Kissimmee Luxury Rentals

We selected the 72 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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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

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.

Mickey's Melody

Mickey's Melody

  • 15 guests

  • 5 bedrooms

Osceola County, Florida

This home sets the stage for magical stay in Florida. It’s just a short drive to Disney World, Disney Springs as well as the centre of Kissimmee where you’ll find all the amenities you could need.

Feel the Joy

Feel the Joy

  • 24 guests

  • 10 bedrooms

Polk County, Florida

With a games room, a private pool, a home cinema and themed bedrooms, we don’t think anyone will be bored in this home. There’s also a Jacuzzi spa outside for long relaxing soaks and you’ll find plenty of space in the living room to stretch out and unwind.

A True Joy

A True Joy

  • 28 guests

  • 11 bedrooms

Polk County, Florida

With a private pool, arcade room and movie theatre, this home sets the stage for a fun-filled stay in Florida. You can enjoy long soaks in the spa and there’s an outdoor kitchen for magical evening meals.


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

Explore the 72 most perfect homes in our collection

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Most popular homes in Kissimmee

Your Bliss

Your Bliss

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Pure Love

Pure Love

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

All The Lights

All The Lights

  • 28 guests

  • 11 bedrooms

Polk County, Florida

The Starlight Sky

The Starlight Sky

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Hero Forever

Hero Forever

  • 34 guests

  • 12 bedrooms

Polk County, Florida

So Much Better

So Much Better

  • 34 guests

  • 12 bedrooms

Polk County, Florida

Find Your Happiness

Find Your Happiness

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

Stone Whistle

Stone Whistle

  • 24 guests

  • 10 bedrooms

Polk County, Florida

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Frequently asked questions

A handpicked selection of the best luxury homes in Kissimmee, as chosen by the experts who've visited and vetted thousands of the city's homes. Luxurious interiors, sumptuous bedrooms and prime city centre locations. Available for short and extended stays.

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