Book Luxury Holiday Lettings in Kissimmee

Award-winning homes from £98

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Age 13+

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Age 1 to 12

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Home spotlights in Kissimmee

The Canyoneer

The Canyoneer

  • 11 guests

  • 4 bedrooms

Osceola County, Florida

This stunning brand new vacation rental is a four-bedroom, three-bathroom property with a private pool located in the beautiful Storey Lake Resort. The bedrooms are spacious and include a king bedroom downstairs, a king suite upstairs, one bedroom with full and twin beds, and another with full over full bunk beds.

Villa Lake Breeze

Villa Lake Breeze

  • 14 guests

  • 6 bedrooms

Kissimmee, Osceola County

This bright and spacious home is perfect for families or groups of friends looking for a relaxing vacation in Orlando. The home features a large, sun-kissed terrace with stunning lake views, a sparkling pool, and a spa.

The Palm Tree Home

The Palm Tree Home

  • 15 guests

  • 4 bedrooms

Osceola County, Florida

This brand new single-family home boasts 5 bedrooms and 5 bathrooms, with 2 bedrooms located on the lower level. Equipped with a fully-stocked kitchen, washer and dryer, and internet and cable, this property is perfect for families or groups of friends.

Body of Evidence

Body of Evidence

  • 15 guests

  • 4 bedrooms

Kissimmee, Osceola County

This beautiful brand new single-family home in the Storey Lake community is equipped with five bedrooms and five bathrooms, with two bedrooms conveniently located downstairs. The kitchen is fully equipped and the house also features a screened private pool and spa, as well as a game room for entertainment.


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

Explore the 97 most perfect homes in our collection

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Most popular homes in Kissimmee

Sea View Sanctuary

Sea View Sanctuary

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

The Master of the House

The Master of the House

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

All Around The House

All Around The House

  • 12 guests

  • 4 bedrooms

Osceola County, Florida

The Oceanaire

The Oceanaire

  • 8 guests

  • 3 bedrooms

Osceola County, Florida

Coral Reef Blue

Coral Reef Blue

  • 17 guests

  • 5 bedrooms

Osceola County, Florida

Paradise on the Shore

Paradise on the Shore

  • 12 guests

  • 5 bedrooms

Osceola County, Florida

A View to a Dream

A View to a Dream

  • 13 guests

  • 5 bedrooms

Osceola County, Florida

An Ocala of Ocala

An Ocala of Ocala

  • 16 guests

  • 5 bedrooms

Osceola County, Florida

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Frequently asked questions

Explore our selection of the finest luxury Holiday Lettings 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 Lettings for your trip.

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