Kissimmee vacation rentals

We found 32,351 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Kissimmee by choosing from 15199 houses, 1780 apartments, and other vacation rentals. Vacation homes provide the best amenities for you and your friends, family, or even pets, like WiFi and parking. At the end of the day, you'll find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Kissimmee

Why visit Kissimmee

  1. Proximity to Disney: Enjoy easy access to world-famous Disney attractions, making it a perfect family vacation spot.
  2. Outdoor Adventures: Explore beautiful lakes and parks for activities like fishing, hiking, and picnicking.
  3. Charming Downtown: Experience local culture with quaint shops, dining, and family-friendly events in downtown Kissimmee.
  4. Variety of Accommodations: Choose from spacious vacation rentals, luxurious villas, or cozy condos catering to all needs.
  5. Welcoming Atmosphere: Enjoy the friendly locals and a community spirit that makes you feel right at home.

Popular types of accommodation in Kissimmee

Kissimmee vacation rentals offer a variety of accommodations to suit every traveler's needs. Whether you're looking for spacious houses, luxurious villas, or cozy condos, you'll find the perfect spot to relax after exploring the area. With numerous options available, our vacation rentals in Kissimmee provide the flexibility and comfort you need for an unforgettable getaway. Discover the ideal vacation rental that fits your plans and makes your trip truly memorable.

  • Houses: The top choice for visitors in Kissimmee, these homes offer spacious living, ideal for families or groups looking for a personal touch during their stay.
  • Villas: These luxurious properties provide a blend of comfort and elegance, perfect for those seeking a more upscale vacation experience.
  • Condos: A popular option for travelers, offering convenient amenities and often located near attractions.
  • Apartments: These cozy rentals are great for individuals or couples wanting a home-like atmosphere while exploring the area.
  • Cottages: Quaint and charming, cottages provide a unique, intimate setting for a relaxing getaway.**

Top attractions in and around Kissimmee

Kissimmee, Florida, is a fantastic destination for families and those seeking entertainment or business-themed vacations. With its popular attractions like theme parks, lakes, and arts centers, visitors can enjoy outdoor adventures and cultural experiences. Don't forget to explore Kissimmee vacation rentals for a comfortable stay while discovering all the exciting activities this vibrant area has to offer!

  1. SeaWorld® Orlando: Experience thrilling rides, captivating shows, and up-close encounters with marine life at this dynamic theme park. Perfect for families, SeaWorld® Orlando offers a blend of entertainment and education, making it a must-visit just 9 miles from Kissimmee.
  2. Orange County Convention Center: Immerse yourself in the vibrant arts and culture scene at this expansive convention center, located 10 miles away. With various events and exhibitions, it’s a hub for creativity and inspiration.
  3. Kissimmee Lakefront Park: Enjoy scenic views and outdoor activities at this urban park in Kissimmee. Perfect for families, it features walking trails, picnic areas, and a playground, offering a relaxing city vibe.

Things to do recommended for couples

For a romantic getaway in Kissimmee, try mini-golf at Congo River Golf, enjoy a captivating dinner at Pirate's Dinner Adventure, or experience the thrill of indoor skydiving at iFly Orlando. Each offers unique vibes perfect for couples looking to create lasting memories together.

Things to do recommended for families

Your family will love the thrills at Aquatica waterpark, only 9 miles from Kissimmee, where fun awaits. For sports enthusiasts, Austin-Tindall Regional Park offers great facilities, while Kissimmee Go-Karts promises exciting racing adventures right in town!

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

When planning your trip—whether you're traveling with a group, family, pets, or seeking longer accommodations—be sure to set your priorities with the appropriate filters. Here are some helpful booking tips for Vrbo.

  • Traveling to Kissimmee with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group get-togethers. The good news is that you can easily refine your search for these options and much more on Vrbo.
  • Traveling to Kissimmee with young kids: Traveling with young kids can be demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Kissimmee: For many families, a vacation is not truly fulfilling unless they can bring along their furry companions. If you relate to this, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of your family feel comfortable and at home.
  • Planning for a long term stay visiting Kissimmee: If you're in search of vacation rentals that offer special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Kissimmee

Kissimmee, Florida, is the ideal destination for family vacations, offering a vibrant mix of entertainment and sunny weather. Explore the charming downtown Kissimmee, perfect for family outings, or enjoy excursions to nearby Disney attractions. With friendly locals and a welcoming atmosphere, you'll find the ultimate home away from home. Whether you're seeking adventure or relaxation, Kissimmee promises unforgettable experiences for everyone in the family.

