Kissimmee, FL Vacation Rentals: house rentals & more

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 $105 per night, and houses and resorts are popular options for a stay in Kissimmee. Either way, you'll find a rental for everyone's needs.

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Find the best place to stay — Kissimmee

Search 24,103 vacation rentals

Stayed Oct 2021

Would stay again!

Great for our extended family of 7 adults. Will look for this place again for our next trip. Enjoyed our access to the clubhouse (White House) pool and outdoor charcoal grill. Hope the gym & theater are available next time. Accommodating homeowner an...

Stayed Oct 2021

Wonderful Stay

We had a wonderful stay! Perfect location, very convenient to everything, comfortable, plenty of room for our family, the kids loved the pool each night after returning from the parks. The owner was a pleasure to work with, very helpful with informat...

Stayed Oct 2021

Very clean and very close to the Disney parks!

My husband, our 2 kids (6 and 7), two grandmothers, and I had a great Disney vacation in Orlando. This property was the perfect home base. It's a cute home in a quiet neighborhood and literally minutes to the Disney Parks. Plus there were no addition...

Stayed Sep 2021

Family Vacation

This was a wonderful property! We visited with extended family, there was something for everyone! The kids took full advantage of the playroom, and they didn’t want to leave to go back to their boring old bedrooms at home. This property was clean and...

Stayed Sep 2021

Perfect for a family of 5!

We wanted a condo instead of an on-site resort so we could have the space and rooms. My girls shared the Mickey room and loved it. It was just perfect for them. My son had his own room and my husband and I had ours. It was great having a full kitchen...

Stayed Sep 2021

Perfect Hideaway for a Quiet and Relaxing Girls' Getaway

This property was PERFECT for the quiet relaxing getaway I planned for my bestie's birthday. We spent our days by the pool watching a gator and crane play cat and mouse in the lake. Our nights curled up on the couch watching tv with our wine. We were...

Stayed Sep 2021

A++++ HIGHLY RECOMMEND!!! Absolutely perfect from start to finish!

I can't say enough positive things about our experience! Everything was as described and then some! Nothing but pleasant surprises here! Maria was warm and welcoming...an absolute pleasure to deal with and an unbelievably gracious host! She made ever...

Stayed Sep 2021

PERFECT spot!

I have stayed in many rentals in Orlando and this is honestly the first one I plan to return to. Ken and Michelle have made a beautiful place for families to stay. The beds were very comfortable, everything was immaculately clean, and the kitchen h...

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Destination guide

Experience Kissimmee with your pet in a vacation rental

If you're looking for pet-friendly rentals while you vacation in Florida, Kissimmee is a great option. Located in central Florida, Kissimmee is close enough to all the attractions but far enough away from Orlando that you can find great pet-friendly rentals at cheaper prices. There are plenty of things to do in Kissimmee, whether you're looking for daytime activities or nighttime entertainment. Within 30 minutes, you can be at Walt Disney World Resort. With fun for kids and adults alike, Kissimmee really is an optimal place to stay.

History

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.

Things to do

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

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.

Weather

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.

Natural features

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 there

Transportation to and around Kissimmee

The nearest airport is in Kissimmee, FL (ISM-Kissimmee Gateway), located 1.9 mi (3 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Orlando, FL (MCO-Orlando Intl.), which is 11.2 mi (18 km) away.

If you're traveling by train, the main station serving the city is Kissimmee Station.

Good for couples

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.

How many vacation rentals are available around Kissimmee, FL?

Our 2021 property listings offer a large selection of 24,103 vacation rentals around Kissimmee. From 18,516 house rentals to 1,271 resort rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Kissimmee?

Vrbo offers a large selection of vacation rentals near lovely places in Kissimmee. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

Reunion Resort Golf Course: 26,324 vacation rentals
Old Town: 26,589 vacation rentals
Kissimmee Lakefront Park: 22,560 vacation rentals
Remington Golf Club: 22 vacation rentals
Mystic Dunes Golf Club: 26,146 vacation rentals

But there are many other points of interest around Kissimmee listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Kissimmee?

Yes, of course. Vrbo has 18,516 Houses in Kissimmee. Our other popular types of vacation rentals in Kissimmee include:

Resorts: 1,271 rentals available
Villas: 5,114 rentals available
Cabins: 49 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Townhouses and more.

Can I find a vacation rental with pool in Kissimmee?

Yes, you can select your preferred vacation rental with pool among our 22,814 vacation rentals with pool available in Kissimmee. Please use our search bar to access the selection of vacation rentals available.