Kissimmee Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Kissimmee

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very good, (1536)
"Perfect location for a short stay as amenities very close and some transportation available "
The price is AU$186
includes taxes & fees
9 Mar - 10 Mar
Vacation Village at Parkway

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1209)
"Great stay. 4/3 villa exceeded our expectations! Resort is beautiful. Well worth the price."
Margaritaville Resort Orlando Cottages by Rentyl

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1690)
"Really friendly people at the desk and the room was cozy. I would stay again. "
The price is AU$191
includes taxes & fees
5 Mar - 6 Mar
Barefoot Suites

Reunion Resort & Golf Club

5.0 star property
8.6 out of 10, Excellent, (1221)
"The front desk staff were absolutely amazing! Christina went above and beyond to accommodate my family in our stay. The stay was so nice, we called and extended our reservation! Our kids loved the lazy River and the access to a yard area."
The price is AU$511
includes taxes & fees
10 Mar - 11 Mar
Reunion Resort & Golf Club

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.4 out of 10, Exceptional, (13)
"Good stay, clean."
The price is AU$236
includes taxes & fees
24 Feb - 25 Feb
Barefoot'n Resort Kissimmee Orlando

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very good, (2838)
"Roomy, quiet, nice pool."
The price is AU$584
includes taxes & fees
16 Mar - 17 Mar
Regal Oaks Resort Vacation Townhomes by IDILIQ

Luxury 20 bedroom Reunion Villas @ Disney's Doorstep

9.2 out of 10, Wonderful, (87)
"Location was great! The water park was an added bonus, the kids loved it!! Pool a plus! Enough room for us all! Side by side homes were a plus! Thanks for allowing us to stay!! Hopefully we win Nationals again and can come back! "
Luxury 20 bedroom Reunion Villas @ Disney's Doorstep

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1681)
"Great place to stay!"
The price is AU$420
includes taxes & fees
9 Mar - 10 Mar
The Berkley, Orlando

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1121)
"We had an amazing time. I highly recommend staying here. All the comforts of home while enjoying your time in Florida. Super easy access to Disney parks. The front desk staff was phenomenal "
Magic Village Yards, Trademark Collection by Wyndham

Club Wyndham Cypress Palms

3.5 star property
9.0 out of 10, Wonderful, (1663)
"It was well equipped suite to fill all your needs. Spacious and clean. A wonderful place to stat. Close ti Disney"
Club Wyndham Cypress Palms

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1328)
"I recently stayed at Encantada Resort Vacation Townhomes by IDILIQ in Four Corners, Florida, from December 23 to January 2, and it was absolutely fantastic! The resort provided the perfect balance of relaxation and convenience. The townhome was spacious, clean, and well-maintained, with all the amenities we needed to feel at home. The fully equipped kitchen made it easy to prepare meals, and the private patio with a hot tub was an incredible touch for unwinding after a day of exploring. The...
The price is AU$495
includes taxes & fees
24 Feb - 25 Feb
Encantada Resort Vacation Townhomes by IDILIQ

3 Miles to Disney! Themed Home FREE Heated Pool & Spa Theater Grill & 7 Bedrooms

10.0 out of 10, Exceptional, (173)
"As lovers of Disney, this home was well themed to our liking. The theater was our favorite because of the details in theming and the surround sound was crazy good. It was also nice to enjoy the hot tub after long days at the parks. The changing lights in the hot tub was also a plus. We also appreciated the washer and 2 dryers to be able to keep up with laundry. Our party of 11 had more than enough room to spread out and be comfortable. Would highly recommend "
3 Miles to Disney! Themed Home FREE Heated Pool & Spa Theater Grill & 7 Bedrooms

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (139)
"Very clean and large with everything you need"
Formosa Valley Resort by UNE Homes

Modern Luxury Villa with Everything

9.8 out of 10, Exceptional, (373)
"Just as advertised, lots of parking , great place. The audio Video was not hooked up right was the only complaint other than that would book again!"
Modern Luxury Villa with Everything

Marvelous Villa with Galactic Themed Bedroom at Encore

9.2 out of 10, Wonderful, (43)
"10/10 experience!"
Marvelous Villa with Galactic Themed Bedroom at Encore

Lakeview Luxury Villa with Everything

9.8 out of 10, Exceptional, (323)
"We enjoyed our stay here. We've rented houses in various cities and states, and I appreciated that this property was well-stocked. We didn't have to take time from our trip to get extra dish soap, paper towels, pool towels, etc. Especially for a shorter trip, this was wonderful! It was convenient enough to all the parks and our needs. The home was well-appointed and just as pictured. The kids enjoyed the themed rooms, video games and theater room. The community may not have been as charming as...
Lakeview Luxury Villa with Everything

Blissful Bay

3.0 star property
7.2 out of 10, Good, (13)
"All of house is great. Meet new people vacationing from other places really great stay."
Blissful Bay

Lifetime of Vacations Resort

3.0 star property
9.2 out of 10, Wonderful, (121)
"Amazing for families. Great location and amenities. "
Lifetime of Vacations Resort

Encore Resort

4.0 star property
6.4 out of 10, (114)
"It was a very nice home. My family had a great time"
Encore Resort

The Bear's Den Resort Orlando

5.0 star property
8.0 out of 10, Very good, (22)
"Great place , I recommend it to everyone."
The Bear's Den Resort Orlando
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Kissimmee
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Kissimmee you may be interested in

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very good, (1536)
"Perfect location for a short stay as amenities very close and some transportation available "
The price is AU$186
includes taxes & fees
9 Mar - 10 Mar
Vacation Village at Parkway

Margaritaville Resort Orlando

4.0 star property
9.0 out of 10, Wonderful, (3237)
"Beautiful property and close to Disney!"
The price is AU$430
includes taxes & fees
24 Feb - 25 Feb
Margaritaville Resort Orlando

Ramada by Wyndham Hotel & Water Park

3.0 star property
7.0 out of 10, Good, (1013)
"Comfy beds "
The price is AU$119
includes taxes & fees
25 Feb - 26 Feb
Ramada by Wyndham Hotel & Water Park
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find holiday rentals in Kissimmee?

Yes, there are holiday rentals in Kissimmee close to Disney's Animal Kingdom® Theme Park, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Kissimmee like the fun-filled theme parks and lively festivals. The array of shops and entertainment choices are some other things you might want to check out while you're here.

What are some of the best holiday rentals that Kissimmee has to offer?

The Berkley, Orlando: This highly rated holiday home rental in Kissimmee offers a furnished patio, a terrace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave and a coffee maker. You can relax into your holiday with an arcade/games room and 1 hot tub. Another good choice for your trip to Kissimmee is Luxury 20 bedroom Reunion Villas @ Disney's Doorstep.

How many holiday rentals are there in Kissimmee?

Choose from 15069 Expedia holiday rentals in Kissimmee for a memorable holiday.

What can I see and do in Kissimmee?

Disney's Animal Kingdom® Theme Park and Walt Disney World® Resort are a couple of the family-friendly sights, whereas cultural attractions include Osceola Performing Arts Center and Medieval Times. Other popular places to visit in the area include Old Town and Disney Springs™.

What are holiday rentals like in Kissimmee?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Kissimmee. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a small group gathering.