Kissimmee: Vacation Rental By Owner

Showing 20 Of 5324 Vacation Rentals
  • Property-1 Image 1
    Resort $181 / Nightly
    • 3 Bed
    • 2 Baths
    • (17) Exceptional
    Kissimmee, FL

    Tuscana Resort has all of what you need to make your stay in the Orlando area great. This 3 bedroom 2 bath unit accommodates the needs of all types of travelers... ...more

  • Property-2 Image 1
    Villa $211 / Nightly
    • 4 Bed
    • 3 Baths
    • (42) Exceptional
    Kissimmee, FL

    Need more than one villa close together? We own the 4-bedroom villa to the left of this one (VRBO number 838300) and the 5-bedroom villa on the other side of... ...more

  • Property-3 Image 1
    Condo Select Dates for Price
    • 3 Bed
    • 2 Baths
    Kissimmee, FL

    Tropical….Luxury…. This is the place to Enjoy, Relax and Dream. A one of a kind condo that will not disappoint! Mickey & Friends themed bedroom! The Owner’s suite... ...more

  • Property-4 Image 1
    Townhome $224 / Nightly
    • 3 Bed
    • 3 Baths
    • (39)
    Kissimmee, FL

    Looking for the ultimate in accommodations while visiting Disney World or any of the other world renowned theme parks in Orlando, then look no further. On your... ...more

  • Property-5 Image 1
    Villa $663 / Nightly
    • 4 Bed
    • 3 Baths
    Kissimmee, FL

    Paradise Palms - Kissimmee is a lovely vacation community located just 15 minutes from the magical world of Disney. This prime location lends itself to visit the... ...more

  • Property-6 Image 1
    Villa $661 / Nightly
    • 4 Bed
    • 3 Baths
    Kissimmee, FL

    About Windsor Palms Resort: Enjoy The Windsor Palms Resort's distinctiveclubhouse that features a huge community pool with sun deck and hot tub to sports courts,... ...more

  • Property-7 Image 1
    House $351 / Nightly
    • 6 Bed
    • 5 Baths
    Kissimmee, FL

    Welcome to this modern , 6 bedroom home which easily accommodates up to 13 people. This well-appointed property located in Paradise Palms Resort offers luxury,... ...more

  • Property-8 Image 1
    House $214 / Nightly
    • 3 Bed
    • 2 Baths
    Kissimmee, FL

    Welcome to this Cozy , 3 bedroom townhome which easily accommodates up to 6 people. This well-appointed property located in Encantada Resort offers luxury,... ...more

  • Property-9 Image 1
    Condo $652 / Nightly
    • 3 Bed
    • 3 Baths
    Kissimmee, FL

    Welcome to this beautiful 3 bedroom, 3 bathroom Villa which easily accommodates a large group of up to 8 people. This fully equipped property offers everything... ...more

  • Property-10 Image 1
    Villa $655 / Nightly
    • 4 Bed
    • 3 Baths
    Kissimmee, FL

    Welcome to this beautiful 4 bedroom, 3 bathroom Villa which easily accommodates a large group of up to 10 people. This fully equipped property offers everything... ...more

  • Property-11 Image 1
    Villa $661 / Nightly
    • 4 Bed
    • 3 Baths
    Kissimmee, FL

    This beautiful townhouse in the gated community of Windsor Hills is the perfect choice for your vacation, this Villa has all the conveniences of home right in... ...more

  • Property-12 Image 1
    Villa Select Dates for Price
    • 5 Bed
    • 4 Baths
    Kissimmee, FL

    Welcome to this beautiful 5 bedroom Villa which easily accommodates a large group of up to 10 people. This fully equipped property offers everything one would... ...more

  • Property-13 Image 1
    Villa Select Dates for Price
    • 3 Bed
    • 3 Baths
    Kissimmee, FL

    Welcome to this beautiful 4 bedroom, 3 bathroom Villa which easily accommodates a large group of up to 8 people. This fully equipped property offers everything... ...more

  • Property-14 Image 1
    Villa $658 / Nightly
    • 4 Bed
    • 3 Baths
    Kissimmee, FL

    Championsgate resort - Kissimmee, Florida is a  gorgeous resort located just 12 miles from Walt Disney World and is one of the most desired tourist areas in the... ...more

  • Property-15 Image 1
    Villa Select Dates for Price
    • 3 Bed
    • 3 Baths
    Kissimmee, FL

    Get ready to stay in a gorgeous 3 bedroom 3 bathroom Villa when you book this vacation home today! Located in Windsor Hills, a guarded, fun packed community only... ...more

  • Property-16 Image 1
    Villa $650 / Nightly
    • 4 Bed
    • 3 Baths
    Kissimmee, FL

    Paradise Palms - Kissimmee, is the perfect getaway if you plan on visiting Florida. This luxury resort sits nestled just 5 miles from Disney's main... ...more

  • Property-17 Image 1
    House $228 / Nightly
    • 7 Bed
    • 6 Baths
    • (13) Very Good
    Kissimmee, FL

    7 bedroom + 6 bathroom vacation villa! Perfect for multiple families/generations that want to vacation together! Gated community with community clubhouse, pool,... ...more

  • Property-18 Image 1
    Townhome Select Dates for Price
    • 5 Bed
    • 4 Baths
    Kissimmee, FL

    This brand new 5 Bedroom 4,5 Bathroom, 2,265 Sq.Ft. home with private splash pool is perfectly located, just minutes to Walt Disney World in Windsor at Westside.... ...more

  • Property-19 Image 1
    Villa Select Dates for Price
    • 7 Bed
    • 5 Baths
    • (15)
    Kissimmee, FL

    We invite you to enjoy our wonderful home on your next trip to Orlando. Absolutely perfect for multi-family groups, or golf groups, this property features all the... ...more

  • Property-20 Image 1
    House Select Dates for Price
    • 5 Bed
    • 4 Baths
    • (3)
    KISSIMMEE, FL

    Newly Remodeled ultra-luxurious 5-bedroom, 4-bath, 5-bed home lets you and your family visit the best that Orlando has to offer and not break your vacation budget... ...more

loader

Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Kissimmee. Many accommodations in Kissimmee provide "Pool - Spa", there are 1848, or there are 1810 of Vacation Rentals in Kissimmee with a "Non Smoking Only", there are also 1693 with "Pets Not Allowed", which is another great reason to visit Kissimmee.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Kissimmee. The most expensive month of the next 12 months is in July, where prices hit an average of $83 a night. In November, prices will hit an average low of $90 per night.