Luxury Long Stay Rentals in Osceola County

We selected the 290 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

Pineapple Peach

Pineapple Peach

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

One thing’s for sure in this Floridian home – you’ll never be bored. Jam-packed with entertainment options including a home cinema, games room, private pool and hot tub, there’s something for everyone here.

Blue Ridge View

Blue Ridge View

  • 34 guests

  • 11 bedrooms

Polk County, Florida

This luxurious 7,200-square-foot mansion in Orlando can accommodate up to 34 guests. The great room features stylish furniture, an oversized TV, and modern décor.

The Swamp Orelse

The Swamp Orelse

  • 15 guests

  • 5 bedrooms

Four Corners, Osceola County

This brand new single-family home is located in Champions Gate and boasts 5 bedrooms and 5 bathrooms, with 2 bedrooms located downstairs. The fully equipped kitchen leads to a screened-in private pool and spa, perfect for relaxing after a long day at Disney or shopping at nearby centers.

Taller Than Life

Taller Than Life

  • 13 guests

  • 4 bedrooms

Osceola County, Florida

This brand new single-family home is perfect for those looking for a luxurious stay in the heart of Orlando. The cozy house features five bedrooms and five bathrooms, with two bedrooms conveniently located on the ground floor.


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

Explore the 290 most perfect homes in our collection

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Most popular homes in Osceola County

The Ocean's Voice

The Ocean's Voice

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

The Oceanaire

The Oceanaire

  • 8 guests

  • 3 bedrooms

Osceola County, Florida

Sea View Sanctuary

Sea View Sanctuary

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

Sugar Sky

Sugar Sky

  • 24 guests

  • 10 bedrooms

Polk County, Florida

The Blue Otter's Nest

The Blue Otter's Nest

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Pineview Villa

Pineview Villa

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Siesta Shade

Siesta Shade

  • 15 guests

  • 5 bedrooms

Loughman, Polk County

Parlour Peace

Parlour Peace

  • 34 guests

  • 12 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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