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

Kissimmee Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Kissimmee holiday rentals

A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

1. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (5,230 reviews)
"Awesome place to stay!"
United States
Richard Allen
The price is HK$566
HK$838 total
includes taxes & fees
10 Nov - 11 Nov
Vacation Village Orlando, Celebration
An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.

2. 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, (2,335 reviews)
"The cottages wonderful will book again"
United States
Cadine
The price is HK$1,443
HK$3,742 total
includes taxes & fees
2 Nov - 3 Nov
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
A two-story house with a porch, surrounded by palm trees and greenery.

3. Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (381 reviews)
"My favorite place to stay in Kissimmee"
United States
James
The price is HK$803
HK$1,009 total
includes taxes & fees
30 Oct - 31 Oct
Barefoot'n Resort Kissimmee Orlando
An aerial view of a resort with two large swimming pools, a tennis court, and a small playground.

4. Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,941 reviews)
"Our favorite hotel to book in Orlando!"
United States
Mary
The price is HK$865
HK$1,136 total
includes taxes & fees
27 Oct - 28 Oct
Barefoot Suites
A rustic outdoor seating area with wooden chairs and a fire pit, surrounded by a wooden fence and palm trees.

5. Disney's Animal Kingdom Villas - Kidani Village

Disney's Animal Kingdom Villas - Kidani Village
4.0 star property
Bay Lake
9.0 out of 10, Wonderful, (174 reviews)
"Outstanding customer service. The Savannah view was amazing!"
United States
Mansi
The price is HK$4,196
HK$4,720 total
includes taxes & fees
1 Nov - 2 Nov
Disney's Animal Kingdom Villas - Kidani Village
A pool area with lounge chairs and umbrellas, surrounded by a fence and buildings.

6. Villas at Fortune Place

Villas at Fortune Place
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (268 reviews)
"Love it nice place to stay"
United States
iris
The price is HK$660
HK$820 total
includes taxes & fees
8 Nov - 9 Nov
Villas at Fortune Place
A resort with a large central pool, multiple guest villas, and a scenic view of the surrounding landscape.

7. 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, (3,266 reviews)
"Nice property friendly place"
United States
Tina
Regal Oaks Resort Vacation Townhomes by IDILIQ
A swimming pool with a curved design, surrounded by a paved deck and a fence.

8. Lyrios Vacation Rentals - The Palms

Lyrios Vacation Rentals - The Palms
4.0 star property
Kissimmee
The price is HK$699
HK$1,496 total
includes taxes & fees
27 Oct - 28 Oct
Lyrios Vacation Rentals - The Palms
A modern living room with a glass dining table, leather sofas, and a flat-screen TV.

9. Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (273 reviews)
"Very nice room for families! Loved having the kitchen will come back to explore more next time."
United States
Leslie
The price is HK$630
HK$786 total
includes taxes & fees
8 Nov - 9 Nov
Grand Lake Resort
A modern kitchen with a dining area, featuring a large island, grey and beige furniture, and a TV mounted on the wall.

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 HK$753
HK$1,906 total
includes taxes & fees
3 Nov - 4 Nov
Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
A view of a park with a lake, benches, and trees.

11. 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 HK$630
HK$848 total
includes taxes & fees
8 Nov - 9 Nov
Lifetime of Vacations Resort
A spacious lobby with a grand chandelier, large windows offering a view of a pool, and a second-floor balcony with a railing.

12. The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,480 reviews)
"Excellent place to stay and CLEAN"
United States
Kristyn
The price is HK$989
HK$1,201 total
includes taxes & fees
15 Nov - 16 Nov
The Berkley, Orlando
A spacious lobby with modern furniture, large windows, and a high ceiling.

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, (1,480 reviews)
"Nice stay"
United States
Pamela
The price is HK$494
HK$2,110 total
includes taxes & fees
27 Oct - 28 Oct
Vacation Townhomes by IDILIQ at Encantada Resort
A pool area with a waterfall, palm trees, and a rocky backdrop.

14. Reunion Resort & Golf Club

Reunion Resort & Golf Club
5.0 star property
Reunion
8.8 out of 10, Excellent, (1,632 reviews)
"Huge property - not a golfer but still enjoyed the stay"
United States
Karen G
The price is HK$2,322
HK$3,007 total
includes taxes & fees
27 Oct - 28 Oct
Reunion Resort & Golf Club
A hotel room with two beds, a desk, a chair, a TV, and a window with a view of greenery.

15. Hotel-Style Room Pool, Disney Shuttle

Hotel-Style Room Pool, Disney Shuttle
3.0 star property
Kissimmee
The price is HK$254
HK$858 total
includes taxes & fees
27 Oct - 28 Oct
Hotel-Style Room Pool, Disney Shuttle
A hotel room with two beds, a desk, a chair, and a TV.

16. Budget Disney Room Pool & Parking

Budget Disney Room Pool & Parking
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"⭐ 0-Star – Unacceptable Conditions and Terrible Customer Service We booked a room for my elderly mother through Hotels.com, and the conditions were absolutely unacceptable. There was visible mold in the room, creating serious concerns about her health and safety. What made matters worse was that a staff member openly admitted that mold is a problem throughout the hotel and that they regularly wipe down the walls to keep it from returning. He also stated that management had been informed...
United States
Kevin
The price is HK$233
HK$834 total
includes taxes & fees
2 Nov - 3 Nov
Budget Disney Room Pool & Parking
A decorative stone fountain with a twisted base, surrounded by vibrant red flowers and tropical foliage, set against a backdrop of a pool and palm trees.

17. Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
6.8 out of 10, (72 reviews)
"The room was clean and the staff was okay "
United States
Shaneka
The price is HK$463
HK$525 total
includes taxes & fees
27 Oct - 28 Oct
Maple Leaf Inn & Suites
A swimming pool with a hot tub, surrounded by a glass enclosure with a view of a residential area.

18. Harmony Ensuite Room Shared Home No Car

Harmony Ensuite Room Shared Home No Car
2.5 star property
Kissimmee
The price is HK$345
HK$1,015 total
includes taxes & fees
27 Oct - 28 Oct
Harmony Ensuite Room Shared Home No Car
A balcony with a table and chairs, overlooking a parking area and a body of water.

19. Sunset Bliss Retreat Condo - Near Disney

Sunset Bliss Retreat Condo - Near Disney
Kissimmee
9.6 out of 10, Exceptional, (61 reviews)
"Will stay again ! Amazing place . Host was very responsive to our needs"
United States
marie c.
The price is HK$408
HK$1,234 total
includes taxes & fees
27 Oct - 28 Oct
Sunset Bliss Retreat Condo - Near Disney
A modern kitchen with white cabinets, a central island, and pendant lighting. There is a dining area with a bar stool and a TV mounted on the wall.

20. 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$459
HK$1,310 total
includes taxes & fees
1 Nov - 2 Nov
Luxe Condo Double Bed Bliss Getaway 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kissimmee Hotel Reviews

Embassy Suites By Hilton Orlando Sunset Walk

Embassy Suites By Hilton Orlando Sunset Walk

8/10 Good
"Estuvo bueno pero lleven pasta de dientes q no ponen jij y la ducha no echa bien agua"
Jenifer 2-night trip
Posted 2 hours ago
Embassy Suites By Hilton Orlando Sunset Walk

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
  • Use the map to find apartments and other holiday homes in the Kissimmee neighbourhood you prefer
  • 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?

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.