Windsor Hills Resort

Join Windsor Hills Resorts’ fastest growing property management company

Brian – Vacation Home Expert

We know Windsor Hills Resort as no other

Windsor Hills Resort in Kissimmee is one of the top vacation rental resorts in the area. With a huge 140.000-gallon swimming pool next to the clubhouse, a hot tub that easily fits 10 people, fitness area, basketball, tennis, and mini gold court, you have all the sports amenities you could wish for.  If you prefer a more relaxed time passing, go to the game room or watch a movie at the movie theatre!

Pick up a few sundries & grocery items or enjoy a fresh burger, sandwich or beverage from the grill! The Market Place stocks basic food items including milk, eggs, juice, bread & other essentials.

At Windsor Hills, we pride ourselves on our distinctive vacation rental homes dedicated to provide a safe, comfortable & enjoyable environment for families visiting top attractions including Disney World, Universal Studios Florida, Sea World, Gatorland and more!

Find out what you could earn 

Two straightforward pricing plans

Casiola offers two straightforward pricing plans: get your income based on the revenue your property makes or opt for the 100% guaranteed monthly income. Choose the plan that works best for you!

Performance-based income
We fully manage your property, for a low 20% commission fee.

100% Guaranteed income
We fully manage your property, and you collect the same income every month. Due to Covid, we updated our procedures. Contact us via if you’re interested in 100% Guaranteed Income.

Michelle – Owner Relations Manager

NEW! Real-time Property Dashboard

Everything going on in your vacation home in
real-time. FREE for every Casiola homeowner.

Full-service vacation home property management. We take care of every aspect of your Bella Vida Resort vacation rental home.

Powerful Marketing

We create standout listings, research and set the best nightly rates, and post them on major platforms.

More Bookings

We quickly respond to all booking inquiries and attract the right guests for your property.

24/7 Guest Support

We care for your guests 24/7 to ensure a great stay and secure rave reviews.

5-Star Property Care

We take great care of your property and quickly resolve any guest or maintenance issues that arise.

What our owners say about Casiola

We advertise your vacation home on the world’s largest booking websites

Casiola: vacation home management you’ll love!