Kissimmee Vacation Rentals, Homes, & More

1-50 of 1188 Kissimmee Rentals

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1 / 9

Kissimmee Condo
4 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”1 Review

from

$99

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Villa
1 / 21

Kissimmee Villa
8 Bedrooms / 4.5 Bathrooms / Sleeps 20

“ Excellent ”5 Reviews

from

$800

/ night

Email Owner
Plasma TV in living room with dining area - opens to your own private pool
1 / 9

Kissimmee Townhouse
3 Bedrooms / 3 Bathrooms / Sleeps 6

from

$99

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Villa
1 / 15

Kissimmee Villa
7 Bedrooms / 6 Bathrooms / Sleeps 16

from

$275

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Condo
1 / 28

Kissimmee Condo
3 Bedrooms / 3 Bathrooms / Sleeps 6

from

$115

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Villa
1 / 13

Kissimmee Villa
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$89

/ night

Email Owner
Front of Home
1 / 8

Kissimmee Home
5 Bedrooms / 3 Bathrooms / Sleeps 12

“ Excellent ”3 Reviews

from

$139

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Condo
1 / 18

Kissimmee Condo
3 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”2 Reviews

from

$115

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Villa
1 / 43

Kissimmee Villa
7 Bedrooms / 5.5 Bathrooms / Sleeps 16

“ Excellent ”16 Reviews

from

$150

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Home
1 / 16

Kissimmee Home
4 Bedrooms / 3 Bathrooms / Sleeps 10

“ Excellent ”1 Review

Kissimmee Florida Vacation Rentals - Condo
1 / 23

Kissimmee Condo
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

from

$69

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Home
1 / 16

Kissimmee Home
8 Bedrooms / 5.5 Bathrooms / Sleeps 18

“ Excellent ”1 Review

from

$259

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Home
1 / 20

Kissimmee Home
4 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”4 Reviews

from

$165

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Villa
1 / 16

Kissimmee Villa
4 Bedrooms / 3 Bathrooms / Sleeps 8

from

$140

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Home
1 / 25

Kissimmee Home
5 Bedrooms / 5.5 Bathrooms / Sleeps 13

from

$325

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Condo
1 / 11

Kissimmee Condo
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”10 Reviews

from

$99

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Townhouse
1 / 21

Kissimmee Townhouse
4 Bedrooms / 3 Bathrooms / Sleeps 8

from

$165

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Home
1 / 23

Kissimmee Home
4 Bedrooms / 3 Bathrooms / Sleeps 10

from

$140

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Townhouse
1 / 10

Kissimmee Townhouse
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”5 Reviews

from

$75

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Townhouse
1 / 20

Kissimmee Townhouse
3 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”17 Reviews

from

$55

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Villa
1 / 14

Kissimmee Villa
5 Bedrooms / 5 Bathrooms / Sleeps 12

from

$150

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Townhouse
1 / 24

Kissimmee Townhouse
3 Bedrooms / 2 Bathrooms / Sleeps 8

from

$120

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Home
1 / 35

Kissimmee Home
5 Bedrooms / 4.5 Bathrooms / Sleeps 10

from

$250

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Villa
1 / 16

Kissimmee Villa
6 Bedrooms / 4 Bathrooms / Sleeps 12

“ Excellent ”11 Reviews

from

$160

/ night

Email Owner
Front of villa
1 / 10

Kissimmee Villa
4 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”1 Review

from

$105

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Villa
1 / 26

Kissimmee Villa
7 Bedrooms / 5.5 Bathrooms / Sleeps 16

from

$315

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Home
1 / 15

Kissimmee Home
4 Bedrooms / 2 Bathrooms / Sleeps 10

“ Excellent ”51 Reviews

from

$109

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Villa
1 / 13

Kissimmee Villa
4 Bedrooms / 3 Bathrooms / Sleeps 10

“ Excellent ”1 Review

from

$100

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Townhouse
1 / 12

Kissimmee Townhouse
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$100

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Home
1 / 49
Kissimmee Florida Vacation Rentals - Villa
1 / 22

