Luxury Long Stay Rentals in Osceola County

We selected the 233 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

An extra fee may apply

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Home spotlights in Osceola County

Sugar Sky

Sugar Sky

  • 24 guests

  • 10 bedrooms

Polk County, Florida

This Orlando villa is the perfect family vacation home, with plenty of entertainment options for kids and adults alike. The themed bedrooms are a hit with the little ones, including a toy room and basketball-themed bedroom complete with over-the-top bunk beds.

The Entertainment Enclave

The Entertainment Enclave

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Welcome to a haven of fun for the whole family. Home entertainment of every type is available here, for both children and adults – kids will love the dedicated arcade room, themed bedrooms including integrated bunk beds, and a video games room complete with karaoke.

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.

Non-Stop Fun

Non-Stop Fun

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Just a quick drive away from Orlando’s world-famous parks, this spacious home is designed to maximize family fun at every turn. Kids will go adore for the “Secret Galaxy” bedroom, where they can climb ladders, zip down a twisty slide, and sleep in treehouse-style bunks – and discover a hidden game room through a closet door.


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

Sounds of Fun

Sounds of Fun

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Wonder Mansion

Wonder Mansion

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

Family Adventure Base

Family Adventure Base

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

Harmony's Place

Harmony's Place

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

Orlando Sunshine

Orlando Sunshine

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

Sunshine Ranch

Sunshine Ranch

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

Mickey's Melody

Mickey's Melody

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

Orlando Adventure

Orlando Adventure

  • 20 guests

  • 9 bedrooms

Four Corners, Osceola County

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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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