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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Kissimmee vacation 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, (5,108 reviews)
"Great place"
United States
Wilbert
$98 nightly
The price is $111
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village Orlando, Celebration
A two-story house with a porch, surrounded by palm trees and greenery.

2. Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (374 reviews)
"Nice rooms pool was great definitely will be back"
United States
Gilbert
$100 nightly
The price is $114
Oct 13 - Oct 14
Total with taxes and fees
Barefoot'n Resort Kissimmee Orlando
An aerial view of a resort with two large swimming pools, a tennis court, and a small playground.

3. Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,927 reviews)
"Great place to stay!"
United States
David
$103 nightly
The price is $117
Oct 4 - Oct 5
Total with taxes and fees
Barefoot Suites
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
9.2 out of 10, Wonderful, (243 reviews)
"Second time staying here, clean, safe, pools are great! absolutely love this location"
United States
Raymond
$98 nightly
The price is $110
Oct 20 - Oct 21
Total with taxes and fees
Villas at Fortune Place
An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.

5. 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, (2,292 reviews)
"Clean property, friendly staff, close to everything!"
United States
Matthew
$391 nightly
The price is $444
Oct 26 - Oct 27
Total with taxes and fees
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
A covered outdoor area with a wooden picnic table and benches, a grill, and a ceiling fan.

6. Lyrios Vacation Rentals - The Palms

Lyrios Vacation Rentals - The Palms
4.0 star property
Kissimmee
$162 nightly
The price is $184
Nov 3 - Nov 4
Total with taxes and fees
Lyrios Vacation Rentals - The Palms
A hotel room with a large bed, a colorful abstract painting, a window with a view, and a chair.

7. Hotel-Style Room Pool, Disney Shuttle

Hotel-Style Room Pool, Disney Shuttle
3.0 star property
Kissimmee
$92 nightly
The price is $104
Oct 4 - Oct 5
Total with taxes and fees
Hotel-Style Room Pool, Disney Shuttle
A hotel with a swimming pool, palm trees, and outdoor seating areas.

8. Club Wyndham Cypress Palms

Club Wyndham Cypress Palms
3.5 star property
Kissimmee
9.0 out of 10, Wonderful, (1,980 reviews)
"The place was nice clean and amazing will return in December"
United States
Natarisha
$125 nightly
The price is $142
Oct 14 - Oct 15
Total with taxes and fees
Club Wyndham Cypress Palms
A thatched-roof gazebo with a wooden fence, surrounded by white lounge chairs on a sandy area.

9. Lifetime of Vacations Resort

Lifetime of Vacations Resort
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (182 reviews)
"We absolutely love coming to lifetime and grand lake resort. This is our favorite place to stay!!"
United States
Alena
$99 nightly
The price is $110
Oct 6 - Oct 7
Total with taxes and fees
Lifetime of Vacations 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, (59 reviews)
"Will stay again ! Amazing place . Host was very responsive to our needs"
United States
marie c.
$141 nightly
The price is $157
Oct 10 - Oct 11
Total with taxes and fees
Sunset Bliss Retreat Condo - Near Disney
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.

11. 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
$59 nightly
The price is $67
Oct 5 - Oct 6
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.

12. Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (258 reviews)
"I enjoyed my stay at this hotel and the pool was clean and refreshing"
United States
LeeAnna
$93 nightly
The price is $105
Oct 5 - Oct 6
Total with taxes and fees
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.

13. 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, (11 reviews)
"Would stay again and so should you! "
United States
katie
$236 nightly
The price is $265
Oct 12 - Oct 13
Total with taxes and fees
Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
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.

14. 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
$148 nightly
The price is $165
Oct 4 - Oct 5
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.

15. The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,435 reviews)
"Clean rooms, great pool area, reasonably priced"
United States
Dean
$150 nightly
The price is $169
Nov 1 - Nov 2
Total with taxes and fees
The Berkley, Orlando
A modern kitchen with a refrigerator, stove, microwave, and dishwasher.

16. Pond Access & Grill! Group Escape, 19 Mi to WDW

Pond Access & Grill! Group Escape, 19 Mi to WDW
3.0 star property
Kissimmee
$178 nightly
The price is $202
Oct 4 - Oct 5
Total with taxes and fees
Pond Access & Grill! Group Escape, 19 Mi to WDW
A rustic outdoor seating area with wooden chairs and a fire pit, surrounded by a wooden fence and palm trees.

17. 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, (173 reviews)
"Clean room. Staff was friendly. My grand daughter loved getting Disney character stickers from the gift shop staff. Pool was amazing!"
United States
Katrina
$535 nightly
The price is $602
Oct 5 - Oct 6
Total with taxes and fees
Disney's Animal Kingdom Villas - Kidani Village
A modern kitchen with dark cabinetry, stainless steel appliances, and a granite countertop.

18. LOVELY LUXURY APARTMENT CLOSE DISNEY

LOVELY LUXURY APARTMENT CLOSE DISNEY
3.5 star property
Kissimmee
8.4 out of 10, Very good, (11 reviews)
"Nice appartment, everything you needed and clean and modern"
United Kingdom
Martyn
$281 nightly
The price is $318
Oct 4 - Oct 5
Total with taxes and fees
LOVELY LUXURY APARTMENT CLOSE DISNEY
A swimming pool with lounge chairs and palm trees, surrounded by buildings with green roofs.

19. Dazzling Newly Renovated Condo 1.5 miles to Disney

Dazzling Newly Renovated Condo 1.5 miles to Disney
Kissimmee
9.4 out of 10, Exceptional, (113 reviews)
"Enjoyed our stay!"
United States
Richard H.
$157 nightly
The price is $176
Oct 6 - Oct 7
Total with taxes and fees
Dazzling Newly Renovated Condo 1.5 miles to Disney
A hotel room with a bed, a TV mounted on the wall, a small table with a vase, and a trash can.

20. Sophisticated Retreat

Sophisticated Retreat
Kissimmee
9.2 out of 10, Wonderful, (12 reviews)
"Everything was as expected and really comfortable "
United States
Vincent T.
$173 nightly
The price is $194
Oct 4 - Oct 5
Total with taxes and fees
Sophisticated Retreat
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

Legacy Vacation Resorts - Kissimmee/Orlando

Legacy Vacation Resorts - Kissimmee/Orlando

10/10 Excellent
"Very good"
Angelo 2-night trip
Posted less than an hour ago
Legacy Vacation Resorts - Kissimmee/Orlando

Price trends for vacation rentals in Kissimmee

Less expensive
More expensive
This month
Next month
May
December
$219
$228
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 $105 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?

Beautiful 9-bedroom house with AC in serene Kissimmee , Bring the whole Family !: This Kissimmee vacation home rental has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Other favorite 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 vacation rentals are there in Kissimmee?

Choose from 1618 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 Osceola Center for the Arts. 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.