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Kissimmee Apartments & Vacation Rentals - 2095 Rentals Available

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2,095 Vacation rentals

(11)

1 / 33

Kissimmee House

  • 8
  • 22
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 35 minutes

“We loved this home and would definitely book it again when traveling with a large group. Whether you have a toddler or a teenager in your group, this house has everything you?ll need. The pool is awesome and the house was very clean. The location is...”
- Review left on 10/13/2019

$264.00

Excellent (11 reviews)

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from $264.00 / night

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(75)

1 / 51

Kissimmee Villa

  • 5
  • 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“This home was perfect for us just as it has been for previous stays. We keep coming back to this wonderful home because it accommodates us so well. Thank you again for letting us call this house home for another week...”
- Review left on 02/18/2019

$144.00

Excellent (75 reviews)

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from $144.00 / night

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(23)

1 / 28

Kissimmee Townhouse

  • 3
  • 8
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
“The location is perfect for a Disney vacation. You can't get much closer to DisneyWorld without staying onsite. I prefer to stay offsite whenever we visit, because it's nice to be able to "escape" from all the Disney magic every now and then. The...”
- Review left on 10/27/2017

$98.00

Excellent (23 reviews)

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from $98.00 / night

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(8)

1 / 27

Kissimmee House

  • 3
  • 8
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly

$98.00

Average (8 reviews)

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from $98.00 / night

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(5)

1 / 29

Kissimmee Villa

  • 6
  • 14
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 50 minutes

“This home was beautiful and clean better than what we thought. The home was conveniently located near shopping centers...”
- Review left on 12/29/2019

$224.00

Very Good (5 reviews)

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from $224.00 / night

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(3)

1 / 23

Kissimmee Apartment

  • 3
  • 8
  • 3 nights min
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 22 minutes

$91.00

Excellent (3 reviews)

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from $91.00 / night

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(54)

1 / 27

Kissimmee Townhouse

  • 3
  • 8
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
“The accommodations were excellent, all the amenities required for a comfortable stay, the place was very clean, the HVAC worked fine no issues. I recommend staying here to anyone. Than you for everything Manny and Carmen we will be back soon...”
- Review left on 01/23/2017

$98.00

Very Good (54 reviews)

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from $98.00 / night

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(43)

1 / 43

Kissimmee House

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

Responds fast! Avg. 2 hours 42 minutes

“Great location. Near Disney and shops. The owner were very nice ? called to see if everything is o.k, and agreed to a late departure. The view of the lake is wonderful and the pool is great. The kids rooms upstairs was the one thing I liked less....”
- Review left on 10/17/2018

$180.00

Excellent (43 reviews)

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from $180.00 / night

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(5)

1 / 50

Kissimmee House

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 34 minutes

$233.00

Excellent (5 reviews)

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from $233.00 / night

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(14)

1 / 40

Kissimmee Apartment

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 59 minutes

“Great value for your money. The condo was very clean. I was really impressed with the unit. There was plenty of space for everyone to spread out and enjoy themselves. It was well stocked with linen. The washer and dryer worked great. Unit has a...”
- Review left on 04/30/2015

$104.00

Very Good (14 reviews)

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from $104.00 / night

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(9)

1 / 45

Kissimmee House

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“All around great stay. Bob and Diane were extremely helpful. Would highly recommend them for your vacation needs...”
- Review left on 07/29/2018

$114.00

Very Good (9 reviews)

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from $114.00 / night

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(22)

Certificate of Excellence

1 / 48

Kissimmee Villa

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 27 minutes

Travelers’ Choice award

“This house is everything the ad states and more!! The location is perfect and is so conveniently located to Disney, fantastic mini putts, a beautiful golf course, and restaurants. The lay out of the house is fantastic allowing everyone in your party...”
- Review left on 03/05/2018

$228.00

Excellent (22 reviews)

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from $228.00 / night

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(4)

1 / 50

Kissimmee Villa

  • 7
  • 16
  • 3 nights min
  • Nearest beach 97 mi
  • Swimming pool
  • Child friendly
“The location is great. Close to all the parks. Restaurants and grocery right up the street. The house was fabulous. We had 14 people stay in the house, plenty of room. The pool and hot tub were used every night...”
- Review left on 11/25/2014

$115.00

Excellent (4 reviews)

