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Kissimmee Vacation Rentals

(197 rentals)
Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms
9 reviews

Distance to park: 4 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to La Casita on the Island (The Little House on the Island) "Our house, our casita" If you want a place to relax and enjoy the beautiful weather of Florida, I invite you to see the "encanto" (charm) that you can experience during your stay at La Casita on the Island.Enjoy...

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Featured review

"Great Villa"

Had a fantastic stay in the villa. Would definitely stay again and highly recommend. It was extremely clean and in a great location near shops, resturaunts and 192 and Disney. Would highly recommend and...

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$152
avg per night
Kissimmee Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This well maintained 3 bedroom 2 baths home located in the renowned Lindfields Estate.It is perfectly placed to maximize your family’s vacation fun here in the entertainment capital of Florida!You will not want to miss this lovely vacation home close to Disney and on the doorsteps of local...

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Featured review

"Great"

A great family vacation rental.booking was easy and check in process was flawless. We had an issue with the internet but the manager resolved it as soon as possible.The rental was safe clean and convenient...

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$140
avg per night
Kissimmee Condo
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

My place offers all you need for a perfect family vacation. Minutes to Disney World, close to all the other attractions. Gated community Villas at Island Club. Two large saltwater swimming pools (my unit is steps from the swimming pool), a tennis court, a volleyball court, and two clubhouses with exercise...

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$106
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
5 reviews

Distance to park: 8 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this...

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Featured review

"Very nice"

We really enjoyed our stay. Community was really nice and house was huge. Had some good amenities and was a real easy drive to all the parks. Pool was nice… wish we paid for heat but we didn’t. ...

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$346
avg per night
Kissimmee House
Sleeps 10, 5 bedrooms, 4 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our stunning spacious 5 bedroom, 4 bath home located in the much sought after community of Tuscan Hills near DisneyThis beautiful home offers 2 masters en-suite bedrooms and 3 sitting rooms.Full air con and hi-speed WiFi throughout.The villa uniquely has 3 sitting rooms, two of...

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Featured review

"Amazing villa"

My family and I stayed at this wonderful villa for 5 nights. The house is very spacious,.clean and in a secured gated community. Watersong community is the best area for villa rentals close to Disney. We...

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$200
avg per night

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Kissimmee Villa
Sleeps 24, 9 bedrooms, 6 bathrooms
14 reviews

Distance to park: 2 miles to Sunday's Grill

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

For last minute rentals or longer extended rentals, please inquiry about our discounted rates.This luxury vacation home is located in the Windsor at Westside upscale resort community - A perfect destination for DISNEY WORLD (10 minutes away), golf, and relaxing and celebrating with family and friends....

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Featured review

"Excellent"

Thank You Ann great service. Me and my family will be renting from you again in the future

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$319
avg per night
Kissimmee House
Sleeps 15, 5 bedrooms, 5 bathrooms
15 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Enjoy this family friendly, five bedroom Orlando vacation home that sleeps 15 people and features a private pool, a Super Mario game and movie room, and themed rooms for the kids including a Beauty and The Beast castle room and Transformers! The entire interior of this home is brand new, so you'll...

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$202
avg per night
Kissimmee House
Sleeps 20, 9 bedrooms, 6 bathrooms
3 reviews

Distance to park: 2 miles to Disney’s Animal Kingdom Park

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, This 24 hour guard gated...

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Featured review

"Very comfortable"

I went with my family, very comfortable. Beds 6 out of 10. Pool 7 out of 10. Rest of amenities 10 out of 10.

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$389
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
6 reviews

Distance to park: 8 miles to Disney Animal Kingdom

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee, Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this...

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Featured review

"Awesome"

Verry nice villa, warm jacuzzi. It was awesome. Bathrooms and bedrooms were good. Everthing was clean when we arrived. Great

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$353
avg per night
Kissimmee Villa
Sleeps 12, 6 bedrooms, 5 bathrooms
5 reviews

Distance to park: 4 miles to Disney

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

We are only 3.5 miles from Disney!! So close to all the fun, Hollywood Studios, Sea World, beaches, walks, restaurants and shopping!! We are in the middle of it all! You will enjoy our lovely villa by yourself or with a group. Our pool is one of the biggest among the rental communities. When comparing...

