We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Kissimmee, FL

Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 4,261 Rentals in Kissimmee
loading...
Sort by
Show Prices
3 Bedrooms, 2 Bathrooms, Sleeps 8
6 photos Details
Reviews (1) Make Inquiry
Show Prices
5 Bedrooms, 3 Bathrooms, Sleeps 10
24 photos Details
Reviews (5) Make Inquiry
Show Prices
3 Bedrooms, 3 Bathrooms, Sleeps 8
9 photos Details
Reviews (3) Make Inquiry
Also consider
WINDSOR HILLS TOWNHOUSE With POOL From $399/wk!
3 Bedrooms, sleeps 8
$57 - $171 / night
Bargain Vacation Home near Disney
2 Bedrooms, sleeps 6
$80 - $90 / night
Brand New Villa Windsor Hill 3ml to Disney SF Pool
6 Bedrooms, sleeps 12
$160 - $350 / night
3 Miles to Disney So close Come back for a dip
5 Bedrooms, sleeps 12
$125 / night
Show Prices
3 Bedrooms, 2 Bathrooms, Sleeps 8
27 photos Details
Reviews (7) Make Inquiry
Show Prices
3 Bedrooms, 2 Bathrooms, Sleeps 8
27 photos Details
Reviews (10) Make Inquiry
Show Prices
3 Bedrooms, 3 Bathrooms, Sleeps 6
15 photos Details
Reviews (4) Make Inquiry
Show Prices
3 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (1) Make Inquiry
Show Prices
3 Bedrooms, 3 Bathrooms, Sleeps 8
31 photos Details
Reviews (1) Make Inquiry
Get the List
Show Prices
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
10 photos Details
Reviews (2) Make Inquiry
Show Prices
4 Bedrooms, 3 Bathrooms, Sleeps 10
14 photos Details
Reviews (4) Make Inquiry
Show Prices
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
32 photos Details
Reviews (15) Make Inquiry
Show Prices
1 Bedroom, 1 Bathroom, Sleeps 4
15 photos Details
Reviews (17) Make Inquiry
Show Prices
4 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
17 photos Details
Reviews (4) Make Inquiry
Show Prices
4 Bedrooms, 3 Bathrooms, Sleeps 8
12 photos Details
Reviews (1) Make Inquiry
Show Prices
3 Bedrooms, 2 Bathrooms, Sleeps 8
48 photos Details
Reviews (22) Make Inquiry
Show Prices
3 Bedrooms, 2 Bathrooms, Sleeps 8
65 photos Details
Reviews (15) Make Inquiry
Show Prices
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
20 photos Details
Reviews (5) Make Inquiry
Show Prices
3 Bedrooms, 2 Bathrooms, Sleeps 8
18 photos Details
Reviews (7) Make Inquiry
Show Prices
4 Bedrooms, 2 Bathrooms, Sleeps 10
20 photos Details
Reviews (3) Make Inquiry
Show Prices
2 Bedrooms, 2 Bathrooms, Sleeps 6
30 photos Details
Reviews (2) Make Inquiry
Show Prices
4 Bedrooms, 2 Bathrooms, Sleeps 10
23 photos Details
Reviews (9) Make Inquiry
Show Prices
3 Bedrooms, 2 Bathrooms, Sleeps 6
38 photos Details
Reviews (1) Make Inquiry
Show Prices
3 Bedrooms, 2 Bathrooms, Sleeps 8
17 photos Details
Reviews (14) Make Inquiry
Show Prices
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
36 photos Details
Reviews (7) Make Inquiry
Show Prices
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
21 photos Details
Reviews (2) Make Inquiry
Show Prices
4 Bedrooms, 2 Bathrooms, Sleeps 10
30 photos Details
Reviews (1) Make Inquiry
Show Prices
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
23 photos Details
Reviews (2) Make Inquiry
Show Prices
4 Bedrooms, 2 Bathrooms, Sleeps 8
13 photos Details
Reviews (6) Make Inquiry
Show Prices
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
12 photos Details
Reviews (2) Make Inquiry
Show Prices
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
35 photos Details
Reviews (2) Make Inquiry
Show Prices
4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
11 photos Details
Reviews (1) Make Inquiry
Show Prices
4 Bedrooms, 3 Bathrooms, Sleeps 10
17 photos Details
Reviews (14) Make Inquiry
Show Prices
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
30 photos Details
Reviews (3) Make Inquiry
Show Prices
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
24 photos Details
Reviews (3) Make Inquiry
Show Prices
6 Bedrooms, 6 Bathrooms, Sleeps 13
24 photos Details
Reviews (9) Make Inquiry
Show Prices
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
14 photos Details
Reviews (4) Make Inquiry
Show Prices
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
47 photos Details
Reviews (28) Make Inquiry
Show Prices
4 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
18 photos Details
Reviews (1) Make Inquiry
Show Prices
3 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (18) Make Inquiry
Show Prices
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
10 photos Details
Reviews (2) Make Inquiry
Go to map view
Book Online(2778)
Use filters to find the best results!

