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Kissimmee Apartments & Vacation Rentals - 1191 Rentals Available

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1,191 Vacation rentals

(11)

1 / 33

Kissimmee House

  • 8
  • 22
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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

$412.00

Excellent (11 reviews)

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from $412.00 / night

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(80)

1 / 41

Kissimmee Villa

  • 5
  • 10
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 24 minutes

“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

$172.00

Excellent (80 reviews)

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from $172.00 / night

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(24)

1 / 28

Kissimmee Townhouse

  • 3
  • 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 60 mi
  • Swimming pool
“Clean, comfortable, and very close to all the area's attractions. We would definitely stay here again...”
- Review left on 11/16/2021

$102.00

Excellent (24 reviews)

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from $102.00 / night

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(8)

1 / 27

Kissimmee House

  • 3
  • 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 60 mi
  • Swimming pool

$102.00

Average (8 reviews)

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from $102.00 / night

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(6)

1 / 29

Kissimmee Villa

  • 6
  • 14
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

Responds fast! Avg. 36 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

$258.00

Very Good (6 reviews)

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from $258.00 / 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 35 minutes

$91.00

Excellent (3 reviews)

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from $91.00 / night

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(55)

1 / 27

Kissimmee Townhouse

  • 3
  • 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 60 mi
  • Swimming pool
“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

$102.00

Very Good (55 reviews)

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from $102.00 / night

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(43)

1 / 43

Kissimmee House

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

$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. 1 hour 2 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

$125.00

Very Good (14 reviews)

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from $125.00 / night

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(22)

1 / 48

Kissimmee Villa

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

Responds fast! Avg. 1 hour 35 minutes

“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
  • Beach/lakeside relaxation
  • Nearest beach 90 mi
  • Swimming pool
“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

$298.00

Excellent (1 reviews)

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from $298.00 / 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 15 minutes

$126.00

Excellent (17 reviews)

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from $126.00 / 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 52 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 15 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

$93.00

Excellent (12 reviews)

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from $93.00 / 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

Responds fast! Avg. 3 hours 58 minutes

“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

$161.00

Excellent (27 reviews)

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from $161.00 / 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
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 2 hours 28 minutes

$86.00

Excellent (4 reviews)

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from $86.00 / night

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(4)

1 / 27

Kissimmee Villa

  • 5
  • 11
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 115 mi
  • Swimming pool

$149.00

Very Good (4 reviews)

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from $149.00 / night

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(6)

1 / 28

Kissimmee Townhouse

  • 3
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 42 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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(15)

1 / 59

Kissimmee Villa

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

Responds fast! Avg. 2 hours 28 minutes

$104.00

Very Good (15 reviews)

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from $104.00 / night

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(60)

1 / 41

Kissimmee House

  • 4
  • 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 125 mi
  • Swimming pool

Responds fast! Avg. 3 hours 27 minutes

“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 (60 reviews)

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from $194.00 / night

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(55)

1 / 30

Kissimmee Townhouse

  • 3
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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

$102.00

Very Good (55 reviews)

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from $102.00 / night

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(7)

1 / 47

Kissimmee House

  • 3
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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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(51)

1 / 70

Kissimmee House

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

Responds fast! Avg. 2 hours 2 minutes

“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

$184.00

Excellent (51 reviews)

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from $184.00 / night

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(8)

1 / 57

Kissimmee House

  • 9
  • 24
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 70 mi
  • Swimming pool

Responds fast! Avg. 3 hours 11 minutes

“Our family vacation was wonderful! The house was beautiful, very well decorated, and spacious, it was everything we expected and much-much more. We enjoyed sitting outside on the screened in patio and outdoor furniture, the pool, and hot tub every...”
- Review left on 05/02/2018

$367.00

Excellent (8 reviews)

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from $367.00 / 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. 2 hours 28 minutes

$98.00

Excellent (5 reviews)

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from $98.00 / night

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(9)

1 / 19

Kissimmee House

  • 5
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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

$229.00

Very Good (9 reviews)

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from $229.00 / night

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(3)

1 / 41

Kissimmee Villa

  • 7
  • 18
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 90 mi
  • Swimming pool
“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

$259.00

Excellent (3 reviews)

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from $259.00 / night

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(3)

1 / 63

Kissimmee House

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

Responds fast! Avg. 1 hour 2 minutes

$344.00

Very Good (3 reviews)

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from $344.00 / night

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(17)

1 / 31

Kissimmee Villa

  • 7
  • 15
  • 4 nights min
  • Nearest beach 112 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 49 minutes

“the home was all that and more, the only dissatisfaction was the games were not working but the kids were still enterained”
- Review left on 08/11/2016

$258.00

Excellent (17 reviews)

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from $258.00 / night

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(9)

1 / 12

Kissimmee House

  • 2
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 95 mi
  • Child friendly

Responds fast! Avg. 3 hours 26 minutes

“I stayed for 5months at this house and it was great. Had everything needed to cook, fenced in backyard for my dog, neighbors were great and I was only 10 minutes from give kids the world where I volunteered. Lots of places to eat and close to all...”
- Review left on 04/11/2016

$114.00

Excellent (9 reviews)

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from $114.00 / night

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(11)

1 / 16

Kissimmee Condo

  • 2
  • 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“My family and I stayed at this place for a week. We loves it the house is super clean it's close to every disney park the pool was really clean too. The only thing we didn't like was the parking spot every nigth when we got home we had to park on the...”
- Review left on 06/29/2016

$74.00

Excellent (11 reviews)

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from $74.00 / night

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(6)

1 / 110

Kissimmee House

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

Responds fast! Avg. 2 hours 28 minutes

$115.00

Excellent (6 reviews)

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from $115.00 / night

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(3)

1 / 19

Kissimmee Villa

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

Responds fast! Avg. 2 hours 52 minutes

$109.00

Very Good (3 reviews)

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from $109.00 / night

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(28)

1 / 48

Kissimmee Townhouse

  • 4
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 90 mi
  • Swimming pool
“Bom condom?nio, bem localizado e organizado. As casas s?o todas iguais, apenas com um quarto a mais nas maiores. S? n?o dei 5 estrelas devido a cobran?a de U$5 por pacote entregue. Muitas vezes s? descobrimos o n?mero da casa que vamos ficar no dia...”
- Review left on 02/24/2016

$94.00

Very Good (28 reviews)

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from $94.00 / night

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(17)

1 / 18

Kissimmee Villa

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

Responds fast! Avg. 3 hours 3 minutes

“We used the home for 4 days during the Halloween season. It was very clean and well maintained. Easy access to all of the area attractions made this the perfect location for our needs. I would highly recommend this property...”
- Review left on 10/21/2015

$167.00

Very Good (17 reviews)

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from $167.00 / 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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