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Kissimmee Vacation Rentals

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Our Favorite Vacation Rentals in Kissimmee

  • ULTRA LUXURY 6 BR Villa Massimo w/POOL by DISNEY
     6br Villa
    RedAwning
    From
    $440
  • Villas at Fortune Place
     100br Home/Apartment
    Booking.com
    From
    $150
  • Disney World... Minutes Away! Luxury 6 BR/4 BA
    Good6br Country House
    Flipkey
    From
    $356
  • holiday apartment for max. 8 persons in Kissimmee, Florida
     Home/Apartment
    TUIvillas
    From
    $327
  • Poinciana
     4br Country House
    Interhome
    From
    $271
  • ULTRA LUXURY The Addison 3BR w/ POOL by DISNEY
     3br Home/Apartment
    RedAwning
    From
    $265
  • NUOVO - Disney/Kissimmee
     Home/Apartment
    Booking.com
    From
    $79
  • Single Parent Retreat 14 miles to Disney!
     Home/Apartment
    HolidayLettings
    From
    $58
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Check prices for these upcoming dates

Kissimmee Vacation Rentals with a Pool

  • Candle Cay Vacation Townhome at Coral Cay Resort
     4br Villa
    RedAwning
    From
    $354
  • Bright + Spacious Deluxe Suite | Theme Park Shuttles!
     3br Home/Apartment
    RedAwning
    From
    $230
  • Disney Penthouse Amazing Lake Bryan view
     2br Home/Apartment
    RedAwning
    From
    $384
  • RENOVATED Sunny + Cozy Orlando Retreat | Minutes from Theme Parks!
     2br Home/Apartment
    RedAwning
    From
    $274
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Kissimmee Vacation Rentals with Wi-Fi

  • One Bedroom Suite Hotel in Celebration
     Home/Apartment
    RedAwning
    From
    $297
  • FREE Disney Shuttle + No Resort Fee | Spacious Suite Near Orlando Theme Parks
     Home/Apartment
    RedAwning
    From
    $170
  • 905SRD-Roodys Place (B)
     4br Home/Apartment
    RedAwning
    From
    $338
  • 117ADC- Bells Palace (G)
     5br Home/Apartment
    RedAwning
    From
    $396
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Kissimmee Pet-Friendly Vacation Rentals

  • Bright Kissimmee Apt - Pool Access, Near Disney
     2br Home/Apartment
    HolidayLettings
    From
    $239
  • NEW! Duplex Home 5Mi to Gatorland & 15Mi to Disney
     3br Home/Apartment
    HolidayLettings
    From
    $214
  • 1 Private Room/ 1 Bath/ Kitchenette- Pets Allowed
     Home/Apartment
    HolidayLettings
    From
    $129
  • 1 Bedroom/ Bath/ Kitchenette- Pets Allowed
     Home/Apartment
    HolidayLettings
    From
    $129
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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.
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Price and Availability in Kissimmee

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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.
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The Weather in Kissimmee

Rainy days
84° 39°
2
88° 46°
1
91° 42°
1
90° 53°
1
95° 66°
2
99° 71°
2
96° 69°
3
94° 74°
4
96° 69°
2
91° 67°
1
88° 45°
0
85° 41°
2
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Kissimmee. The hottest month in Kissimmee is July, when temperatures peak at 99 ˚F. The coolest month is December, when temperatures drop to 39 ˚F. The wettest month in Kissimmee is May with 3.55 inches of rain, while the driest month is February with 0.44 inches of rain.

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What Expert Travelers Think

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  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

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    Whitney WearTravel Better Guide
    Travel Better Guide

Vacation Rentals in Kissimmee

At AllTheRooms.com we have rentals from all of the best providers - Airbnb, RedAwning, Priceline and more. We have 119,122 vacation rentals, hotels and other accommodation types in Kissimmee ranging from low-cost options to extravagant places to stay. The average price of a vacation rental is $574 per night.

If you want to stay connected during your vacation, then you can choose from over 29,471 accommodations in Kissimmee that have WiFi. We have 834 accommodations that come with breakfast included. Fitness fanatics can get a workout in during their stay by choosing from 18,248 accommodations that have gym facilities. If you're planning on arriving in Kissimmee by car, be sure to choose from 27,455 accommodations that provide parking. 29,606 hotels and vacation rentals have a a pool or jacuzzi

Those traveling with a cat, dog or some other animal can stay in one of 2,587 accommodations that are designated as pet-friendly.

AllTheRooms aggregates vacation rentals, hotels and other bespoke accommodation types from loads of providers in Kissimmee, including 27,065 places to stay from Airbnb, 2,526 accommodations from RedAwning and 2,436 places to stay from Priceline

28,026 of the rentals in Kissimmee have been reviewed by previous guests. They rated 18% as great. You can instantly book any of 51,067 places to stay right now.

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