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Featured review

"Wow!!!! Perfect 10 out of 10!!!!"

We stayed at the property for 6 nights during our recent family's Disney World vacation. Right from the start of the process, the owner was very courteous and prompt with her responses to our many questions....

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$429
avg per night
Kissimmee House
Sleeps 18, 9 bedrooms, 6 bathrooms
6 reviews

Distance to park: 8 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this...

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Featured review

"Great property!!"

What a great property! It was perfect for our family. Very spacious and clean. Definitely staying there again on our next stay in Florida.

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$396
avg per night
Kissimmee Villa
Sleeps 12, 5 bedrooms, 3 bathrooms
17 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This villa is a stunning 5 Bed 3 Bath villa that can comfortably sleep 12 guests.A stunning, larger than average, 5 Bed 3 Bathroom villa with a fantastic private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard.The villa is spaciously arranged...

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Featured review

"Ahhh-Mazing Villa"

Our family of 5 were sooo comfortable in this villa! Close to shopping and experiences. We will definitely be back!

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$130
avg per night
Kissimmee Condo
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Distance to park: 3 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Surrounded in Magic! Please check your spam for any quotes.Kids of all ages will love this magical, bright and spacious Disney & Universal Studios themed (1400 sq ft), 3-bedroom, 2-bath, 1st floor condo. Set in a quiet location at the renowned Windsor Hills Resort within walking distance...

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Featured review

"Disney vacation"

We moved into the condo for 4 nights to finish out our vacation, after staying at a Disney Property for three nights. Wow, this property was fantastic, very clean. The two themed bedrooms were such a hit...

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$184
avg per night
Kissimmee Villa
Sleeps 14, 7 bedrooms, 4.5 bathrooms
16 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This luxury villa is perfectly located on the exclusive Emerald Island Resort community less than 3 miles from Walt Disney World, Florida. The property has 7 bedrooms two of which are master bedrooms with en suite bathrooms and a further two and a half bathrooms.This stunning elegant and spacious...

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Featured review

"Great stay"

Great stay at this villa in Emerald Island, location is perfect for all the parks as well as going to the beaches. Katrina was very responsive12 in our party, 4 of which were children, the property...

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$149
avg per night
Kissimmee Townhome
Sleeps 10, 5 bedrooms, 3 bathrooms
3 reviews

Distance to park: 6 miles to Disney,Seaworld

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to the beautiful Coral Cay Resort. It is one of the most popular resort destinations in the Kissimmee/Orlando area for its proximity to the theme parks and other major attractions. Situated 6 miles from Disney World, 1 mile to Walmart and target. 8 miles to Seaworld and Convention center. Minutes...

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Featured review

"Comfortable place to stay....."

We stayed here while in Florida for my daughter's dance competition. It was so nice to come "home" after a long day of dance. I loved that the driveway was right up to the door. I also loved that it...

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$141
avg per night
New
Kissimmee House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Perfect home for SUMMERS, WINTERS, HOLIDAYS. This IMMACULATE, CLEAN, LUXURIOUS, WATERFRONT PROPERTY WITH AMAZING SUNSET VIEWS, PRIVATE HEATED POOL, 2 suites KING and QUEEN. Great for ROMANTIC GETAWAYS or FAMILY REUNIONS, LONG TERM STAYS OR VACATIONS to Sea World and Universal Studios, minutes to Orlando...

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$371
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
17 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A stunning, larger than average 4 Bed 3 Bathroom villa.There are 2 sitting rooms both with lots of comfortable seating. Both rooms have large screen TVs, ideal for when the adults want to watch the latest sports programme whilst the kids enjoy the latest Disney film. Netflix subscription is also included...

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Featured review

"Highly recommend this villa"

We have just returned home after spending two great weeks at this amazing villa.It was spacious,spotlessly clean, with very comfortable beds and all the amenities you need for a relaxing, enjoyable holiday. The...

