Luxury Long Stay Rentals in Osceola County

We selected the 233 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

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

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.

Orlando Sunshine

Orlando Sunshine

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

This family home offers plenty of space and style for your dream Florida getaway. The kitchen is fully equipped, perfect for whipping up meals to enjoy outside by the screened private pool and spa.

Sunset Haze

Sunset Haze

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

Visiting Orlando's hotspots like Disney World and Universal Studios? Here's the perfect base for just that.

Citrus Garden Breeze

Citrus Garden Breeze

  • 9 guests

  • 3 bedrooms

Osceola County, Florida

Wake up in your Orlando hideaway and decide what the day will bring: a family adventure at Disney, just minutes away, or a lazy morning floating down a winding river under the Florida sun. Return to the perfect spot for a coffee or an evening wine, the the balcony overlooking the garden.


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

Casa Rosita

Casa Rosita

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Playcation Retreat

Playcation Retreat

  • 20 guests

  • 9 bedrooms

Four Corners, Osceola County

Sugar Sky

Sugar Sky

  • 24 guests

  • 10 bedrooms

Polk County, Florida

Harmony's Place

Harmony's Place

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

Sunshine Ranch

Sunshine Ranch

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

The Starlight Sky

The Starlight Sky

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Lakeview Terrace

Lakeview Terrace

  • 8 guests

  • 2 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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