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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (5,075 reviews)
"Nice hotel and great location close to the Parks."
United States
Monica
$97 nightly
The price is $110
Oct 25 - Oct 26
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, (369 reviews)
"Nice rooms pool was great definitely will be back"
United States
Gilbert
$143 nightly
The price is $162
Sep 27 - Sep 28
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, (1,925 reviews)
"Great place to stay!"
United States
David
$107 nightly
The price is $121
Sep 27 - Sep 28
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, (235 reviews)
"Definitely coming back and all the staff was amazing 😍😍"
United States
Shannon
$98 nightly
The price is $110
Oct 20 - Oct 21
Total with taxes and fees
Villas at Fortune Place
A modern kitchen with a central island, built-in appliances, and a large window providing natural light.

5. Resort Stay~Near Disney~Bright~Gym~Hot Tub

Resort Stay~Near Disney~Bright~Gym~Hot Tub
Kissimmee
10.0 out of 10, Exceptional, (9 reviews)
"Property was very clean and convenient and host communication was excellent"
United States
John
$378 nightly
The price is $399
Oct 3 - Oct 4
Total with taxes and fees
Resort Stay~Near Disney~Bright~Gym~Hot Tub
A spacious lobby with a grand chandelier, large windows offering a view of a pool, and a second-floor balcony with a railing.

6. The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,426 reviews)
"Great place"
Canada
Stefanny
$134 nightly
The price is $150
Sep 28 - Sep 29
Total with taxes and fees
The Berkley, Orlando
A balcony with a table and chairs, overlooking a parking area and a body of water.

7. Sunset Bliss Retreat Condo - Near Disney

Sunset Bliss Retreat Condo - Near Disney
Kissimmee
9.6 out of 10, Exceptional, (58 reviews)
"Will stay again ! Amazing place . Host was very responsive to our needs"
United States
marie c.
$133 nightly
The price is $148
Sep 27 - Sep 28
Total with taxes and fees
Sunset Bliss Retreat Condo - Near Disney
A covered outdoor area with a wooden picnic table and benches, a grill, and a ceiling fan.

8. Lyrios Vacation Rentals - The Palms

Lyrios Vacation Rentals - The Palms
4.0 star property
Kissimmee
$178 nightly
The price is $202
Oct 3 - Oct 4
Total with taxes and fees
Lyrios Vacation Rentals - The Palms
A hotel with a swimming pool, palm trees, and outdoor seating areas.

9. Club Wyndham Cypress Palms

Club Wyndham Cypress Palms
3.5 star property
Kissimmee
9.0 out of 10, Wonderful, (1,979 reviews)
"The place was nice clean and amazing will return in December"
United States
Natarisha
$134 nightly
The price is $152
Oct 14 - Oct 15
Total with taxes and fees
Club Wyndham Cypress Palms
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
$266 nightly
The price is $302
Sep 27 - Sep 28
Total with taxes and fees
Regal Oaks Resort Vacation Townhomes by IDILIQ
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, (182 reviews)
"We absolutely love coming to lifetime and grand lake resort. This is our favorite place to stay!!"
United States
Alena
$94 nightly
The price is $105
Sep 27 - Sep 28
Total with taxes and fees
Lifetime of Vacations Resort
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.

12. 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
$141 nightly
The price is $157
Sep 28 - Sep 29
Total with taxes and fees
Luxe Condo Double Bed Bliss Getaway near Disney
A modern living room with a glass dining table, leather sofas, and a flat-screen TV.

13. 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
$93 nightly
The price is $105
Sep 27 - Sep 28
Total with taxes and fees
Grand Lake Resort
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.

14. 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
Sep 27 - Sep 28
Total with taxes and fees
Maple Leaf Inn & Suites
A modern bedroom with a large bed, a ceiling fan, and a view of a pool and building.

15. Private Resort Access~King Bed~Hot Tub~Balcony

Private Resort Access~King Bed~Hot Tub~Balcony
Kissimmee
10.0 out of 10, Exceptional, (3 reviews)
"Great host and fantastic pool"
United States
paul m.
$329 nightly
The price is $348
Oct 22 - Oct 23
Total with taxes and fees
Private Resort Access~King Bed~Hot Tub~Balcony
An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.

16. 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, (2,278 reviews)
"Clean property, friendly staff, close to everything!"
United States
Matthew
$435 nightly
The price is $494
Sep 28 - Sep 29
Total with taxes and fees
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
A bedroom with a large bed, a wooden headboard, two bedside tables with lamps, a view of a swimming pool, and a sliding door.

17. Heated Pool~Game Room~Modern~Resort~Disney Magic

Heated Pool~Game Room~Modern~Resort~Disney Magic
Lake Berkley
10.0 out of 10, Exceptional, (2 reviews)
"We absolutely loved our stay in this home. The host's were extremely kind and responsive. The home was squeaky clean and the beds were super comfy. We cannot wait to book again. Thank you Derek & Lauren!!!"
United States
Kelly F.
$412 nightly
The price is $435
Sep 30 - Oct 1
Total with taxes and fees
Heated Pool~Game Room~Modern~Resort~Disney Magic

18. 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
$365 nightly
The price is $415
Oct 7 - Oct 8
Total with taxes and fees
Sunset Greens Villa
A modern kitchen with white cabinets, a central island with bar stools, a stainless steel microwave, and a built-in oven.

19. 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.
$141 nightly
The price is $158
Sep 28 - Sep 29
Total with taxes and fees
Luxe King Suite Bliss Getaway Condo Near Disney
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

20. Storey Lake Resort~Heated Pool~Brand New~Designer

Storey Lake Resort~Heated Pool~Brand New~Designer
Kissimmee
10.0 out of 10, Exceptional, (7 reviews)
"We had a great stay. Host was very attentive and responded back quickly anytime we had a question before or during our stay. Resort amenities were wonderful and location was great! We would stay again! "
United States
Amber K.
$435 nightly
The price is $459
Oct 12 - Oct 13
Total with taxes and fees
Storey Lake Resort~Heated Pool~Brand New~Designer
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

Galleria Palms Hotel

Galleria Palms Hotel

10/10 Excellent
"Genuinely one of the nicest hotels I’ve stayed at: no bugs, pleasant staff, comfortable beds"
Samantha 1-night trip
Posted 2 hours ago
Galleria Palms Hotel

Price trends for vacation rentals in Kissimmee

Less expensive
More expensive
Next month
May
December
$219
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 The Most Fun House with tons of room, huge pool, pickleball and an amazing view..

How many vacation rentals are there in Kissimmee?

Choose from 1602 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.