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from $115.00 / night

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(1)

1 / 47

Kissimmee Villa

  • 7
  • 14
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“Location, location, location! This well- equipped neat, spacious and cozy luxury home is close to everything you'd ever want to do in Orlando,Florida. Children open the patio doors and they are in their own pool, while the family relax in or out of...”
- Review left on 03/22/2016

$188.00

Excellent (1 reviews)

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from $188.00 / night

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(17)

1 / 38

Kissimmee Villa

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 20 minutes

$109.00

Excellent (17 reviews)

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from $109.00 / night

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(4)

1 / 23

Kissimmee Villa

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

Responds fast! Avg. 1 hour 44 minutes

“From the time we viewed this beautiful home on the website, we knew this was the place we wanted to celebrate our 2nd. Anniversary here. This place is decorated with a touch of sophistication and elegance yet it made you feel at home once you walked...”
- Review left on 10/07/2015

$129.00

Average (4 reviews)

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from $129.00 / night

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1 / 94

Kissimmee Villa

  • 7
  • 16
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 113 mi
  • Swimming pool

Responds fast! Avg. 3 hours 20 minutes

$172.00

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from $172.00 / night

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(12)

1 / 25

Kissimmee Townhouse

  • 3
  • 7
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“Will recommended to friends when they are planning to go Orlando in July/August.Closed to Disney world, shopping centres, etc...”
- Review left on 04/18/2016

$70.00

Excellent (12 reviews)

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from $70.00 / night

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(13)

1 / 26

Kissimmee House

  • 7
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Our stay was just breathtaking. The best stay ever! For most of us it was our first time experiencing a Vacation home and they definitely suggest to come back again! Everything was in place , everything was clean and well taken care of, the pool was...”
- Review left on 09/12/2017

$252.00

Very Good (13 reviews)

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from $252.00 / night

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(27)

1 / 64

Kissimmee Villa

  • 4
  • 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“My wife and I had an enjoyable, relaxing 8 week stay at the villa this past winter and were impressed with the cleanliness while the neighborhood itself is quiet and serene. We were close to a local park with basketball and tennis courts along with...”
- Review left on 03/28/2016

$138.00

Excellent (27 reviews)

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from $138.00 / night

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(2)

1 / 56

Kissimmee Villa

  • 8
  • 18
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“We had the best vacation ever and this property was everything a family my size needed and more.. I will recommend this to anyone that I come in contact with because it was so comfortable,convenient,spacious,nicely decorated and it was not far from...”
- Review left on 04/07/2016

$306.00

Average (2 reviews)

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from $306.00 / night

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(4)

1 / 118

Kissimmee House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 3 hours 14 minutes

$75.00

Excellent (4 reviews)

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from $75.00 / night

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(4)

1 / 2

Kissimmee Villa

  • 5
  • 11
  • min stay varies
  • Nearest beach 115 mi
  • Swimming pool
  • Child friendly

$125.00

Very Good (4 reviews)

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from $125.00 / night

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(6)

1 / 28

Kissimmee Townhouse

  • 3
  • 6
  • 1 night min
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 51 minutes

“Oakwater was very clean. The pictures were true. My family and I stayed for two weeks. We would definitely stay here again in the future...”
- Review left on 08/28/2017

$114.00

Very Good (6 reviews)

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from $114.00 / night

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(10)

1 / 40

Kissimmee Villa

  • 6
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 120 mi
  • Swimming pool

Responds fast! Avg. 19 minutes

“We went with two families and everyone loved the place! It was close to Disney. Relaxing in the hot tub after a day a Disney was perfect...”
- Review left on 12/23/2017

$229.00

Excellent (10 reviews)

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from $229.00 / night

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(15)

1 / 59

Kissimmee Villa

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

Responds fast! Avg. 3 hours 4 minutes

$81.00

Very Good (15 reviews)

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from $81.00 / night

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(59)

Certificate of Excellence

1 / 41

Kissimmee House

  • 4
  • 8
  • 3 nights min
  • Nearest beach 125 mi
  • Swimming pool
  • Child friendly

Travelers’ Choice award

“A well equipped, well maintained vacation home. Plenty of room for our group of 4 adults and 3 children. The private pool was great. This was our first experience renting a whole house. We enjoyed our stay...”
- Review left on 03/31/2018

