Osceola County Properties

We selected the 235 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Osceola County

Sunflower Sun

Sunflower Sun

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

If you're planning an action-packed trip to Florida and want to be close to the good stuff, this family home may do the trick. It's set in a resort – the closest to Walt Disney World – and well-positioned to make the most of the nearby shopping malls and top attractions.

The Moon Smile

The Moon Smile

  • 28 guests

  • 11 bedrooms

Polk County, Florida

If you’ve been dreaming of a magical family getaway in Florida, this home offers an easy solution. From the private pool and spa to the golf simulator room and arcade room, every detail has been considered to bring fun to your stay.

Strawberry Sunrise

Strawberry Sunrise

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Just a short drive from Disney World, this home opens its doors to a magical stay in Florida. Days can be spent exploring the nearby attraction parks as well as Downtown Orlando and Kissimmee.

Wonder Mansion

Wonder Mansion

  • 26 guests

  • 10 bedrooms

Four Corners, Osceola County

Step inside this show-stopping Orlando mansion and you’ll discover a world of fun, luxury, and relaxation. Set in a luxurious gated resort, days here are never ordinary.


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

Explore the 235 most perfect homes in our collection

View on map

Most popular homes in Osceola County

Family Adventure Base

Family Adventure Base

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

Wonderland Mansion

Wonderland Mansion

  • 18 guests

  • 6 bedrooms

Polk County, Florida

Sunset Haze

Sunset Haze

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

Harmony's Place

Harmony's Place

  • 12 guests

  • 5 bedrooms

Four Corners, Osceola County

Disney Daydreams

Disney Daydreams

  • 17 guests

  • 5 bedrooms

Osceola County, Florida

Castle and Cape Villa

Castle and Cape Villa

  • 24 guests

  • 9 bedrooms

Four Corners, Osceola County

The Blue Ocean

The Blue Ocean

  • 7 guests

  • 2 bedrooms

Kissimmee, Osceola County

For You Love

For You Love

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

View all

Check upcoming rates & availability for Osceola County Properties


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.

Search Our Collection