Kissimmee Vacation Rentals

Compare 29,826 available properties from 44 providers
Kissimmee
Save up to 19%

Best vacation home deals in Kissimmee

$131
from $107
-18%
1290 ft² House
8 3
Kissimmee, Osceola County, Florida, United States
Found on
$130
from $105
-19%
1520 ft² House
8 4
Osceola County, Florida, United States
Found on
$130
from $105
-19%
1500 ft² House
8 4
Osceola County, Florida, United States
Found on

Find a welcoming property from $71 per night by exploring the 29,826 options available in Kissimmee. All of the vacation rentals from the different providers are instantly compared on our website so you can save up to 19%.

Recommended vacation rentals in Kissimmee

Rent a vacation accommodation in Kissimmee: from $71 per night

from $86
House
6 3
Osceola County, Florida, United States
4.5
"Outstanding" 11 reviews
Found on VRBO
from $116
House
6 3
Kissimmee, Osceola County, Florida, United States
4.7
"Excellent" 6 reviews
Found on VRBO
from $105
1500 ft² House
8 4
Osceola County, Florida, United States
4.8
"Excellent" 4 reviews
Found on VRBO
from $105
1520 ft² House
8 4
Osceola County, Florida, United States
4.8
"Excellent" 42 reviews
Found on VRBO
from $89
1440 ft² House
8 4
Osceola County, Florida, United States
5.0
"Excellent" 1 review
Found on VRBO
from $89
1520 ft² House
8 4
Osceola County, Florida, United States
4.1
"Very good" 22 reviews
Found on VRBO
from $89
1520 ft² House
8 4
Osceola County, Florida, United States
4.8
"Excellent" 16 reviews
Found on VRBO
from $89
1520 ft² House
8 4
Osceola County, Florida, United States
4.4
"Outstanding" 29 reviews
Found on VRBO
See all offers

 Vacation houses with pools

from $125
1490 ft² House
8 3
Kissimmee, Osceola County, Florida, United States
4.5
"Outstanding" 56 reviews
Found on VRBO
from $87
1290 ft² House
8 3
Kissimmee, Osceola County, Florida, United States
4.9
"Excellent" 7 reviews
Found on VRBO
from $81
1460 ft² House
6 3
Buena Ventura Lakes, Osceola County, Florida, United States
4.0
"Very good" 56 reviews
Found on VRBO
from $128
1400 ft² House
6 3
Kissimmee, Osceola County, Florida, United States
4.5
"Excellent" 2 reviews
Found on Owner Direct
See all offers

 Apartments with a balcony or patio

from $105
1500 ft² House
8 4
Osceola County, Florida, United States
4.4
"Outstanding" 75 reviews
Found on VRBO
from $111
1270 ft² House
8 3
Osceola County, Florida, United States
4.2
"Outstanding" 5 reviews
Found on VRBO
from $152
1190 ft² Apartment
6 2
Kissimmee, Osceola County, Florida, United States
4.4
"Outstanding" 23 reviews
Found on VRBO
from $89
1500 ft² House
8 3
Kissimmee, Osceola County, Florida, United States
4.3
"Outstanding" 10 reviews
Found on Owner Direct
See all offers

 Vacation homes with fishing spots nearby

from $111
2290 ft² House
8 4
Kissimmee, Osceola County, Florida, United States
4.9
"Excellent" 12 reviews
Found on VRBO
from $98
House
8 4
Osceola County, Florida, United States
4.6
"Excellent" 22 reviews
Found on VRBO
from $153
1500 ft² House
6 3
Kissimmee, Osceola County, Florida, United States
4.8
"Excellent" 64 reviews
Found on VRBO
from $90
2130 ft² House
8 4
Kissimmee, Osceola County, Florida, United States
4.3
"Outstanding" 67 reviews
Found on VRBO
See all offers

Popular rental amenities in Kissimmee

  • Kitchen (23,917)
  • TV (20,689)
  • AC (20,560)
  • Internet (20,160)
  • Pool (20,067)
  • No smoking (16,405)
  • No pets (15,555)
  • Parking (13,968)
  • Washer (13,494)
  • Microwave (12,476)
  • Dishwasher (12,059)
  • Grill (7,007)

Properties can be chosen based on various criteria. Above, you will find the number of properties that offer a specific feature in Kissimmee. You can easily compare and find a vacation rental fitting your expectations in Kissimmee if you never miss an episode of your favorite show or you need internet access during your vacation, as most accommodations provide "TVs" or "internet." Not as many vacation homes in Kissimmee are available if you want to sweat it out in a sauna or if you like to end your days curled up by the fire as "fireplaces" and "saunas" are not very popular amenities in Kissimmee.

