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Vacation Rentals in Kissimmee, FL

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$240
Per Night
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6 Bedrooms, 6 Bathrooms, Sleeps 14
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$157
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6 Bedrooms, 4 Bathrooms, Sleeps 12
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$120
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4 Bedrooms, 3 Bathrooms, Sleeps 10
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Also consider
MAGICAL DREAMS, Fantastic 5 bed 4.5 Bath
5 Bedrooms, sleeps 12
$111 - $140 / night
PP04TL/8889- Jessica Rabbit's Chateau
4 Bedrooms, sleeps 10
$150 - $200 / night
2/2 Luxury Resort Apt./Condo- Orlando, FL.
2 Bedrooms, sleeps 8
$200 / night
One of the closest communities to Disney
4 Bedrooms, sleeps 8
$99 - $130 / night
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$97
Per Night
1 / 23
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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5 of 5 stars Reviewed November 4, 2014
I love Florida I've been coming there since my son was 6, he's 19. This is the first time I stayed in a house I usually rent a hotel room on the grounds at the Disney park. I plan...
5 of 5 stars Reviewed September 19, 2014
We stayed here in April 2014 for 2 weeks, and had a great time. The villa was beautiful, spacious, exceptionally clean, well laid out with everything you could need for a great...
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$110
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed November 12, 2014
We stayed for two weeks at the end of October/early November 2014 - we were a party of 6 including two children ages 12 and 7 and thoroughly enjoyed staying in this wonderful...
5 of 5 stars Reviewed October 8, 2014
Our 2 night stay was perfect! We booked this trip at the last minute to celebrate my 40th birthday! The kids loved the pool and game room, there was plenty for everyone to do...
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$225
Per Night
1 / 24
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6 Bedrooms, 5 Bathrooms, Sleeps 14
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5 of 5 stars Reviewed October 30, 2014
We really enjoyed our stay and the property more than met our expectations. We traveled with two of our children ages 11 and 13 and my wife's parents. The property is nicely...
5 of 5 stars Reviewed May 31, 2014
Family of 9, stayed for 7 days. Beautiful, well-maintained home. Clean, clean, clean. Loads of room for all of us. Kids loved the gameroom and especially loved having pool...
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$55
Per Night
1 / 24
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed September 21, 2014
The House was very nicly decorated. 3 good sized bedrooms, with comfortable beds. Kitchen was fully equipped. Netflix was very good to have for the kids. Short drive to...
5 of 5 stars Reviewed August 25, 2014
We were there end of June 2014 for about 3 weeks. The owner Paul sent us an email with all the useful informations for the relevant stay, which is very kind and helpful. Perfect...
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$94
Per Night
1 / 23
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3 Bedrooms, 2 Bathrooms, Sleeps 7
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5 of 5 stars Reviewed November 4, 2014
Fantastic service from first email to phone call on arrival to check everything was in order. Sue couldn’t have been more helpful. The accommodation was beautiful, clean and very...
5 of 5 stars Reviewed July 13, 2014
Stayed at this accommodation with a 19 year old and 18 year old and it provided everything we could want or need. Great location, extremely clean and a lovely place to come back...
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$1,082
Per Week
1 / 24
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4 Bedrooms, 3 Bathrooms, Sleeps 10
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5 of 5 stars Reviewed November 22, 2014
We stayed in this beautiful villa from 27th oct to 10 nov 2014 and we had the best holiday we've ever had! The villa was spotless and had everything we possibly needed. There is a...
5 of 5 stars Reviewed October 28, 2014
We all enjoyed our stay at Dolphin Villa. The house is lovely, and the pool and hot tub make it a very relaxing and chilled out place to spend quality time.
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$118
Per Night
1 / 23
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4 Bedrooms, 3 Bathrooms, Sleeps 9
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4 of 5 stars Reviewed September 10, 2014
Having been to Orlando before (this our 4th stay) and having stayed in condos previously, we decided to try the villa experience. We were not disappointed!! Firstly...
5 of 5 stars Reviewed July 29, 2014
Even before the holiday started when we were trying to decide just which of the very many villa's to choose from. Jan Staines responded to all my questions promptly and clearly...
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$225
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1 / 22
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7 Bedrooms, 5 Bathrooms, Sleeps 16
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5 of 5 stars Reviewed July 7, 2014
My family and I just returned from an excellent stay at Sri's property, Simba's Magic! The home is beautifully decorated and the pictures don't do it justice! It was the...
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$71
Per Night
1 / 16
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed September 9, 2014
We had a great Stay at the Terra Verde Townhome. It has all your basic needs. The Kitchen was well equiped. The furnishings are low budget items. Townhome has a washer and...
