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Kissimmee Apartments & Vacation Rentals - 3429 Rentals Available

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3,429 Vacation rentals

Filters applied: 2+ Bedrooms

1 / 18

Kissimmee Townhouse

  • 3
  • 7
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

$69.00

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from $69.00 / night

1 / 43

Kissimmee Townhouse

  • 4
  • 10
  • min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Child friendly

$86.00

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from $86.00 / night

1 / 53

Kissimmee Villa

  • 7
  • 14
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

$155.00

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from $155.00 / night

(4)

1 / 44

Kissimmee Villa

  • 7
  • 17
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$281.00

Average (4 reviews)

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from $281.00 / night

1 / 14

Kissimmee House

  • 4
  • 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$126.00

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from $126.00 / night

1 / 59

Kissimmee Villa

  • 8
  • 18
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

$258.00

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from $258.00 / night

1 / 44

Kissimmee Villa

  • 7
  • 18
  • min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Child friendly

$144.00

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from $144.00 / night

1 / 42

Kissimmee Villa

  • 10
  • 22
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$705.00

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from $705.00 / night

(1)

1 / 11

Kissimmee Villa

  • 4
  • 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“My only small issues were with the pool/bathrooms. Some railings for elderly/handicapped people would be nice for the pool and maybe the master brm. toilet The house was wonderful!!!!! Thanks again”
- Review left on 04/28/2019

$144.00

Excellent (1 reviews)

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from $144.00 / night

1 / 37

Kissimmee Villa

  • 4
  • 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$212.00

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from $212.00 / night

1 / 58

Kissimmee Villa

  • 7
  • 14
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$161.00

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from $161.00 / night

1 / 46

Kissimmee Villa

  • 7
  • 18
  • min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Child friendly

$144.00

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from $144.00 / night

1 / 51

Kissimmee Villa

  • 6
  • 14
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$161.00

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from $161.00 / night

1 / 58

Kissimmee Villa

  • 8
  • 18
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

$264.00

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from $264.00 / night

1 / 48

Kissimmee Villa

  • 6
  • 14
  • 3 nights min
  • Nearest beach 97 mi
  • Swimming pool
  • Child friendly

$172.00

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from $172.00 / night

1 / 58

Kissimmee Villa

  • 7
  • 14
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$161.00

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from $161.00 / night

1 / 18

Kissimmee Villa

  • 7
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 17 minutes

$258.00

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from $258.00 / night

1 / 46

Kissimmee Townhouse

  • 4
  • 10
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

$86.00

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from $86.00 / night

1 / 48

Kissimmee Villa

  • 6
  • 14
  • 3 nights min
  • Nearest beach 97 mi
  • Swimming pool
  • Child friendly

$172.00

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from $172.00 / night

1 / 17

Kissimmee Townhouse

  • 3
  • 7
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

$70.00

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from $70.00 / night

1 / 43

Kissimmee Townhouse

  • 4
  • 10
  • min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Child friendly

$86.00

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from $86.00 / night

1 / 64

Kissimmee Villa

  • 9
  • 18
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$229.00

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from $229.00 / night

1 / 47

Kissimmee Villa

  • 7
  • 16
  • 3 nights min
  • Nearest beach 97 mi
  • Swimming pool
  • Child friendly

$149.00

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from $149.00 / night

1 / 63

Kissimmee Villa

  • 9
  • 22
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$218.00

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from $218.00 / night

1 / 51

Kissimmee Villa

  • 6
  • 14
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$161.00

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from $161.00 / night

1 / 28

Kissimmee Condo

  • 3
  • 6
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

$69.00

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from $69.00 / night

1 / 18

Kissimmee Townhouse

  • 3
  • 7
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

$69.00

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from $69.00 / night

1 / 58

Kissimmee Villa

  • 8
  • 18
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly

$258.00

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from $258.00 / night

(5)

Certificate of Excellence

1 / 27

Kissimmee Villa

  • 5
  • 10
  • 3 nights min
  • Nearest beach 77 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 0 minutes

