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 41 family 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 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.
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 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.