Holiday rentals in Kissimmee

Compare 46,656 available properties from 46 providers
Kissimmee
Save up to 45%

Best holiday rental deals in Kissimmee

-18%
e.g. 19/01 - 26/01
House ∙ 2 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
from £71 £86
EveryStay
5.0
View deal
-31%
e.g. 5/01 - 12/01
House ∙ 2 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
from £70 £101
EveryStay
4.5
View deal
-45%
e.g. 8/12 - 15/12
House ∙ 4 guests ∙ 2 bedrooms
Kissimmee, Osceola County, Florida, United States
from £47 £86
EveryStay
5.0
View deal

Explore 46,656 rentals listed in Kissimmee and find the ideal place for your getaway. Our search engine instantly compares each of the accommodation options, allowing you to save up to 45%.

Recommended holiday lettings in Kissimmee

Rent a holiday apartment, home or cottage in Kissimmee: from £38 per night

House ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from £32
Airbnb
5.0
View deal
Villa ∙ 4 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from £41
Airbnb
5.0
View deal
Apartment ∙ 4 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from £38
Airbnb
4.0
View deal
Villa ∙ 2 guests ∙ 1 bedroom
Orlando, Orange County, Florida, United States
from £36
Airbnb
4.0
View deal
Private room ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from £39
Airbnb
4.5
View deal
Private room ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from £27
Airbnb
5.0
View deal
Private room ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from £25
Airbnb
5.0
View deal
Private room ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from £36
Airbnb
5.0
View deal
Private room ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from £40
Airbnb
5.0
View deal
See all offers

Best holiday cottages with a pool

Pool
House ∙ 4 guests ∙ 2 bedrooms
Kissimmee, Osceola County, Florida, United States
from £55
HomeAway
4.4
View deal
Pool
Apartment ∙ 8 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
from £39
HomeAway
4.7
View deal
Pool
Motel ∙ 4 guests
Kissimmee, Osceola County, Florida, United States
from £39
Booking.com
4.3
View deal
See all offers

Best holiday homes with a patio or terrace

Balcony/Patio
House ∙ 4 guests ∙ 2 bedrooms
Kissimmee, Osceola County, Florida, United States
from £78
HomeAway
4.4
View deal
Balcony/Patio
House ∙ 6 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
from £82
HomeAway
4.1
View deal
Balcony/Patio
Apartment ∙ 6 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
from £60
HomeAway
4.7
View deal
See all offers

Top holiday accommodation with fishing spots nearby

Fishing
House ∙ 6 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
from £58
HomeAway
4.8
View deal
Fishing
House ∙ 6 guests ∙ 3 bedrooms
Kissimmee, Osceola County, Florida, United States
from £82
HomeAway
4.5
View deal
Fishing
House ∙ 2 guests ∙ 1 bedroom
Kissimmee, Osceola County, Florida, United States
from £88
HomeAway
4.7
View deal
See all offers

Popular holiday rental amenities in Kissimmee

  • Kitchen (43,538)
  • Pool (32,227)
  • Internet (31,731)
  • AC (30,554)
  • TV (30,498)
  • No smoking (29,220)
  • No pets (24,432)
  • Parking (23,341)
  • Washer (19,391)
  • Microwave (17,923)
  • Dishwasher (17,664)
  • BBQ (10,913)
You will have a large selection of properties to choose from if you are looking for a short stay accommodation with a pool in Kissimmee. House rentals with pools in Kissimmee are a fantastic choice for groups of 11 and usually cost around £253 a night. Among these rentals, a few of them are within 2 kilometres of water. Kissimmee is a wonderful holiday destination if you travel with a pet, as a lot of properties in Kissimmee allow you to bring your pet. Most pet-friendly rentals in Kissimmee are house rentals. Furthermore, their average price is £216. a night. If you prefer to stay central, a few of the pet-friendly holiday rentals are less than 2 kilometres away from the city centre.

Price and Availability Index in Kissimmee

Holiday Letting Price Information in Kissimmee

The price graph will give you the nightly price average for the upcoming months. The most expensive week to book a holiday letting in Kissimmee is in December (22/12 - 29/12). Conversely, the cheapest average prices are in a week of September (07/09 - 14/09).

Holiday Home Availability Information in Kissimmee

Have a look at the above graph to see the global availability of holiday rentals in Kissimmee. The week with the lowest percentage of available accommodations is in December (22/12 - 29/12). More accommodations are available in a week of August (31/08 - 07/09) as the booking rate is only 21%.

The weather in Kissimmee

24°
14°
23°
13°
26°
15°
29°
19°
30°
21°
32°
23°
32°
24°
33°
24°
31°
23°
29°
20°
25°
16°
24°
15°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Find the Kissimmee climate diagram. During August, maximum temperatures go up to more than 33° Conversely, February is the coolest month in Kissimmee, with temperatures going under 13°. The rainiest month is August while the driest month is January.

Accommodations in Kissimmee

In Kissimmee, many of the holiday accommodation options are house rentals, which represent 60.83% of Kissimmee's short-term lettings. Additionally, the average price of house rentals is £252 a night, with an average size of 215 m². Furthermore, if you're travelling in a group of 10, house rentals are the perfect type of accommodation in Kissimmee, as they usually accommodate 10 people. You could also search and compare other accommodation options in Kissimmee. Apartment rentals are another popular accommodation type in Kissimmee with 10,823 properties to compare. Our analysis reveals that the average price of apartment rentals is £218 a night for an area of 157 m².

Book Kissimmee holiday lettings for an unforgettable family break

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 holiday letting for the perfect, adrenalin-filled adventure with the family.

Show all 46,656 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 holiday letting would be by taxi or by letting car.

Food & Drinks

Foodie's Paradise

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 holiday letting .

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 holiday home well in advance during this period, so that you can ensure you find your perfect holiday letting . 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 holiday for kids

Kids will love Kissimee. 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 Centre 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 Centre 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 holiday letting . 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 favourites 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 holiday letting 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 centre

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 Holiday Rentals in Kissimmee Novasol Holiday Rentals in Kissimmee TripAdvisor Holiday Rentals in Kissimmee Inter Chalet Holiday Rentals in Kissimmee HomeAway Holiday Rentals in Kissimmee EveryStay Holiday Rentals in Kissimmee Interhome Holiday Rentals in Kissimmee 9flats.com Holiday Rentals in Kissimmee HouseTrip Holiday Rentals in Kissimmee Belvilla Holiday Rentals in Kissimmee Sykes Cottages Holiday Rentals in Kissimmee Homestay.com Holiday Rentals in Kissimmee Ski Planet Holiday Rentals in Kissimmee Only-apartments Holiday Rentals in Kissimmee James Villa Holidays Holiday Rentals in Kissimmee

Holiday destinations near Kissimmee