5 of 5 stars Reviewed September 26, 2014
Rente la casa sin tener la opinión de nadie para orientarme, pero valió la pena el resort es hermoso tiene un lago, picina, espacios recreacionales y la casa en si es muy cómoda...
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$88
Per Night
1 / 21
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4 Bedrooms, 2 Bathrooms, Sleeps 8
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5 of 5 stars Reviewed November 23, 2014
A beautiful house, very clean and well maintained. Felt like home from home but with sunshine and a pool!! Everything is thought of for a great holiday home. Very speedy response...
5 of 5 stars Reviewed June 24, 2014
We stayed at the villa for a week and loved it. Dealing with Wally was so easy, he was helpful and got back to us quickly with any questions we had. The villa is in a beautiful...
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$102
Per Night
1 / 22
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed September 26, 2014
I stayed in this home for 3 weeks - it was amazing !! It had everything you needed and more, the living room is nicely decorated and the house was very clean. The house was an end...
5 of 5 stars Reviewed March 16, 2014
The quality of service from the owner of this property is more than enough to inspire us to return! The residence was far better than we could have expected. The place was clean...
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$55
Per Night
1 / 15
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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5 of 5 stars Reviewed August 27, 2014
The condo is in a great location, not far from Disney. It was clean & well kept, all facilities supplied, TVs in all rooms. Nice area, pool was great too.
4 of 5 stars Reviewed August 13, 2014
Nice, clean and great size condo Very close to Disney and close to a lot of restaurants and other facilities Quiet Have good fun at the pool
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$97
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1 / 22
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4 Bedrooms, 2 Bathrooms, Sleeps 10
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5 of 5 stars Reviewed June 23, 2014
We had a fabulous holiday at this villa. Everything was as described. The area was very quiet and peaceful. Supermarkets and restaurants are close by. It took a bit longer to get...
5 of 5 stars Reviewed May 1, 2014
Our first trip to Florida and Ventura Villa. This defiantly won't be my last. The house was super clean and spacious. Its located in a quiet neighborhood only minutes from all...
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$78
Per Night
1 / 20
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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4 of 5 stars Reviewed August 24, 2013
Excellent accommodation. Very clean and very comfortable. Looks over a lake at back with lots of wildlife to watch from the lounge or conservatory. The club house is good and the...
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$71
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1 / 24
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2 Bedrooms, 2 Bathrooms, Sleeps 7
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5 of 5 stars Reviewed August 24, 2014
We arrived during a summer downpour but it did not affect our very good impression of the place, a very nice condo, very quiet and extremely well located, close to all parks and...
5 of 5 stars Reviewed July 24, 2014
My son and I traveled to Disney for a short summer visit to celebrate his 13th birthday. This is a great condo - very comfortable, clean, well furnished/stocked and in a nice...
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$63
Per Night
1 / 24
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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4 of 5 stars Reviewed August 23, 2014
A big thank you to Mary, the booking process was simple and I was in touch with her throughout the whole process, from general enquiry to booking and even questions via email...
5 of 5 stars Reviewed August 6, 2014
the complex was well maintained and looked after,the condo was clean and tidy with all the amenities that you needed . The pool was great after a long day at the parks to relax...
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$102
Per Night
1 / 12
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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5 of 5 stars Reviewed October 21, 2014
This house was just right had everything we needed and was close to publix and lots of restaurants! I would deffernatly book this villa again
5 of 5 stars Reviewed January 24, 2014
This home was everything we needed for our stay in Florida, it was quiet and had all the amenities we required. There was plenty of space and the pool and hot tub were both much...
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$47
Per Night
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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5 of 5 stars Reviewed October 30, 2014
Myself, my partner and a friend have just returned from a 2 week stay in Caballero. I can honestly say it became our home for those 2 weeks and we were very sad to leave...
5 of 5 stars Reviewed September 8, 2014
This holiday home has it all under 1 roof, 4 bedrooms, 3.5 bathrooms a spacious kitchen, dinning room and lounge, it also boasts an impressive outdoor patio for relaxing and a...
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$102
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1 / 10
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4 Bedrooms, 2 Bathrooms, Sleeps 9
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4 of 5 stars Reviewed October 8, 2014
