Discover a selection of more than 10,000 vacation rentals in Kissimmee, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including private pools and swimming pools. Prices start at $65 per night, and houses and villas are popular options for a stay in Kissimmee. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Kissimmee
Destination guide

The sunny setting of Kissimmee is ready to explore

Take a vacation 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. There are plenty of places to find the perfect souvenir including Disney Springs™, Orlando International Premium Outlets and Old Town. A vacation rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Things to do

Activities and attractions in and around Kissimmee

Do you want to discover attractions to see while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Kissimmee a fun place to get away. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Epcot® (10.2 mi / 16.4 km)
  • Disney's Hollywood Studios® (10.3 mi / 16.6 km)
  • Walt Disney World® Resort (11.4 mi / 18.4 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)

Seasonal weather in Kissimmee

If warm-weather activities are high on your list, August, July, June and September are the hottest months to visit, when temperatures average 85°F.

Natural features

Exploring the natural landscape of Kissimmee

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Kissimmee is a great place to get out in nature. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Kissimmee Lakefront Park (0.2 mi / 0.3 km)
  • Osceola Heritage Park (2.4 mi / 3.9 km)
  • Lake Bryan (7.5 mi / 12.1 km)
  • Austin-Tindall Regional Park (8.3 mi / 13.4 km)
  • Bill Frederick Park (15.1 mi / 24.3 km)
  • Northeast Regional Park (15.8 mi / 25.4 km)
How to get there

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.

What are the top vacation rentals in or near Kissimmee?

Whatever your getaway needs, you'll find a rental in or around Kissimmee that's a match made in heaven. Here are some of our favorites:

  • Take advantage of handy amenities like high-speed internet services and a nearby zoo at "Theme Rooms, Splashpad, Movie Theater". Located around 12 miles from Kissimmee, this property has 7 bedrooms and is a hit with guests.
  • Alternatively, make yourself comfy at "Luxurious Family - 4bedroom - Privacy Fenced Pool Hot Tub". Located around 12 miles from the heart of Kissimmee, it has 4 bedrooms and comes with a nearby hospital and a fenced yard.

For even more great options, use the search bar at the top of the page to find the perfect Kissimmee vacation rental for you.

What are the best tiny house vacation rentals in or near Kissimmee?

You need only open the door to Vrbo's tiny house vacation rentals in Kissimmee to figure out that awesome things really do come in little packages. Cleverly designed to maximize every spare inch of space, these pint-sized pads deliver a big vacation experience:

  • Get ready for a simpler way of living at "Brand New Tiny House Near Orlando Attractions And Central Florida Beaches". Amenities at this tiny house in Clermont include a separate dining area, a toaster and more.
  • Alternatively, settle in at "The Cottage - Quaint Tiny Home Filled With Charm". Located in Princeton - Silver Star, this little gem comes with off-street parking options and outdoor furniture.

What are the top-rated vacation rentals for weekend getaways in or near Kissimmee?

Clock out on Friday afternoon and then pack your overnight bag. If you're ready for some fun and relaxation, these retreats in and near Kissimmee are the perfect weekend getaway:

  • "Welcome To The Windsor Fantasy" is a favorite option around 12 miles west of central Kissimmee. You'll never have to wander far to find something fun to do around this property. Pull out your map and head for Princeton Park and Split Oak Forest Mitigation Park. Activities like fishing and kayaking will perfectly round off your weekend trip.
  • Alternatively, enjoy some downtime at "Minutes To Disney5 - Starman". About 12 miles west of Kissimmee, activities around here include golf and tennis. Prefer to go sightseeing? Pencil in a visit to Split Oak Forest Mitigation Park and Orange County National Golf Club.

Can I find studio apartments for rent in and around Kissimmee?

Typically small, easy on the pocketbook and well located, it's not difficult to fall for the charms of a studio apartment. Get comfy in one of these options and experience the energy of Kissimmee up close:

  • Make "Sensational Water View 1 Mile To Disney Newly Renovated Superb Location" your home for a couple of days or more. This great vacation rental features amenities including a microwave oven and a balcony.
  • Another awesome choice is "Upgraded Huge Lakefront 1br/2ba Blue Heron Beach Resort Condominium". Make use of nearby birdwatching activities, a kitchen and other conveniences during your getaway.

There are many sights around Kissimmee you shouldn't miss. Nourish the culture vulture in you by visiting Wizardz Magic Theater and Orlando Repertory Theater.

Can I find short term rentals in or near Kissimmee?