Kissimmee Villa
4 Bedrooms / 3 Bathrooms / Sleeps 8

from

$165

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Villa
1 / 55

Kissimmee Villa
5 Bedrooms / 5 Bathrooms / Sleeps 12

“ Excellent ”7 Reviews

from

$172

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Home
1 / 24

Kissimmee Home
5 Bedrooms / 3 Bathrooms / Sleeps 12

“ Excellent ”7 Reviews

from

$100

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Home
1 / 14

Kissimmee Home
6 Bedrooms / 4 Bathrooms / Sleeps 15

“ Excellent ”2 Reviews

from

$200

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Condo
1 / 21

Kissimmee Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$99

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Home
1 / 12

Kissimmee Home
5 Bedrooms / 4.5 Bathrooms / Sleeps 12

“ Excellent ”6 Reviews

from

$135

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Condo
1 / 30

Kissimmee Condo
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$119

/ night

Email Owner
1 / 18

Kissimmee Home
5 Bedrooms / 3.5 Bathrooms / Sleeps 12

from

$145

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Townhouse
1 / 9
Kissimmee Florida Vacation Rentals - Condo
1 / 27

Kissimmee Condo
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$125

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Townhouse
1 / 11

Kissimmee Townhouse
3 Bedrooms / 3.5 Bathrooms / Sleeps 10

“ Excellent ”1 Review

Kissimmee Florida Vacation Rentals - Home
1 / 40

Kissimmee Home
7 Bedrooms / 5 Bathrooms / Sleeps 16

from

$250

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Condo
1 / 24

Kissimmee Condo
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”4 Reviews

from

$70

/ night

Email Owner
1 / 7

Kissimmee Villa
7 Bedrooms / 4.5 Bathrooms / Sleeps 16

from

$190

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Townhouse
1 / 10

Kissimmee Townhouse
3 Bedrooms / 3 Bathrooms / Sleeps 8

from

$99

/ night

Email Owner
Front of Villa
1 / 26

Kissimmee Villa
6 Bedrooms / 3.5 Bathrooms / Sleeps 14

“ Excellent ”11 Reviews

from

$159

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Villa
1 / 24

Kissimmee Villa
8 Bedrooms / 4.5 Bathrooms / Sleeps 20

from

$199

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Home
1 / 18

Kissimmee Home
4 Bedrooms / 3 Bathrooms / Sleeps 10

from

$187

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Condo
1 / 25

Kissimmee Condo
3 Bedrooms / 2 Bathrooms / Sleeps 8

from

$109

/ night

Email Owner
Kissimmee Florida Vacation Rentals - Home
1 / 25

Kissimmee Home
7 Bedrooms / 4.5 Bathrooms / Sleeps 14

“ Excellent ”6 Reviews

from

$185

/ night

Email Owner
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Kissimmee, Florida Travel Tips

Located only moments from Orlando, the beautiful resort town of Kissimmee offers the best that Florida has to offer. 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 renting by owner ensures that homes are very well maintained and updated. Keep reading to learn more tips about how to have a memorable Florida vacation in Kissimmee.
Beaches and Parks
Because it is such a popular tourist destination, there is an abundance of available vacation homes in Kissimmee. Families interested in spending time at the beach can easily find great accommodations, but hurry! Beach houses for rent in Kissimmee, FL are quickly snapped up. Make sure to reserve your spot online well in advance to save time and money.
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.
Things to Do
A great feature of Kissimmee vacation homes is their central location to a number of popular attractions. Theme parks, outdoor activities, and fun things for the kids can all be found within a short drive. Read on to find out more about the variety of activities waiting for you in the Kissimmee area.
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
Airboat Tours are available via Aquatic Adventures Airboat Tours . Go bird watching, look out for alligators, or take a combination hiking tour/boat ride and learn all about the wildlife of the Florida wetlands.
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 vacation homes. Kids and parents will have all the comforts of home while having 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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