Luxury Vacation Rentals for Families in Osceola County

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 959 family vacation rentals – enter your dates for availability.

Top-rated family vacation rentals in Osceola County

Home in Kissimmee

12 bedrooms•11.5 baths

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Home in Davenport

4 bedrooms•5 baths

New

Home in Kissimmee

5 bedrooms•4 baths

New

Home in Kissimmee

4 bedrooms•3 baths

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Home in Kissimmee

12 bedrooms•11.5 baths

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Home in Kissimmee

5 bedrooms•5 baths

Townhome in Kissimmee

4 bedrooms•3 baths

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Home in Kissimmee

4 bedrooms•3 baths

Welcome to family adventures in Osceola County

Bring everyone together with space to spread out and unwind. Wander offers luxury family vacation rentals in Osceola County that blend hotel-grade consistency with the comfort of a private home. Each stay is designed so parents can relax and kids can play without compromise.

Enjoy generous multi-bedroom layouts, open-plan kitchens for shared meals, and living areas that flow outdoors for sunshine and poolside downtime. Many homes include private pools, game rooms, and bunk-friendly sleeping options, while every Wander delivers ultra fast WiFi, pristine cleaning, and 24/7 concierge support.

Available soon in Osceola County

Home in Davenport

4 bedrooms•5 baths

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New

Home in Kissimmee

4 bedrooms•3 baths

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Home in Kissimmee

12 bedrooms•11.5 baths

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Townhome in Kissimmee

4 bedrooms•3 baths

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Home in Kissimmee

4 bedrooms•3 baths

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Home in Polk County

6 bedrooms•4 baths

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New

Home in Davenport

4 bedrooms•5 baths

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New

Home in Davenport

6 bedrooms•6 baths

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New

Featured family vacation rentals in Osceola County

Home in Four Corners

9 bedrooms•9.5 baths

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Home in Four Corners

10 bedrooms•10 baths

New

Luxury

Home in Kissimmee

9 bedrooms•10.5 baths

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Home in Kissimmee

11 bedrooms•10 baths

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New

Luxury

Home in Kissimmee

6 bedrooms•6 baths

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New

Home in Kissimmee

9 bedrooms•9 baths

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New

Luxury

Home in Kissimmee

10 bedrooms•11 baths

New

Home in Kissimmee

11 bedrooms•15 baths

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Highlights in Osceola County

Discover endless family fun in Osceola County, featuring thrilling airboat rides, classic amusement parks, and vibrant entertainment districts for all ages.

Old Town Kissimmee

Fun Spot America - Kissimmee

Wild Florida Airboats & Gator Park

Medieval Times Dinner & Tournament

Celebration Town Center

Shingle Creek Regional 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 Osceola County

Home in Kissimmee

12 bedrooms•11.5 baths

•

Home in Davenport

4 bedrooms•5 baths

New

Home in Kissimmee

5 bedrooms•4 baths

New

Home in Kissimmee

4 bedrooms•3 baths

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Home in Kissimmee

12 bedrooms•11.5 baths

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Home in Kissimmee

5 bedrooms•5 baths

Townhome in Kissimmee

4 bedrooms•3 baths

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Home in Kissimmee

4 bedrooms•3 baths

View all homes

Most popular amenities for family vacation rentals in Osceola County

Basketball court (28)

More popular family destinations near Osceola County

Family vacation rentals in Kissimmee

Family vacation rentals in KISSIMMEE

Family vacation rentals in Davenport

Family vacation rentals in Orlando

Family vacation rentals in Orlando,

Family vacation rentals in Four Corners

Other popular amenities & vacation types in Osceola County

Private pool vacation rentals in Osceola County

Discover more family fun in Osceola County

Osceola County pairs the magic of Central Florida with room to breathe. Lakes like Tohopekaliga and the headwaters of the Everglades at Shingle Creek create a scenic backdrop for paddling and wildlife spotting.

Family days come easy here, from playgrounds and splash zones at Kissimmee Lakefront Park to the Silver Spurs Rodeo and Celebration's lakeside paths. Add effortless proximity to Orlando’s world-famous theme parks. This is why Wander's luxury family vacation rentals in Osceola County are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Osceola County

Why should I book a Wander in Osceola County 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 Osceola County 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 Osceola County?

Some of our most popular family vacation rentals in Osceola County include 4473 Monado, Beautiful large home, conservation views, 5 beds, and Cheerful 5 bed - 4 bath Spacious Home. 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 Osceola County?

Wander offers 959 family vacation rentals in Osceola County, 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 Osceola County?

You can check-in to Wander family vacation rentals in Osceola County after 4.00pm and check-out before 10.00am.

Do Wander’s family vacation rentals in Osceola County have WiFi access?

Yes. Every Wander home in Osceola County 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.