Certificate of Excellence

“The house was wonderful! The home was is in great condition, very clean. Had all the amenities to keep the family busy. The pool was fantastic, with lots of toys for the kiddos, as well as separate pool towels. Lots of extras such as blankets, towels...”
- Review left on 04/03/2014

$139.00

Very Good (5 reviews)

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from $139.00 / night

1 / 41

Kissimmee House

  • 5
  • 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$229.00

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from $229.00 / night

(4)

1 / 31

Kissimmee House

  • 4
  • 10
  • min stay varies
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 22 minutes

“This home is both beautiful and clean with plenty to do. It was so nice to relax while the children played pool and air hockey. We all loved the pool and hot tub! It was also nice having two bedrooms with bathrooms in them! The other two bedrooms...”
- Review left on 09/03/2015

$137.00

Very Good (4 reviews)

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from $137.00 / night

1 / 56

Kissimmee House

  • 8
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 49 minutes

$336.00

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from $336.00 / night

(4)

1 / 19

Kissimmee Townhouse

  • 3
  • 7
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“This was a great experience! There were a few things but they were reported once the service guy came out the same day that I called. I was celebrating my birthday and I enjoyed it immensely. Thank You...”
- Review left on 12/19/2015

$69.00

Very Good (4 reviews)

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from $69.00 / night

1 / 36

Kissimmee Villa

  • 8
  • 20
  • min stay varies
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 18 minutes

$343.00

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from $343.00 / night

(2)

1 / 71

Kissimmee House

  • 4
  • 10
  • min stay varies
  • Child friendly
  • Car not necessary

Responds fast! Avg. 3 hours 55 minutes

$81.00

Average (2 reviews)

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from $81.00 / night

(8)

1 / 25

Kissimmee Townhouse

  • 3
  • 7
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“This was a nice, spacious townhouse style condo. We were happy and comfortable. It was as advertised. Would stay there again...”
- Review left on 06/25/2016

$70.00

Very Good (8 reviews)

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from $70.00 / night

1 / 37

Kissimmee House

  • 7
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$453.00

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from $453.00 / night

(4)

1 / 31

Kissimmee Villa

  • 7
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 59 minutes

“We enjoyed the home. It had all the amenities we needed. It was 13 of us and the house had enough room for us to enjoy. The pooo was nice and the neighborhood was quite. I like that we were close to Disney, Walmart and a lot of restaurants. I would...”
- Review left on 08/20/2018

$230.00

Very Good (4 reviews)

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from $230.00 / night

(33)

1 / 27

Kissimmee Apartment

  • 3
  • 8
  • min stay varies
  • Nearest beach 97 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 38 minutes

“The place was great and spacious! It was so clean and close to everything we needed (grocery, restaurants, and Disney). Best vacation place we have ever stayed at! Iverson was great to work with. I would stay here again or stay at another one of his...”
- Review left on 12/31/2016

$92.00

Very Good (33 reviews)

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from $92.00 / night

(5)

1 / 63

Kissimmee House

  • 9
  • 20
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 38 minutes

$321.00

Excellent (5 reviews)

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from $321.00 / night

About Kissimmee

Whether you want to visit theme parks or nature preserves, Kissimmee is the place to be in Central Florida. Take your pick from dozens of luxurious Kissimmee villas, and enjoy a dip in the pool and plenty of fun in the Florida sun.

Introduction to Kissimmee

Located just a short hop away from Orlando, Kissimmee is a small city that offers quick and convenient access to a whole range of family friendly activities. When you want to take the kids on a trip to Central Florida but don’t want the stress or expense of vacationing at the theme parks, consider staying at one of the affordable Kissimmee villas. Vacation properties in Kissimmee give you the space to have a good time without breaking the bank.

Kissimmee Climate

Like most of Central Florida, Kissimmee enjoys hot, humid summers followed by mild winters. If you visit in December or January, you’ll find temperatures around 60 degrees, while temperatures top out around 90 in July and August.

How to Get Around Kissimmee

If you’re flying to Kissimmee, Orlando International Airport is an easy 25-minute drive away. Public busses and private shuttles can transport visitors around the Kissimmee area, but if you want to explore on your own, renting a car is your best bet. You can easily get from your vacation home to the theme parks, or to the natural attractions, on your own schedule with a car.

