Book Luxury Holiday Rentals in Kissimmee

Award-winning homes from £98

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Adults

Age 13+

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Children

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.

The Skyline

The Skyline

  • 15 guests

  • 4 bedrooms

Osceola County, Florida

This newly furnished and decorated single family home boasts 5 bedrooms, 5 bathrooms, equipped kitchen, and a private screened pool and spa. With 2 bedrooms located downstairs, this property is perfect for families or groups of friends.

Halfnote

Halfnote

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

This brand new 4 bedroom, 3 bathroom vacation rental with a pool is located in Storey Lake Resort, providing guests with an exceptional vacation experience. The bedrooms include a king bedroom downstairs, a king suite upstairs, and two bedrooms with one full and one twin bed each.

Sea View Sanctuary

Sea View Sanctuary

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

This newly furnished and decorated single-family home is located in the Storey Lake community, close to Disney, Disney Springs, restaurants, and shopping centers. The cozy 7-bedroom home features 5 bathrooms, a game room with pool table and air hockey, a fully equipped kitchen, private screened pool and spa, and internet and cable.


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

Explore the 91 most perfect homes in our collection

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Most popular homes in Kissimmee

A History of the Sun

A History of the Sun

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

The Canyoneer

The Canyoneer

  • 11 guests

  • 4 bedrooms

Osceola County, Florida

The Lazy River

The Lazy River

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

The Black Marble

The Black Marble

  • 17 guests

  • 5 bedrooms

Osceola County, Florida

The Sun & White

The Sun & White

  • 8 guests

  • 3 bedrooms

Osceola County, Florida

Summer's Insomniac Dream

Summer's Insomniac Dream

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Black & White Paradise

Black & White Paradise

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

Fuzzy Dreams

Fuzzy Dreams

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

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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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