Osceola County Weekend House Rentals

We selected the 232 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Osceola County

Sugar Sky

Sugar Sky

  • 24 guests

  • 10 bedrooms

Polk County, Florida

This Orlando villa is the perfect family vacation home, with plenty of entertainment options for kids and adults alike. The themed bedrooms are a hit with the little ones, including a toy room and basketball-themed bedroom complete with over-the-top bunk beds.

Fun-Filled Getaway

Fun-Filled Getaway

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Tailor-made for family fun, this five-bedroom home on the outskirts of Orlando is close to all the excitement of the city’s famous theme parks – but it’s just as entertaining in this sprawling house. The kids will be ecstatic with the two themed kids’ rooms – think Minions mischief and superhero adventures – and a Mario-inspired game room packed with slides, nets, hoops, Nintendo Switch, and PS4.

Wondrous Villa

Wondrous Villa

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

If you're looking to stay somewhere that little ones will never forget, which also gives plenty of thought to older guests, this expansive vacation villa is full of charming surprises. The home sleeps sixteen guests across six bedrooms, with two very much aimed at the kids – one bottom bunk can only be accessed through a giant pair of goggles – and one master bedroom having an obvious edge with its larger en-suite bathroom and private balcony.

Lake Escapes

Lake Escapes

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

This Orlando resort condo was made for both relaxation and excitement. Wake up to lake views from the private balcony, then dive into the fun with access to resort amenities including pools, a lazy river, golf course, gym, clubhouse, restaurant, and cinema.


We selected the top 3% holiday homes in Osceola County Weekend House Rentals

Explore the 232 most perfect homes in our collection

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Most popular homes in Osceola County

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

Orlando Sunshine

Orlando Sunshine

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

The Starlight Sky

The Starlight Sky

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Castle and Cape Villa

Castle and Cape Villa

  • 24 guests

  • 9 bedrooms

Four Corners, Osceola County

Maitland Hills

Maitland Hills

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

 King of the Lake

King of the Lake

  • 7 guests

  • 2 bedrooms

Osceola County, Florida

The Blue Ocean

The Blue Ocean

  • 7 guests

  • 2 bedrooms

Kissimmee, Osceola County

The Magic of Osceola

The Magic of Osceola

  • 17 guests

  • 4 bedrooms

Four Corners, Osceola County

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Frequently asked questions

Looking to book a holiday rental for the weekend in Osceola County, Florida, United States? You've come to the right place: we’re the official selection of the world’s best homes. Our collection of weekend rentals in Osceola County, Florida, United States come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. We obsessively check each home for you, so you can book with peace of mind. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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