The villa is MASSIVE. A little outdated in places and not quite up to my standards cleanliness-wise. However, the layout of the villa is very well thought out and looks...
4 of 5 stars Reviewed May 11, 2014
We had a wonderful time in the house, was clean and had everything you needed, was a real home from home. The house was situated near to all the attractions and was convenient...
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$157
Per Night
1 / 9
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6 Bedrooms, 3 Bathrooms, Sleeps 14
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$225
Per Night
1 / 23
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7 Bedrooms, 4 Bathrooms, Sleeps 16
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$118
Per Night
1 / 15
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4 Bedrooms, 3 Bathrooms, Sleeps 10
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From
$140
Per Night
1 / 24
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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$225
Per Night
1 / 24
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7 Bedrooms, 4 Bathrooms, Sleeps 16
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From
$79
Per Night
1 / 13
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$140
Per Night
1 / 16
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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From
$94
Per Night
1 / 14
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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From
$110
Per Night
1 / 16
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4 Bedrooms, 2 Bathrooms, Sleeps 10
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$100
Per Night
1 / 24
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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$132
Per Night
1 / 19
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5 Bedrooms, 3 Bathrooms, Sleeps 12
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$110
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1 / 15
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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$149
Per Night
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5 Bedrooms, 3 Bathrooms, Sleeps 12
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$121
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1 / 14
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4 Bedrooms, 2 Bathrooms, Sleeps 8
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5 of 5 stars Reviewed June 17, 2014
After a lengthy search for a villa that ticked all the boxes, we chose to stay at Witcomb Villa for our fortnight holiday in Florida, and were certainly not disappointed! The...
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$956
Per Week
1 / 20
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4 Bedrooms, 2 Bathrooms, Sleeps 8
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4 of 5 stars Reviewed November 14, 2014
Plenty of room for us all. Easy routes to parks etc. if you are happy to drive in US. House had everything we needed. Pool was perfect.
5 of 5 stars Reviewed July 16, 2014
We have stayed in villas for the last 10 years and have enjoyed many great holidays, but this villa was just superb. We couldn't rate it anything other than magnificent...
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$138
Per Night
1 / 20
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5 Bedrooms, 4 Bathrooms, Sleeps 10
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5 of 5 stars Reviewed September 5, 2014
We chose this rental through Trip Advisor and from the moment we booked we had nothing but fantastic service from Maureen. Any questions we raised she answered and the whole...
5 of 5 stars Reviewed March 21, 2014
The house was simply perfect for our entire family and we had the most enjoyable time there. We could not have asked for anything more. There were 12 of us, eight adults and 4...
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$102
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4 Bedrooms, 2 Bathrooms, Sleeps 10
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5 of 5 stars Reviewed July 17, 2014
We stayed in this Villa for 2 weeks in June. 4 Adults and a small child and it was brilliant. The villa is in a great setting, very quiet and ideal for visiting Disney...
5 of 5 stars Reviewed February 3, 2014
My husband and I traveled to FL to visit the parks and have a leisurely time with our two children (ages 18 and 3). This home was the best choice we could've made. It was very...
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$95
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1 / 15
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4 Bedrooms, 2 Bathrooms, Sleeps 8
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5 of 5 stars Reviewed July 24, 2014
"Our stay has been outstanding .We couldn't fault the villa or its location in any way. Steve the owner was very friendly and helpfull...nothing was too much trouble. The photos...
5 of 5 stars Reviewed May 28, 2014
I stayed in this villa with my family at the end of April and the first week in May. It is a well equipped and maintained villa with a lovely pool area. The master bedroom and en...
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Suitability

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  • Suitable for children (2,100)
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Book Online(2683)

Suitability

  • Wheelchair access (594)
  • Elder access (1,568)
  • Suitable for children (2,100)
  • Pet friendly (193)
  • Smoking allowed (9)

Amenities

  • Air Conditioning (2,766)
  • Internet (2,720)
  • All pools (2,234)
  • Washer/Dryer (1,819)
  • Other outdoor space (1,817)
  • 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.