Price and Availability Index Kissimmee

Vacation Rental Price Information in Kissimmee

We analyzed vacation houses, cottages and apartments to display a price graph showing the average price per night in Kissimmee. The most expensive week to book a rental in Kissimmee is in December (12/22 - 12/29). The cheapest week is in September (9/15 - 9/22). Prices fall to an average of $180 per night.

Rental Availability Information in Kissimmee

Check how busy Kissimmee is with our availability graph. The week with the highest booking rate in the next 6 months is in June (6/30 - 7/7), where 53% of the vacation rentals are booked. On the contrary, only 22% of the rentals are booked during a week in December (12/8 - 12/15).

The weather in Kissimmee

75°
57°
73°
55°
79°
59°
84°
66°
86°
70°
90°
73°
90°
75°
91°
75°
88°
73°
84°
68°
77°
61°
75°
59°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

You can see our climate diagram above. On average, the warmest month is August. Conversely, February is the coolest month in Kissimmee, with temperatures going under 55° It may rain 14 days in June while it typically rains only 2 days in January.

Accommodations in Kissimmee

20,976 among the 29,826 available properties in Kissimmee are house rentals. They account for two-thirds of the accommodation types in this destination (72.59%). In addition, the median size of house rentals in Kissimmee is 2,600 ft² with an average price of $308 a night. Moreover, these properties are excellent for 10 as that is the average number of people house rentals can accommodate in Kissimmee. If you would like to rent something else, you can search and compare many other offers, such as apartment rentals, which are the second most popular type of accommodation in Kissimmee. These accommodations cost $240 a night on average and have an average size of 1,930 ft².

Book Kissimmee Vacation Rentals for an Unforgettable Family Trip

Located directly between St. Cloud and Disney World, Kissimmee is a popular stop for vacationers headed to the Disney World theme parks. This popular central Florida destination beckons with its sunny skies, gastronomic delights, theme parks and family-centered activities.

Since Disney World opened in 1971, the town is primarily visitor-oriented and does a great job of it. Book your Kissimmee vacation rental for the perfect, adrenalin-filled adventure with the family.

Show all 29,826 properties
Getting There

Getting to Kissimmee

The easiest way to get to Kissimmee is by the Orlando International Airport (MCO) which is an arrival point for most domestic and international flights. The Kissimmee Gateway Airport (ISM) is the nearest aviation facility to Walt Disney World, Sea World and UNIVERSAL Orlando. The quickest way to get to your Kissimmee vacation rental would be by taxi or by rental car.

Food & Drinks

A Paradise for Foodies

Kissimmee doesn't let down foodies with its myriad of gastronomic options ranging from Middle Eastern delicacies to Dominican Republic fare. The town is proud of its award-winning breakfasts that feature hash browns, omelets, pancakes, cheese, ham and good coffee. Pick up some Middle Eastern takeaway such as hummus, Baba ghanoush and Kibbeh to snack on back at your Kissimmee vacation rental.

Savion's Place in downtown Kissimmee treats diners to Caribbean-inspired delicacies fused with modern American flavors. For dishes as varied as Cajun-grilled mahi-mahi, seafood and smoked baby back rib, Chef John’s Place does the trick. Germans Restaurant & Bierhouse, situated right on the edge of Walt Disney World, excels with its smoked meat, potatoes and bratwurst, washed down with good, full-bodied German ales.

Weather & Climate

A Good Time to Visit Kissimmee

Spring and summer are predictably peak seasons in Kissimmee, when college students descend for spring break in March/April, and when families with kids arrive between June and August. Be sure to book your Kissimmee vacation home well in advance during this period, so that you can ensure you find your perfect vacation rental. For a quieter time, late fall and winter are ideal, as the temperature can be anywhere between 47ºF and 84ºF.

