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Kissimmee Apartments & Vacation Rentals - 3870 Rentals Available

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3,870 Vacation rentals

(56)

1 / 64

Kissimmee House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“My grandson was invited to Select 30 at ESPN. Graham told me this house was only 15 minutes away. This house is a perfect location for Disney facilities. Once out of the subdivision, you make one turn and you are at Disney. We enjoyed the pool at...”
- Review left on 08/31/2017

$114.00

Excellent (56 reviews)

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from $114.00 / night

(57)

1 / 51

Kissimmee Villa

  • 5
  • 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great big house Excellent location for parks Very reasonable Owner gave great directions for when you show up Also pool really came in handy”
- Review left on 06/28/2018

$125.00

Excellent (57 reviews)

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from $125.00 / night

(16)

1 / 17

Kissimmee Apartment

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 9 minutes

$89.00

Excellent (16 reviews)

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from $89.00 / night

(51)

1 / 41

Kissimmee House

  • 4
  • 8
  • min stay varies
  • Nearest beach 125 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 18 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

$119.00

Excellent (51 reviews)

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from $119.00 / night

(2)

1 / 18

Kissimmee House

  • 8
  • 19
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$199.00

Excellent (2 reviews)

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from $199.00 / night

(69)

1 / 23

Kissimmee Townhouse

  • 3
  • 8
  • min stay varies
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 28 minutes

“My Wife and I and Her Brother and his wife ( we are all in our mid sixties) stayed in this rental for the month of February. When we arrived everything was set up well for us from clean linens to the dining room table all set for a meal. The...”
- Review left on 03/08/2017

$55.00

Very Good (69 reviews)

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from $55.00 / night

(1)

1 / 41

Kissimmee Villa

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

$396.00

Excellent (1 reviews)

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from $396.00 / night

(24)

Certificate of Excellence

1 / 64

Kissimmee Villa

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

Responds fast! Avg. 3 hours 21 minutes

Certificate of Excellence

“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

$120.00

Excellent (24 reviews)

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from $120.00 / night

(4)

1 / 29

Kissimmee Villa

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 57 minutes

“We had a wonderful time at this home. The house is spotless and the bedrooms are all very comfortable. The pool is lovely and we also took advantage of having access to the huge clubhouse pool . The commute to Disney was easy and quick. The owner...”
- Review left on 05/16/2016

$196.00

Very Good (4 reviews)

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from $196.00 / night

(42)

1 / 36

Kissimmee House

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$150.00

Excellent (42 reviews)

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from $150.00 / night

(5)

1 / 27

Kissimmee House

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

$79.00

Average (5 reviews)

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from $79.00 / night

(1)

1 / 47

Kissimmee Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 32 minutes

$99.00

Excellent (1 reviews)

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from $99.00 / night

(3)

1 / 43

Kissimmee House

  • 8
  • 18
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 52 minutes

“This vacation home is absolutely beautiful! It looks identical to the pictures on the website. We stayed at the Reunion Emperor in March 2017 for a total of 8 nights. Our group consisted of 6 adults and 7 children - three families all under one...”
- Review left on 01/20/2018

$370.00

Excellent (3 reviews)

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from $370.00 / night

(1)

1 / 49

Kissimmee House

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

Responds fast! Avg. 3 hours 51 minutes

$250.00

Excellent (1 reviews)

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from $250.00 / night

(6)

1 / 37

Kissimmee Villa

  • 8
  • 18
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 138 mi
  • Swimming pool

Responds fast! Avg. 49 minutes

$299.00

Excellent (6 reviews)

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from $299.00 / night

(5)

1 / 39

Kissimmee House

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

Responds fast! Avg. 3 hours 0 minutes

“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

$115.00

Excellent (5 reviews)

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from $115.00 / night

(3)

1 / 23

Kissimmee Apartment

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

Responds fast! Avg. 3 hours 23 minutes

$69.00

Excellent (3 reviews)

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from $69.00 / night

(29)

1 / 105

Kissimmee Villa

  • 7
  • 20
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Went to Disney for six days, adults and kids had a blast. The house was in fine condition and the amenities were great. Plenty of room for the 12 of us...”
- Review left on 05/31/2018

$179.00

Very Good (29 reviews)

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from $179.00 / night

(53)

1 / 27

Kissimmee Townhouse

  • 3
  • 8
  • 2 nights min
  • 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

$89.00

Very Good (53 reviews)

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from $89.00 / night

(20)

