Book Family Friendly Rentals in Osceola County

We selected the 176 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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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.

All The Lights

All The Lights

  • 28 guests

  • 11 bedrooms

Polk County, Florida

Whether you’re in search of a sun kissed stay or a fun-filled family adventure, this home will not disappoint. Outside, there’s a private pool and a Jacuzzi for long relaxing soaks.

Mickey's Melody

Mickey's Melody

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

This home sets the stage for magical stay in Florida. It’s just a short drive to Disney World, Disney Springs as well as the centre of Kissimmee where you’ll find all the amenities you could need.

Friends, Family & Fun

Friends, Family & Fun

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

On the outskirts of Orlando, just a quick twenty-minute drive from Disney World, this spacious family home promises a stay packed with memories. Upon crossing the threshold, you’ll be hit immediately by this home’s airiness, compounded by high ceilings and a large open-plan living space.


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

Explore the 176 most perfect homes in our collection

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Most popular homes in Osceola County

Maitland Hills

Maitland Hills

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Family Fun in Florida

Family Fun in Florida

  • 24 guests

  • 10 bedrooms

Polk County, Florida

Pineview Villa

Pineview Villa

  • 34 guests

  • 12 bedrooms

Polk County, Florida

The Blue Ledge

The Blue Ledge

  • 18 guests

  • 6 bedrooms

Polk County, Florida

The Starlight Sky

The Starlight Sky

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Fun-Filled Getaway

Fun-Filled Getaway

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Casa Rosita

Casa Rosita

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Orlando Sunshine

Orlando Sunshine

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

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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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