Luxury Long Stay Rentals in Osceola County

We selected the 233 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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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Osceola County

Florida Adventure

Florida Adventure

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

This fun and family-friendly lakeside retreat is just a short drive from Disney, yet offers the peace of a private escape. Kids will love the themed bedrooms.

Electric Ocean

Electric Ocean

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

If you’re looking to soak up the sunny spirit of Florida, this home offers an uplifting solution. It’s just a short drive to Disney World so you’ll be spoiled for choice when it comes to family fun.

Moon Over Lake

Moon Over Lake

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Adults and kids alike won’t be able to resist the amenities included at this lavish villa. A notable highlight is the themed children’s rooms – they’ll have a blast pretending to be pirates and astronauts.

Mansion Adventure

Mansion Adventure

  • 34 guests

  • 12 bedrooms

Polk County, Florida

This family-friendly mansion makes every day of your Orlando holiday feel special. Kids will love the playful themed bedrooms while grown-ups can unwind in the stylish living room or cook together in the sleek, fully equipped kitchen.

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

Explore the 233 most perfect homes in our collection

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Most popular homes in Osceola County

Sunset Haze

Sunset Haze

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

Pineview Villa

Pineview Villa

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Sugar Sky

Sugar Sky

  • 24 guests

  • 10 bedrooms

Polk County, Florida

Family Adventure Base

Family Adventure Base

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

Sunflower Sun

Sunflower Sun

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Friends, Family & Fun

Friends, Family & Fun

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

The Blue Ledge

The Blue Ledge

  • 18 guests

  • 6 bedrooms

Polk County, Florida

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Check upcoming rates & availability for Osceola County Long Stay Rentals

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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