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 1,015 family vacation rentals – enter your dates for availability.

Top-rated family vacation rentals in Kissimmee

4473 Monado

12 bedrooms•11.5 baths

•

~$175 less than other sites

Home in Kissimmee

8 bedrooms•6 baths

•

~$55 less than other sites

Large Orlando Home, Great Location

8 bedrooms•5 baths

New

Pool, Resort Home Near Disney

4 bedrooms•3 baths

•

New

~$60 less than other sites

Gated community townhouse next to Disney

4 bedrooms•3.5 baths

•

New

~$45 less than other sites

Townhouse with BBQ next to the club house

4 bedrooms•3.5 baths

•

New

~$55 less than other sites

Heated Pool Game Room Modern Resort Disney Magic

4 bedrooms•3 baths

•

~$35 less than other sites

Star Wars, Princess, Arcade Games, Disney 5334

4 bedrooms•3 baths

•

New

~$90 less than other sites

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.

Available soon in Kissimmee

Home in Kissimmee

8 bedrooms•6 baths

•

~$55 less than other sites

Pool, Resort Home Near Disney

4 bedrooms•3 baths

•

New

~$60 less than other sites

Gated community townhouse next to Disney

4 bedrooms•3.5 baths

•

New

~$45 less than other sites

Townhouse with BBQ next to the club house

4 bedrooms•3.5 baths

•

New

~$55 less than other sites

Heated Pool Game Room Modern Resort Disney Magic

4 bedrooms•3 baths

•

~$35 less than other sites

Star Wars, Princess, Arcade Games, Disney 5334

4 bedrooms•3 baths

•

New

~$90 less than other sites

Townhome in Kissimmee

4 bedrooms•3 baths

•

~$60 less than other sites

Home in Kissimmee

12 bedrooms•11.5 baths

•

~$155 less than other sites

Featured family vacation rentals in Kissimmee

Themed Rooms, Mario Kart, Private Pool, Disney

15 bedrooms•14.5 baths

•

New

~$380 less than other sites

Harry Potter, Toy Story, Game Room, Disney 2505

15 bedrooms•14 baths

•

New

~$415 less than other sites

Luxury

NM501L Legends Palazzo

9 bedrooms•10.5 baths

•

~$970 less than other sites

Luxury

500ML - 10 Bed - Michael's Manor - W001

10 bedrooms•11 baths

•

New

~$405 less than other sites

1200GT - 10 Bed - Alyssa's Abode - W261

10 bedrooms•10 baths

•

New

~$345 less than other sites

Luxury

W402E - The Eclectic Colonial Estate

14 bedrooms•14 baths

•

New

~$680 less than other sites

Luxury

BD012E - The Luxurious Bear's Den Oasis

6 bedrooms•6 baths

•

New

~$510 less than other sites

Luxury

W320E - The Entertainment Mansion

9 bedrooms•12 baths

•

New

~$660 less than other sites

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.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Kissimmee

4473 Monado

12 bedrooms•11.5 baths

•

~$175 less than other sites

Home in Kissimmee

8 bedrooms•6 baths

•

~$55 less than other sites

Large Orlando Home, Great Location

8 bedrooms•5 baths

New

Pool, Resort Home Near Disney

4 bedrooms•3 baths

•

New

~$60 less than other sites

Gated community townhouse next to Disney

4 bedrooms•3.5 baths

•

New

~$45 less than other sites

Townhouse with BBQ next to the club house

4 bedrooms•3.5 baths

•

New

~$55 less than other sites

Heated Pool Game Room Modern Resort Disney Magic

4 bedrooms•3 baths

•

~$35 less than other sites

Star Wars, Princess, Arcade Games, Disney 5334

4 bedrooms•3 baths

•

New

~$90 less than other sites

View all homes

Most popular amenities for family vacation rentals in Kissimmee

Basketball court (26)

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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 4473 Monado, 226, and Large Orlando Home | 8BR | Great Location. 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 1015 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.