  • Four Corners: Situated in the Kissimmee area, Four Corners is a vibrant village that serves as a gateway to family-friendly adventures. Known for its entertainment and outdoor experiences, this locale offers easy access to a variety of resorts and golf courses. Visitors can enjoy nearby attractions like renowned theme parks, a film studio, and a stadium, making it an ideal spot for those looking to immerse themselves in Florida’s famed amusement culture. Whether you're teeing off on a golf course or relaxing at a resort, Four Corners promises a memorable getaway.
  • Windsor Hills: Located around Kissimmee, Windsor Hills is a charming neighborhood that caters to families and entertainment seekers alike. This area boasts a range of activities, from shopping to outdoor recreation, with several resorts and golf options within reach. Attractions nearby include vibrant theme parks, a film studio, and a stadium, ensuring there's always something exciting to do. Windsor Hills is perfect for those looking to balance relaxation with fun, making it a popular choice for vacationers.
  • Reunion: Reunion is another enticing neighborhood close to Kissimmee, celebrated for its outdoor activities and sports experiences. This picturesque area is home to luxurious resorts and beautiful golf courses, providing ample opportunities for relaxation and recreation. Visitors can explore nearby attractions such as theme parks, a film studio, and even a beach, making it a versatile destination for all types of travelers. Whether you're planning a family trip or a sports getaway, Reunion has something to offer everyone.

Booking with Vrbo is a breeze

Are you hoping to save money on your upcoming journey? Being flexible with your travel dates can really help, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to narrow down your options by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve an eligible Vrbo for your group getaway, you'll receive OneKeyCash™ on the full booking amount. It's certainly beneficial to be the planner! Become a member of our One Key rewards program to unlock special savings just for members and earn OneKeyCash™ on qualifying stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers an easy-to-use platform for organizing your travel plans. You can create new trips, continue from where you last left off, or review and arrange your itinerary. Your saved or booked properties will be neatly organized into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Explore Kissimmee from vacation home rentals

Set just south of Orlando in Florida's Osceola County, Kissimmee's population has doubled twice since Walt Disney World opened nearby in 1971. Once a rural outpost where citrus groves and cattle ranches flourished, the city has maintained a sense of the past with a historic downtown, antique shops, and vintage amusement parks. Its sunny weather and wetlands make it a destination for anyone seeking warm temps, whether you prefer a weekend relaxing poolside or a more vigorous outdoor adventure. Its family attractions and close proximity to Disney make it a draw for the young and the young-at-heart.

Historic sites near Kissimmee vacation homes

Kissimmee has numerous historic sites and museums to explore during your trip. Vacation rentals are available near fascinating places like the Museum of Military History, a museum with military relics, photographs, and personal stories, and Osceola County Welcome Center and History Museum, a local history museum with dioramas and interactive exhibits of the county’s history. You can also visit the Monument of the States, a mid-century monument with stones sourced from the 50 states to celebrate American unity.

Places to visit near Kissimmee vacation rentals

Don't list the attractions in Kissimmee out loud to your kids. The excitement might be too much for them. Luckily, the amusements on offer are fun for grown-ups, too. Green Meadows Farm is a peaceful countryside getaway where you can pet the animals, milk a cow, and have a picnic on the grass. Gatorland is a theme park with a playful, vintage feel. There are live animal shows and plenty of alligators in its breeding marsh, and you can buy hot dogs to feed them. Fun Spot America features old-time carnival rides and go-kart tracks.

Activities near Kissimmee vacation homes

Kissimmee's historic downtown is the center of commercial life and offers a mix of family-owned businesses, shops, and restaurants. Consider a Kissimmee vacation rental within walking distance of Main Street, where you can enjoy breakfast at an outdoor cafe before deciding how you'll take in the surrounding wetland wilderness. Eco-tours via horseback, zipline, or airboat are just a few of your options. You'll likely have the chance to spot alligators, black bears, and dozens of bird species. Nighttime helicopter tours over the city provide a unique thrill, as the region's theme park lights twinkle below.

Best time to travel to Kissimmee vacation homes

You don't have to worry about the cold in Kissimmee, even in winter. January temperatures average in the 70s, and skies are typically sunny. The city is crowded during the Christmas holiday but otherwise peaceful, and you might score a Kissimmee vacation rental at a low rate. Spring weather is mild, with highs between the 60s and 80s, and rental prices are still low. Summer is the busy season and also the hottest, so look for lodging with air-conditioning. Temperature-wise, autumn is as lovely as spring, but it's also the height of hurricane season, so check local forecasts.

Blow a kiss to a bald eagle from your Kissimmee kayak

Set on the headwaters of the Everglades, the largest subtropical wilderness in the U.S., and on the northern border of Lake Tohopekaliga, your Kissimmee vacation rental is surrounded by wetlands and animal habitats. Many of these are protected in Nature Conservancy's Disney Wilderness Preserve, 15 miles south of Kissimmee. It's an 11,500-acre home to gopher tortoises, bald eagles, and sandhill cranes. The Shingle Creek Regional Park is another natural wonder, this one right in the city itself, with rivers for kayaking and canoeing, and nature trails for spotting birds.

How to get to and around Kissimmee

The nearest airport is in Orlando Intl. Airport (MCO), located 11.4 mi (18.3 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Kissimmee, FL (ISM-Kissimmee Gateway), which is 1.8 mi (2.9 km) away.

If you're traveling by train, the main station is Kissimmee Station. Consider catching the metro at Tupperware Station or Poinciana Station to see more of the city.

