Kissimmee Vacation Rentals

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Vacation Rentals in Kissimmee

Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.6 out of 10, Excellent, (2950)
"Had every thing you would need for a family trip Perfect loved it "
$111 nightly
The price is $127
Oct 12 - Oct 13
Total with taxes and fees
Vacation Village at Parkway
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Interior

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1651)
"It was a great stay !"
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Club Wyndham Cypress Palms
2 outdoor pools, sun loungers

Club Wyndham Cypress Palms

3.5 star property
9.0 out of 10, Wonderful, (1820)
"Nice place to stay"
Club Wyndham Cypress Palms
The Berkley, Orlando
Lobby

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1937)
"Great stay!"
$137 nightly
The price is $154
Oct 12 - Oct 13
Total with taxes and fees
The Berkley, Orlando
Reunion Resort & Golf Club
Water park

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (1410)
"amazing place for families"
Reunion Resort & Golf Club
Regal Oaks Resort Vacation Townhomes by IDILIQ
View from property

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very Good, (2986)
"Loved the location of the property and that the property was gated"
$285 nightly
The price is $324
Oct 26 - Oct 27
Total with taxes and fees
Regal Oaks Resort Vacation Townhomes by IDILIQ
Encantada Resort Vacation Townhomes by IDILIQ
2 outdoor pools, pool umbrellas, sun loungers

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1385)
"The unit was great for our large group of people. The only issue was some cheaply made furniture that seemed very wobbly. "
$264 nightly
The price is $299
Oct 14 - Oct 15
Total with taxes and fees
Encantada Resort Vacation Townhomes by IDILIQ
Magical Dreams
Outdoor pool

Magical Dreams

4.0 star property
10.0 out of 10, Exceptional, (1)
"estaba algo caliente pero nos contactamos con los encargados y nos solucionaron el problema "
$114 nightly
The price is $130
Oct 11 - Oct 12
Total with taxes and fees
Magical Dreams
Barefoot'n Resort Kissimmee Orlando
Exterior

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.0 out of 10, Wonderful, (147)
"Loved being able to walk across the street to Old Town. Large space and a great price. "
$104 nightly
The price is $119
Oct 15 - Oct 16
Total with taxes and fees
Barefoot'n Resort Kissimmee Orlando
Magic Village Yards, Trademark Collection by Wyndham
Outdoor pool, pool umbrellas, sun loungers

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1146)
"Spacious accommodations near Disney, with some amenities. "
Magic Village Yards, Trademark Collection by Wyndham
Club Wyndham Star Island
2 outdoor pools, sun loungers

Club Wyndham Star Island

3.5 star property
8.2 out of 10, Very Good, (440)
"The rooms were very clean & equipped with every little item we were going to need in the kitchen/bedrooms/bedrooms. We also had washer/dryer to leave with clean clothes from our stay. I will definitely recommend this place for a family/friend getaway. "
Club Wyndham Star Island
Grand Lake Resort
Dock

Grand Lake Resort

3.0 star property
9.2 out of 10, Wonderful, (141)
"Amber was great we had a ball definitely coming back resort was beautiful "
Grand Lake Resort
Barefoot Suites
Dock

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1772)
"Much better than the last stay there!"
$94 nightly
The price is $107
Oct 14 - Oct 15
Total with taxes and fees
Barefoot Suites
Enchanted Fantasy
Terrace/patio

Enchanted Fantasy

3.5 star property
$119 nightly
The price is $136
Oct 11 - Oct 12
Total with taxes and fees
Enchanted Fantasy
Lifetime of Vacations Resort
Lake view

Lifetime of Vacations Resort

3.0 star property
9.4 out of 10, Exceptional, (147)
"Quiet place "
Lifetime of Vacations Resort
Formosa Valley Resort by UNE Homes
Private pool

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (171)
"Great stay"
$432 nightly
The price is $480
Nov 2 - Nov 3
Total with taxes and fees
Formosa Valley Resort by UNE Homes
Modern Luxury Villa with Everything
TV, foosball, stereo

Modern Luxury Villa with Everything

9.8 out of 10, Exceptional, (441)
"It was a great stay. The house was clean and close to everything."
Modern Luxury Villa with Everything
Enchanted Dreams
Full-size fridge, microwave, oven, stovetop

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. "
$128 nightly
The price is $146
Oct 13 - Oct 14
Total with taxes and fees
Enchanted Dreams
Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38
Outdoor pool, a heated pool

Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38

10.0 out of 10, Exceptional, (27)
"Very spacious and fun house, very easy to get to Parks, groceries, and outletsHost was amazing and available!"
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
Outdoor pool, a heated pool

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!"
Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool
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

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"⭐️⭐️⭐️⭐️⭐️ Outstanding service from Matthew at the front desk I stayed at Kompose Hotel recently and had a great experience, thanks to Matthew at the front desk. He was incredibly professional, kind, and helpful throughout my stay. He went out of his way to assist me and made check-in smooth and stress-free. It’s rare to come across someone who genuinely cares about guests, and Matthew definitely stood out. Big thanks to him and the Kompose team for making my visit so comfortable! Brand new hotel with an awesome swimming pool and bar! "
Steven 4-night trip
Posted 15 hours ago
Kompose Boutique Resort at Theme Parks

Price trends for vacation rentals in Kissimmee

Less expensive
More expensive
This month
Next month
September
December
$215
$211
Month
Price
January
$202
February
$218
March
$211
April
$199
May
$179
June
$184
July
$184
August
$173
September
$160
October
$215
November
$211
December
$231
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 $107 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?

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 15208 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.