Luxury Long Stay Rentals in Osceola County

We selected the 236 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Osceola County

Family Adventure Base

Family Adventure Base

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

A private pool, resort access, and just twenty minutes from Walt Disney World – this villa is a dream for families. Inside, it’s bright and airy, with plenty of space to gather or unwind.

The Sunshine of Your Eyes

The Sunshine of Your Eyes

  • 28 guests

  • 11 bedrooms

Polk County, Florida

Just a short drive from Disney, this Florida home places you right in the heart of the action. You’ll find plenty to keep the whole gang entertained at local attraction parks.

Magic Retreat

Magic Retreat

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

If you're planning a trip to Disney, this home is a great choice. It's set in a resort just twenty minutes away by car, so it couldn't be easier to go and see Mickey and the gang.

The Blue Dunes

The Blue Dunes

  • 24 guests

  • 10 bedrooms

Polk County, Florida

With a private pool and Jacuzzi, a game loft, and even a twelve-seat cinema, this villa delivers on every front. Calling out for a multi-generational family stay, expect ten en-suite bedrooms – including two themed bunk rooms for little ones – and banquet-worthy dining spaces in the free-flowing living spaces downstairs to gather together.


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

Explore the 236 most perfect homes in our collection

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Most popular homes in Osceola County

 The Fairy Godmother

The Fairy Godmother

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Maitland Hills

Maitland Hills

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Fun-Filled Getaway

Fun-Filled Getaway

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Harmony's Place

Harmony's Place

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

Siesta Shade

Siesta Shade

  • 15 guests

  • 5 bedrooms

Loughman, Polk County

Orlando Sunshine

Orlando Sunshine

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

Casa Rosita

Casa Rosita

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Sunshine Residence

Sunshine Residence

  • 24 guests

  • 10 bedrooms

Polk 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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