Vacation Homes
Firelight, good wine, and great company. Evenings in Kissimmee feel effortlessly unforgettable.
Kissimmee is the Vacation Home Capital of the World
When planning a meeting in a vacation home, contact our team for the best options to fit your specific needs.
Kissimmee, Florida, is home to more than 30,000 professionally managed vacation home rentals, ranging from affordable single-family homes to 15-bedroom villas. These one-of-a-kind properties make unique spaces for a board retreat or corporate incentive trip. Whether you’re looking for a large private pool, a chef’s kitchen, or any other modern amenity, the Experience Kissimmee team can guide you to the best options. Contact the team to connect with the options that provide commission and event support services.
Magic Village Yards & Magic Village Views
These complexes feature on-site dining, elevated services, and uniform condo-style guest rooms with bold, modern décor.
Attendees get the privacy and security of a vacation home in a gated community while enjoying the perks of a boutique luxury resort. The properties feature a clubhouse, indoor and outdoor event space, on-site dining, and countless activities for after-hours entertainment. With world-famous theme parks right next door, the post-meeting activities are easy to plan.
Westgate Town Center Resort
An on-site town center offers attendees a convenient hub for dining, entertainment, and outdoor fun.
This centrally located resort offers all the comforts of a fully furnished home with units ranging from studios to four-bedroom villas. There’s also more than 8,500 square feet of flexible event space. After a day of meetings, attendees can find plenty to do right on-site at the Westgate Town Center, which features 14 outdoor pools, mini golf, fitness center, a movie theater, and more.
Hilton Vacation Club Mystic Dunes Orlando
Spacious suites on a golf course will delight attendees.
A trusted lodging brand located just minutes from Florida's famous theme parks, this Hilton Vacation Club property offers nearly 1,000 guest rooms, a championship golf course, and 3,300 square feet of meeting and event space, including a large ballroom with stunning natural light. Hilton’s on-site catering team keeps attendees fueled for on-site meetings and off-site adventures.
Encore Resort at Reunion
The perfect blend of a luxury hotel and vacation home experience.
The resort’s meeting space includes a private dining room that accommodates up to 50 people and a third-floor terrace that accommodates 120 guests. Attendees can enjoy the space, privacy, and security of a curated resort residence, with resort-style amenities including on-site restaurants, bars, and access to Encore Resort’s own water park.
Jeeves Vacation Rentals
Elevate your meeting with luxury vacation home rentals offering the ultimate in privacy, comfort, and style.
The collection of outstanding rental properties from Jeeves includes everything from 12-bedroom homes with elaborate pools to homes decked out with home theaters, bowling alleys, or private gyms. Jeeves helps simplify meetings with concierge services, private chefs for meal functions, and airport transportation support.
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Discover Kissimmee
Minutes from famous theme parks and attractions but also convenient to the natural wonders of Central Florida's great outdoors, Kissimmee offers the best of both worlds.