Kissimmee Vacation Rentals

Our Favorite Vacation Rentals in Kissimmee

  • ACO FAMILY – 4 bd TOWNHOME WITH POOL (1515)
     4br Home/Apartment
    RedAwning
    From
    $347
  • Windsor Hills/Windsor Palms by Orlando Select Vacation Rental
    GoodCountry House
    Booking.com
    From
    $225
  • NEW! Updated Kissimmee Condo 20 Mins to Disney!
     2br Home/Apartment
    HolidayLettings
    From
    $191
  • holiday home for max. 8 persons in Kissimmee, Florida
     Country House
    TUIvillas
    From
    $244
  • Candle Cay Vacation Townhome at Coral Cay Resort
     4br Villa
    RedAwning
    From
    $277
  • Two-Bedroom Bonfire Apartment #1103
     Home/Apartment
    Booking.com
    From
    $79
  • GREAT FIND, 3 x 2BR VILLAS for 27! POOL, HOT-TUB, TENNIS, GRILL, PARKING
     6br Home/Apartment
    HolidayLettings
    From
    $435
  • holiday home for max. 8 persons in Kissimmee, Florida
    OkayCountry House
    TUIvillas
    From
    $238

Check prices for these upcoming dates

Kissimmee Vacation Rentals with a Pool

  • 3 Bedrooms Townhouse at The Villas at Seven Dwarfs (gvs)
     3br Home/Apartment
    RedAwning
    From
    $278
  • VOS-2739PB-73 - Somerset Gardens (B)
     3br Home/Apartment
    RedAwning
    From
    $246
  • 4639EPD - Comfort Island (G)
     3br Country House
    RedAwning
    From
    $329
  • Bright + Spacious Deluxe Suite | Theme Park Shuttles!
     3br Home/Apartment
    RedAwning
    From
    $253

Kissimmee Vacation Rentals with Wi-Fi

  • 4983BS - Bawtry Estate (B)
     4br Home/Apartment
    RedAwning
    From
    $315
  • Villas at Fortune Place
    Good100br Home/Apartment
    Booking.com
    From
    $92
  • RENOVATED Sunny + Cozy Orlando Retreat | Minutes from Theme Parks!
     2br Home/Apartment
    RedAwning
    From
    $265
  • 4970PMS - Don Caster Home (B)
     4br Home/Apartment
    RedAwning
    From
    $315

Kissimmee Pet-Friendly Vacation Rentals

  • Exclusive Orlando Vacation Home
    Nice4br Home/Apartment
    Flipkey
    From
    $210
  • 1 Private Room/ 1 Bath/ Kitchenette- Pets Allowed
     Home/Apartment
    HolidayLettings
    From
    $129
  • 1 Bedroom/ Bath/ Kitchenette- Pets Allowed
     Home/Apartment
    HolidayLettings
    From
    $129
  • 4 Bedroom/2 1/2 bath beautiful townhouse - Close to Disney
    Excellent4br Home/Apartment
    Flipkey
    From
    $195

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
Most availability
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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
95 º73
3
92 º52
2
89 º39
1
87 º40
2
83 º0
2
88 º47
0
87 º37
0
90 º51
1
92 º61
8
95 º70
3
95 º72
1
94 º71
3
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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

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

    ArtMatters.Info
    ArtMatters.InfoArtMatters.Info
  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    Jaz
    JazThe Life of a Social Butterfly
  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad

Vacation Rentals in Kissimmee

Pick the perfect vacation rental for your vacation at AllTheRooms.com. We aggregate Airbnb, RedAwning, TUIVillas and more. AllTheRooms has 133,451 vacation rentals, hotels and other great places to stay while you enjoy Kissimmee, with everything from inexpensive hostels and homestays to luxury Airbnbs and hotels. A typical vacation rental in Kissimmee costs on average $612 a night.

If you would like to stay connected during your vacation, then you can choose from over 37,611 accommodations in Kissimmee that have WiFi. We have 565 accommodations that come with breakfast included. You can maintain your workout routine by staying at one of 19,023 accommodations that provide gym facilities. If you're planning on arriving in Kissimmee by car, be sure to choose from 31,160 accommodations that provide parking. We track 26,031 accommodations that have a pool or jacuzzi.

If you're traveling with your best friend, then make sure to select one of the 2,529 pet-friendly accommodations available.

In Kissimmee AllTheRooms currently compares hotels, vacation rentals, hostels from more than 6 providers, including 22,406 places to stay from Airbnb, 871 accommodations from RedAwning and 871 places to stay from TUIVillas.

26,572 accommodations in Kissimmee have been reviewed; 18% are rated highly. You can instantly book any of 52,819 places to stay right now.

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