Windsor Hills
Vacation Rental Management
SunnySide Properties manages short-term rental homes throughout Windsor Hills, one of Kissimmee's oldest established resort communities, 2 miles from Disney's main gate.
Why Windsor Hills?
Kissimmee's Closest Established Resort to Disney
Windsor Hills sits just 2 miles from the Walt Disney World main gate, the closest major resort community to the parks, and is a decade-plus into a track record of steady occupancy and strong reviews.
- Private Pool HomesWindsor Hills is known for detached single-family homes with private heated pools, a key driver of consistent bookings from family groups who want space and privacy.
- Resort AmenitiesA clubhouse, fitness center, tennis courts, and a games room in addition to each home's private pool.
- 2 Miles from DisneyUnder 10 minutes from the main gate, the closest major resort community to the parks.
- Proven Long-Term PerformanceA longer operating history than most communities in this market, which shows up in more consistent occupancy.
- Established STR ProcessThe HOA has a long-established process supporting short-term rentals.
Owner Testimonial
"Windsor Hills has been our family's investment for eight years. SunnySide took over management and immediately improved our occupancy and our reviews. I wish we'd made the switch sooner."
Free Vacation Rental Revenue Estimate
What could your Windsor Hills property earn?
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Our Windsor Hills Services
Full-Service Management in Windsor Hills
Everything you need to run a profitable short-term rental (STR), handled by our local team.
Professional Photos
HDR photography that showcases your Windsor Hills property at its best.
Dynamic Pricing
Real-time rate optimization tuned to Windsor Hills demand patterns.
Professional Cleaning
Trusted local housekeepers who know Windsor Hills properties.
24/7 Guest Support
We handle every guest inquiry so you never get a 2am call.
Common Questions
Windsor Hills FAQ
About 2 miles, under 10 minutes by car, the closest major resort community to the main gate.
It has a decade-plus track record of consistent occupancy, longer than most communities in this market.
A clubhouse, community pool, fitness center, tennis courts, and a games room, on top of private pools at each home.
Where We Work
Orlando's Top Resort Communities
We specialize in STR management across Orlando's most popular resort communities, from Champions Gate to Windsor Island and beyond.
Own a Property in Windsor Hills?
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