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

Kissimmee Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Kissimmee vacation rentals

A living room with a sofa, two armchairs, a coffee table, a TV stand, a ceiling fan, and a large window with a view of greenery.

1. Alhambra Villas by Coolvacay

Alhambra Villas by Coolvacay
3.0 star property
Solivita
9.2 out of 10, Wonderful, (1,015 reviews)
"Great place, clean, and convenient for our trip to Disney and universal."
United States
Tanya
$80 nightly
The price is $90
Sep 1 - Sep 2
Total with taxes and fees
Alhambra Villas by Coolvacay
An outdoor patio area with wicker furniture, a fire pit, and a view of a pool and greenery.

2. Parkway International Resort by Coolvacay

Parkway International Resort by Coolvacay
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (2,551 reviews)
"Great for families and kids clean room and nice pool area"
United States
Eusebio
$120 nightly
The price is $136
Sep 1 - Sep 2
Total with taxes and fees
Parkway International Resort by Coolvacay
A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

3. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (4,948 reviews)
"Enjoyed the stay booked again"
United States
Joseph
$97 nightly
The price is $110
Sep 10 - Sep 11
Total with taxes and fees
Vacation Village Orlando, Celebration
A pool area with lounge chairs and umbrellas, surrounded by a fence and buildings.

4. Villas at Fortune Place

Villas at Fortune Place
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (214 reviews)
"Great stay for the cost. Close to all the parks & the airport. Would definitely book this spot again."
United States
Joseph
$85 nightly
The price is $95
Sep 21 - Sep 22
Total with taxes and fees
Villas at Fortune Place
A two-story house with a porch, surrounded by palm trees and greenery.

5. Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (364 reviews)
"Great aminities"
United States
Carlos
$119 nightly
The price is $135
Sep 7 - Sep 8
Total with taxes and fees
Barefoot'n Resort Kissimmee Orlando
An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.

6. 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, (2,230 reviews)
"nice place to stay!"
United States
Victor
$440 nightly
The price is $500
Sep 1 - Sep 2
Total with taxes and fees
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
A hotel with a swimming pool, multiple balconies, and outdoor seating areas.

7. The Irlo

The Irlo
3.0 star property
Kissimmee
7.6 out of 10, Good, (101 reviews)
"Great rooms staff was nice"
United States
Hargeni
$76 nightly
The price is $86
Sep 9 - Sep 10
Total with taxes and fees
The Irlo
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.

8. 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
$59 nightly
The price is $67
Sep 1 - Sep 2
Total with taxes and fees
Maple Leaf Inn & Suites
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, (240 reviews)
"Loved it! Would definitely stay again."
United States
Lissette
$90 nightly
The price is $101
Sep 7 - Sep 8
Total with taxes and fees
Grand Lake Resort
A balcony with a table and chairs, overlooking a parking area and a body of water.

10. Sunset Bliss Retreat Condo - Near Disney

Sunset Bliss Retreat Condo - Near Disney
Kissimmee
9.6 out of 10, Exceptional, (57 reviews)
"Everything was perfect, next time I will stay here again"
United States
Luis Pedro L.
$147 nightly
The price is $165
Sep 1 - Sep 2
Total with taxes and fees
Sunset Bliss Retreat Condo - Near Disney
A thatched-roof gazebo with a wooden fence, surrounded by white lounge chairs on a sandy area.

11. Lifetime of Vacations Resort

Lifetime of Vacations Resort
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (178 reviews)
"Best value option in the area. May be a bit out of date and directly on the strip, but clean, well maintained, and a really nice view. Great value for the money."
United States
Kevin
$89 nightly
The price is $98
Sep 14 - Sep 15
Total with taxes and fees
Lifetime of Vacations Resort
A spacious living room with grey sofas, a coffee table with flowers, and a kitchen area visible through large windows.

12. Cozy 2BD/2BTH Condo Near Disney

Cozy 2BD/2BTH Condo Near Disney
Kissimmee
9.2 out of 10, Wonderful, (35 reviews)
"Comfy, cute, clean and affordable place to stay!"
United States
Anna W.
$173 nightly
The price is $194
Sep 1 - Sep 2
Total with taxes and fees
Cozy 2BD/2BTH Condo Near Disney
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

13. 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.
$261 nightly
The price is $292
Sep 8 - Sep 9
Total with taxes and fees
Charming 2-bedroom Florida Getaway! Sleeps 6
A modern kitchen with white cabinets, a central island with two stools, and a dining area with a sofa and coffee table.

