Kissimmee Holiday Rentals

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Holiday Rentals in Kissimmee

Vacation Village at Parkway
3.0 star property
8.6 out of 10, Excellent, (2956)
"Had every thing you would need for a family trip Perfect loved it "
The price is AU$193
includes taxes & fees
23 Oct - 24 Oct
Vacation Village at Parkway
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
4.0 star property
8.8 out of 10, Excellent, (1654)
"It was a great stay !"
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Club Wyndham Cypress Palms
3.5 star property
9.0 out of 10, Wonderful, (1822)
"Nice place to stay"
Club Wyndham Cypress Palms
The Berkley, Orlando
4.0 star property
9.6 out of 10, Exceptional, (1947)
"Great stay!"
The price is AU$237
includes taxes & fees
14 Oct - 15 Oct
The Berkley, Orlando
Reunion Resort & Golf Club
5.0 star property
8.8 out of 10, Excellent, (1410)
"amazing place for families"
Reunion Resort & Golf Club
Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
8.4 out of 10, Very good, (2986)
"Loved the location of the property and that the property was gated"
Regal Oaks Resort Vacation Townhomes by IDILIQ
Encantada Resort Vacation Townhomes by IDILIQ
3.0 star property
8.6 out of 10, Excellent, (1386)
"The unit was great for our large group of people. The only issue was some cheaply made furniture that seemed very wobbly. "
Encantada Resort Vacation Townhomes by IDILIQ
Magical Dreams
4.0 star property
10.0 out of 10, Exceptional, (1)
"estaba algo caliente pero nos contactamos con los encargados y nos solucionaron el problema "
The price is AU$199
includes taxes & fees
14 Oct - 15 Oct
Magical Dreams
Magic Village Yards, Trademark Collection by Wyndham
4.0 star property
9.2 out of 10, Wonderful, (1146)
"Spacious accommodations near Disney, with some amenities. "
Magic Village Yards, Trademark Collection by Wyndham
Barefoot'n Resort Kissimmee Orlando
2.5 star property
9.0 out of 10, Wonderful, (149)
"Awesome place to stay. This is my 3rd time staying at this resort. Its my favorite place, its roomy, calm, an apt all to myself what else can i ask for."
The price is AU$155
includes taxes & fees
14 Oct - 15 Oct
Barefoot'n Resort Kissimmee Orlando
Club Wyndham Star Island
3.5 star property
8.2 out of 10, Very good, (440)
"The rooms were very clean & equipped with every little item we were going to need in the kitchen/bedrooms/bedrooms. We also had washer/dryer to leave with clean clothes from our stay. I will definitely recommend this place for a family/friend getaway. "
Club Wyndham Star Island
Grand Lake Resort
3.0 star property
9.2 out of 10, Wonderful, (141)
"Amber was great we had a ball definitely coming back resort was beautiful "
Grand Lake Resort
Barefoot Suites
3.0 star property
9.0 out of 10, Wonderful, (1775)
"Barefoot Suites is just an overall an awesome place to stay."
Barefoot Suites
Enchanted Fantasy
3.5 star property
The price is AU$208
includes taxes & fees
14 Oct - 15 Oct
Enchanted Fantasy
Formosa Valley Resort by UNE Homes
4.0 star property
9.4 out of 10, Exceptional, (173)
"Great stay"
Formosa Valley Resort by UNE Homes
Lifetime of Vacations Resort
3.0 star property
9.4 out of 10, Exceptional, (147)
"Quiet place "
Lifetime of Vacations Resort
Modern Luxury Villa with Everything
9.8 out of 10, Exceptional, (441)
"It was a great stay. The house was clean and close to everything."
Modern Luxury Villa with Everything
Enchanted Dreams
3.5 star property
8.0 out of 10, Very good, (4)
"Clean, comfortable home. Everything was excellent from the security to amenities. I will book again, share with friends and family. "
The price is AU$225
includes taxes & fees
14 Oct - 15 Oct
Enchanted Dreams
Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38
10.0 out of 10, Exceptional, (27)
"Very spacious and fun house, very easy to get to Parks, groceries, and outletsHost was amazing and available!"
Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38
Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool
9.6 out of 10, Exceptional, (48)
"The home was perfect for our family trip to Disney! Its conveniently located near all of the FUN!! Great place to stay! I would definitely stay here again!"
Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool
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.
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Top Kissimmee Hotel Reviews

Find out more about Kissimmee

Everything you need to know about Kissimmee holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kissimmee holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kissimmee holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Kissimmee holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kissimmee. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kissimmee holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kissimmee holiday rentals we have selected for you start as low as AU$155 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Kissimmee rentals

At Expedia, we put the best Kissimmee holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Kissimmee rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kissimmee holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kissimmee. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 renowned opera 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. Other favourite homes for rent in Kissimmee are Formosa Valley Resort by UNE Homes and Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool.

How many holiday rentals are there in Kissimmee?

Choose from 15140 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 Medieval Times and Osceola County Welcome Center and History Museum. 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.