Kissimmee holiday lettings

We found 30,608 holiday rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Find the perfect place for you stay in Kissimmee by choosing from 19272 houses, 2026 apartments and other holiday rentals. Holiday homes provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Frequently asked questions

What is the best area to stay in Kissimmee when booking a holiday rental?

If you're on you way to Kissimmee, Bellavida is one of the most sought-after neighbourhoods to stay. No matter your travel style, Vrbo is bound to have a property here that matches your needs.

What is the most popular type of holiday rental accommodation in Kissimmee?

The most in-demand types of holiday rentals in Kissimmee are houses. Looking for something different? Vrbo offers a variety of options to match our guests' needs, so you'll see holiday homes in loads of shapes and sizes. The ideal fit is ready and waiting for you — book yours today.

How much does it cost to rent a holiday rental in Kissimmee?

A range of things can determine the price of a holiday rental in Kissimmee, including the season, length of stay and type of property. Still, all our holiday homes have one thing in common — amazing value. Simply enter your travel dates to find your ideal fit.

How much does it cost to rent a beach house in Kissimmee?

When you travel and the style and size of the property will determine the cost of your beachside holiday rental. Enter your Kissimmee travel dates to see your options on Vrbo. Can't live without a hot tub? Use our filters to pick the amenities and features you want in your beach house.

Are there pet-friendly holiday rentals in Kissimmee?

Yes. You can pick from 14,063 holiday rentals that allow pets in Kissimmee. Many of our pet-friendly holiday rentals come with an area outdoors for your four-legged friend to have fun in, dog beds, complimentary treats and proximity to parks and green space. Apply the "Pets allowed" filter to find your pawfect place on Vrbo.

Can I rent a house with a pool in Kissimmee?

Tick the "pool" box in our filter tool and select from 13,636 houses with private pools in Kissimmee on Vrbo. Morning swim, afternoon splash or midnight soak? Leisure time is up to you when your Vrbo holiday property comes with its own swimming pool.

What are popular rental amenities in Kissimmee?

The most popular rental amenities people are searching for in Kissimmee include a nearby river, a barbecue grill and a firepit. Whether you're on the road with family, friends or even pets, Vrbo holiday rentals have the best amenities for fun and relaxation with the people closest to you.

Are there large group holiday rentals in Kissimmee?

With 6,071 properties that can host 10 guests or more in Kissimmee, you won't have to keep anyone off the invite list. From family holidays to special events like birthday and Christmas parties, Vrbo will help you find a large group rental to suit the occasion.

Are there holiday rentals in Kissimmee that welcome kids?

With 14,021 family-friendly holiday rentals to choose from in Kissimmee, now is an awesome time to introduce your children to the joys of travel. Simply click on our "Properties good for families" filter box to look for stays that come with conveniences perfect for holidaying families, like extra bedrooms, swimming pools, bunk beds and entertainment units.

What are the top attractions for families in Kissimmee?

Keep your kids entertained at these leading family-friendly attractions in Kissimmee:

  • Aquatica
  • Discovery Cove
  • Disneys Typhoon Lagoon Water Park

Are there one-bedroom holiday rentals in Kissimmee?

You can choose from 319 one-bedroom rentals in Kissimmee. Whether you're searching for a secluded cottage or an upmarket condo, our one-bedroom properties are great if you don't require a huge amount of space. One of the best things about having your own digs? You won't have to share your getaway with strangers.

Can I find two-bedroom holiday rentals in Kissimmee?

Pick from 889 two-bedroom holiday rentals in Kissimmee. Settle the kids into the second room or fill it with a couple of your best buddies. There's a spot for whoever's lucky enough to be joining your adventure.

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