Luxury Long Stay Rentals in Kissimmee

We selected the 74 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Kissimmee

Lake Escapes

Lake Escapes

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

This Orlando resort condo was made for both relaxation and excitement. Wake up to lake views from the private balcony, then dive into the fun with access to resort amenities including pools, a lazy river, golf course, gym, clubhouse, restaurant, and cinema.

 The Magic Hour

The Magic Hour

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

If you’re planning a fun-filled trip to Florida, this two-bedroom home is a handy launchpad for exploring Orlando’s theme parks. It’s ideally set up for a family holiday, with a comfortable living space that opens onto a balcony, and a modern kitchen for home-cooked meals.

Lazy River Retreat

Lazy River Retreat

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

This home is located in Storey Lake Resort – the closest community to Walt Disney World – making it a great choice if you plan on discovering the Magic Kingdom during your stay. And, with golf courses and shopping destinations just a short drive away, there's lots to see and do around here.

Yachts & Yacht Houses

Yachts & Yacht Houses

  • 15 guests

  • 4 bedrooms

Campbell, Osceola County

This beautiful newly furnished and decorated single-family home boasts 5 bedrooms and 5 bathrooms, with 2 bedrooms located downstairs. Equipped with a fully stocked kitchen, washer and dryer, internet, and cable, this home has everything guests need for a comfortable stay.


We selected the top 3% holiday homes in Kissimmee Long Stay Rentals

Explore the 74 most perfect homes in our collection

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Most popular homes in Kissimmee

Halfnote

Halfnote

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Disney Daydreams

Disney Daydreams

  • 17 guests

  • 5 bedrooms

Osceola County, Florida

Body of Evidence

Body of Evidence

  • 15 guests

  • 4 bedrooms

Kissimmee, Osceola County

Sunshine on the Seaside

Sunshine on the Seaside

  • 11 guests

  • 4 bedrooms

Campbell, Osceola County

Paradise on the Shore

Paradise on the Shore

  • 12 guests

  • 5 bedrooms

Osceola County, Florida

Maitland Hills

Maitland Hills

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

Lake Majesty

Lake Majesty

  • 5 guests

  • 2 bedrooms

Osceola County, Florida

Lakeview Terrace

Lakeview Terrace

  • 8 guests

  • 2 bedrooms

Osceola County, Florida

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Check upcoming rates & availability for Kissimmee Long Stay Rentals


Frequently asked questions

Explore our collection of luxury Extended Stay Rentals available for you to rent in Kissimmee. Each and every home you'll find has been through a meticulous, multi-stage vetting process to ensure quality our guests can always count on. The Long Stay Rentals in our Kissimmee collection come fully furnished with well-equipped kitchens, all linens, and essential bathroom toiletries included. And if you need any assistance, our friendly team of experts is always on hand to help plan your perfect stay.

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