A pathway through a park with Spanish moss hanging from trees and a body of water in the background.

Kissimmee Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Kissimmee holiday rentals

Exterior

1. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (4,974 reviews)
"It's is a very nice resort my family enjoyed it and use way they rooms are designed is awesome you can get a little privacy from your kids and love ones at the same time."
United States
Vernon
The price is HK$528
HK$795 total
includes taxes & fees
10 Sept - 11 Sept
Vacation Village Orlando, Celebration
Pool

2. Villas at Fortune Place

Villas at Fortune Place
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (219 reviews)
"Great stay for the cost. Close to all the parks & the airport. Would definitely book this spot again."
United States
Joseph
The price is HK$604
HK$756 total
includes taxes & fees
9 Sept - 10 Sept
Villas at Fortune Place
Outdoor pool

3. Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,915 reviews)
"All in the property was wonderful"
United States
Michelle
The price is HK$748
HK$1,004 total
includes taxes & fees
8 Sept - 9 Sept
Barefoot Suites
Lobby sitting area

4. The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,397 reviews)
"Great place"
Canada
Stefanny
The price is HK$883
HK$1,082 total
includes taxes & fees
7 Oct - 8 Oct
The Berkley, Orlando
Exterior

5. Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (364 reviews)
"Great aminities"
United States
Carlos
The price is HK$952
HK$1,178 total
includes taxes & fees
8 Sept - 9 Sept
Barefoot'n Resort Kissimmee Orlando
Pool

6. The Irlo

The Irlo
3.0 star property
Kissimmee
7.8 out of 10, Good, (108 reviews)
"Clean, cozy and equipped with everything for comfortable stay! We loved it!"
United States
Ismael
The price is HK$447
HK$685 total
includes taxes & fees
9 Sept - 10 Sept
The Irlo
Pool

7. Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
6.8 out of 10, (71 reviews)
"The room was clean and the staff was okay "
United States
Shaneka
The price is HK$463
HK$525 total
includes taxes & fees
8 Sept - 9 Sept
Maple Leaf Inn & Suites
Living area

8. Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (243 reviews)
"Great price and size"
United States
Scott
The price is HK$559
HK$705 total
includes taxes & fees
13 Sept - 14 Sept
Grand Lake Resort
Exterior

9. Lifetime of Vacations Resort

Lifetime of Vacations Resort
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (180 reviews)
"We absolutely love coming to lifetime and grand lake resort. This is our favorite place to stay!!"
United States
Alena
The price is HK$521
HK$725 total
includes taxes & fees
13 Sept - 14 Sept
Lifetime of Vacations Resort
Private kitchen

10. Cloud Nine • 1BR 15 MIN from Kissimmee Main Street

Cloud Nine • 1BR 15 MIN from Kissimmee Main Street
Kissimmee
10.0 out of 10, Exceptional, (5 reviews)
"Space was great for a single traveler or couple. Fairly quiet apartment complex with a couple pools on the property. Was great for my quick stay in the area. "
United States
Shea H.
The price is HK$823
HK$1,816 total
includes taxes & fees
13 Sept - 14 Sept
Cloud Nine • 1BR 15 MIN from Kissimmee Main Street
Terrace/patio

11. Sunset Bliss Retreat Condo - Near Disney

Sunset Bliss Retreat Condo - Near Disney
Kissimmee
9.6 out of 10, Exceptional, (58 reviews)
"Everything was perfect, next time I will stay here again"
United States
Luis Pedro L.
The price is HK$433
HK$1,262 total
includes taxes & fees
11 Sept - 12 Sept
Sunset Bliss Retreat Condo - Near Disney
Dining

12. Freshly Updated~Near Disney~Private Pool~Resort

Freshly Updated~Near Disney~Private Pool~Resort
Crystal Cove
10.0 out of 10, Exceptional, (3 reviews)
"Everything was amazing would love to rent more properties in the future!!"
United States
Dijaun B.
The price is HK$480
HK$4,070 total
includes taxes & fees
8 Sept - 9 Sept
Freshly Updated~Near Disney~Private Pool~Resort
Lounge

13. Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
4.0 star property
Kissimmee
10.0 out of 10, Exceptional, (10 reviews)
"Would stay again and so should you! "
United States
katie
The price is HK$753
HK$1,905 total
includes taxes & fees
15 Sept - 16 Sept
Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
Exterior

14. Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
Kissimmee
9.0 out of 10, Wonderful, (2,242 reviews)
"nice place to stay!"
United States
Victor
The price is HK$1,599
HK$3,919 total
includes taxes & fees
8 Sept - 9 Sept
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
Private kitchen

15. Luxe Condo Double Bed Bliss Getaway near Disney

Luxe Condo Double Bed Bliss Getaway near Disney
Kissimmee
8.8 out of 10, Excellent, (47 reviews)
"This place is nice. Easy access and the pools are nice. Property is a bit dated but for the price you can’t beat it. I will stay here again."
United States
Jeremy
The price is HK$480
HK$1,333 total
includes taxes & fees
20 Sept - 21 Sept
Luxe Condo Double Bed Bliss Getaway near Disney
Living area

16. Cozy 2BD/2BTH Condo Near Disney

Cozy 2BD/2BTH Condo Near Disney
Kissimmee
9.4 out of 10, Exceptional, (36 reviews)
"Comfy, cute, clean and affordable place to stay!"
United States
Anna W.
The price is HK$627
HK$1,588 total
includes taxes & fees
27 Sept - 28 Sept
Cozy 2BD/2BTH Condo Near Disney
Private kitchen

17. Luxe King Suite Bliss Getaway Condo Near Disney

Luxe King Suite Bliss Getaway Condo Near Disney
Kissimmee
9.0 out of 10, Wonderful, (48 reviews)
"We had a fantastic time staying here for the second year in a row. It is in a great and safe location. The host is very kind, responsive and helpful. Very comfortable and homey property. I just rebooked the property and I am excited to come back in February!"
United States
Adrienne G.
The price is HK$480
HK$1,315 total
includes taxes & fees
8 Sept - 9 Sept
Luxe King Suite Bliss Getaway Condo Near Disney
Private kitchen

18. Think Pink in Kissimmee - Gorgeous 2BD with free WIFI, free parking and more!!

Think Pink in Kissimmee - Gorgeous 2BD with free WIFI, free parking and more!!
Kissimmee
9.6 out of 10, Exceptional, (12 reviews)
"This was a cute, quiet, and convenient rental location."
United States
Tabitha W.
The price is HK$925
HK$1,929 total
includes taxes & fees
28 Sept - 29 Sept
Think Pink in Kissimmee - Gorgeous 2BD with free WIFI, free parking and more!!
Private kitchen

19. Charming 2-bedroom Florida Getaway! Sleeps 6

Charming 2-bedroom Florida Getaway! Sleeps 6
Kissimmee
9.8 out of 10, Exceptional, (21 reviews)
"Great little place. We would book it again."
United States
Jack Francis G.
The price is HK$682
HK$2,376 total
includes taxes & fees
8 Sept - 9 Sept
Charming 2-bedroom Florida Getaway! Sleeps 6
Room

20. Private Resort Access~King Bed~Hot Tub~Balcony

Private Resort Access~King Bed~Hot Tub~Balcony
Kissimmee
10.0 out of 10, Exceptional, (3 reviews)
"Great host and fantastic pool"
United States
paul m.
The price is HK$388
HK$2,967 total
includes taxes & fees
17 Sept - 18 Sept
Private Resort Access~King Bed~Hot Tub~Balcony
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

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"❤️Love this play, 10x better than any Disney property for kids+Adults"
Fredrick 3-night trip
Posted 6 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Find out more about Kissimmee

Search for holiday rentals in Kissimmee on Expedia! You can easily find your home rentals, villas, holiday apartments in Kissimmee using one of the methods below:

  • View our selection of featured holiday rentals in Kissimmee
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  • Enter your travel dates to view the best deals on holiday rentals in Kissimmee while they last

Look no further and take a look at our great range of rental properties in Kissimmee!

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?

Formosa Valley Resort by UNE Homes: This highly rated holiday home rental in Kissimmee is equipped with an outdoor pool, air conditioning and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop. Some other homes for rent in Kissimmee include Spacious 4-bedroom Pool house in charming Kissimmee Close to Disney with Wi-fi and 🌴Beautiful home in Windsor Hills Resort -Disney 2.5 miles 🌴.

How many holiday rentals are there in Kissimmee?

Choose from 1619 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 Kissimmee Air 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.