
Luxury Vacation Rentals for Families 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 44 family vacation rentals – enter your dates for availability.

Welcome to family adventures in Kissimmee
Bring everyone together with Wander’s luxury family vacation rentals in Kissimmee. Choose from spacious contemporary homes and modern villas that pair the polish of a five star stay with the comfort of a private residence, giving kids space to play and adults room to unwind.
Expect thoughtful layouts with multiple bedrooms, generous living areas, and outdoor lounges fit for family downtime. Every stay includes hotel-grade amenities, pristine cleaning, ultra fast WiFi, and 24/7 concierge service. Many homes add private pools, game nooks, and quiet workspaces, so work and play never compete. What you see is exactly what you arrive to, ensuring a stress-free family escape.
Highlights in Kissimmee
Discover a world of family fun, from world-famous theme parks and thrilling airboat rides to charming downtowns and natural escapes.
Walt Disney World® Resort
Universal Orlando Resort
SeaWorld Orlando
Old Town Kissimmee
Fun Spot America Kissimmee
Gatorland
Wild Florida Airboats, Gator Park & Drive-thru Safari
Kissimmee Lakefront Park
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, FL
Wander Orlando Charm
Next avail.
Jan 26 - Jan 28
36
Kissimmee, FL
Wander Orlando Haze
Next avail.
Feb 2 - Feb 4
36
Most popular amenities for family vacation rentals in Kissimmee
More popular family destinations near Kissimmee
Other popular amenities & vacation types in Kissimmee

Discover more family fun in Kissimmee
Kissimmee puts you minutes from Orlando’s most celebrated parks while keeping a relaxed lakeside pace. Walt Disney World Resort sits just up the road, with Universal Orlando and SeaWorld within easy reach for big days of thrills.
Off the coaster track, families find airboat rides on the headwaters of the Everglades, paddling on Shingle Creek, boardwalk sunsets at Lake Tohopekaliga, and classic fun at Old Town. Seasonal festivals, weekend car shows, and kid-friendly attractions keep the schedule full without the crowds.
With sunshine, convenience, and a wide spectrum of family activities, Kissimmee makes planning simple. That is why Wander’s luxury family vacation rentals in Kissimmee are the perfect choice, whether you are traveling for work or leisure.
FAQs: Vacation Rentals in Kissimmee
Why should I book a Wander in Kissimmee over other family vacation rentals?
Wander offers a level of consistency and quality you won’t find with most family 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 family vacation rentals in Kissimmee?
Some of our most popular family vacation rentals in Kissimmee include Wander Orlando Fairway, Wander Orlando Estate, and Wander Orlando Park. 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 family vacation rentals does Wander have available in Kissimmee?
Wander offers 44 family 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 family vacation rentals in Kissimmee?
You can check-in to Wander family vacation rentals in Kissimmee after 4.00pm and check-out before 10.00am.
Do Wander’s family 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.

















