Book Family Friendly Rentals in Osceola County

We selected the 173 homes worth renting in this location

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Home spotlights in Osceola County

For You Love

For You Love

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Nestled in a private resort, this home is perfectly placed for a fun-filled adventure in Florida. It’s just a short drive to Walt Disney World and the main attractions in Kissimmee – including walking paths, playgrounds and restaurants.

The Sweet Palm

The Sweet Palm

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Step into this Orlando retreat, where every corner will make you feel the excitement and fun of childhood, all over again. With clean-lined interiors, a private pool and entertainment at every bend (including a home theatre, arcade, and loft lounge), you’ll never run out of ways to be entertained.

Orlando Sunshine

Orlando Sunshine

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

This family home offers plenty of space and style for your dream Florida getaway. The kitchen is fully equipped, perfect for whipping up meals to enjoy outside by the screened private pool and spa.

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

This is the perfect vacation home for families looking for a fun-filled getaway. Kids will love the superhero and Fashionista-themed bedrooms, complete with over-the-top bunk beds and decor.


We selected the top 3% holiday homes in Osceola County Family Friendly Rentals

Explore the 173 most perfect homes in our collection

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Most popular homes in Osceola County

Pines & Greenwood

Pines & Greenwood

  • 28 guests

  • 11 bedrooms

Polk County, Florida

Mickey's Melody

Mickey's Melody

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

Strawberry Sunrise

Strawberry Sunrise

  • 18 guests

  • 6 bedrooms

Polk County, Florida

The Blue Dunes

The Blue Dunes

  • 24 guests

  • 10 bedrooms

Polk County, Florida

Lazy River Retreat

Lazy River Retreat

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

The Starlight Sky

The Starlight Sky

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Pineview Villa

Pineview Villa

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Town & Country Retreat

Town & Country Retreat

  • 10 guests

  • 4 bedrooms

Four Corners, Osceola County

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Check upcoming rates & availability for Osceola County Family Friendly Rentals


Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Osceola County, Florida, United States. Here at Plum Guide, we prioritise customer satisfaction over everything, which is why we are so meticulous in what we do. Every home in our collection has been put through a vigorous 150-step vetting process, so we promise consistent quality you can count on. Each rental also comes fully furnished will essential bathroom toiletries, an excellently-equipped kitchen, and all linen included. Rent Osceola County Family Friendly Homes now and secure yourself a trip to remember for all the right reasons. And call on the help of our friendly team, on standby night and day to ensure that your decision process is made as straightforward as possible.

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