Kissimmee Vacation Rentals

Compare 55,476 available properties from 51 providers
Kissimmee
Save up to 42%

Best Vacation Home Deals in Kissimmee

-37%
House ∙ 2 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
from $85 $135
EveryStay
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-42%
House ∙ 4 guests ∙ 2 bedrooms
Kissimmee, Osceola County, Florida, United States
from $89 $155
HomeAway
4.4
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-19%
House ∙ 6 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
from $90 $111
VRBO
4.5
View deal

Find a welcoming property from $46 per night by exploring the 55,476 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 42%.

Recommended Vacation Rentals in Kissimmee

Find your perfect vacation rental in Kissimmee: from $46 per night

House ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from $33
Airbnb
5.0
View deal
House ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from $45
Airbnb
5.0
View deal
House ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from $46
Airbnb
5.0
View deal
House ∙ 3 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from $43
Airbnb
5.0
View deal
House ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from $46
Airbnb
5.0
View deal
House ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from $47
Airbnb
5.0
View deal
House ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from $40
Airbnb
5.0
View deal
House ∙ 3 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from $43
Airbnb
5.0
View deal
House ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from $41
Airbnb
5.0
View deal
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Vacation Houses With Pools

Pool
House ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from $45
Airbnb
5.0
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Pool
House ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from $30
Airbnb
5.0
View deal
Pool
House ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from $40
Airbnb
5.0
View deal
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Apartments With Balconies or Patios

Balcony/Patio
House ∙ 4 guests ∙ 2 bedrooms
Kissimmee, Osceola County, Florida, United States
from $89
HomeAway
4.4
View deal
Balcony/Patio
House ∙ 6 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
from $106
VRBO
4.1
View deal
Balcony/Patio
Apartment ∙ 6 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
from $82
VRBO
4.7
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Dog-Friendly Vacation Rentals

Pet-friendly
House ∙ 6 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
from $119
HomeAway
4.0
View deal
Pet-friendly
House ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from $132
VRBO
4.7
View deal
Pet-friendly
House ∙ 2 guests ∙ 1 bedroom
Meadow Woods, Orange County, Florida, United States
from $27
Airbnb
4.5
View deal
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Popular Rental Amenities in Kissimmee

  • Kitchen (51,182)
  • Pool (44,098)
  • TV (43,481)
  • Internet (43,425)
  • AC (40,973)
  • No smoking (31,763)
  • Washer (31,249)
  • No pets (24,938)
  • Parking (22,777)
  • Microwave (21,907)
  • Dishwasher (20,938)
  • Grill (13,498)
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 want to tune out with some TV time or you're dreaming of days spent poolside, as most accommodations provide "TVs" or "pools." Not as many vacation homes in Kissimmee are available if you love sweating the stress away in saunas 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 in Kissimmee

Vacation Rental Price Information in Kissimmee

The graph shows average prices of rental prices in Kissimmee for the next twelve months. The most expensive dates to travel to Kissimmee are in December (12/22 - 12/29). The week with the lowest average prices is in September (9/7 - 9/14).

Rental Availability Information in Kissimmee

The availability graph shows the percentage of available rentals in Kissimmee. More people travel to Kissimmee a week in December (12/22 - 12/29). So far, 92% of the rentals are occupied this week. On the contrary, you will find the highest number of available rentals in a week of August (8/31 - 9/7).

The Weather in Kissimmee

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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.
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Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

This is the climate diagram in Kissimmee. August is the warmest month of the year in Kissimmee with temperatures reaching a maximum average of 91°. On the other hand, you could have temperatures dropping under 55° in February. The rainiest month is August while the driest month is January.

Accommodations in Kissimmee

37,844 among the 55,476 available properties in Kissimmee are house rentals. They account for many of the accommodation types in this destination (61.3%). In addition, the median size of house rentals in Kissimmee is 2,220 ft² with an average price of $317 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 $245 a night on average and have an average size of 1,510 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 55,476 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 300 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 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

Vacation Destinations Near Kissimmee