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, (5,095 reviews)
"Nice hotel and great location close to the Parks."
United States
Monica
The price is ￥11,099
￥16,533 total
includes taxes & fees
Oct 20 - Oct 21
Vacation Village Orlando, Celebration
A pool area with lounge chairs and umbrellas, surrounded by a fence and buildings.

2. Villas at Fortune Place

Villas at Fortune Place
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (238 reviews)
"Second time staying here, clean, safe, pools are great! absolutely love this location"
United States
Raymond
The price is ￥12,644
￥15,768 total
includes taxes & fees
Oct 20 - Oct 21
Villas at Fortune Place
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, (1,926 reviews)
"Great place to stay!"
United States
David
The price is ￥12,249
￥17,011 total
includes taxes & fees
Oct 4 - Oct 5
Barefoot Suites
A balcony with a table and chairs, overlooking a parking area and a body of water.

4. 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.
The price is ￥6,920
￥23,318 total
includes taxes & fees
Sep 30 - Oct 1
Sunset Bliss Retreat Condo - Near Disney
A hotel with a swimming pool, palm trees, and outdoor seating areas.

5. 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
The price is ￥21,092
￥23,938 total
includes taxes & fees
Oct 14 - Oct 15
Club Wyndham Cypress Palms
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
The price is ￥13,558
￥29,502 total
includes taxes & fees
Oct 6 - Oct 7
Lyrios Vacation Rentals - The Palms
A two-story house with a porch, surrounded by palm trees and greenery.

7. Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (372 reviews)
"Nice rooms pool was great definitely will be back"
United States
Gilbert
The price is ￥15,827
￥19,931 total
includes taxes & fees
Oct 11 - Oct 12
Barefoot'n Resort Kissimmee Orlando
A modern kitchen with white cabinets, a central island with two stools, and a dining area with a sofa and coffee table.

8. 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.
The price is ￥14,533
￥33,385 total
includes taxes & fees
Oct 5 - Oct 6
Cloud Nine • 1BR 15 MIN from Kissimmee Main Street
A spacious lobby with a grand chandelier, large windows offering a view of a pool, and a second-floor balcony with a railing.

9. The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,430 reviews)
"Great place"
Canada
Stefanny
The price is ￥21,437
￥25,886 total
includes taxes & fees
Oct 1 - Oct 2
The Berkley, Orlando
A resort with a large central pool, multiple guest villas, and a scenic view of the surrounding landscape.

10. 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, (3,238 reviews)
"We had an amazing time ,the facility was spotless very roomy and great access to everything you may need."
United States
Sobeyda F
The price is ￥13,424
￥46,297 total
includes taxes & fees
Sep 30 - Oct 1
Regal Oaks Resort Vacation Townhomes by IDILIQ
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.

11. 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 ￥7,792
￥24,677 total
includes taxes & fees
Sep 30 - Oct 1
Luxe Condo Double Bed Bliss Getaway near Disney
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

12. Think Pink in Kissimmee - Gorgeous 2BD with free WIFI, free parking and more!!

Think Pink in Kissimmee - Gorgeous 2BD with free WIFI, free parking and more!!
Kissimmee
9.6 out of 10, Exceptional, (14 reviews)
"Great spot!"
United States
Candice M.
The price is ￥15,712
￥34,365 total
includes taxes & fees
Sep 30 - Oct 1
Think Pink in Kissimmee - Gorgeous 2BD with free WIFI, free parking and more!!
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.

13. 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
Maple Leaf Inn & Suites
A modern living room with a glass dining table, leather sofas, and a flat-screen TV.

14. Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (254 reviews)
"I enjoyed my stay at this hotel and the pool was clean and refreshing"
United States
LeeAnna
The price is ￥11,678
￥14,672 total
includes taxes & fees
Sep 30 - Oct 1
Grand Lake Resort
Interior

15. Sunset Greens Villa

Sunset Greens Villa
2.0 star property
Reunion
10.0 out of 10, Exceptional, (1 review)
"Very nice property"
United States
Richard
The price is ￥12,417
￥63,534 total
includes taxes & fees
Oct 7 - Oct 8
Sunset Greens Villa
A thatched-roof gazebo with a wooden fence, surrounded by white lounge chairs on a sandy area.

16. 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
The price is ￥10,853
￥14,994 total
includes taxes & fees
Sep 30 - Oct 1
Lifetime of Vacations Resort
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

17. 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.
The price is ￥13,695
￥45,492 total
includes taxes & fees
Sep 30 - Oct 1
Charming 2-bedroom Florida Getaway! Sleeps 6
A modern kitchen with white cabinets, a central island with bar stools, a stainless steel microwave, and a built-in oven.

18. Luxe King Suite Bliss Getaway Condo Near Disney

Luxe King Suite Bliss Getaway Condo Near Disney
Kissimmee
9.2 out of 10, Wonderful, (49 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.
The price is ￥8,210
￥24,781 total
includes taxes & fees
Sep 30 - Oct 1
Luxe King Suite Bliss Getaway Condo Near Disney
An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.

19. 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, (2,285 reviews)
"Clean property, friendly staff, close to everything!"
United States
Matthew
The price is ￥25,373
￥71,024 total
includes taxes & fees
Oct 28 - Oct 29
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
A spacious living room with grey sofas, a coffee table with flowers, and a kitchen area visible through large windows.

20. Cozy 2BD/2BTH Condo Near Disney

Cozy 2BD/2BTH Condo Near Disney
Kissimmee
9.4 out of 10, Exceptional, (37 reviews)
"Comfy, cute, clean and affordable place to stay!"
United States
Anna W.
The price is ￥10,900
￥29,799 total
includes taxes & fees
Oct 4 - Oct 5
Cozy 2BD/2BTH Condo 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.
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Top Kissimmee Hotel Reviews

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark

10/10 Excellent
"Good"
Yadira 2-night trip
Posted 1 hour ago
Margaritaville Resort Orlando with H2O Waterpark

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
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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.