Luxury Long Stay Rentals in Osceola County

We selected the 277 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

Take Me to the Ball Game

Take Me to the Ball Game

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

This Orlando vacation villa is a dream come true for families with kids who love Minions and Disney Princesses. The two themed bedrooms are decked out with bunk beds and decor from the beloved characters, sure to delight little ones.

The Heart of Osceola

The Heart of Osceola

  • 17 guests

  • 6 bedrooms

Four Corners, Osceola County

This newly furnished and decorated luxury single-family home is located at the Solara Resort, just a short distance from Disney, restaurants, and shopping centers. With 7 bedrooms and 6.

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.

The Magic of Ketchikan

The Magic of Ketchikan

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

This luxurious vacation home has everything you need for a fun-filled family vacation. The game room features seven arcade favorites, while the gaming loft offers pool and giant scrabble competitions, karaoke, and a full bar.


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

Explore the 277 most perfect homes in our collection

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Most popular homes in Osceola County

Sunshine on the Seaside

Sunshine on the Seaside

  • 11 guests

  • 4 bedrooms

Campbell, Osceola County

Bulletproof Blue

Bulletproof Blue

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Sugar Sky

Sugar Sky

  • 24 guests

  • 10 bedrooms

Polk County, Florida

Black & White Paradise

Black & White Paradise

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

The Old Ore Mine

The Old Ore Mine

  • 6 guests

  • 2 bedrooms

Four Corners, Osceola County

All Around The House

All Around The House

  • 12 guests

  • 4 bedrooms

Osceola County, Florida

Sunflower Sun

Sunflower Sun

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

The Blue Otter's Nest

The Blue Otter's Nest

  • 16 guests

  • 6 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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