Luxury Long Stay Rentals in Osceola County

We selected the 235 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

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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.

 Castle of Champions

Castle of Champions

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

For families or groups of friends visiting Orlando's hot spots, this home is the perfect balance of adventure and relaxation. There are rooms made for excited young ones, with Disney decorations and shared sleeping arrangements (single beds and bunk beds).

Family Adventure Base

Family Adventure Base

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

A private pool, resort access, and just twenty minutes from Walt Disney World – this villa is a dream for families. Inside, it’s bright and airy, with plenty of space to gather or unwind.

Sunflower Sun

Sunflower Sun

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

If you're planning an action-packed trip to Florida and want to be close to the good stuff, this family home may do the trick. It's set in a resort – the closest to Walt Disney World – and well-positioned to make the most of the nearby shopping malls and top attractions.


We selected the top 3% holiday homes in Osceola County Long Stay Rentals

Explore the 235 most perfect homes in our collection

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Most popular homes in Osceola County

Sunshine Residence

Sunshine Residence

  • 24 guests

  • 10 bedrooms

Polk County, Florida

Sunshine on the Lake

Sunshine on the Lake

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Wondrous Villa

Wondrous Villa

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

The Starlight Sky

The Starlight Sky

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Sun and Games

Sun and Games

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

The Magic of Love

The Magic of Love

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Moon Over Lake

Moon Over Lake

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Pineapple Peach

Pineapple Peach

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

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Frequently asked questions

Explore our collection of luxury Extended Stay Rentals available for you to rent in Osceola County, Florida, United States. Each and every home you'll find has been through a meticulous, multi-stage vetting process to ensure quality our guests can always count on. The Long Stay Rentals in our Osceola County, Florida, United States collection come fully furnished with well-equipped kitchens, all linens, and essential bathroom toiletries included. And if you need any assistance, our friendly team of experts is always on hand to help plan your perfect stay.

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