14. 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.
$221 nightly
The price is $246
Sep 1 - Sep 2
Total with taxes and fees
Cloud Nine • 1BR 15 MIN from Kissimmee Main Street
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.

15. Luxe Condo Double Bed Bliss Getaway near Disney

Luxe Condo Double Bed Bliss Getaway near Disney
Kissimmee
8.8 out of 10, Excellent, (46 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
$157 nightly
The price is $175
Sep 13 - Sep 14
Total with taxes and fees
Luxe Condo Double Bed Bliss Getaway near Disney
A spacious lobby with a grand chandelier, large windows offering a view of a pool, and a second-floor balcony with a railing.

16. The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,388 reviews)
"The place was wonderful, clean, spacious and staff was very friendly. This is our go to place when we go to Disney!!"
United States
Lauren
$128 nightly
The price is $144
Sep 3 - Sep 4
Total with taxes and fees
The Berkley, Orlando
A modern kitchen with white cabinets, a central island with bar stools, a stainless steel microwave, and a built-in oven.

17. 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.
$163 nightly
The price is $182
Sep 1 - Sep 2
Total with taxes and fees
Luxe King Suite Bliss Getaway Condo Near Disney
A modern kitchen with a central island, stainless steel appliances, and a blue accent wall.

18. 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.
$204 nightly
The price is $227
Sep 1 - Sep 2
Total with taxes and fees
Lovely remodeled 1 bed, 1 bath Condo, Just miles from Disney! Great location.
A modern kitchen with a dining area, featuring a large island, grey and beige furniture, and a TV mounted on the wall.

19. 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
$227 nightly
The price is $255
Sep 7 - Sep 8
Total with taxes and fees
Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
A modern living room with a grey couch, a coffee table, and a TV mounted on the wall. There are large windows providing a view of the street and houses outside.

20. Completely Renovated 3/2 Close to Disney parks

Completely Renovated 3/2 Close to Disney parks
Royal Palm Bay
10.0 out of 10, Exceptional, (35 reviews)
"Rental was spacious and met all of our needs."
United States
Nikolaus K.
$214 nightly
The price is $239
Sep 1 - Sep 2
Total with taxes and fees
Completely Renovated 3/2 Close to Disney parks
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

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

10/10 Excellent
"The property was beautiful and relaxing, with a fun vibe."
Susan 2-night trip
Posted less than an hour ago
Margaritaville Resort Orlando with H2O Waterpark

Price trends for vacation rentals in Kissimmee

Less expensive
More expensive
Next month
May
December
$212
Month
Price
January
$264
February
$232
March
$221
April
$191
May
$186
June
$226
July
$219
August
$212
September
$212
October
$219
November
$228
December
$269
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Kissimmee. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Kissimmee

Everything you need to know about Kissimmee vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kissimmee vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kissimmee vacation 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 low season months. For more hustle and bustle, you may prefer to visit Kissimmee in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $86 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Kissimmee rentals

At Expedia, we put the best Kissimmee vacation 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 vacation.

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 vacation rentals in Kissimmee?

Yes, we have vacation rentals in Kissimmee close to Disney's Animal Kingdom® Theme Park, or you can select a secluded option if you'd like a relaxing place to 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's the top vacation rental that Kissimmee has to offer?

Formosa Valley Resort by UNE Homes: This Kissimmee vacation home rental 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. Another good choice for your trip to Kissimmee is Charming 3-bedroom house w/ AC in Kissimmee, nearby Disney, Walmart, Ross & more.

How many vacation rentals are there in Kissimmee?

Choose from 1624 Expedia vacation rentals in Kissimmee for a memorable vacation.

What can I see and do in Kissimmee?

Disney's Animal Kingdom® Theme Park and Walt Disney World® Resort are a couple of 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 vacation rentals like in Kissimmee?

Vacation rentals are privately owned properties you can book for several days or more in Kissimmee. Vacation rentals offer amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family trip.