Luxury Long Stay Rentals in Osceola County

We selected the 305 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

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Home spotlights in Osceola County

Black & White Paradise

Black & White Paradise

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

This brand new vacation rental condo is located in the beautiful Storey Lake Resort and is perfect for a family or group of friends. With two bedrooms and two bathrooms, this condo comfortably accommodates up to four guests.

A Disney Mania

A Disney Mania

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

This 6-bed/5-bath villa in Orlando is perfect for a family vacation. The villa features two epic-themed bedrooms, including a Minions and Ironman bedroom, that will keep the kids entertained all night long.

The Tallest Tree

The Tallest Tree

  • 28 guests

  • 10 bedrooms

Polk County, Florida

This is a luxurious and spacious 11-bedroom vacation home that offers a wide range of amenities for guests of all ages. The grand entrance welcomes visitors into an upscale central living area with sleek couches and modern furnishings.

The Time Traveler's Daughter

The Time Traveler's Daughter

  • 20 guests

  • 9 bedrooms

Four Corners, Osceola County

This vacation home is perfect for families looking to have a fun-filled retreat. The kids will love the jungle-themed bedroom with tree trunk bunk beds and the toy-themed bedroom with floor-to-ceiling wall art of their favorite toys.


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

Explore the 305 most perfect homes in our collection

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Most popular homes in Osceola County

So Much Better

So Much Better

  • 34 guests

  • 12 bedrooms

Polk County, Florida

The Dead Man's Chest

The Dead Man's Chest

  • 34 guests

  • 11 bedrooms

Polk County, Florida

Under the Sea Escape

Under the Sea Escape

  • 12 guests

  • 6 bedrooms

Polk County, Florida

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

Magical Disney Haven

Magical Disney Haven

  • 25 guests

  • 9 bedrooms

Four Corners, Osceola County

The Last Frontier

The Last Frontier

  • 11 guests

  • 3 bedrooms

Four Corners, Osceola County

The Soul of an Old Fisherman

The Soul of an Old Fisherman

  • 14 guests

  • 6 bedrooms

Osceola County, Florida

Westside Oasis

Westside Oasis

  • 20 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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