Vacation rentals have the best mix of premium home luxuries, common area amenities and convenient location. Vacation rentals do not have recognizable national brands and ample advertising behind them, but they do have a long history of satisfied guests who rent time and time again. As they say, once you have stayed in a vacation home rental, you’ll never stay in a cramped hotel again.

Our site reviews over 80+ resorts and vacation home communities that cater to the short term rental market. Vacation rental houses in Orlando, Kissimmeee and Davenport come in all shapes and sizes, but are most commonly available in a minimum size of three bedrooms to five bedrooms and higher. We believe you’ll have a superior vacation stay in these vacation home communities. However, all home communities and resorts are not created equal.

The highest rated resorts near Disney on our site include:

• Windsor Hills Resort – Outstanding clubhouse, top community pool and manicured lawns
• Emerald Island Resort – Gated entry, walking trails and well landscaped homes
• Windsor Palms – Maximum privacy, full amenities, excellent villa homes
• Bella Vida Resort – New Mediterranean style community, beautiful pool area
• Encantada Resort – Dual pools and spas, gated, and great location
• Terra Verde Resort – Modern clubhouse, tennis, basketball with premium homes and townhomes
• Tuscan Hills – Luxurious villa homes with tile roofs on rolling hills in Davenport
• Acadia Estates – Smaller cul-de-sac community with mostly large spacious vacation homes
• Reunion Resort – Beautiful villas adjacent to a world class golf course
• Watersong Resort – Located a little further out, this community contains beautiful homes in a natural setting along with a luxurious resort clubhouse

This is only a sample listing of some of the top properties. For full resort details, video and profiles on each of these resorts and more, please consult the community reviews section of our main page. These reviews will help you find the best values that meet your vacationing needs.

Best Orlando Vacation Home Resorts

To further help our readers, we have selected what in our opinion are the top eight Kissimmee vacation rental home communities.

We define “vacation homes” as detached dwelling structures with multiple bedrooms and are similar, if not synonymous, to single family residential homes. A complete explanation of the various vacation rental options are linked here.

Here we go. The top eight vacation home picks for short term rentals in Kissimmee, Florida based on vacation rental evaluator reviews are (in alphabetical order):

Acadia Estates

Bella Vida Resort

Emerald Island Resort

Formosa Gardens Estates 

Rolling Hills Estates

Terra Verde Resort

Windsor Hills Resort

Windsor Palms Vacation Homes 

Just click on any of the communities above for detailed review scores, video tours, photos and interactive maps.

Best Kissimmee Vacation Homes

Bella Vida is a gated and guarded vacation home community located approximately 6 miles from the Walt Disney World Resort ®. It is located behind Medieval Times.

Although located a little further out than some communities relative to Walt Disney World ®, the quality of the community is of the highest caliber. Check out our Video Review of Bella Vida Resort and interactive map below.

View Larger Map