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$120
avg per night
Kissimmee Villa
Sleeps 14, 6 bedrooms, 5.5 bathrooms
2 reviews

Distance to park: 3 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This "Tropical Magic" villa is proudly offered to you by "Emerald Island Rentals"Air Conditioning • Free Wi-Fi • Free Internet • Outdoor Grill • Parking Included • Pool • SMART TVs through-out • Full-size laundry facilities • Children Welcome...

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Featured review

"Excellent vacation & house"

we were a family of 10 staying in this beautiful house was well equipt with everything we needed room was a big hit ..The heated pool was sure a big catcher the 4 children loved it so did the adults.....

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$298
avg per night
Kissimmee House
Sleeps 16, 7 bedrooms, 4 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Relax in the comfort of this luxurious, family friendly, seven bedroom, resort vacation home that sleeps 16-18 people. Featuring a private pool, Avengers movie room, themed rooms for the kids including Star Wars, Harry Potter and Pirates themes, and resort amenities included at the exclusive Terra Verde...

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$248
avg per night
Kissimmee House
Sleeps 10, 5 bedrooms, 4 bathrooms

Distance to park: 6 miles to Disney World

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This beautiful 5 bedroom house is located in Crystal cove gated community. Perfect vacation home for families with small children or large groups. This vacation villa offers a sunny private pool, relaxing spa overlooking the lake. There are 2 master suites, private pool, community pool / gym. Pool...

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$238
avg per night
Kissimmee Villa
Sleeps 12, 6 bedrooms, 3.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Bring your family to this stunning 6BR 3.5BA in the luxurious gated community just minutes from the world-famous Disney World. Have hours of fun in the game room and scenic pool backyard, or set out to explore local theme parks, golf clubs, restaurants, shops, and more!6 Comfy Bedrooms (2 Themed) ...

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Featured review

"Wonderful Stay!"

The house was lovely and had everything we needed for my family of 6 week long stay. Kitchen was well stocked with everything we needed, house and pool were clean, and the beds were comfortable. The 80s...

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$189
avg per night
Kissimmee House
Sleeps 14, 5 bedrooms, 5 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This lakefront resort pool home sleeps 14 and is steps from the Paradise Palms clubhouse, and only minutes from Disney World, Universal, and all Orlando attractions. Featuring 5 bedrooms with three king beds, private pool, a Tron themed game & movie room, and themed rooms for the kids including Mickey...

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$243
avg per night
Kissimmee Villa
Sleeps 10, 5 bedrooms, 3 bathrooms
9 reviews

Distance to park: 8 miles to Disney

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come stay in our spacious one story single family home that features 5 bedrooms, 3 bathrooms fully kitchen and a private pool (can be heated for additional fee)Our home is very well located in Lake Berkley Resort with short walking distance to the lake berkley, where you may walking or fishing....

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Featured review

"Our stay for Disney trip"

The house was very comfortable and we were very pleased with all the options including the pool. We will definitely recommend and use this resort again. Thank you

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$160
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 6 bathrooms
8 reviews

Distance to park: 8 miles to Disney World

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Windsor at Westside Resort is one of the newest and most luxurious resort communities in the Orlando/Kissimmee,Developed by one of the nation's largest developer , the Pulte Homes. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area, this...

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Featured review

"GREAT"

Great home for large family .. home is located close to shops … it’s a great location to be at! Very nice

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$346
avg per night
Kissimmee Villa
Sleeps 18, 8 bedrooms, 4.5 bathrooms
17 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

One of the closest communities to Walt Disney World (less than 3 miles away), Emerald Island Resort is a quiet oasis in which to spend your vacation. Emerald Island is an exclusive man gated resort community less than a mile from the world famous US Highway 192 where you will find shops, restaurants,...

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Featured review

"One of the best rentals to date"

Everything that was in house info was delivered. Safe neighborhood and close to everything. House was clean and well set up for our family. Pool and hot tub were our favorite with plenty of room for everyone.

