Kissimmee Vacation Rentals from $42: Search Short-Term Rentals

Q: What's the top vacation rental that Kissimmee has to offer?

The Berkley, Orlando : This Kissimmee vacation home rental offers a furnished patio, a terrace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave, and a coffee maker. You can relax into your vacation with an arcade game room and a spa tub. Another good choice for your trip to Kissimmee is Upstay - Theme Rooms|Movie Theatre|Pool|Sleeps 18 .

Check Kissimmee vacation rental availability

Vacation Rentals in Kissimmee

Kissimmee Vacation Rental Travel Info

Number of vacation rentals	2,837
Popular accommodation	Kissimmee private vacation homes
Known landmarks	Discovery Cove, Aquatica and Disney's Typhoon Lagoon Water Park
International airport	Orlando, FL (MCO-Orlando Intl.)

Price trends for vacation rentals in Kissimmee

Less expensive	More expensive	This month	Next month
September	March	$136	$146

Month	Price
January	$130
February	$148
March	$152
April	$119
May	$110
June	$136
July	$146
August	$120
September	$107
October	$126
November	$113
December	$142

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.

Other types of properties in Kissimmee you may be interested in

In-room safe, laptop workspace, blackout drapes, iron/ironing board

"Great staff, Good stay"

$84 total

includes taxes & fees

Jun 17 - Jun 18

4 outdoor pools, cabanas (surcharge), pool umbrellas

"The property was wonderful! The staff were helpful and friendly. The property was close to everything. My kids and husband loved the pool. Music and pool made me feel like we were at a pool party. Would definitely stay again!"

$133 total

includes taxes & fees

Jul 8 - Jul 9

"Gorgeous hotel and property! We loved our room."

$214 total

includes taxes & fees

Jun 23 - Jun 24

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 $42 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.

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 renowned opera. The array of shops and lively festivals 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?

The Berkley, Orlando: This Kissimmee vacation home rental offers a furnished patio, a terrace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave, and a coffee maker. You can relax into your vacation with an arcade game room and a spa tub. Another good choice for your trip to Kissimmee is Upstay - Theme Rooms|Movie Theatre|Pool|Sleeps 18.

How many vacation rentals are there in Kissimmee?

Choose from 19272 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 Osceola Performing Arts Center and Medieval Times. 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.

Recent reviews of Kissimmee properties
Expedia verified reviews

5/5 Excellent

"Breakfast was great. Staff was great. Area was great and the hotel was nice. I recommend "

A verified traveler stayed at Palazzo Lakeside Hotel

Posted 1 day ago

5/5 Excellent

Vacation

"The hotel is good, the pool is heated, the area is very safe and they have a security guard walking around at night. The rooms are spacious enough, at least the one I had was very clean. I was able to check it by wiping it and it came out clean, this has not happened in other hotels I've been to. They don't have breakfast but there are restaurants nearby. I would definitely stay there again. And I will try to give me the same room every time I return. I recommend it."

A verified traveler stayed at Sonder Cirrus

Posted 1 day ago

Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel

5/5 Excellent

Great stay but skip the timeshare!

"We stayed 5 nights in a 2 bedroom villa with our 3 children, ages 3 to 8. Our location in the West Village was perfect. Our unit had been renovated; it was spacious and clean. Variety of great pools on property. Charges for additional activities, but reasonably priced. Our only regret was agreeing to timeshare presentation in exchange for free play passes. It took 3 hours, not the 90 minutes promised. Otherwise, this was a great vacation! "

A verified traveler stayed at Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel

Posted 2 days ago

Red Lion Hotel Orlando Lake Buena Vista South

5/5 Excellent

Lovely stay

"Myself and my friend stayed from Friday to Wednesday. We had a great room overlooking the pool. Had a fab breakfast included. Reasonable price but great location next to everything you need. Very comfy. Nice pool and gym. Would stay here again. Special mention to the nice lady who served us breakfast every morning "

A verified traveler stayed at Red Lion Hotel Orlando Lake Buena Vista South

Posted 2 days ago