In the heart of Central Florida’s booming vacation rental market, Orlando and Kissimmee continue to dominate the map for both travelers and real estate investors. With over 70 million visitors heading to the area each year, many of them families looking for space, comfort, and convenience, demand for short-term rentals near Disney World has never been stronger.
That’s where Windsor Hills stands out.
Just 2 miles from the gates of Walt Disney World, Windsor Hills Resort has become one of the most searched and trusted vacation rental communities in the Disney area. It’s a favorite on TripAdvisor, Facebook travel groups, and direct booking platforms for one key reason: it consistently delivers on guest expectations.
Whether you’re a frequent Disney-goer, a family planning your first trip, or a property investor looking for a high-performing short-term rental, Windsor Hills checks every box.
1. Prime Location Just Minutes from Disney
When it comes to vacation rentals, location isn’t just important—it’s everything. Windsor Hills Resort is located at 2600 N Old Lake Wilson Rd, Kissimmee, FL 34747, just 2 miles from Walt Disney World. It’s one of the closest short-term rental communities to the parks, and it’s a major reason travelers seek it out year-round.
Families love how quickly they can get to Magic Kingdom in the morning (and back for naptime in the afternoon). Investors love the effect that proximity has on occupancy rates and search visibility.
But it’s not just Disney. Windsor Hills offers easy access to:
- Universal Studios Florida – 20 minutes
- SeaWorld Orlando – 15 minutes
- Gatorland – 20 minutes
- Shops and restaurants along Highway 192 – under 5 minutes
In short, Windsor Hills nails that sweet spot: close enough for ultimate convenience, yet far enough to enjoy peace and quiet after the parks.
2. Gated Security and Peace of Mind
One thing guests consistently mention in reviews? Feeling safe and at ease. Windsor Hills delivers with a 24/7 manned security gate, giving guests a true sense of security from the moment they arrive.
It’s a standout feature, especially for:
- Families with young children
- International travelers unfamiliar with the area
- First-time vacation renters looking for reassurance
The gated entry also adds perceived value and supports higher nightly rates, particularly when competing with less secure communities.
And while it’s just minutes from the excitement of Disney, the resort itself feels tucked away and peaceful, like a private retreat built for recharging after long park days.
3. A Variety of Rental Options for Every Group Size
Not every guest wants a giant house, and not every family fits in a condo. That’s what makes Windsor Hills Resort such a smart choice for both travelers and property owners: it offers a flexible mix of vacation rental options to match just about any group size or budget.
Visitors can choose from:
- 2- and 3-bedroom condos – great for couples and small families
- Townhomes with splash pools – perfect for mid-sized groups
- Large single-family homes with private pools – ideal for family reunions or multiple families traveling together
Every property is individually owned, often beautifully furnished and well-maintained, with layouts that cater to vacationers. Whether it’s a quick weekend getaway or a two-week Disney trip, Windsor Hills has something that fits.
This kind of variety attracts a wider guest base, and that means more booking potential for owners.
4. Resort-Style Amenities That Guests Actually Use
One of the biggest reasons Windsor Hills keeps guests coming back? The amenities. These aren’t just add-ons or brochure fillers; they’re the kind of features families plan their entire stay around.
Top-rated amenities include:
- Lagoon-style resort pool with 140,000 gallons of swimming space
- On-site water park with dueling slides and a splash pad
- Game room, fitness center, and private movie theater
- Tennis courts, putting green, and multiple playgrounds
- The Marketplace & Grill for quick meals, drinks, and essentials
It’s everything you’d expect from a high-end Orlando resort, but available without the theme park prices.
Families can spend entire days at the resort without ever needing to leave. That means longer bookings, happier guests, and more 5-star reviews for your property.
5. A Community Built for Short-Term Rentals
Windsor Hills isn’t just friendly to short-term rentals—it was built for them. The entire community is zoned and approved for vacation rentals, meaning investors don’t have to worry about unexpected HOA restrictions or gray areas that can complicate hosting.
The result?
- No red tape
- No stress over local ordinances
- No HOA surprises down the line
This kind of hosting-friendly environment makes it easier to list on platforms like Airbnb, VRBO, Booking.com, and more with complete confidence that you’re operating legally and efficiently.
It’s the kind of setup every vacation rental investor hopes for: simple, smooth, and built for results.
6. Proven Popularity and Positive Reviews
While some communities come and go in popularity, Windsor Hills has stayed consistently top-of-mind for both vacationers and property owners, and the reviews prove it.
Just check:
- TripAdvisor: Hundreds of glowing reviews from happy families
- Facebook groups: Active, supportive community with ongoing praise
- Direct testimonials from guests and investors alike
Whether you’re listing your home or planning your next stay, Windsor Hills’ reputation gives you a head start.
7. Strong Investment Opportunity
Windsor Hills is a smart investment, plain and simple. It stays booked year-round because it’s only 2 miles from Disney. That location alone keeps calendars full, but the resort-style features like the water park, lagoon pool, and gated security let owners charge higher nightly rates than in regular neighborhoods.
That means more income, more often.
Unlike other communities that struggle with off-season gaps, Windsor Hills has low vacancy because people always want to stay there.
And while you’re earning steady short-term rental income, your property is also gaining long-term value. If you want a vacation rental that actually performs, this is the kind of place you want to own.
Why Windsor Hills Is Perfect for Your Next Stay (or Investment)
If you’re looking for a vacation rental that performs and a community guests actually love, Windsor Hills checks every box. It’s perfect for first-time investors, seasoned Airbnb hosts, and families alike. With built-in demand from its unbeatable location near Disney, top-tier resort amenities, and a secure, family-friendly atmosphere, this community consistently delivers five-star experiences and strong returns.
Whether you’re thinking of buying, booking, or listing your property here, Windsor Hills offers everything you need to succeed in the short-term rental game.
