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. Mac: Safari.

Kissimmee

Check availability
Refine search

Search within

 

Desired stay

 

Price range

 
$100$5,150
 

Bedrooms

Studio10+
 

Bathrooms

14+
 

Sleeps

110+
 

Traveler rating

1.05.0
 

Property type

 

Amenities

 

Suitability

 
Own a rental property?
Want more exposure for your rental? Get listed in TripAdvisor Vacation Rentals (in partnership with FlipKey).
Vacation Rental Calculator
Compare & Save »
Free Newsletter

Sign up to hear about gorgeous vacation rentals, the latest deals, exciting destinations, and more.

Rental properties provided by
Learn more
Don't see the property you rented? Tell us more about it »

Vacation Rentals in Kissimmee, Central Florida

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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.

 
more     
Nearby rentals
Tip: Refine your search by price, amenities, & more (see left column).
Searching … 0% complete
1,340 Trusted Kissimmee Rentals
List View
loading...
Showing 0 plottable rentals of 0 total
Map nearby restaurants, attractions & more
Restaurants
Things to Do
Coffee shops
Rail stations
Also consider
$275 - $350 / night
4 Bedrooms, sleeps 12
4 Bathrooms
4 Bedrooms, sleeps 10
3 Bathrooms
$135 - $158 / night
4 Bedrooms, sleeps 8
3 Bathrooms
$1,029 - $1,345 / week
5 Bedrooms, sleeps 10
4 Bathrooms
$59 - $125 / night
3 Bedrooms, sleeps 8
2 Bathrooms

Traveler Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews
Florida, Central Florida, Kissimmee Vacation Rentals
  • Villa
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Week:
$467 - $712
Minimum rental - 1 week
Check availability
Florida, Central Florida, Kissimmee Vacation Rentals
  • Villa
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
$95 - $119
Week:
$657 - $839
Minimum rental - 1 night
Check availability
Map unavailable
Florida, Central Florida, Kissimmee Vacation Rentals
  • Rental Home
  • 4 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$149 - $189
Week:
$1,043 - $1,323
Minimum rental - 1 night
Check availability
Map unavailable
Also consider
$275 - $350 / night
4 Bedrooms, sleeps 12
4 Bathrooms
4 Bedrooms, sleeps 10
3 Bathrooms
$135 - $158 / night
4 Bedrooms, sleeps 8
3 Bathrooms
$1,029 - $1,345 / week
5 Bedrooms, sleeps 10
4 Bathrooms
$59 - $125 / night
3 Bedrooms, sleeps 8
2 Bathrooms
  • Rental Home
  • 4 Bedrooms, sleeps 10
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$110 - $159
Minimum rental - 1 night
Check availability
Florida, Central Florida, Kissimmee Vacation Rentals
  • Rental Home
  • 4 Bedrooms, sleeps 10
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$139 - $189
Week:
$953 - $1,323
Minimum rental - 1 night
Check availability
Florida, Central Florida, Kissimmee Vacation Rentals
  • Rental Home
  • 4 Bedrooms, sleeps 10
  • 3 Bathrooms
  • Owner
EMAIL OWNER
Night:
$150 - $180
Week:
$1,050 - $1,260
Minimum rental - 3 nights
Check availability
  • Rental Home
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$90 - $105
Minimum rental - 3 nights
Check availability
  • Rental Home
  • 4 Bedrooms, sleeps 10
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Month:
$3,000
Minimum rental - 2 nights
Check availability
  • Rental Home
  • 3 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$119 - $149
Minimum rental - 2 nights
Check availability
Map unavailable
Florida, Central Florida, Kissimmee Vacation Rentals
  • Rental Home
  • 4 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$175 - $214
Minimum rental - 3 nights
Check availability
Map unavailable
  • Condo/Apartment
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$105 - $135
Minimum rental - 2 nights
Check availability
  • Rental Home
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$79 - $159
Minimum rental - 2 nights
Check availability
Florida, Central Florida, Kissimmee Vacation Rentals
  • Rental Home
  • 4 Bedrooms, sleeps 10
  • 4 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$255 - $355
Minimum rental - 2 nights
Check availability
Map unavailable
  • Condo/Apartment
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$74 - $149
Minimum rental - 2 nights
Check availability
  • Rental Home
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Week:
$885 - $1,060
Minimum rental - 4 nights
Check availability
  • Rental Home
  • 4 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
$85 - $135
Minimum rental - 4 nights
Check availability

Kissimmee Vacation Rental Advice

Posted by denang18, Aug 19, 2011
... one of the Go Disney Vacation rentals. My family of 7 stayed in April for our Disney vacation. The condo was amazing and sooo clean. Everything was clean! We had a faucet problem and they came over and took care of it ASAP! I am getting ready to book another ... more
Posted by countyfolk, Aug 6, 2011
Has anyone ever used this company? We are going to Orlando in February and looking for a vacation rental and it is overwhelming what is available! We are leery of doing an owner direct rental. Any recommendations? ... more
Posted by BelfastSkeet, Aug 15, 2011
... t referring to Florida Sun Vacation Rentals. When I asked the owner for a price, I asked him for a price which included everything which we have always done. He then passed us on to his management company and told them the rate he quoted us. They completely disregarded his ... more
Posted by Novalobster, Oct 9, 2010
Did you leave a review on the "vacation rentals" site for this home? You can usually "tell it like it is" on that part of Trip Advisor. ... more
Posted by FLMom2boys, Jul 11, 2010
... most of the homes are vacation rentals. Some will have amenities, playgrounds or tennis courts, some not. Neighborhoods close to Disney are Rolling Hills (next to Windsor Hills), Indian Creek, Indian Ridge, Sunset Lakes, Lindfields, Oak Island. There are many other communities farther out. The easiest way to judge is ... more
Posted by madcustomer_12, Jul 21, 2010
LOWERY'S VACATION RENTALS is the MOST UNPROFESSIONAL company I have ever booked with!! The pictures on the web are very misleading and the management could care less about customer satisfaction. When we arrived at the rental we were disappointed with what we found... but it was too late to ... more
Posted by theKteam, Sep 13, 2009
... are trying to find a vacation rental in ... ... nearer the Disney Parks area and miles away from downtown. Presuming that the downtown area is a decent place to stay in does anyone know a website where I can find vacation rentals specifically in this area? All advice gratefully received - thanks ... more
Posted by CruisingtoRetirement, Feb 2, 2009
mcc0004, I believe these two developments are in good areas. For future reference, the "bad" areas are clustered in two small rectangles at least ten miles away from where the majority of these vacation rentals are located. CTR ... more
Posted by Novalobster, Jul 18, 2009
A lot of the vacation rentals only do week or more during the peak times like Christmas. Gaylord Palms is very nice and has a lot going on at Christmas. ... more
Posted by 1031Orlando, Jul 18, 2009
... brings a good point that vacation rentals will likely have a minimum night stay which you won't meet not to mention many of the best probably booked already. For hotels, the Waldorf will be the newest. Gaylord Palms is a nice recommendation and close to Disney. Marriott World Center ... more
Featured Events
The festival features arts and fine crafts, children activities, chalk street painting, street performers & great foods!
See all sites
Cruise Critic

The ultimate cruise resource: cruise reviews, deals, news and advice.

SeatGuru

The world's most comprehensive source for airline seats, airline info, & in-flight amenities.

Family Vacation Critic

The best family vacations start here.

Get the #1 travel app FREE>>
Take TripAdvisor with you

Find 50 million reviews & opinions of hotels, things to do, restaurants and more

GET IT
Named "#1 Travel App" by Frommer's