Couple's retreat in Kissimmee vacation homes

Couples will find plenty of romantic experiences and locations in Kissimmee. Vacation homes are available near places like Lake Tohopekaliga, a huge fishing lake with wildlife viewing, airboat rides, and swimming, and Kissimmee Lakefront Park, a waterside park with walking paths and fishing areas. You’ll also enjoy Main Gate Flea Market, an indoor flea market with booths selling clothing, accessories, and other goods.

Frequently asked questions

What is the best area to stay in Kissimmee when booking a vacation rental?
Bellavida is among the more in-demand neighborhoods for a vacation home in Kissimmee. Spend your stay here to enjoy all the privacy and comfort that comes with having the entire place to yourself.
What is the most popular type of vacation rental accommodation in Kissimmee?
Villas are the most popular kind of vacation rental in Kissimmee, according to our data. Even if you have something different in mind, Vrbo has properties in a variety of sizes and shapes. Look over our options to find your perfect pad.
How much does it cost to rent a vacation rental in Kissimmee?
The average price for a vacation home in Kissimmee is based on several factors, including season, property type and length of stay. Whether you're dreaming about a sprawling villa with lots of space or a cozy condo for just you and your sweetheart, just enter your dates of travel to find stays with terrific value.
How much does it cost to rent a beach house in Kissimmee?
When you travel and the size and style of the property will help determine the cost of your beachside escape. Type in your Kissimmee travel dates to see all your options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to pick the amenities and features you want in your rental.
Are there pet-friendly vacation rentals in Kissimmee?
Pack a travel bag for your puppy dog because Kissimmee has 20,419 properties that roll out the welcome mat to pets. Let your happy hound join in with the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates then check the "Pets allowed" filter box.
Can I rent a house with a pool in Kissimmee?
Grab your swimsuit and pool noodle, because there are 19,323 houses with a private pool in Kissimmee. Unwind at one of these terrific vacation rentals and enjoy a pool day every day. Simply enter your dates into Vrbo, then check the "pool" filter to find the ideal place for a splashing good time!
What are popular rental amenities in Kissimmee?
A water view, a garden and an electric car charging station top the list of most popular rental amenities in Kissimmee. Whether you plan to go alone, with a partner or a group of dear friends, Vrbo will help you find a vacation rental that fits your tastes with all the conveniences you're looking for.
Are there large group vacation rentals in Kissimmee?
Kissimmee has 9,105 vacation homes that can accommodate 10 or more people. These stays come with enough space to share good times with family and friends.
Are there vacation rentals in Kissimmee that welcome kids?
Gather your whole crew for fun-filled adventures in Kissimmee at one of our 19,863 family-friendly vacation rentals. Lots of these stays come with amenities that are ideally suited to trips with youngsters, including full kitchens, extra bedrooms and pools. Just click on the "Properties good for families" filter and pick your favorite option.
What are the top attractions for families in Kissimmee?
Keeping the kids entertained during your Kissimmee vacation is child's play with these top family-friendly attractions:

  • Kissimmee Golf Club
  • Osceola Square Mall
  • 192 Flea Market

Are there one-bedroom vacation rentals in Kissimmee?
Yes, Kissimmee has 719 one-bedroom rentals available. Typically located in desirable areas because of their smaller size, a one-bedroom vacation property is perfect if you're traveling with your partner or a friend. And with plenty of home comforts like laundry facilities and more privacy than a standard hotel, you'll be able to kick back and relax while sightseeing around this amazing destination.
Can I find two-bedroom vacation rentals in Kissimmee?
Gather your loved ones and enjoy total privacy and comfort in one of the 1,495 two-bedroom vacation homes Kissimmee has to offer.
Are there vacation rentals with WiFi in Kissimmee?
Kissimmee has 6,862 vacation rentals with WiFi, so you can stay connected while you're traveling. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to updating your social media, these Vrbo homes make it a cinch to get online.
How can I find vacation rentals with air conditioning in Kissimmee?
Pick from 19,898 vacation homes with air conditioning in Kissimmee offering that cooling breeze and extra level of comfort. Just enter your preferred dates of travel and then make use of our filter tool to search for properties with air conditioning.
How old do you have to be to rent a vacation rental in Kissimmee?
We advise checking with the Kissimmee vacation rental you're considering on Vrbo as the age limit differs. However, normally it's 16, 18 or 21.
How long can I rent a vacation rental in Kissimmee for?
The length of time you can book a vacation rental in Kissimmee is down to the property. Simply enter your chosen dates to display a list of options offering extended stays. With lots of features like washing machines and kitchens, as well as some offering weekly or monthly discounts, you're sure to find somewhere just right to call your home away from home in Kissimmee.
Does Vrbo offer discounts for vacation homes in Kissimmee?
Whether you're interested in one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you're sure to find some fabulous bargains and discounts on Vrbo. From mini stays to extended vacations, we've got the ideal space for your next Kissimmee escape.

Explore destinations around Kissimmee

People also search for

More Vacation Rentals ideas