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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Home spotlights in Osceola County

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.

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.

Orange Vista

Orange Vista

  • 18 guests

  • 6 bedrooms

Polk County, Florida

It's all about location with this villa, set in a family-friendly resort. Not only is it less than twenty-five minutes in the car to Disney, but it's also a great base for exploring Universal Studios, SeaWorld and other local attractions.

Wonder Mansion

Wonder Mansion

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

Step inside this show-stopping Orlando mansion and you’ll discover a world of fun, luxury, and relaxation. Set in a luxurious gated resort, days here are never ordinary.


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

The Old Cabin

The Old Cabin

  • 10 guests

  • 4 bedrooms

Four Corners, Osceola County

Pineapple Peach

Pineapple Peach

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Fun-Filled Getaway

Fun-Filled Getaway

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Sugar Sky

Sugar Sky

  • 24 guests

  • 10 bedrooms

Polk County, Florida

The Magic of Osceola

The Magic of Osceola

  • 17 guests

  • 4 bedrooms

Four Corners, Osceola County

Maitland Hills

Maitland Hills

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Sunny Meadows

Sunny Meadows

  • 28 guests

  • 11 bedrooms

Polk County, Florida

Siesta Shade

Siesta Shade

  • 15 guests

  • 5 bedrooms

Loughman, Polk 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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