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

Holiday Rentals in Kissimmee

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Our top choices for Kissimmee holiday rentals

1. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (5,264 reviews)
"Great place to stay at a great place."
United States
Desiree
The price is €93
includes taxes & fees
29 Nov - 30 Nov
Vacation Village Orlando, Celebration

2. Hotel-Style Room Pool, Disney Shuttle

Hotel-Style Room Pool, Disney Shuttle
3.0 star property
Kissimmee
The price is €104
includes taxes & fees
2 Dec - 3 Dec
Hotel-Style Room Pool, Disney Shuttle

3. Lyrios Vacation Rentals - The Palms

Lyrios Vacation Rentals - The Palms
4.0 star property
Kissimmee
The price is €171
includes taxes & fees
3 Nov - 4 Nov
Lyrios Vacation Rentals - The Palms

4. Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
Kissimmee
8.4 out of 10, Very good, (3,269 reviews)
"Nice property friendly place"
United States
Tina
The price is €245
includes taxes & fees
3 Nov - 4 Nov
Regal Oaks Resort Vacation Townhomes by IDILIQ

5. Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,943 reviews)
"Our favorite hotel to book in Orlando!"
United States
Mary
The price is €100
includes taxes & fees
3 Nov - 4 Nov
Barefoot Suites

6. Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (384 reviews)
"My favorite place to stay in Kissimmee"
United States
James
The price is €117
includes taxes & fees
8 Nov - 9 Nov
Barefoot'n Resort Kissimmee Orlando

7. Villas at Fortune Place

Villas at Fortune Place
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (275 reviews)
"Love it nice place to stay"
United States
iris
The price is €94
includes taxes & fees
16 Nov - 17 Nov
Villas at Fortune Place

8. 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, (2,351 reviews)
"The cottages wonderful will book again"
United States
Cadine
The price is €443
includes taxes & fees
3 Nov - 4 Nov
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

9. Sunset Bliss Retreat Condo - Near Disney

Sunset Bliss Retreat Condo - Near Disney
Kissimmee
9.6 out of 10, Exceptional, (62 reviews)
"Will stay again ! Amazing place . Host was very responsive to our needs"
United States
marie c.
The price is €139
includes taxes & fees
3 Nov - 4 Nov
Sunset Bliss Retreat Condo - Near Disney

10. 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, (12 reviews)
"Would stay again and so should you! "
United States
katie
The price is €209
includes taxes & fees
6 Nov - 7 Nov
Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

11. Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (279 reviews)
"Everyone and everything was awesome clean friendly"
United States
LaShonda
The price is €90
includes taxes & fees
16 Nov - 17 Nov
Grand Lake Resort

12. Lifetime of Vacations Resort

Lifetime of Vacations Resort
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (186 reviews)
"We absolutely love coming to lifetime and grand lake resort. This is our favorite place to stay!!"
United States
Alena
The price is €96
includes taxes & fees
29 Nov - 30 Nov
Lifetime of Vacations Resort

13. Vacation Townhomes by IDILIQ at Encantada Resort

Vacation Townhomes by IDILIQ at Encantada Resort
3.0 star property
Kissimmee
8.4 out of 10, Very good, (1,481 reviews)
"Nice stay"
United States
Pamela
The price is €241
includes taxes & fees
3 Nov - 4 Nov
Vacation Townhomes by IDILIQ at Encantada Resort

14. Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
7.0 out of 10, Good, (73 reviews)
"Yes recomende"
United States
Alex
The price is €60
includes taxes & fees
3 Nov - 4 Nov
Maple Leaf Inn & Suites

15. Luxe Condo Double Bed Bliss Getaway near Disney

Luxe Condo Double Bed Bliss Getaway near Disney
Kissimmee
8.8 out of 10, Excellent, (48 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
Luxe Condo Double Bed Bliss Getaway near Disney

16. Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
Kissimmee
9.2 out of 10, Wonderful, (177 reviews)
"Nicely kept and very roomy. "
United States
Sheila M.
The price is €178
includes taxes & fees
3 Nov - 4 Nov
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney

17. Every Bedroom Has Its Own Bathroom ~ 1.4 Miles to Disney`s Animal Kingdom

Every Bedroom Has Its Own Bathroom ~ 1.4 Miles to Disney`s Animal Kingdom
Kissimmee
9.6 out of 10, Exceptional, (47 reviews)
"Great location and space and gist was great"
United States
terri
The price is €327
includes taxes & fees
3 Nov - 4 Nov
Every Bedroom Has Its Own Bathroom ~ 1.4 Miles to Disney`s Animal Kingdom

18. The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,492 reviews)
"Excellent place to stay and CLEAN"
United States
Kristyn
The price is €125
includes taxes & fees
29 Nov - 30 Nov
The Berkley, Orlando

19. Magical Newly Renovated,1.5 miles to Disney with Tons of Eateries Near By 754

Magical Newly Renovated,1.5 miles to Disney with Tons of Eateries Near By 754
Kissimmee
9.4 out of 10, Exceptional, (36 reviews)
"My stay here was very good ! Thank you so much!"
United States
Glenda F.
The price is €158
includes taxes & fees
3 Nov - 4 Nov
Magical Newly Renovated,1.5 miles to Disney with Tons of Eateries Near By 754

20. Luxe King Suite Bliss Getaway Condo Near Disney

Luxe King Suite Bliss Getaway Condo Near Disney
Kissimmee
9.2 out of 10, Wonderful, (50 reviews)
"I was very pleased and happy with my stay at this property. It was clean, convenient to where I needed to be daily and I felt very safe. I definitely would return as it was a great stay!"
United States
Sarah M.
The price is €133
includes taxes & fees
9 Nov - 10 Nov
Luxe King Suite Bliss Getaway Condo Near Disney
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, apart-hotels, 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 favorite 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 depends 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 €90 per night. Entering your travel dates in the search wizard you might find 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. 

Explore a world of travel with Expedia

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?

Beautiful 9-bedroom house with AC in serene Kissimmee , Bring the whole Family !: This highly rated holiday home rental in Kissimmee has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Other favourite homes for rent in Kissimmee are Newly Totally Renovated-Video Game Room-Private Pool and Spacious villa with themed bedrooms and private pool.

How many holiday rentals are there in Kissimmee?

Choose from 1618 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 Center for the Arts. 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.