Every once in a while, you've just got to take a break from it all, even if it's only for two or three days. Enjoy a nice mix of sightseeing and relaxation at one of these short-term rentals in or around Kissimmee:

  • If you're eager to be near the action, "Welcome To The Windsor Magic" is calling your name. It's within easy reach of the center of Kissimmee and a handy base to explore sights like Amway Center and Camping World Stadium.
  • "Clean Themed Rooms, Private Lakeview Yard" is another appealing option. Remember to add Mall at Millenia and Orlando Science Center to your to-do list when it's time to sightsee.

What are the best romantic weekend getaways in or near Kissimmee?

Forget about flowers and chocolates. Sometimes all you need is to take off for the weekend, just you and your honey. At Vrbo, we've got romantic getaways in and around Kissimmee that would make even old Cupid swoon. Here are some to tempt you:

  • Sneak off on Friday for a few nights of passion at "Theme Rooms, Splashpad, Movie Theater". Roughly 12 miles from Kissimmee, it comes with lots of nice touches, like air conditioning and a swimming pool.
  • "Luxurious Family - 4bedroom - Privacy Fenced Pool Hot Tub" is another top option that'll impress. It's approximately 12 miles from Kissimmee and has beauty services and winery tours.

What are the best large group vacation rentals in or near Kissimmee?

Vacation with others and multiply the fun. Whether you're organizing an adventurous getaway with pals or a big family gathering, you'll have your pick of large group vacation rentals in and around Kissimmee:

  • There's plenty of space to enjoy yourselves at "Theme Rooms, Splashpad, Movie Theater". Around 12 miles west of Kissimmee, this grand retreat has 7 bedrooms sleeping up to 16 guests. Quality amenities include a swimming pool and a kitchen.
  • "Welcome To The Windsor Fantasy" is another terrific option. It's around 12 miles to the west of Kissimmee, has 5 bedrooms and sleeps as many as 12 guests. A kitchen and a swimming pool are just a couple of things that'll help make your group getaway even more comfortable.

Are there large vacation rentals that sleep 30 or more in or near Kissimmee?

Whether you're hosting a big event like a wedding or an unforgettable vacation with your favorite people, we'll help you find the right place for your group. Bring together the troops and explore these large vacation rentals in or around Kissimmee:

  • "Championsgate, 9 Bed Luxury Exec Villa": With 9 bedrooms accommodating up to 30 people, space isn't a problem at this sizable rental. A water park and a kitchen are a sample of its numerous amenities.
  • "24 Bedrooms In Two Homes Just One House Between. All Set Up And Ready For You": Offering space, comfort and privacy, this vacation home houses up to 76 people in its 24 bedrooms. A swimming pool and a kitchen will help keep your crew happy and comfortable.

What are the best houses for rent with a pool in or near Kissimmee?

Nothing says fun times like a pool. Grab your inflatable flamingo and check out these rental houses in or near Kissimmee that feature this added perk:

  • Treat your loved ones to an unforgettable stay at "5 Stars House With Wifi, Game Room". There's plenty to love about this getaway apart from its pool, such as a porch and nearby birdwatching activities.
  • Spend leisurely days swimming or simply unwinding beside the water at "Awesome Deals - Fantastic 5bedroom House". This property is also a firm favorite and offers childrens activities, coffee and tea making facilities and more.

Not sure how to pack for your Kissimmee escape? This impressive destination has a humid subtropical climate. In the summertime, expect average temperatures ranging from 75 ºF to 90 ºF. Browse our selection of Kissimmee vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more inspiration on where to stay.

What are the best large family vacation rentals in or near Kissimmee?

It's always more fun when you share the great times with the people you care about the most. Whether you're planning a family get-together or taking time out with good friends, we'll have a large vacation rental that's perfect for you. Here are two of our best in and around Kissimmee:

  • Get everyone together at "Theme Rooms, Splashpad, Movie Theater", which has 7 bedrooms that sleep up to 16 guests. This retreat is located 12 miles to the west of Kissimmee and features amenities such as cable/satellite TV services and a swimming pool.
  • "Luxurious Family - 4bedroom - Privacy Fenced Pool Hot Tub" also offers the space you need to live it up with loved ones. This option is around 12 miles to the west of central Kissimmee and accommodates 8 guests in its 4 bedrooms. A dishwasher and nearby birdwatching activities will help keep everyone content and comfortable.

When it's time to explore, there are plenty of family-friendly attractions in the area to keep everyone happy and entertained. Walt Disney World®, Universal Studios Florida and Magic Kingdom® Park should be on your list.