Osceola County Properties

We selected the 266 homes worth renting in this location

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Age 13+

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Children

Age 1 to 12

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Home spotlights in Osceola County

The Bayou Breeze

The Bayou Breeze

  • 18 guests

  • 6 bedrooms

Polk County, Florida

This luxurious Orlando villa is perfect for groups seeking a fun-filled vacation. The grand entrance leads to a spacious great room that feels like a resort-style lobby, complete with an oversized TV and plenty of seating.

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.

The Pineapple Gate

The Pineapple Gate

  • 24 guests

  • 9 bedrooms

Polk County, Florida

This villa is a perfect vacation destination for families with children, featuring themed bedrooms that include the ocean princess and Galactica rooms. Children will also love the arcade, game loft, and home theater.

The Blue Ocean

The Blue Ocean

  • 7 guests

  • 2 bedrooms

Kissimmee, Osceola County

This brand new 2 bedroom, 2 bathroom vacation rental condo is located in the beautiful Storey Lake Resort, providing guests with an amazing vacation experience. The condo boasts a king bedroom with an en-suite bathroom, as well as another bedroom featuring a full bed, twin bed and sofa bed.


We selected the top 3% holiday homes in Osceola County Properties

Explore the 266 most perfect homes in our collection

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Most popular homes in Osceola County

The Lazy River

The Lazy River

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

The Magic of Osceola

The Magic of Osceola

  • 17 guests

  • 4 bedrooms

Four Corners, Osceola County

The Blue Otter's Nest

The Blue Otter's Nest

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Moon Over Lake

Moon Over Lake

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Sargasso Seas

Sargasso Seas

  • 7 guests

  • 2 bedrooms

Osceola County, Florida

The Old Cabin

The Old Cabin

  • 10 guests

  • 4 bedrooms

Four Corners, Osceola County

Sunshine Ranch

Sunshine Ranch

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

The Indian Village

The Indian Village

  • 9 guests

  • 3 bedrooms

Osceola County, Florida

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Frequently asked questions

Plum guide offers a handpicked selection of the most luxurious properties in Osceola County, Florida, United States. Our homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book a short or extended stay and find your dream property in Osceola County, Florida, United States for a memorable holiday. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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