Book Luxury Holiday Rentals in Kissimmee

Award-winning homes from £98

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Age 1 to 12

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Home spotlights in Kissimmee

Floridian Dream

Floridian Dream

  • 12 guests

  • 4 bedrooms

Osceola County, Florida

This brand new 4-bedroom, 3-bathroom vacation rental is located in the beautiful Storey Lake Resort and promises a wonderful vacation experience. The property features one king bedroom downstairs, a king suite, one bedroom with a full and twin beds, and one bedroom with a bunk bed full over full + twin trundle.

Lakeview Terrace

Lakeview Terrace

  • 8 guests

  • 2 bedrooms

Osceola County, Florida

Florida is known for delivering fun around the clock. And, this resort – the closest community to Walt Disney World, in fact – does just that.

 Disney Magic

Disney Magic

  • 8 guests

  • 3 bedrooms

Osceola County, Florida

Hitting up classic Orlando hotspots like Disney World and Universal Studios? This family condo inside a resort is a great base for round-the-clock fun.

For You Love

For You Love

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Nestled in a private resort, this home is perfectly placed for a fun-filled adventure in Florida. It’s just a short drive to Walt Disney World and the main attractions in Kissimmee – including walking paths, playgrounds and restaurants.


We selected the top 3% holiday homes in Kissimmee Holiday Rentals

Explore the 73 most perfect homes in our collection

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Most popular homes in Kissimmee

Sunshine on the Seaside

Sunshine on the Seaside

  • 11 guests

  • 4 bedrooms

Campbell, Osceola County

Disney Daydreams

Disney Daydreams

  • 17 guests

  • 5 bedrooms

Osceola County, Florida

Sunset Haze

Sunset Haze

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

 King's Castle

King's Castle

  • 8 guests

  • 3 bedrooms

Osceola County, Florida

 The Fairy Godmother

The Fairy Godmother

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Mickey's Melody

Mickey's Melody

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

Body of Evidence

Body of Evidence

  • 15 guests

  • 4 bedrooms

Kissimmee, Osceola County

Sunflower Sun

Sunflower Sun

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

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Check upcoming rates & availability for Kissimmee Holiday Rentals


Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Kissimmee. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Kissimmee has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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