Kissimmee Vacation Homes & Villa Rentals
Villas in Kissimmee's gated resorts along the US-192 corridor
Kissimmee is a city in Osceola County, Florida, directly south-east of Walt Disney World. Our Kissimmee vacation homes are villas in gated resort communities off US-192 and Osceola Parkway, a short drive from the Disney gates. Most have a private pool, and every one is rented whole and booked direct with the local manager.
Right now that is 242 homes across Encore Resort, Paradise Palms Resort, Reunion Resort, Solara Resort, Storey Lake Resort and Windsor Hills Resort, sleeps 4 to 46.
Kissimmee sits in Osceola County, immediately south and east of Walt Disney World. For anyone renting a villa it mostly means one road and its side turnings: US-192, signed as W Irlo Bronson Memorial Highway, with Osceola Parkway running roughly parallel to the north. The gated resort communities are set back off both, so you keep the access without the traffic outside your gate.
Windsor Hills Resort is the closest of our Kissimmee resorts to Disney, under three miles from the gates, and the others are a short drive further out. What you get for staying on this side is that everything else is close too: Old Town's vintage rides and weekend car cruises are on US-192 itself, the go-karts at Fun Spot America are fifteen to twenty minutes up towards International Drive, and The Loop on John Young Parkway covers the arrival-day grocery run and a cinema trip in one stop.
The homes range from townhomes with resort pool access up to very large villas with their own cinema rooms. If the specification matters to you more than which side of the parks you are on, the luxury vacation homes page sets a floor on size, pool, cinema and games room instead.
Kissimmee villas
24 properties found
Common questions
Is Kissimmee close to Walt Disney World?
Very. Our Kissimmee resorts sit within about ten miles of the Disney gates and the closest of them is under three miles out, with each resort page carrying its own measured distance table. Allow fifteen to twenty minutes door to gate once you have parked and taken the tram.
Kissimmee or Davenport — which is the better base for a villa?
Kissimmee is nearer the Disney gates and nearer the US-192 restaurants and attractions, which suits a first Orlando trip. Davenport sits further west off I-4, where the communities tend to be newer and the roads quieter, and it is closer to LEGOLAND. Both are a comfortable drive from every park.
Do we need a car to stay in Kissimmee?
In practice, yes. The resorts are residential communities set back off the main roads, and while buses do run along US-192 they are not built for getting a family to a park gate on schedule. The supermarket, the restaurants and the park entrances are all a short drive, and every home we manage has free parking.
What is US-192?
US-192 is the main east-west highway through Kissimmee, signed as West Irlo Bronson Memorial Highway along the tourist stretch. It carries most of the area's restaurants, shops, mini-golf and supermarkets, and the gated villa communities sit on the roads leading off it rather than on the highway itself.
Are the Kissimmee resorts gated?
Every community in this set is gated, with a controlled entrance, and access to the resort's own facilities is included in the stay — typically a pool complex, a fitness centre, and on-site dining or a cafe where the community has one. What is on site differs by resort, and each resort page lists it.
Send us your dates and your headcount and we will point you at the homes in these resorts that genuinely fit, rather than the ones that merely survive a filter. Our Davenport-side resorts — ChampionsGate, Windsor Island and Windsor at Westside — are not in the set above, and they are listed on the Orlando villas page along with everything else we manage.