Attractions

Sights and Sounds of Kissimmee

Kissimmee's Old Town is wonderful to stroll around for its many shops, restaurants, and bars. You will also be able to check out the Ferris wheel and a classic car show held over the weekends. From late February through early April, catch some Major League Baseball at the Osceola County Stadium.

For insights into the restoration of WW2 aircrafts to working condition, visit the Warbird Air Museum. The Osceola County Historical Society is a traditional village and museum which features an interesting cracker house and horse stables. History buffs will enjoy a visit to the Museum of Military History which features the history of the American military experience through fun interactive exhibits.

Family Activities

A Dream Vacation for Kids

Kids will love Kissimmee. Take them down to the Green Meadows Petting Farm where hands-on guided tours will introduce them to over 300 species of animals. The Paddling Center at Shingle Creek meanwhile, offers kayaking, paddling, canoeing and camping activities. The Wild Florida Airboats & Wildlife Park is a place to hang out with the sloths, bobcats and lemurs, and see alligators in the wild.

Learn how chocolate miraculously transitions from a humble bean into a luscious chocolate bar at Chocolate Kingdom. The Happy Days Family Fun Center in Kissimmee's Old Town boasts the world's largest indoor bumper car ride, as well as laser tag. At the LEGOLAND Florida Resort, adults and children alike are blown away by the structures built from LEGO blocks.

Kissimmee packs a punch, so go on and book your Kissimmee vacation rental. Your first port-of-call to Florida awaits.

Local Attractions

Excursion Destinations Galore

While in Kissimmee, a day trip to Walt Disney World Resort becomes an obligation! Come and discover the fantasy and magic of your favorite Disney characters. To take a look at what a real movie set looks like, your next stop should be the Universal Orlando Resort, where you can immerse yourself in Harry Potter's magical universe, or even mount an attack on space aliens. Smaller kids will love the Ranch Buggy Tour, which takes you to one of America's oldest working cattle operations.

Just an hour’s drive from Kissimmee are the Atlantic beaches of Cape Canaveral and Cocoa Beach. Animal lovers should not miss Forever Florida, a 4,700 acre ecological ranch and wildlife conservation area that is home to alligators, black bears and the Florida panther. For bass fishing, Lake Tohopekaliga is your best bet. At the end of the day, you can unwind at your Kissimmee vacation rental and exchange stories from the day.

For something a little further afield, take a short drive to St. Cloud and visit the Peghorn National Park and Trail for great hiking and kite flying.

Sights & things to do in Kissimmee

Florida Adventures and More in the Kissimmee Area

Museum of Military History

Find out about American military history at Kissimmee's military museum, where interactive exhibits explore American conflicts from the Civil War to the wars in Iraq and Afghanistan.

Gaylord Palms Resort and Convention Center

The glass atrium of the Gaylord Palms hotel encloses 4.5 acres of lush gardens and water features. Highlights include the luxurious spa and the organic black angus steaks in the restaurant.

Shingle Creek Regional Park

An oasis of green within the urban sprawl of Orlando, Shingle Creek can be explored by foot, bicycle or boat. Try to spot the deer, alligators and birds.

Fun Spot America

The family-owned theme park of Fun Spot America offers fun for all the family, with high-adrenaline roller coasters teamed with more gentle rides for younger children.

Kissimmee Lakefront Park

Appealing to both locals and visitors, Kissimmee Lakefront Park features wide walkways for jogging or walking, a splash park and two children's playgrounds.

We compare more than 250 providers, including:

Booking.com Vacation Rentals in Kissimmee VRBO Vacation Rentals in Kissimmee HomeAway Vacation Rentals in Kissimmee TripAdvisor Vacation Rentals in Kissimmee VacationRentals.com Vacation Rentals in Kissimmee HouseTrip Vacation Rentals in Kissimmee FlipKey Vacation Rentals in Kissimmee Wimdu Vacation Rentals in Kissimmee 9flats.com Vacation Rentals in Kissimmee VaycayHero Vacation Rentals in Kissimmee PerfectPlaces.com Vacation Rentals in Kissimmee Homestay.com Vacation Rentals in Kissimmee only-apartments Vacation Rentals in Kissimmee Interhome Vacation Rentals in Kissimmee Bedycasa Vacation Rentals in Kissimmee Novasol Vacation Rentals in Kissimmee HomeEscape Vacation Rentals in Kissimmee