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, (2813)
"Lovely property will stay here everytime"
The price is AU$162
includes taxes & fees
28 Sept - 29 Sept
Vacation Village at Parkway

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1590)
"Great place"
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (1383)
"The best hotel "
Reunion Resort & Golf Club

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$211
includes taxes & fees
7 Sept - 8 Sept
Magical Dreams

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1892)
"Beautiful, perfect for a family getaway"
The price is AU$216
includes taxes & fees
1 Sept - 2 Sept
The Berkley, Orlando

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very good, (2969)
"Excellent service and stay "
The price is AU$478
includes taxes & fees
4 Sept - 5 Sept
Regal Oaks Resort Vacation Townhomes by IDILIQ

Club Wyndham Cypress Palms

3.5 star property
9.0 out of 10, Wonderful, (1797)
"Great stay, excellent rooms, ample and clean. Resort facilities are good."
Club Wyndham Cypress Palms

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.0 out of 10, Wonderful, (138)
"Great place, would definitely stay there again "
The price is AU$195
includes taxes & fees
27 Sept - 28 Sept
Barefoot'n Resort Kissimmee Orlando

Enchanted Dreams

3.5 star property
6.0 out of 10, (2)
"Clean, comfortable home. Everything was excellent from the security to amenities. I will book again, share with friends and family. "
The price is AU$240
includes taxes & fees
9 Sept - 10 Sept
Enchanted Dreams

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1373)
"Love that there was a private as well as a community pool"
The price is AU$434
includes taxes & fees
9 Sept - 10 Sept
Encantada Resort Vacation Townhomes by IDILIQ

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1145)
"Spacious accommodations near Disney, with some amenities. "
Magic Village Yards, Trademark Collection by Wyndham

Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38

10.0 out of 10, Exceptional, (26)
"Great communication from the host and a fun house"
Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38

Grand Lake Resort

3.0 star property
9.2 out of 10, Wonderful, (136)
"It’s a great place "
Grand Lake Resort

Lifetime of Vacations Resort

3.0 star property
9.4 out of 10, Exceptional, (144)
"Fairly quiet, beautiful view. We would 100% stay here again."
Lifetime of Vacations Resort

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (170)
"Great stay"
The price is AU$786
includes taxes & fees
31 Aug - 1 Sept
Formosa Valley Resort by UNE Homes

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1764)
"We have stayed numerous times. We love the property and love staying across the street from Fun Spot. Its nice to be able to stroll out every evening, shop, dine and have some fun. The 2 bedroom was very nice, clean and super roomy! We will be back as usual."
Barefoot Suites

Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool

9.6 out of 10, Exceptional, (48)
"Great location Sun all day and communication with management company was fantastic Will definitely stay again I’ve stayed for over 30 yrs and the best villa yet"
Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool

Lakeview Luxury Villa with Everything

9.8 out of 10, Exceptional, (384)
"Location was great! House was great lots to do, lots of space, clean, absolutely loved it!"
Lakeview Luxury Villa with Everything

Modern Luxury Villa with Everything

9.8 out of 10, Exceptional, (434)
"This the best place I’ve stayed at!!! Thank you so much and we made many sweet memories!!! "
Modern Luxury Villa with Everything

Summerville Vacation Homes by Columbia Management

4.0 star property
8.4 out of 10, Very good, (151)
"Not enough parking "
Summerville Vacation Homes by Columbia Management
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

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$162 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 Summerville Vacation Homes by Columbia Management.

How many holiday rentals are there in Kissimmee?

Choose from 15053 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.