$194.00

Excellent (59 reviews)

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from $194.00 / night

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(55)

1 / 30

Kissimmee Townhouse

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Clean, beautiful and all you need to feel in home, close to parks, restaurants and everything, I will stay here again, Thanks to Harish and Jaya...”
- Review left on 05/28/2017

$86.00

Very Good (55 reviews)

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from $86.00 / night

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(12)

1 / 19

Kissimmee Villa

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

Responds fast! Avg. 2 hours 16 minutes

“Accommodation was perfect. We wanted a relaxing weekend getaway and this home more than exceeded our expectations. We will definitely book this house again...”
- Review left on 09/19/2017

$115.00

Very Good (12 reviews)

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from $115.00 / night

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(7)

1 / 47

Kissimmee House

  • 3
  • 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“I was here from 1/29-2/26 and the stay was awesome. The house was everything that was advertised and the pictures were right on. The house was very clean and equipped with all the thing a person needs to enjoy a month in sunny Orlando. We didn't...”
- Review left on 02/27/2017

$132.00

Excellent (7 reviews)

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from $132.00 / night

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(50)

Certificate of Excellence

1 / 75

Kissimmee House

  • 4
  • 8
  • 5 nights min
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 4 minutes

Travelers’ Choice award

“This house was the perfect setting for our Disney vacation! Each young person in our group of 5 enjoyed having the privacy of having their own bedroom and bathroom. The house was extremely clean, well-equipped and convenient to all! Although we...”
- Review left on 07/13/2018

$172.00

Excellent (50 reviews)

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from $172.00 / night

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(15)

1 / 28

Kissimmee House

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“The property is perfect. The pictures don't do the pool justice. It is one of the nicest pools you'll see on a vacation property. We had 3 children all 3 and under and it was no problem at all. The drive to Disney was a very quick and easy drive and...”
- Review left on 12/02/2017

$104.00

Excellent (15 reviews)

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from $104.00 / night

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(3)

1 / 41

Kissimmee House

  • 6
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$401.00

Excellent (3 reviews)

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from $401.00 / night

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(2)

1 / 49

Kissimmee House

  • 6
  • 16
  • min stay varies
  • Nearest beach 114 mi
  • Swimming pool
  • Child friendly
“We loved our recent trip to Florida with family. Some flew in and some drove. We loved the nice and clean big house with lots of space for everyone to retreat to if they wanted. The pool was great and very well used for the 10 days we were there. We...”
- Review left on 03/24/2016

$295.00

Excellent (2 reviews)

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from $295.00 / night

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(6)

1 / 19

Kissimmee House

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This vacation was a winner and Bob and Dianne provided us with a fantastic and welcoming vacation home rental. It was so peaceful and relaxing. The home was very clean and well maintained. I would strongly recommend this property to anyone visiting...”
- Review left on 05/13/2018

$98.00

Excellent (6 reviews)

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from $98.00 / night

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(5)

1 / 84

Kissimmee House

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

Responds fast! Avg. 3 hours 4 minutes

$92.00

Excellent (5 reviews)

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from $92.00 / night

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(3)

1 / 27

Kissimmee Condo

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“**I made the contact and found this condo for my daughter that is active duty Military, the following were her comments on the the rental: Lots of room, owner was very helpful with information, answered emails quickly. Easy deal on short notice....”
- Review left on 09/27/2016

$86.00

Excellent (3 reviews)

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from $86.00 / night

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(9)

1 / 19

Kissimmee House

  • 5
  • 12
  • 10 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“The house the perfect size for my family. The pool was great. The game room was awesome and had great games. Overall one of the best rental homes you can get...”
- Review left on 11/25/2017

$258.00

Very Good (9 reviews)

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from $258.00 / night

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(3)

1 / 41

Kissimmee Villa

  • 7
  • 18
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“This is a big house! Three families would have no problems here and plently of space not to be under each others feet. Close to Disney and main route to all the normal popular attractions. House was clean and tidy, kitchen had everything should you...”
- Review left on 04/20/2015

$188.00

Excellent (3 reviews)

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from $188.00 / night

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(3)

1 / 63

Kissimmee House

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

Responds fast! Avg. 59 minutes

$287.00

Very Good (3 reviews)

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from $287.00 / night

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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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