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 40 large group vacation rentals – enter your dates for availability.
Kissimmee, Florida
Wander Orlando Halo
Next avail.
Jan 21 - Jan 24
824
Kissimmee, Florida
Wander Orlando Horizon
Next avail.
Jan 17 - Jan 20
719
Kissimmee, Florida
Wander Orlando Manor
Next avail.
Jan 25 - Jan 28
828
Kissimmee, Florida
Wander Orlando Golden
Next avail.
Jan 26 - Jan 29
1028
Kissimmee, Florida
Wander Orlando Palace
Next avail.
Jan 25 - Jan 28
924
Kissimmee, Florida
Wander Orlando Haven
Next avail.
Jan 17 - Jan 20
410
Kissimmee, Florida
Wander Orlando Oasis
Next avail.
Jan 19 - Jan 21
1140
Kissimmee, Florida
Wander Orlando Modern
Next avail.
Jan 17 - Jan 19
820
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.
Jan 19 - Jan 21
1140
Kissimmee, Florida
Wander Orlando Modern
Next avail.
Jan 17 - Jan 19
820
Kissimmee, Florida
Wander Orlando Fairway
Next avail.
Jan 31 - Feb 3
1025
Kissimmee, Florida
Wander Orlando Grand
Next avail.
Jan 17 - Jan 19
512
Kissimmee, Florida
Wander Orlando Estate
Next avail.
Jun 30 - Jul 9
1246
Kissimmee, Florida
Wander Orlando Park
Next avail.
Jan 30 - Feb 2
718
Kissimmee, Florida
Wander Orlando Springs
Next avail.
Jan 22 - Jan 26
822
Kissimmee, Florida
Wander Orlando Golden
Next avail.
Jan 26 - Jan 29
1028
Highlights in Kissimmee
Discover thrilling theme parks, exciting dinner shows, and outdoor adventures perfect for accommodating large groups and creating lasting memories together.
Walt Disney World® Resort
Universal Orlando Resort
SeaWorld® Orlando
Old Town Kissimmee
Gatorland
Medieval Times Dinner & Tournament
Boggy Creek Airboat Adventures
Fun Spot America Kissimmee
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 Halo
Next avail.
Jan 21 - Jan 24
824
Kissimmee, Florida
Wander Orlando Horizon
Next avail.
Jan 17 - Jan 20
719
Kissimmee, Florida
Wander Orlando Manor
Next avail.
Jan 25 - Jan 28
828
Kissimmee, Florida
Wander Orlando Golden
Next avail.
Jan 26 - Jan 29
1028
Kissimmee, Florida
Wander Orlando Palace
Next avail.
Jan 25 - Jan 28
924
Kissimmee, Florida
Wander Orlando Haven
Next avail.
Jan 17 - Jan 20
410
Kissimmee, Florida
Wander Orlando Oasis
Next avail.
Jan 19 - Jan 21
1140
Kissimmee, Florida
Wander Orlando Modern
Next avail.
Jan 17 - Jan 19
820
Most popular amenities for large group vacation rentals in Kissimmee
More popular large group destinations near Kissimmee
Other popular amenities & vacation types in Kissimmee
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.
FAQs: Vacation Rentals in Kissimmee
Why should I book a Wander in Kissimmee over other large group vacation rentals?
Wander offers a level of consistency and quality you won’t find with most large group vacation rentals.
Every home in Kissimmee delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?
Which are Wander’s most popular large group vacation rentals in Kissimmee?
Some of our most popular large group vacation rentals in Kissimmee include Wander Orlando Oasis, Wander Orlando Modern, and Wander Orlando Fairway. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.
How many different large group vacation rentals does Wander have available in Kissimmee?
Wander offers 40 large group vacation rentals in Kissimmee, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.
What time is check-in and check-out at Wander’s large group vacation rentals in Kissimmee?
You can check-in to Wander large group vacation rentals in Kissimmee after 4.00pm and check-out before 10.00am.
Do Wander’s large group vacation rentals in Kissimmee have WiFi access?
Yes. Every Wander home in Kissimmee has ultra fast, reliable WiFi so you can stay connected throughout your stay.
What is Wander’s cancellation policy?
You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.