Kissimmee Vacation Rentals

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USA > Florida > Kissimmee

Make Kissimmee your next getaway—choose from 201 great vacation rentals

With geography unlike any other, the Sunshine State combines emerald-green waters, swamplands, and inland cities. If you’re looking for a blend of both world-class tourist attractions and small-town charm, our Kissimmee vacation rentals are the perfect choice for you! Whether you're planning a relaxing retreat or an adventure-filled experience, our vacation homes serve as the perfect home base as you explore all that the eventful Central Florida region has to offer. 

Explore Kissimmee condo rentals, house rentals, townhouses, and more


Condo rentals

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House rentals

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Kissimmee vacation rentals for every getaway

Dog-friendly Hot tub Internet
Grand Hideaway 3D Tour
6 Bed | 5.5 Bath | Sleeps 14

Grand Hideaway - Kissimmee, FL

From $202
Caribe Cove Resort 10309 3D Tour
3 Bed | 2 Bath | Sleeps 8

Caribe Cove Resort 10309 - Kissimmee, FL

From $91
Caribe Cove Resort 40306 3D Tour
3 Bed | 2 Bath | Sleeps 8

Caribe Cove Resort 40306 - Kissimmee, FL

From $91
Mickey's Magical Escape 3D Tour
3 Bed | 3 Bath | Sleeps 6

Mickey's Magical Escape - Kissimmee, FL

From $110
Oakwater Resort 3D Tour
2 Bed | 2 Bath | Sleeps 6

Oakwater Resort - Kissimmee, FL

From $94

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Recent Kissimmee vacation rental reviews

Adventure Awaits was a great place for us to rest after visiting theme parks all day. The condo had everything we needed and was quiet and comfortable! We also enjoyed the pool area - well maintained, clean and relaxing. One thing I will note that could be updated - the glass shower door in the master bath, as one side of the door is missing and the other side is rather stuck on the track. A person with poor agility would be a little challenged getting in and out of the shower, as the door was somewhat blocking your entrance and exit. A shower curtain has been added over the door, so you can shower without splashing water everywhere. Overall, a great stay for our family of 5!
Sharon V. | Oct 2021
There were roaches in every room. The twin beds were very hard. No dust pan the garage had a smell and the pool was freezing with no jacuzzi. But the house was beautiful and king beds were very soft.
Whitney T. | Oct 2021
My husband and I took our kids and daughter in law to Disney and Universal Studios. Since we would have to get 3 hotel rooms for 4 nights, I looked into renting a house/condo instead. WHAT A FIND! I am SUPER picky about where I stay. It has to be fresh, smell good, comfortable and most of all, clean. The Sunrise Condo fit the bill. There were 5 of us; all adults. We gave our son and his wife the master (had a king); our daughter the double double bed room and we took the queen bedroom. All of the bedrooms had en suite full baths. Even though my hubby and I didn't take the master, we loved our room! It had ample room, great closet and the bathroom was roomy enough for us both. The kids all enjoyed their rooms very much. The air conditioning worked great and that was very nice since the Florida heat and humidity can be a lot! It was fully furnished, meaning their was a complete living room area with TV, a full kitchen and a dining room. The only meals we ate at the condo was breakfast but I had everything I needed to prepare a full breakfast. There is a Publix grocery store within 2 miles of the condo. There are many other fast food places , liquor store, and other convenient stores in the same center. 5-10 minutes away, is also the Championsgate shopping area. There are many restaurants, a Publix and stores there as well. The Disney parks are within 10 minutes of the condo; Universal Studios is about 20 minutes away-both very easy to access from the condo's location. There is a washer/dryer combo in the unit for guest's use. That is very helpful BUT it was a little tricky to figure out; at least for me! The building has an elevator which was very nice for getting all of our luggage to the second floor but this unit is right off of the stairs so it's an easy climb if your arms aren't carrying a load. The complex is located right next to I-4 but we had no issues with highway noise. In fact, the whole complex was very quiet. The area is very pretty and well kept. We felt totally safe. It is gated and you will receive a parking pass to display on your dashboard for coming and going. We were super pleased with the condo and all it had to offer. It was very comfortable for all 5 of us but it could easily sleep a total of 8 in beds. It also has a nice balcony with patio furniture. We would go back in a heartbeat!
Jimi D. | Oct 2021

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
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Where is Kissimmee, FL?

Kissimmee sits just 23 miles south of the bustling metropolis of Orlando, but the atmosphere that you'll find in this quaint and charming town is remarkably different from Orlando's more lively city vibe. Although you won’t see any skyscrapers, downtown Kissimmee’s unique shops, restaurants, and historic Old Town are ideal for travelers wanting to experience a piece of the action while enjoying the quiet neighborhood and the comforts of home! 

Old Town Kissimmee

Arts, culture, and entertainment come alive in Old Town! The outdoor shopping mall and amusement park offer 18 amusement rides (including both a merry-go-round and roller coasters), 10 restaurants, and upwards of 75 specialty boutiques. The brick streets come alive every weekend with a parade of hundreds of hot rods and classic cars during the Nite Car Cruise. 

Old Town is home to an arcade, laser tag, and even a shooter alley so you try your luck at some classic arcade games! Brave travelers can visit the haunted house and ghost tours at the Legends Dark Amusements, while those hoping for a more family-friendly experience can crash into each other at Happy Days Extreme Bumper Cars. With something for everyone, Old Town Kissimmee offers fun - with a little flair - for the whole family! 

Day trips from Kissimmee, FL

Our diverse selection of Kissimmee vacation rentals vary in size and included amenities, but each home boasts a location that is conveniently close to well-known family attractions like Walt Disney World Resort, SeaWorld, and Universal Orlando Resort! Spend your day exploring the parks or just seeing Orlando's many sights, before heading back to your relaxing rental for a good night's sleep. 

During your stay, make sure to take some time and explore the surrounding area! Go pick citrus fruits in Haines City or shop at one of the many farmer's markets, before heading back to your vacation rental to make a delicious homemade meal using local ingredients from the market. Cool off on a hot summer's day with a splash at the water park in Reunion, only 15 miles away. 

Outdoor adventures in Kissimmee, FL

If you're looking for an outdoor adventure or hoping for a bit of an adrenaline rush during your stay, you're in luck! Tee off at Kissimmee golf courses, including the Remington Golf Club, or view the city by sky in a hot air balloon with Thompson Aire. Discover the Florida Everglades and alligators on an airboat ride with Boggy Creek Airboat Rides, an unforgettable experience that is guaranteed to amaze guests of all ages! 

Invite your friends, pack your bags, and leave your worries behind when you come to one of our Kissimmee vacation homes. This charming town promises an exciting getaway full of adventure and family-friendly fun that you'll remember for years to come.

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Photo credit: Henry Hazboun via Shutterstock