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$186
avg per night
Kissimmee House
Sleeps 12, 6 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

A Truly Luxurious Executive Retreat, Main Level Features: Quality Ceramic Tile Flooring throughout. Spacious Family Room with Vaulted Ceiling and Corner Leather Sofa.70″ TV with 5.1 surround sound with blue tooth capabilities. Formal Dining Room/ Sitting Area with table for six, Fabulous Kitchen...

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$356
avg per night
Kissimmee Villa
Sleeps 10, 5 bedrooms, 3 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Your villa is located on the gated 5 Star Lake Berkley Resort in Kissimmee. 5 Beds, 3 Bath home that is beautifully furnished throughout (Big TV/Games Room/Heated Pool/Free Internet). Our villa is furnished to a very high standard and being all one level is ideal for one or two families. The villa...

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Featured review

"Lake Berkley Villa"

We have rented from this agent multiple times and are always beyond pleased. Each home we have rented were great and the location is perfect. Any communications before, during and after have always been...

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$130
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
14 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

We invite you to stay at our villa which is a 4 Bedroom 3 Bathroom luxury vacation home.The villa is fully equipped with everything you will need including air con throughout, private pool, WiFi, fully equipped kitchen, laundry room, bed linens, towels etc.Full air con and hi-speed WiFi throughout.As...

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Featured review

"Beautiful villa with all you’ll need"

This is an excellent villa with absolutely everything you might need during your stay. Plenty of towels, kitchen utensils and lots of extras in the garage, like golf clubs and inflatables for the pool....

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$160
avg per night
Kissimmee Villa
Sleeps 10, 5 bedrooms, 4 bathrooms
22 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our stunning, larger than average, 5 Bed 4 Bathroom villa with a beautiful view of the conservation area at the rear as background of our private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard.The villa is located just off US 192...

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Featured review

"Fabulous Villa on Bellavida Resort"

All I can say is fabulous, the villa was everything you promised and more, absolutely superb. Cleaning was done to a high standard throughout. Pool was enjoyed by all, multi coloured pool light at night...

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$160
avg per night
Kissimmee Condo
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Distance to park: 2 miles to Disney’s Animal Kingdom Park

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

This huge 1650 sqft condo has 4 bedrooms and 3 full bathrooms. It is located at Sun Lake Resort, just 2 Miles to Disney world Florida.sleeping accommodations for 8.* King-size Master bedroom with bathroom* One queen size sofa bed in family room for extra guests* One 40" HDTV(free...

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Featured review

"Nice Vacation Condo Rental"

Located near Disney, shopping, restaurants. Everything on 1st floor was wonderful for a group of oldsters!

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$125
avg per night
Kissimmee House
Sleeps 16, 8 bedrooms, 5 bathrooms
20 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This spacious home is designed to impress with top-tier amenities and elegant touches, making it ideal for families or groups craving an unforgettable escape. Enjoy the ultimate blend of comfort and excitement ensuring your stay is spectacular.Bedroom 1: (3) Twin Beds, Bathroom Attached Bedroom 2:...

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$390
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Ideal for your next family vacation, this striking 4-bedroom, 3 bath Disney area vacation home is conveniently located just 10 minutes to the Walt Disney World Resort, 15-20 minutes from Universal Studios Florida and SeaWorld Orlando. Florida’s famous beaches are just a quick 45 minutes away. ...

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Featured review

"Very comfortable villa with a great pond view and beautiful sunsets!"

We stayed in this villa for 20 nights. Upon arrival the house was spotless and we found the furniture to be very comfortable. We used the hot tub and pool a lot and were glad that we could find shade...

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$170
avg per night
Kissimmee House
Sleeps 16, 9 bedrooms, 5 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to your 9-bedroom lakefront villa with a private pool, just minutes from Disney! Race in the Mario Kart room, sleep in a Princess Castle and a Guardians room, explore the glowing Avatar game room, and relax in the vibrant Coco loft. Packed with luxury amenities, themed fun, and endless photo ops—this...

