Kissimmee Summer Rentals, Cottages & Cabins

There are a lot of options in Kissimmee. If you plan on staying in the Kissimmee area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Kissimmee:

• Amazing villa close to Disney with 5* Reviews
• Conservation View - Hot Tub - Free Pool Heat - Very Private
• Our DisneyDreamVilla - minutes to DisneyWorld!
• BEST HOUSE! StarWars Theater, HarryPotter, Princess, Pirates! Disney 8-10 min!
• Mickeys Magical Villa Disney Five Star Pool Villa Home at Windsor Hills
• Magical Getaway - 4BR/3BA with Pool/Spa, Wifi, Games Room
• Beautiful 6 Bedroom Home, 6 Miles from Disney World, South Facing Pool
• Hakuna Ma'Cottage - Minecraft Room, Southern Pool!
• VRBO STAYED! 6 Bedrms, Free Wifi, 2.5 Miles to Disney! Theater, Mickey Pool!
• Welcome to The Windsor Dream!

In 2026, Holidayrentalvillas offers 8160 summer rentals in or around Kissimmee. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.

The average price per night for a summer rental in Kissimmee is $534. Check the full list of summer accommodations in Kissimmee.

There are 8160 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Holidayrentalvillas.

Yes, here are some popular summer holiday rentals in Kissimmee that have a private or indoor pool:

• 4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee off Us192
• Amazing house with a nice private pool near Disney
• 2780 Bookmark Drive
• Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills

Check all holiday rentals with a pool in Kissimmee on Holidayrentalvillas.