Luxury Vacation Rentals for Large Groups in Kissimmee
Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 41 large group vacation rentals – enter your dates for availability.
Kissimmee, Florida
Wander Orlando Haven
Next avail.
Dec 2 - Dec 5
410
Kissimmee, Florida
Wander Orlando Palmer
Next avail.
Dec 6 - Dec 8
510
Kissimmee, Florida
Wander Orlando Drift
Next avail.
Dec 10 - Dec 13
510
Kissimmee, Florida
Wander Orlando Grand
Next avail.
Dec 14 - Dec 16
512
Kissimmee, Florida
Wander Orlando Serenity
Next avail.
Dec 2 - Dec 5
512
Kissimmee, Florida
Wander Orlando Garden
Next avail.
Dec 2 - Dec 5
614
Kissimmee, Florida
Wander Orlando Dream
Next avail.
Dec 7 - Dec 10
716
Kissimmee, Florida
Wander Orlando Enchanted
Next avail.
Jan 28 - Feb 2
816
Welcome to your large group retreat in Kissimmee
Gather your favorite people in style. Our luxury vacation rentals in Kissimmee for large groups provide generous space, real privacy, and a flawless finish. With Wander you get hotel ease with the comfort of a private home, run by experts.
Expect expansive great rooms, multiple primary suites, optional bunk spaces, and kitchens built for big meals. Many homes add private pools, game lounges, and media rooms, plus ultra fast WiFi for work or play. Hotel-grade amenities, pristine cleaning, and 24/7 concierge mean every detail is handled.
Kissimmee, Florida
Wander Orlando Oasis
Next avail.
Dec 2 - Dec 4
1140
Kissimmee, Florida
Wander Orlando Golden
Next avail.
Dec 2 - Dec 5
1028
Kissimmee, Florida
Wander Orlando Paradise
Next avail.
Dec 2 - Dec 5
1036
Kissimmee, Florida
Wander Orlando Estate
Next avail.
Dec 13 - Dec 19
1246
Kissimmee, Florida
Wander Orlando Palace
Next avail.
Dec 5 - Dec 9
924
Kissimmee, Florida
Wander Orlando Cove
Next avail.
Dec 14 - Dec 16
1436
Kissimmee, Florida
Wander Orlando Sanctuary
Next avail.
Dec 2 - Dec 5
1228
Kissimmee, Florida
Wander Orlando Tropic
Next avail.
Dec 2 - Dec 5
1031
Kissimmee, Florida
Wander Orlando Starlight
Next avail.
Dec 4 - Dec 7
924
Kissimmee, Florida
Wander Orlando Treasure
Next avail.
Dec 7 - Dec 10
822
Kissimmee, Florida
Wander Orlando Manor
Next avail.
Dec 2 - Dec 5
828
Kissimmee, Florida
Wander Orlando Bliss
Next avail.
Dec 2 - Dec 5
1024
Kissimmee, Florida
Wander Orlando Sol
Next avail.
Dec 8 - Dec 11
1023
Kissimmee, Florida
Wander Orlando Fairway
Next avail.
Dec 2 - Dec 5
1025
Kissimmee, Florida
Wander Orlando Halo
Next avail.
Dec 7 - Dec 11
824
Kissimmee, Florida
Wander Orlando Modern
Next avail.
Dec 2 - Dec 5
820
IT'S A VACATION HOME, BUT BETTER
The Wander difference
Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.
All homes in Kissimmee
Kissimmee, Florida
Wander Orlando Haven
Next avail.
Dec 2 - Dec 5
410
Kissimmee, Florida
Wander Orlando Palmer
Next avail.
Dec 6 - Dec 8
510
Kissimmee, Florida
Wander Orlando Drift
Next avail.
Dec 10 - Dec 13
510
Kissimmee, Florida
Wander Orlando Grand
Next avail.
Dec 14 - Dec 16
512
Kissimmee, Florida
Wander Orlando Serenity
Next avail.
Dec 2 - Dec 5
512
Kissimmee, Florida
Wander Orlando Garden
Next avail.
Dec 2 - Dec 5
614
Kissimmee, Florida
Wander Orlando Dream
Next avail.
Dec 7 - Dec 10
716
Kissimmee, Florida
Wander Orlando Enchanted
Next avail.
Jan 28 - Feb 2
816
Discover more large groups activities in Kissimmee
Kissimmee puts you at the front door of Central Florida’s icons, including the Walt Disney World Resort, waterparks, and nightly entertainment. Beyond the parks, skim the headwaters of the Everglades by airboat, or chase trophy bass on Lake Tohopekaliga.
Stroll Old Town’s classic car nights, bike shaded paths in Shingle Creek Regional Park, and play championship golf in nearby Reunion and Celebration. Atlantic beaches and the Space Coast sit within an easy day trip. With convenience, variety, and sunshine year round, this is why Wander’s luxury vacation rentals in Kissimmee are the perfect choice, whether you’re traveling for work or leisure.