1 / 16

Kissimmee Villa

  • 7
  • 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“The property itself was very nice with a few small problems. We had to purchase an HDMI cable in order to view the TV in the family room which we left on the set. The lamp in the family room was damaged by a previous renter and inoperable. Upstairs...”
- Review left on 04/15/2018

$143.00

Excellent (20 reviews)

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from $143.00 / night

(3)

1 / 20

Kissimmee Villa

  • 4
  • 10
  • 3 nights min
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 23 minutes

$109.00

Very Good (3 reviews)

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from $109.00 / night

(9)

1 / 16

Kissimmee Condo

  • 2
  • 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 28 minutes

“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

$63.00

Excellent (9 reviews)

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from $63.00 / night

(17)

1 / 38

Kissimmee Villa

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

Responds fast! Avg. 1 hour 30 minutes

$95.00

Excellent (17 reviews)

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from $95.00 / night

(10)

1 / 21

Kissimmee Townhouse

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

Responds fast! Avg. 3 hours 8 minutes

$100.00

Excellent (10 reviews)

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from $100.00 / night

(34)

Certificate of Excellence

1 / 12

Kissimmee Villa

  • 4
  • 8
  • 4 nights min
  • Nearest beach 105 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 23 minutes

Certificate of Excellence

“We had an awesome time and the owner was a pleasure also the property manager was awesome and prompt. Beautiful home spacious and clean. Convienant to all atractions”
- Review left on 12/20/2016

$100.00

Very Good (34 reviews)

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from $100.00 / night

(9)

1 / 98

Kissimmee Villa

  • 7
  • 16
  • min stay varies
  • Nearest beach 81 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 11 minutes

$160.00

Very Good (9 reviews)

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from $160.00 / night

(9)

1 / 33

Kissimmee House

  • 6
  • 15
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 50 minutes

“We've stayed in a lot of vacation homes in this area over the last 20 years and I have to say that this was one of the best equipped that we've ever stayed in. The house has been recently renovated and everything was very nice and clean. The pool is...”
- Review left on 03/11/2017

$189.00

Excellent (9 reviews)

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from $189.00 / night

(2)

1 / 38

Kissimmee House

  • 6
  • 12
  • min stay varies
  • Child friendly

Responds fast! Avg. 59 minutes

$160.00

Excellent (2 reviews)

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from $160.00 / night

(29)

1 / 19

Kissimmee House

  • 4
  • 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 27 minutes

“We had a last minute vacation opportunity and Sheryl was so accommodating and excellent and we loved her place! We had 5 kids and 2 adults and there was tons of space to relax and have private space. The pool was amazing!! It was the perfect temp and...”
- Review left on 07/07/2018

$119.00

Very Good (29 reviews)

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from $119.00 / night

(2)

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

$69.00

Excellent (2 reviews)

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from $69.00 / night

(1)

1 / 21

Kissimmee Townhouse

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 52 minutes

$39.00

Very Good (1 reviews)

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from $39.00 / night

(2)

1 / 66

Kissimmee House

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

$396.00

Excellent (2 reviews)

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from $396.00 / night

(3)

1 / 22

Kissimmee Villa

  • 5
  • 12
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

Responds fast! Avg. 1 hour 25 minutes

“10 of my family stayed at this Villa. It was perfect so much space. The villa is very well equipped with everything you could possibly need Thank you for a wonderful holiday”
- Review left on 07/11/2016

$165.00

Excellent (3 reviews)

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from $165.00 / night

(6)

1 / 22

Kissimmee Villa

  • 6
  • 13
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 6 minutes

$196.00

Excellent (6 reviews)

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from $196.00 / night

(12)

1 / 26

Kissimmee House

  • 7
  • 16
  • min stay varies
  • 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

$150.00

Very Good (12 reviews)

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from $150.00 / night

(1)

1 / 52

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

$131.00

Excellent (1 reviews)

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from $131.00 / night

(22)

1 / 28

Kissimmee Townhouse

  • 3
  • 8
  • 2 nights min
  • 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

$89.00

Excellent (22 reviews)

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from $89.00 / night

(14)

1 / 33

Kissimmee Apartment

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

Responds fast! Avg. 3 hours 51 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

$80.00

Very Good (14 reviews)

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from $80.00 / night

1 / 25

Kissimmee House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 29 minutes

$88.00

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from $88.00 / night

(4)

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

$70.00

Excellent (4 reviews)

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from $70.00 / 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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