Luxury Long Stay Rentals in Osceola County

We selected the 275 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

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.

Florida Vacations

Florida Vacations

  • 20 guests

  • 9 bedrooms

Four Corners, Osceola County

This luxurious vacation home is perfect for families who want to have a fun-filled holiday in Orlando. The kids will love the winter-themed bedroom and superhero-themed bunk bed, as well as the private home theater with arcade games, karaoke system, and mini jungle gym.

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 Old Ore Mine

The Old Ore Mine

  • 6 guests

  • 2 bedrooms

Four Corners, Osceola County

This beautiful brand new vacation rental condo is perfect for a family or group of friends looking for an amazing vacation. Located in Champions Gate Resort, guests will be just a stone's throw away from Disney, restaurants, and shopping.


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

Explore the 275 most perfect homes in our collection

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Most popular homes in Osceola County

Hurricanes in Summer

Hurricanes in Summer

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

The Pineapple Gate

The Pineapple Gate

  • 24 guests

  • 9 bedrooms

Polk County, Florida

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

Summer's Insomniac Dream

Summer's Insomniac Dream

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Lemon Blue

Lemon Blue

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

The Starlight Sky

The Starlight Sky

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Strawberry Bikini

Strawberry Bikini

  • 18 guests

  • 6 bedrooms

Polk County, Florida

All Around The House

All Around The House

  • 12 guests

  • 4 bedrooms

Osceola 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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