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In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
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2 Jan - 4 Jan
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30 Jan - 1 Feb

Top Holiday Rentals in Kissimmee

Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.6 out of 10, Excellent, (2946)
"Really relaxing customer service was extremely nice room was really nice "
Vacation Village at Parkway
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Interior

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1647)
"It was a great stay !"
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Club Wyndham Cypress Palms
2 outdoor pools, pool loungers

Club Wyndham Cypress Palms

3.5 star property
9.0 out of 10, Wonderful, (1820)
"Nice place to stay"
Club Wyndham Cypress Palms
The Berkley, Orlando
Lobby

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1934)
"Great stay!"
The price is ฿4,151
฿5,039 total
includes taxes & fees
6 Nov - 7 Nov
The Berkley, Orlando
Reunion Resort & Golf Club
Water park

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (1410)
"amazing place for families"
Reunion Resort & Golf Club
Regal Oaks Resort Vacation Townhomes by IDILIQ
View from property

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very good, (2986)
"Loved the location of the property and that the property was gated"
Regal Oaks Resort Vacation Townhomes by IDILIQ
Encantada Resort Vacation Townhomes by IDILIQ
2 outdoor pools, pool umbrellas, pool loungers

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1385)
"The unit was great for our large group of people. The only issue was some cheaply made furniture that seemed very wobbly. "
Encantada Resort Vacation Townhomes by IDILIQ
Magical Dreams
Outdoor pool

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 ฿2,271
฿4,787 total
includes taxes & fees
16 Oct - 17 Oct
Magical Dreams
Barefoot'n Resort Kissimmee Orlando
Exterior

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.0 out of 10, Wonderful, (147)
"Loved being able to walk across the street to Old Town. Large space and a great price. "
The price is ฿3,126
฿3,953 total
includes taxes & fees
9 Oct - 10 Oct
Barefoot'n Resort Kissimmee Orlando
Magic Village Yards, Trademark Collection by Wyndham
Outdoor pool, pool umbrellas, pool loungers

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1146)
"Spacious accommodations near Disney, with some amenities. "
Magic Village Yards, Trademark Collection by Wyndham
Club Wyndham Star Island
2 outdoor pools, pool loungers

Club Wyndham Star Island

3.5 star property
8.2 out of 10, Very good, (438)
"The rooms were very clean & equipped with every little item we were going to need in the kitchen/bedrooms/bedrooms. We also had washer/dryer to leave with clean clothes from our stay. I will definitely recommend this place for a family/friend getaway. "
Club Wyndham Star Island
Grand Lake Resort
Dock

Grand Lake Resort

3.0 star property
9.2 out of 10, Wonderful, (141)
"Amber was great we had a ball definitely coming back resort was beautiful "
Grand Lake Resort
Barefoot Suites
Dock

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1772)
"Much better than the last stay there!"
Barefoot Suites
Enchanted Fantasy
Terrace/patio

Enchanted Fantasy

3.5 star property
The price is ฿1,947
฿4,419 total
includes taxes & fees
21 Oct - 22 Oct
Enchanted Fantasy
Lifetime of Vacations Resort
Lake view

Lifetime of Vacations Resort

3.0 star property
9.4 out of 10, Exceptional, (147)
"Quiet place "
Lifetime of Vacations Resort
Formosa Valley Resort by UNE Homes
Private pool

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (170)
"Great stay"
Formosa Valley Resort by UNE Homes
Enchanted Dreams
Full-sized fridge, microwave, oven, stovetop

Enchanted Dreams

3.5 star property
8.0 out of 10, Very good, (4)
"Clean, comfortable home. Everything was excellent from the security to amenities. I will book again, share with friends and family. "
The price is ฿2,271
฿4,787 total
includes taxes & fees
17 Oct - 18 Oct
Enchanted Dreams
Villas at Fortune Place
2 outdoor pools, open 7:00 AM to midnight, pool umbrellas, pool loungers

Villas at Fortune Place

3.0 star property
8.8 out of 10, Excellent, (137)
"Nice place plenty of room, convenient for the event we attended Thanks"
Villas at Fortune Place
Royal Laguna Villas By Magical Memories
Lobby

Royal Laguna Villas By Magical Memories

3.5 star property
7.0 out of 10, Good, (2336)
"the apartment is comfortable and pleasant but the air conditioning does not work, there is only a ceiling fan in the main room and in the living room. They did not give us the card for the pool area and it was a problem to pay and get the lockbox code."
Royal Laguna Villas By Magical Memories
Summerville Vacation Homes by Columbia Management
Captiva-06 (SMV104) | Private kitchen | Fridge, microwave, oven, stovetop

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

Ramada by Wyndham Hotel & Water Park

Ramada by Wyndham Hotel & Water Park

10/10 Excellent
"Very good"
Isaac 3-night trip
Posted 2 days ago
Ramada by Wyndham Hotel & Water Park

Find out more about Kissimmee

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!

Explore a world of travel with Expedia

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?

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 Royal Laguna Villas By Magical Memories.

How many holiday rentals are there in Kissimmee?

Choose from 15208 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.