Kissimmee holiday lettings

We found 31,911 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Kissimmee by choosing from 15120 houses, 1758 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.

Holiday rentals with weekly discounts - Kissimmee

Showing deals for:26 Sept - 3 Oct

Image gallery for Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground

Games room
10 out of 10 rating
Exceptional
(153 reviews)

Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground

Kissimmee, FL

7% off
Price is £2,014
£288 per night
includes taxes & fees
Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground

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

The sunny setting of Kissimmee is ready to explore

Take a holiday to Kissimmee and enjoy the area's festivals, entertainment and opera. Renowned for its theme park, shopping and sporting events, this city welcomes all visitors. Disney's Animal Kingdom® Theme Park and Walt Disney World® Resort are just a couple of the must-see attractions. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Kissimmee

Are you hoping to find attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Kissimmee a one-of-a-kind holiday spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Epcot® (10.2 mi / 16.4 km)
  • Disney's Hollywood Studios® (10.3 mi / 16.6 km)
  • Disney's Animal Kingdom® Theme Park (12.1 mi / 19.5 km)
  • Universal Orlando Resort (13 mi / 21 km)
  • Universal Studios Florida (13.4 mi / 21.6 km)
  • Walt Disney World® Resort (13.6 mi / 21.9 km)

Exploring the natural landscape of Kissimmee

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Kissimmee is a great place to spend some time outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Kissimmee Lakefront Park (0.2 mi / 0.3 km)
  • Osceola Heritage Park (2.4 mi / 3.9 km)
  • Shingle Creek Regional Park (3.1 mi / 5 km)
  • Lake Tohopekaliga (6.1 mi / 9.9 km)
  • Lake Bryan (7.5 mi / 12.1 km)
  • Austin-Tindall Regional Park (8.3 mi / 13.4 km)

Seasonal weather in Kissimmee

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 27°C.

How to get to and around Kissimmee

The nearest airport is in Kissimmee, FL (ISM-Kissimmee Gateway), located 1.8 mi (2.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Orlando International Airport (MCO), which is 11.4 mi (18.3 km) away.

If you prefer train travel, you can make your way to Kissimmee Station. Utilise the area's public transport and catch a ride on the metro at Tupperware Station or Poinciana Station and easily see more of the city.

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.
Are there holiday rentals with WiFi in Kissimmee?
You'll find 4,721 holiday rentals with WiFi in Kissimmee. If you'd like to disconnect from the world on your trip, but still want to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Kissimmee?
Select your travel dates and then use our filters to view holiday rentals with ac in Kissimmee on Vrbo. With 13,802 air-conditioned properties available here, you can enjoy a cool and comfy break.
How old do you have to be to rent a holiday rental in Kissimmee?
The minimum age allowed can vary across properties on Vrbo, so look at the rules of the holiday rental in Kissimmee you want. But typically, it's 16, 18 or 21.
How long can I rent a holiday rental in Kissimmee for?
The length of time you can rent a holiday rental in Kissimmee depends on the property. Simply enter your selected dates to view a list of options offering extended stays. With loads of amenities like air conditioning and full kitchens, as well as some offering weekly or monthly discounted prices, you're sure to find a terrific place to call your home away from home in Kissimmee.

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