Kissimmee Vacation Rentals

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Vacation Rentals in Kissimmee

Vacation Village Orlando, Celebration
3.0 star property
8.6 out of 10, Excellent, (2976)
"Great stay for a family! Cant wait to go back"
United States
jancarlos
$108 nightly
The price is $122
Oct 26 - Oct 27
Total with taxes and fees
Vacation Village Orlando, Celebration
Margaritaville Cottages Orlando by Rentyl
4.0 star property
8.8 out of 10, Excellent, (1664)
"It was a great stay !"
United States
Dianelly
Margaritaville Cottages Orlando by Rentyl
Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
8.4 out of 10, Very Good, (2991)
"Loved the location of the property and that the property was gated"
United States
Darlene
$275 nightly
The price is $312
Oct 23 - Oct 24
Total with taxes and fees
Regal Oaks Resort Vacation Townhomes by IDILIQ
Club Wyndham Cypress Palms
3.5 star property
9.0 out of 10, Wonderful, (1826)
"Beautiful property! Quiet and close to the Disney parks. Would definitely stay here again!"
United States
Angie
Club Wyndham Cypress Palms
The Berkley, Orlando
4.0 star property
9.6 out of 10, Exceptional, (1954)
"Great stay!"
United States
Chris
$137 nightly
The price is $154
Oct 28 - Oct 29
Total with taxes and fees
The Berkley, Orlando
Reunion Resort & Golf Club
5.0 star property
8.8 out of 10, Excellent, (1417)
"Was amazing beautiful and is an special place to go with kids , we love it !! "
United States
Yamila
Reunion Resort & Golf Club
Encantada Resort Vacation Townhomes by IDILIQ
3.0 star property
8.6 out of 10, Excellent, (1391)
"2nd time staying here safe to say this is our second home "
United States
Melanie
$257 nightly
The price is $292
Oct 23 - Oct 24
Total with taxes and fees
Encantada Resort Vacation Townhomes by IDILIQ
Barefoot'n Resort Kissimmee Orlando
2.5 star property
9.0 out of 10, Wonderful, (151)
"Condo has a friendly staff, clean and walking distance to Old Town. "
United States
BONNIE
$102 nightly
The price is $116
Nov 20 - Nov 21
Total with taxes and fees
Barefoot'n Resort Kissimmee Orlando
Magical Dreams
4.0 star property
10.0 out of 10, Exceptional, (2)
"Parking can be an issue but as long as you communicate with the others, you’ll be alright. "
United States
Shana
$111 nightly
The price is $127
Oct 23 - Oct 24
Total with taxes and fees
Magical Dreams
Club Wyndham Star Island
3.5 star property
8.2 out of 10, Very Good, (443)
"Enjoyed our stay here. We got a double unit and it was the perfect size and space for our family"
United States
Melody
Club Wyndham Star Island
Magic Village Yards, Trademark Collection by Wyndham
4.0 star property
9.2 out of 10, Wonderful, (1147)
"Its mising a couple things for a complete kitchen. More utencils and pots"
United States
Jesica
Magic Village Yards, Trademark Collection by Wyndham
Barefoot Suites
3.0 star property
9.0 out of 10, Wonderful, (1775)
"Barefoot Suites is just an overall an awesome place to stay."
United States
Loretta
$86 nightly
The price is $98
Nov 5 - Nov 6
Total with taxes and fees
Barefoot Suites
Grand Lake Resort
3.0 star property
9.2 out of 10, Wonderful, (146)
"Amber was great we had a ball definitely coming back resort was beautiful "
United States
TAIYLAR
Grand Lake Resort
Enchanted Fantasy
3.5 star property
$119 nightly
The price is $136
Oct 23 - Oct 24
Total with taxes and fees
Enchanted Fantasy
Enchanted Dreams
3.5 star property
8.0 out of 10, Very Good, (4)
"Clean, comfortable home. Everything was excellent from the security to amenities. I will book again, share with friends and family. "
United States
Gregory
$128 nightly
The price is $146
Oct 23 - Oct 24
Total with taxes and fees
Enchanted Dreams
Formosa Valley Resort by UNE Homes
4.0 star property
9.4 out of 10, Exceptional, (179)
"Great stay"
United States
Johnny
$458 nightly
The price is $509
Oct 23 - Oct 24
Total with taxes and fees
Formosa Valley Resort by UNE Homes
Lifetime of Vacations Resort
3.0 star property
9.4 out of 10, Exceptional, (148)
"Very nice quiet place... very polite front desk personnel "
United States
Iliana
Lifetime of Vacations Resort
Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38
10.0 out of 10, Exceptional, (27)
"Great spacious house for big families or groups. Kid friendly and minutes away from Orlando! We really enjoyed our stay ! Bowling alley, arcade and theater are great features. "
United States
jeremy s.
Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38
Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool
9.6 out of 10, Exceptional, (48)
"The home was perfect for our family trip to Disney! Its conveniently located near all of the FUN!! Great place to stay! I would definitely stay here again!"
United States
Angela S.
Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool
Modern Luxury Villa with Everything
9.8 out of 10, Exceptional, (446)
"It was a great stay. The house was clean and close to everything."
United States
Jasmine C.
Modern Luxury Villa with Everything
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

Price trends for vacation rentals in Kissimmee

Less expensive
More expensive
Next month
September
December
$215
Month
Price
January
$200
February
$215
March
$209
April
$197
May
$192
June
$196
July
$191
August
$171
September
$152
October
$200
November
$215
December
$238
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 $98 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 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?

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 hot tub. Other favorite homes for rent in Kissimmee are Formosa Valley Resort by UNE Homes and Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool.

How many vacation rentals are there in Kissimmee?

Choose from 15109 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 County Welcome Center and History 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.