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$348
avg per night
Kissimmee House
Sleeps 7, 3 bedrooms, 2 bathrooms
8 reviews

Distance to park: 12 miles to Disney

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Heavenly Retreat, a designated rental vacation home, was just remodeled in a casual and comfortable style. It is a complete turn key ready vacation home with a full equipped kitchen, three bedrooms, and two bathrooms for up to 6 guests. The pool offers lots of privacy and relaxing atmosphere.This...

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Featured review

"Large well kept house"

very nice house. Clean, spacious rooms, nice pool, quiet neighborhood. Very nice owner, she helped several times with tv operation. Enjoyed staying there very much. Good location. Near major roads.

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$158
avg per night
Kissimmee House
Sleeps 12, 6 bedrooms, 5 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Fantastic 2 KING bed EnSuite Villa w heated pool HOT TUB Mins to DisneyFamily-friendly Kissimmee vacation home in Four Corners with water parkContactless one time access code check in! All white linen! Private pool heat up to 104 degree. It’s like a 5 star hotel but better! Pet Friendly...

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Featured review

"Great place"

The owners were very easy to work with. The house was in perfect condition, very clean and well maintained. We had 9 people and plenty of room for everyone. Definitely would recommend the house.

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$294
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

At Calabay near Disney- This 4 bedroom 3 bath home is well maintained and cared for. It is a perfect vacation rental getaway. The spacious foyer leads to a well equipped kitchen/dining room. The master bedroom has a king bed; master bath has double sinks, garden tub, privacy toilet & shower. A second...

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Featured review

"Perfect serene environment"

My family and I thoroughly enjoyed our stay at the villa. It’s truly one of the best private rental properties in Florida, and we would rate it over 100%!

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$155
avg per night
Kissimmee Townhome
Sleeps 8, 4 bedrooms, 3 bathrooms
3 reviews

Distance to park: 6 miles to Disney,Seworld

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to the beautiful Coral Cay Resort. It is one of the most popular resort destinations in the Kissimmee/Orlando area for its proximity to theme parks and other major attractions. Situated 6 miles from Disney,1 mile to Walmart and target, 8 miles to Seaworld and Convention Center.This 1500...

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Featured review

"Wonderful location"

Very nice home, close to Disney and shopping places. Very quiet friendly neighborhood. Def will be booking again in the future

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$134
avg per night
Kissimmee Villa
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Located in the prestigious, gated Windsor Palms resort community in Kissimmee, this privately owned 3-bedroom, 3-bathroom vacation villa comfortably sleeps up to 6 guests. Featuring a private south-facing splash pool with full privacy, spacious en-suite bedrooms, and just a 4-minute walk from world-class...

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$120
avg per night
Kissimmee House
Sleeps 12, 6 bedrooms, 6 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Our 6 Bedrooms 6 Bathroom, luxury villa ideal for you and your families / friend’s vacation.As you enter the home you are greeted with a large living room area. Towards the back of the villa there is an open plan living/dining/kitchen area. There are tri-sliding doors to the pool area where...

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Featured review

"Stunning villa"

Let me start by saying location was Ok.South of I-4 not so good. Traffic very bad to theme park near I-4. Gated community nice. Guards were very nice and pleasant. Now for the Villa. Villa was beautiful.Entry...

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$185
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our fabulous 4-bedroom, 3-bathroom family villa, located in the highly sought-after community of Orange Tree in Clermont, just off Highway 27.This spacious and fully air-conditioned home is ideal for families or groups of up to 8 guests. With two living areas, a fully equipped kitchen,...

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Featured review

"AWESOME!!!!"

This home is just as described. It is clean, well kept, beautifully decorated and spacious with plenty of kitchen utensils. The game room was so much fun. We had a few hiccups but the property management...

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$140
avg per night
Kissimmee Townhome
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Distance to park: 5 miles to Disney,Seworld

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to our new opening 4 Bedroom/3 bathroom Townhouse in CLUB CORTILE,This gated-community is close to every major Orlando attraction: Disney's Magic Kingdom, Epcot, Animal Kingdom, Universal Studios (Harry Potter), Sea World, and many more. Club Cortile is also conveniently close to WalMart,...