Visit the Parks

The rides and attractions at Disney World are just a short drive away, but Kissimmee also boasts several of its own parks. Right on Lake Tohopekaliga, Kissimmee Lakefront Park features a playground and splash park for kids, BBQ grills for family get togethers, and fishing piers for everyone. If you time your visit right, you can even catch one of the many festivals or events on the park’s outdoor stage.

If you’re looking for something more outdoorsy, visit Shingle Creek Regional Park, which encompasses over 1,000 acres. Canoe along the creek, hike the trails, and enjoy a picnic near the park’s historic pioneer homes. Even more impressive is the Disney Wilderness Preserve, which includes 11,500 acres and over 1,000 plant and animal species. Explore wetlands, swamps, and a freshwater marsh while spotting bats, snakes, and even panthers.

Shop and Dine in Old Town

When you’re ready to do some shopping or grab a bite to eat, head straight for Kissimme’s Old Town neighborhood. Here you’ll find everything from souvenir shops to places to stock up on warm weather gear. To fuel up for more adventures, dig into pizza, Tex-Mex, or pub grub. You can even enjoy a night out at one of the live music venues or nightclubs in Old Town.

Just a few miles from Disney, Kissimmee offers the best of everything. With parks and preserves that will keep everyone entertained, Kissimmee villas that comfortably fit the whole family, and easy access to all the fun at Disney World, Kissimmee is a great vacation destination.


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Kissimmee, Florida Travel Tips

Families looking for vacation rentals in Kissimmee, FL have many accommodations to choose from, but renting a home is the best bang for your buck while on a Kissimmee vacation. Rentals by owner offer much more space and privacy than a hotel room, and ensures that homes are very well maintained and updated. Keep reading to learn more tips about how to have a memorable vacation in Kissimmee.

Beaches and Parks

St. Cloud Lakefront Park and Beach offers a fishing pier, splash pad, family picnic area, volleyball court, and playground. Located along the breathtaking Lake Tohopekaliga, this park is a great place to spend a relaxing afternoon.
Cocoa Beach, located just an hour's drive from Kissimmee, features beautiful weather, whale watching, fine dining, and golf.

Theme Parks

What probably comes to mind when looking for houses for rent in Kissimmee, FL is the town's close proximity to world-famous theme parks. The magic of Disney World, Universal Orlando, and SeaWorld are only a short drive away while staying at this delightful vacation spot.
Walt Disney World needs no introduction. As the most visited entertainment complex in the world, this beloved attraction boasts four theme parks and two water parks.
Universal Orlando consists of Universal Studios, Islands of Adventure, and Wet N' Wild Orlando. Visitors can enjoy a variety of shows, dining, and events right within the borders of the park.
SeaWorld is another favorite of those visiting the Orlando area. With tons of shows, exhibits, dining, and shopping, there is surely to be something for everyone to enjoy. Kids will adore seeing killer whales, dolphins, manatees, sharks, polar bears, flamingoes, and penguins up close.

Outdoor Adventures

Golf is a popular sport in Florida because of its year-round sunny weather. If you're a seasoned pro looking for challenging courses or just want to play mini-golf with the kids, Kissimmee has you covered.
Hot Air Balloon Rides are a great way to top off your Kissimmee vacation. Take a sunrise balloon ride over Central Florida's beautiful landscape and check out the wildlife from high above.

Fun With Kids

The kids will have no shortage of things to do while enjoying their time in Kissimmee. Kids and parents will have a blast exploring the nearby attractions. In addition to the great outdoors and amazing theme parks, the Kissimmee area also features lots of relaxing, family-friendly activities.
Medieval Times Dinner & Tournament is guaranteed to always be a fun time. Have dinner while being entertained by a live-action jousting tournament.
Osceola County Pioneer Village and Museum features many exhibits depicting life in the 19th century. Located in northwestern Osceola County, the Pioneer Village has a general store, blacksmith shop, one room schoolhouse, and nature preserve.
Green Meadows Petting Farm , located just minutes from Orlando, teaches kids about a variety of farm animals and even allows them to milk a cow. The farm also has a train ride and offers pony rides.
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