Osceola County Weekend House Rentals

We selected the 363 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.

A Little Hike

A Little Hike

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

This brand new 2-bedroom, 2-bathroom vacation rental condo is located in the beautiful Storey Lake Resort and promises guests an amazing stay. The condo features a king bedroom with an en-suite bathroom and another bedroom with a queen bed.

Westside Oasis

Westside Oasis

  • 20 guests

  • 8 bedrooms

Four Corners, Osceola County

Welcome to Twice-as-Nice, the 9th home in the Overmoon collection. This 8-bedroom, 6-bathroom oasis is located in the Windsor at Westside resort, just a short drive from Orlando's famous thrills.

Crystal Sunrise

Crystal Sunrise

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

This brand new 2-bedroom, 2-bathroom vacation rental condo in Storey Lake Resort offers stunning lake views and promises an unforgettable vacation experience. The bedrooms include a king-sized bed in the en-suite master bedroom and a full-over-full bunk bed in the second bedroom.


We selected the top 3% holiday homes in Osceola County Weekend House Rentals

Explore the 363 most perfect homes in our collection

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Most popular homes in Osceola County

The Bluebonnet Loft

The Bluebonnet Loft

  • 6 guests

  • 3 bedrooms

Four Corners, Osceola County

The Satellite

The Satellite

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Body of Evidence

Body of Evidence

  • 15 guests

  • 4 bedrooms

Kissimmee, Osceola County

Sugar Sky

Sugar Sky

  • 24 guests

  • 10 bedrooms

Polk County, Florida

The Sea Dragon

The Sea Dragon

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Summer's Insomniac Dream

Summer's Insomniac Dream

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

On the Ocean

On the Ocean

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

The Sea Serpent

The Sea Serpent

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

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Frequently asked questions

Looking to book a holiday rental for the weekend in Osceola County, Florida, United States? You've come to the right place: we’re the official selection of the world’s best homes. Our collection of weekend rentals in Osceola County, Florida, United States come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. We obsessively check each home for you, so you can book with peace of mind. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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