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, (5,004 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$534
HK$802 total
includes taxes & fees
16 Sept - 17 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, (221 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$587
HK$736 total
includes taxes & fees
23 Sept - 24 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$749
HK$1,005 total
includes taxes & fees
13 Sept - 14 Sept
Barefoot Suites
Lobby sitting area

4. The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,403 reviews)
"Great place"
Canada
Stefanny
The price is HK$884
HK$1,082 total
includes taxes & fees
8 Oct - 9 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, (366 reviews)
"Nice rooms pool was great definitely will be back"
United States
Gilbert
The price is HK$952
HK$1,178 total
includes taxes & fees
14 Sept - 15 Sept
Barefoot'n Resort Kissimmee Orlando
Terrace/patio

6. 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$395
HK$1,219 total
includes taxes & fees
19 Sept - 20 Sept
Sunset Bliss Retreat Condo - Near Disney
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
13 Sept - 14 Sept
Maple Leaf Inn & Suites
Room

8. Lyrios Vacation Rentals - The Palms

Lyrios Vacation Rentals - The Palms
4.0 star property
Kissimmee
The price is HK$776
HK$1,584 total
includes taxes & fees
5 Oct - 6 Oct
Lyrios Vacation Rentals - The Palms
Exterior

9. Lifetime of Vacations Resort

Lifetime of Vacations Resort
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (182 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
Dining

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

Freshly Updated~Near Disney~Private Pool~Resort
Crystal Cove
10.0 out of 10, Exceptional, (4 reviews)
"Everything was amazing would love to rent more properties in the future!!"
United States
Dijaun B.
The price is HK$660
HK$4,284 total
includes taxes & fees
11 Sept - 12 Sept
Freshly Updated~Near Disney~Private Pool~Resort
Living area

11. Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (244 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
Pool

12. The Irlo

The Irlo
3.0 star property
Kissimmee
7.8 out of 10, Good, (109 reviews)
"Clean, cozy and equipped with everything for comfortable stay! We loved it!"
United States
Ismael
The Irlo
Private kitchen

13. 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$774
HK$1,744 total
includes taxes & fees
14 Sept - 15 Sept
Cloud Nine • 1BR 15 MIN from Kissimmee Main Street
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, (2,250 reviews)
"nice place to stay!"
United States
Victor
The price is HK$1,440
HK$3,738 total
includes taxes & fees
14 Sept - 15 Sept
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
Private kitchen

15. 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$614
HK$2,251 total
includes taxes & fees
29 Sept - 30 Sept
Charming 2-bedroom Florida Getaway! Sleeps 6
Private kitchen

16. 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$466
HK$1,317 total
includes taxes & fees
18 Sept - 19 Sept
Luxe Condo Double Bed Bliss Getaway near Disney
Lounge

17. 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$688
HK$1,833 total
includes taxes & fees
15 Sept - 16 Sept
Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
Private kitchen

18. 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$445
HK$1,276 total
includes taxes & fees
14 Sept - 15 Sept
Luxe King Suite Bliss Getaway Condo Near Disney
Private kitchen

19. LOVELY LUXURY APARTMENT CLOSE DISNEY

LOVELY LUXURY APARTMENT CLOSE DISNEY
3.5 star property
Kissimmee
8.4 out of 10, Very good, (11 reviews)
"Nice appartment, everything you needed and clean and modern"
United Kingdom
Martyn
The price is HK$819
HK$2,345 total
includes taxes & fees
18 Sept - 19 Sept
LOVELY LUXURY APARTMENT CLOSE DISNEY
Private kitchen

20. Lovely remodeled 1 bed, 1 bath Condo, Just miles from Disney! Great location.

Lovely remodeled 1 bed, 1 bath Condo, Just miles from Disney! Great location.
Kissimmee
9.4 out of 10, Exceptional, (91 reviews)
"Having a washer and dryer on site was a plus."
United States
Dorenda W.
The price is HK$529
HK$1,760 total
includes taxes & fees
11 Sept - 12 Sept
Lovely remodeled 1 bed, 1 bath Condo, Just miles from Disney! Great location.
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

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

10/10 Excellent
"Clean"
Luis 1-night trip
Posted 9 hours ago
Vacation Village Orlando, Celebration

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 1620 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.