Kissimmee Vacation Rentals

Our Favorite Vacation Rentals in Kissimmee

  • Windsor Hills/Windsor Palms by Orlando Select Vacation Rental
     Country House
    Booking.com
    From
    $155
  • Single Parent Retreat 14 miles to Disney!
     Home/Apartment
    HolidayLettings
    From
    $58
  • Westgate Lakes Resort & Spa
     Studio
    NextTrip
    From
    $103
  • holiday home for max. 14 persons in Kissimmee, Florida
    OkayCountry House
    TUIvillas
    From
    $270
  • Sunshine Venetian Bay Palace
     Home/Apartment
    Booking.com
    From
    $90
  • Ultimate Orlando Vacay Starts Here! Lovely 1BR Junior Suite, 3 Pools, Shuttle!
     Home/Apartment
    HolidayLettings
    From
    $94
  • holiday home for max. 8 persons in Kissimmee, Florida
     Country House
    TUIvillas
    From
    $274
  • Newly renovated 2 bedroom 2 bath condo close to Disney
     Country House
    Booking.com
    From
    $85

Check prices for these upcoming dates

Kissimmee Vacation Rentals with a Pool

  • Perfect Orlando Getaway, closest to Disney
     8br Home/Apartment
    Airbnb
    From
    $719
  • Luxury Villa-Private Pool lakeside, 20'' to Disney
    Excellent3br Home/Apartment
    Airbnb
    From
    $242
  • A solo 30 minutos de los parques!!
    Good3br Home/Apartment
    Airbnb
    From
    $192
  • Venetian Bay Villages
    Good3br Country House
    Airbnb
    From
    $155

Kissimmee Vacation Rentals with Wi-Fi

  • Villas at Fortune Place
     100br Home/Apartment
    Booking.com
    From
    $131
  • Dassah's Room
    ExcellentHome/Apartment
    Airbnb
    From
    $72
  • Kissimmee!! Close to Disney! Pets welcome
     4br Home/Apartment
    Airbnb
    From
    $267
  • Private, Warm & Cozy Studio in Kissimmee, FL
    ExcellentHome/Apartment
    Airbnb
    From
    $73

Kissimmee Pet-Friendly Vacation Rentals

  • Beautiful 3BR Townhome Villa Near Disney
    Excellent3br Country House
    HolidayLettings
    From
    $166
  • Exclusive Orlando Vacation Home
    Nice4br Home/Apartment
    Flipkey
    From
    $206
  • 1 Private Room/ 1 Bath/ Kitchenette- Pets Allowed
     Home/Apartment
    HolidayLettings
    From
    $123
  • 1 Bedroom/ Bath/ Kitchenette- Pets Allowed
     Home/Apartment
    HolidayLettings
    From
    $129

Kissimmee Travel Guide

Located just south of Orlando, Kissimmee is a small city with a big reputation for theme parks and world-class vacation rentals. Warm weather, endless activities for the kids, good food and a plenty of golf courses make the city a perfect family getaway.

Things to Do in Kissimmee

Kissimmee is known for its wealth of Airbnbs and other short-term vacation rental properties. Families looking for hotels stay up north in the Orlando, but families looking to escape the crowds but still have the parks at their fingertips tend to opt for larger homes and condos in Kissimmee. The rentals are generally spacious homes with private pools and easy access to nearby golf courses. Many sit on Lake Tohopekaliga and set guests up with gorgeous sunset views.

Best Time to Visit Kissimmee

Most visitors book their homes and condos in the winter to escape the northern cold and take in the Florida sun. The spring and fall are also nice and visitors benefit from offseason price dips. The summer is hot and humid and better avoided.

A Local's Guide to Kissimmee Vacation Rentals

The often overlooked jewel of central Florida, Kissimmee offers traveler’s all of the perks and Disney Parks access of Orlando with the added benefit of outdoor adventures along Lake Toho (Lake Tohopekaliga).

The lovely town of Kissimmee is located in Osceola County, Florida just a mere 11 miles from Walt Disney World and 19 miles from Universal Studios, making it the perfect rental destination for families looking for a mix of park access and relaxation.

Family Activities

The community in Kissimmee is family-oriented and there are plenty of off-the-beaten-path activities to do to keep the whole family entertained.

An ideal day in Kissimmee, Florida includes a trip to Disney World with the family, a tour of the Kennedy Space Center, and an unforgettable fan boat experience on Lake Tohopekaliga. Other popular experiences in Kissimmee include scenic treetop zip line tours, hot air balloon adventures, and of course boutique shopping in Kissimmee’s charming downtown area.

When to Book

The classic Florida scene of sunshine and palm trees makes Kissimmee the perfect winter getaway during the bitter cold months of the year. During the summer months, Kissimmee is the ideal destination to avoid the crowds of Orlando, while having access to Florida’s best theme parks.

Price and Availability in Kissimmee

Most expensive
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The cheapest day to stay at a vacation rental in Kissimmee tends to be Monday, while the most expensive day tends to be Saturday. Vacation homes in Kissimmee tend to be busiest on Fridays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Kissimmee is in July, while the cheapest month is in September. The most popular time to book a vacation rental in Kissimmee is in the high season in March. Kissimmee has its low season in September, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Kissimmee

Rainy days
89° 39°
1
87° 40°
2
83°
2
88° 47°
0
87° 37°
0
90° 51°
1
92° 61°
8
95° 70°
3
95° 72°
1
94° 71°
3
95° 73°
3
92° 52°
2
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Kissimmee. The hottest month in Kissimmee is July, when temperatures peak at 95 ˚F. The coolest month is December, when temperatures drop to 0 ˚F. The wettest month in Kissimmee is August with 7.7 inches of rain, while the driest month is November with 0.16 inches of rain.

What Expert Travelers Think

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    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit
  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum
  • — AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

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Vacation Rentals in Kissimmee

Choose the perfect accommodation for your vacation at AllTheRooms.com. We aggregate Airbnb, RedAwning, TUIVillas and more. We have 148,364 vacation rentals, hotels and other places to stay in Kissimmee ranging from low-cost options to extravagant places to stay. In general, a place to stay in Kissimmee will cost you $608 per night.

Those looking to get some work done during their trip to Kissimmee can choose from 32,349 places to stay that provide WiFi. We have 900 accommodations that include a breakfast included. You can keep up with your workout routine by staying at one of 17,957 accommodations that provide gym facilities. If you're planning on getting to Kissimmee by car, be sure to choose from 27,483 accommodations that provide parking. 30,447 vacation rentals come with a pool or jacuzzi

AllTheRooms has 2,643 pet-friendly places to stay in Kissimmee, so if you're traveling with your cat or dog you won't have any trouble.

In Kissimmee AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 6 providers, including 27,009 places to stay from Airbnb, 896 accommodations from RedAwning and 896 places to stay from TUIVillas.

27,130 of the accommodations in Kissimmee have been rated by previous guests. They rated 16% as excellent or good. 61,329 accommodations allow instant booking.

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