Luxury Long Stay Rentals in Osceola County

We selected the 360 homes worth renting in this location

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.

On the Ocean

On the Ocean

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

This brand new 2-bedroom, 2-bathroom vacation rental condo is located in Storey Lake Resort and promises to make your stay unforgettable. The condo features a king bedroom with an en-suite bathroom, as well as a second bedroom with a twin-over-full bunk bed and a sofa bed.

The Sea Dragon

The Sea Dragon

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

This brand new vacation rental condo is located in the Storey Lake Resort and offers guests a fantastic vacation experience. The condo features two bedrooms and two bathrooms, including a king bedroom with an en-suite bathroom and a second bedroom with a full bed, twin bed, and sofa bed.

The Blue Star

The Blue Star

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

This stunning 2-bedroom, 2-bathroom vacation rental condo is located in Storey Lake Resort and boasts a beautiful lake view. The bedrooms consist of one King bedroom on suite and one bedroom with bunk beds twin over full + a Sofabed.


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

Explore the 360 most perfect homes in our collection

View on map

Most popular homes in Osceola County

A Little Hike

A Little Hike

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

The Jessamine

The Jessamine

  • 15 guests

  • 5 bedrooms

Four Corners, Osceola County

Celine Dion

Celine Dion

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Coral Blue Horizon

Coral Blue Horizon

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

The Blue Ocean

The Blue Ocean

  • 7 guests

  • 2 bedrooms

Kissimmee, Osceola County

An Ocala of Ocala

An Ocala of Ocala

  • 16 guests

  • 5 bedrooms

Osceola County, Florida

The Reapers

The Reapers

  • 10 guests

  • 5 bedrooms

Four Corners, Osceola County

Paradise on the Shore

Paradise on the Shore

  • 12 guests

  • 5 bedrooms

Osceola County, Florida

View all


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.

Search our collection