Suitability

  • Wheelchair access (605)
  • Elder access (1,719)
  • Suitable for children (2,411)
  • Pet friendly (201)
  • Smoking allowed (89)

Amenities

  • Internet (2,989)
  • Air Conditioning (2,926)
  • All pools (2,685)
  • Other outdoor space (1,955)
  • Washer/Dryer (1,763)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List

More Family destinations:

More Golf destinations:

Filter search results by:
Book Online(2778)

Suitability

  • Wheelchair access (605)
  • Elder access (1,719)
  • Suitable for children (2,411)
  • Pet friendly (201)
  • Smoking allowed (89)

Amenities

  • Internet (2,989)
  • Air Conditioning (2,926)
  • All pools (2,685)
  • Other outdoor space (1,955)
  • Washer/Dryer (1,763)
  • View all amenities
Kissimmee Vacation Rentals

Don’t automatically think you need to rent a vacation home in Orlando to be close to Walt Disney World. Smart vacationers know that searching for a vacation rental in Kissimmee, Florida often gets you space, luxury and a great rate—as well as a very short commute to the parks.

Kissimmee Vacation Rentals for Families

More and more families are choosing to celebrate major events like birthdays and anniversaries with a multi-generational trip to Disney World. (It’s one of the few destinations where everyone from toddlers to seniors can have an equally great time.) And we can help you find a Kissimmee vacation rental that can handle any size family. Whether you’re interested in a one-bedroom condo rental in Kissimmee or a seven-bedroom luxury villa, our helpful vacation rental reviews make your selection easy.

Advantages of renting a vacation home in Kissimmee

Let’s be honest—while it’s great fun to spend a week visiting the Magic Kingdom, Epcot, Disney’s MGM Studios, Universal Studios and Islands of Adventure, for most of us, it’s a significant strain on our bank accounts. Staying in a hotel and eating in Orlando-area restaurants also adds up. However, we can help you find a great deal on a villa rental in Kissimmee… and even if you just take a few meals in your vacation home instead of in restaurants, your budget will thank you. You’ll even save money on baggage fees with a rental—when you’ve got your own washer and dryer, you can do a few loads of laundry and pack much less clothing.

Rent a vacation house with a pool in Kissimmee, Florida

How do you visit the Orlando theme parks and maintain your sanity? Escape the crowds in the mid-afternoon, when the heat peaks and everybody’s nerves are frazzled. By staying just a short distance away in Kissimmee, you can zip home for a refreshing dip in the pool. Little kids can nap in the comfortable A/C of your Kissimmee vacation rental. You’ll all return to WDW or Universal in a much better mood!

Rental deals in Kissimmee

Remember that Florida’s a year-round vacation destination—but it definitely has an off-season when you can snag a great deal on Kissimmee condo rentals. If you really want a bargain, plan to visit Kissimmee between Thanksgiving and Christmas. Your condo will be cheap, the parks will be less crowded, and if you’re coming from a northern climate, the weather in Kissimmee will still seem great compared to what you’d get at home.

Kissimmee and Orlando beyond Disney

Don’t forget, there’s more to this part of Florida than Mickey and Donald and friends. Animal lovers will want to spend a day at Sea World, or take a day trip to the Everglades. Shoppers should save time (and suitcase space) for bargain-hunting at outlets in Kissimmee and the nearby Orlando Premium Outlets. Just over an hour away, on Florida’s Space Coast, you’ll find the Kennedy Space Center and fantastic sandy beaches like Cocoa Beach. Taking a Disney Cruise departing from Port Canaveral? A vacation rental in Kissimmee is the perfect pre-cruise accommodation.