Book Family Friendly Rentals in Osceola County

We selected the 124 homes worth renting in this location

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Age 13+

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Age 1 to 12

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Home spotlights in Osceola County

ToplessTower

ToplessTower

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Experience luxury living at this villa, a stunning mansion located just minutes away from Orlando's famous attractions and dining destinations. With five spacious and elegant bedrooms, this Midcentury Modern-style villa exudes classic, clean-lined luxury with natural fabrics, soothing colors, and pops of contemporary color.

Fisk Bayview

Fisk Bayview

  • 28 guests

  • 10 bedrooms

Polk County, Florida

This stunning 7,200-square-foot villa in a resort of Orlando is a dream vacation home for families and groups of friends. The mid-century modern decor and amenities are sure to impress guests of all ages.

The Magic of Disney

The Magic of Disney

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

This vacation home in The resort is perfect for families with kids who will love the Winter and Superhero-themed bedrooms, private home theater, game room/loft, and private screened-in pool and spa. The game room has a karaoke system, mini jungle gym, arcade games, and a lounge area with a smart TV.

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 124 most perfect homes in our collection

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Most popular homes in Osceola County

Pineview Villa

Pineview Villa

  • 34 guests

  • 12 bedrooms

Polk County, Florida

So Much Better

So Much Better

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Just One Night at the Hotel

Just One Night at the Hotel

  • 24 guests

  • 10 bedrooms

Polk County, Florida

Old Folks At Home

Old Folks At Home

  • 34 guests

  • 10 bedrooms

Polk County, Florida

The Time Traveler's Daughter

The Time Traveler's Daughter

  • 20 guests

  • 9 bedrooms

Four Corners, Osceola County

The Blue Burdock

The Blue Burdock

  • 24 guests

  • 9 bedrooms

Four Corners, Osceola County

A Little Piece of Sunshine

A Little Piece of Sunshine

  • 28 guests

  • 11 bedrooms

Polk County, Florida

The Blue Forger

The Blue Forger

  • 28 guests

  • 10 bedrooms

Polk 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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