Search Holiday Rentals in Kissimmee

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
26 Sep - 27 Sep
Tomorrow
27 Sep - 28 Sep
This weekend
26 Sep - 28 Sep
Next weekend
3 Oct - 5 Oct

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, (2912)
"Clean rooms and wonderful staff"
The price is 2.335.693 ₫
3.100.894 ₫ total
includes taxes & fees
28 Sept - 29 Sept
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, (1635)
"Great place to 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, (1810)
"Nice place to stay"
Club Wyndham Cypress Palms
Reunion Resort & Golf Club
Water park

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (1402)
"Great place for the family "
Reunion Resort & Golf Club
The Berkley, Orlando
Lobby

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1918)
"Great stay!"
The price is 2.919.079 ₫
3.583.796 ₫ total
includes taxes & fees
28 Sept - 29 Sept
The Berkley, Orlando
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, (2982)
"Loved the location of the property and that the property was gated"
Regal Oaks 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 1.848.070 ₫
3.895.469 ₫ total
includes taxes & fees
28 Sept - 29 Sept
Magical Dreams
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, (1379)
"Very nice resort "
Encantada Resort Vacation Townhomes by IDILIQ
Barefoot'n Resort Kissimmee Orlando
Exterior

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.0 out of 10, Wonderful, (142)
"Great place, would definitely stay there again "
The price is 1.793.473 ₫
2.365.208 ₫ 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, (1145)
"Spacious accommodations near Disney, with some amenities. "
Magic Village Yards, Trademark Collection by Wyndham
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 1.584.060 ₫
3.595.818 ₫ total
includes taxes & fees
28 Sept - 29 Sept
Enchanted Dreams
Barefoot Suites
Dock

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1768)
"We have stayed numerous times. We love the property and love staying across the street from Fun Spot. Its nice to be able to stroll out every evening, shop, dine and have some fun. The 2 bedroom was very nice, clean and super roomy! We will be back as usual."
Barefoot Suites
Grand Lake Resort
Dock

Grand Lake Resort

3.0 star property
9.2 out of 10, Wonderful, (138)
"We stay here often as we are Disney season pass holders. This place is excellent. Always clean, great location, a lot of bang for your buck and staff is very friendly. "
Grand Lake Resort
Club Wyndham Star Island
2 outdoor pools, pool loungers

Club Wyndham Star Island

3.5 star property
8.2 out of 10, Very good, (437)
"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
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
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
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
Encore Resort
Outdoor pool

Encore Resort

4.0 star property
6.4 out of 10, (117)
"Great place "
Encore Resort
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

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

10/10 Excellent
"El desayuno estuvo bien, las habitaciones estaban amplias y el trato muy bien"
Sabrina 2-night trip
Posted 21 hours ago
Palazzo Lakeside Hotel

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.

How many holiday rentals are there in Kissimmee?

Choose from 15166 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.