Kissimmee holiday homes

We found 32,877 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Kissimmee by choosing from 15125 houses, 1959 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:2 Jan - 9 Jan
  • 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, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Kissimmee

  • Family-friendly attractions: Kissimmee is home to numerous theme parks and amusement venues perfect for a fun-filled family holiday.
  • Scenic outdoor spaces: Explore the beautiful Kissimmee Lakefront Park for leisurely walks and stunning views.
  • Exciting excursions: The area offers various nearby attractions and activities for adventure seekers.
  • Relaxing holiday rentals: You'll find a range of comfortable accommodations to unwind after a day of exploring.
  • Sunny weather: Enjoy the warm, inviting climate, ideal for outdoor adventures and relaxation.

Top attractions in and around Kissimmee

Kissimmee is a fantastic destination for family holidays, offering a blend of entertainment, outdoor activities, and cultural experiences. You can explore the scenic Kissimmee Lakefront Park, enjoy various theme and amusement parks, and discover nearby attractions. With plenty of great holiday rentals available, you’ll find plenty to keep everyone entertained, making it an ideal spot for both relaxation and adventure.

  • Universal Orlando Resort: A thrilling theme park offering world-class attractions and rides based on popular films. It's perfect for families seeking adventure and entertainment just 20.9km from Kissimmee.
  • Orange County Convention Center: A vibrant arts centre that hosts various cultural events and exhibitions, located 16.1km from Kissimmee. It's a hub for arts enthusiasts and those looking to immerse themselves in local culture.
  • Osceola Heritage Park: An inviting urban park situated in Kissimmee, ideal for families looking to enjoy outdoor activities and city vibes amidst nature.

Things to do recommended for couples

For a romantic getaway in Kissimmee, try your hand at mini-golf at Pirate's Island Adventure Golf, enjoy a delightful meal at the charming Pirate's Dinner Adventure, or savour exquisite wines at True Blue Winery. Each experience promises to create unforgettable memories together.

Things to do recommended for families

Your family will love the adventure at Disney's Typhoon Lagoon Water Park, just 14.5km from Kissimmee, offering thrilling water rides. For more excitement, try karting at Kissimmee Go-Karts. Relax and unwind at Shingle Creek Regional Park, where you can enjoy nature and wellness activities.

Things to do recommended for groups

In Kissimmee, your group can enjoy the vibrant atmosphere at Disney Springs™ for shopping and dining, explore the lively Old Town for entertainment, and play a round of golf at Mystic Dunes Golf Club, perfect for outdoor enthusiasts.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Kissimmee

If you're planning a trip with friends, family, pets, or looking for extended stays, it's important to filter your options based on what matters most to you. Here are some helpful booking tips for using Vrbo.

  • Traveling to Kissimmee with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group get-togethers. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Kissimmee with young kids: Travelling with young kids can be quite a task. It's important to prioritise their comfort and safety, along with suitable facilities like a private pool. Additionally, keeping in mind your closeness to family-friendly attractions can make a big difference.
  • Taking your pets with you to Kissimmee: For many families, a holiday wouldn't feel complete without their furry companion along for the ride. If this resonates with you, be sure to explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Kissimmee: If you're seeking holiday rentals with great deals for stays of a month or more, you've come to the perfect spot. By using the right filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in Kissimmee

Kissimmee, Florida, offers a fantastic holiday experience for families and adventure seekers alike. With its sunny weather and friendly atmosphere, you’ll find plenty of family-friendly attractions and romantic spots. Explore nearby regions for exciting excursions, or relax in one of the many holiday parks. Whether you’re planning your next vacation or a business trip, Kissimmee’s charm and variety of vacation spots make it a top choice for visitors from all over.

  • Orlando: As a sprawling metropolis, Orlando serves as a central hub for tourists visiting Kissimmee. It is renowned for its family-friendly attractions and vibrant entertainment scene. Orlando boasts a variety of resorts, shopping districts, and cultural venues, making it a perfect destination for a diverse travel experience. Visitors can explore world-famous theme parks, including Walt Disney World and Universal Studios, or soak up the sun at nearby beaches. The city's arts centre also offers a glimpse into local culture, making Orlando a must-visit for those looking to blend excitement with relaxation.
  • Four Corners: Four Corners is a charming village located close to Kissimmee, ideal for families seeking outdoor adventures. This area is known for its beautiful golf courses and resorts, making it a great spot for both leisure and recreation. With easy access to theme parks and film studios, Four Corners provides a balance of relaxation and thrilling experiences. The atmosphere is welcoming, and there are ample opportunities to enjoy family activities, making it a lovely stop for those exploring Central Florida.
  • Windsor Hills: Windsor Hills is a delightful neighbourhood situated near Kissimmee, perfect for families looking for a mix of fun and relaxation. This community is famous for its resort-style amenities, shopping areas, and golf options. Close to popular theme parks and stadiums, Windsor Hills ensures that visitors have plenty to keep them entertained. The serene environment and family-oriented activities make it an appealing choice for those wanting to unwind after a day of adventures.

Booking with Vrbo is a breeze

Are you keen to save on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you could enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of holiday rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy platform to help you plan new trips, resume your previous arrangements, or keep track of your itinerary. You can easily find your saved or booked properties sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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 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)
  • Magic Kingdom® Park (13.7 mi / 22 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)
  • 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)
  • Lake Butler (14.4 mi / 23.2 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 home?
If you're on you way to Kissimmee, Bellavida is one of the most sought-after neighbourhoods to stay. No matter your travel style, Bookabach is bound to have a property here that matches your needs.
What is the most popular type of holiday home accommodation in Kissimmee?
The most in-demand types of holiday homes in Kissimmee are houses. Looking for something different? Bookabach 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 home in Kissimmee?
A range of things can determine the price of a holiday home 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 home. Enter your Kissimmee travel dates to see your options on Bookabach. 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 homes in Kissimmee?
Yes. You can pick from 14,063 holiday homes that allow pets in Kissimmee. Many of our pet-friendly holiday homes 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 Bookabach.
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 Bookabach. Morning swim, afternoon splash or midnight soak? Leisure time is up to you when your Bookabach holiday property comes with its own swimming pool.
What are popular home amenities in Kissimmee?
The most popular home 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, Bookabach holiday homes have the best amenities for fun and relaxation with the people closest to you.
Are there large group holiday homes 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, Bookabach will help you find a large group home to suit the occasion.
Are there holiday homes in Kissimmee that welcome kids?
With 14,021 family-friendly holiday homes 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 homes in Kissimmee?
You can choose from 319 one-bedroom homes 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 homes in Kissimmee?
Pick from 889 two-bedroom holiday homes 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 homes with WiFi in Kissimmee?
You'll find 4,721 holiday homes 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 Bookabach.
How can I find holiday homes with air conditioning in Kissimmee?
Select your travel dates and then use our filters to view holiday homes with ac in Kissimmee on Bookabach. 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 home in Kissimmee?
The minimum age allowed can vary across properties on Bookabach, so look at the rules of the holiday home in Kissimmee you want. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Kissimmee for?
The length of time you can rent a holiday home 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.

Explore destinations around Kissimmee

More Holiday Rentals ideas

People also search for