney magic? Chillax Inn is your answer.
Why Book Chillax Inn?
- Spacious Living: Our 5-bedroom villa in Windsor Hills offers over 2,300 square feet of living space.
- Windsor Hills villa with private pool: Relax in your very own screened-in pool and spa.
- Entertainment: Enjoy themed bedrooms, a fully equipped kitchen, and a game room.
- Ideal Location: Minutes from the Disney parks, shopping, and dining.
Affordable Kissimmee Vacation Rental
Compared to hotels and other rentals, Chillax Inn provides unbeatable value:
- No resort fees
- Free parking
- Fully stocked kitchen saves on dining out
Book Direct for the Best Experience
When you book directly with Chillax Inn, you get:
- Best rates
- Exclusive deals and availability
- Personalized service
Check availability and book your stay now!
Whether you’re planning your first family trip to Disney or returning for another magical experience, choosing the right vacation rental can make all the difference. With options like Windsor Hills and the comfort of Chillax Inn, your perfect Orlando vacation starts now.