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Featured review

"Well located safe townhouse on a lake with good club facilities"

We are a pensioned couple from the Netherlands and in Florida to play golf in the sunshine. We have rented from the owner on several occasions over the last 15 years. This was our first time in the Club...

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$129
avg per night
Kissimmee Condo
Sleeps 8, 4 bedrooms, 3 bathrooms
8 reviews

Distance to park: 2 miles to Disney’s Animal Kingdom Park

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to the Sun Lake Resort. We have 4 identical 1650 sqft units with 4 bedrooms and 3 bathrooms. The beautiful condo faces to sun lake and it has a spacious screened patio. It only takes 1 minute walk to a plaza for shopping and restaurants which is very convenient! More importantly, you are only...

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Featured review

"Awesome stay"

Beautiful resort and room was great. Great location and staff was very helpful. Would highly recommend this property.

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$128
avg per night
Kissimmee Villa
Sleeps 10, 5 bedrooms, 4 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

One of the closest possible communities to Walt Disney World (less than 3 miles away), Emerald Island is a quiet oasis in which to spend your vacation. Emerald Island is an exclusive gated community less than a mile from the world famous US Highway 192 where you will find shops, restaurants, and entertainment....

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Featured review

"Family vacation"

Our family were there for 2 1/2 weeks and everyone loved it. Location very close to parks,restaurants and stores.Grandkids loved the time in the pool. House was big enough for the family and clean.Screens...

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$136
avg per night
Kissimmee House
Sleeps 10, 5 bedrooms, 4.5 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our superb 5-bedroom 4.5-bathroom villa, located in the community of Solana in Davenport. It is fully gated for security.The villa is modern and very spacious with all the amenities you could want. It sleeps up to 10 guests.The villa benefits from 2 sitting rooms. One is classed as...

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Featured review

"Lovely house handy Disney andalltheattractions"

The location of this house was great for visiting all the attractions. There were 10 of us—9 adults and 1 child. We loved everything about this place. It was clean, everything we needed, pool and hot...

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$165
avg per night
Kissimmee Villa
Sleeps 8, 4 bedrooms, 3 bathrooms
16 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Your villa is located in an upscale gated community located just 8 miles from Walt Disney World. Terra Verde Resort is one of the most desired resorts in the Orlando area. Only a 25-minute drive from the Orlando International Airport and is situated central to all of Orlando’s famous attractions....

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Featured review

"Great vacation home"

Very clean, lots of room, vacation home. Great location in the middle of everything. Room for family of 10

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$155
avg per night
Kissimmee House
Sleeps 20, 10 bedrooms, 7 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Exciting NEW 10 bedroom family vacation home Offering privacy and space for everyone 4300 square feet of awesomeness 2 separate large living areas Relaxing pool with spa Covered outdoor dining and seating Games loft with pool table and foosball Windsor Island Resort offers a wide variety of world...

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Kissimmee House
Sleeps 18, 8 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Windsor at Westside Resort features a large 10,000 sq.ft. clubhouse which includes a resort-style pool, lazy river, water slide, & hot tub. Other amenities include a gym, beach volleyball, cabana rentals, basketball court, game room, tiki bar and concierge desk.Location is great with a Kissimmee...

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Kissimmee Weather

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7222°  489°
JANUARY
7323°  499°
FEBRUARY
7725°  5312°
MARCH
8228°  5814°
APRIL
8731°  6418°
MAY
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JUNE
9233°  7222°
JULY
9233°  7222°
AUGUST
9032°  7122°
SEPTEMBER
8429°  6518°
OCTOBER
7926°  5714°
NOVEMBER
7323°  5010°
DECEMBER

FAQ

Proximity to Attractions

How close are Kissimmee rentals to the main entrance of Walt Disney World versus Orlando rentals?

Some Kissimmee vacation rentals are only 12 miles from Walt Disney World. Orlando rentals are a little further away from the amusement park at around 20 miles.

What is the average drive time from Kissimmee to Universal Studios or SeaWorld?

The average drive time from Kissimmee to Universal Studios is 23 minutes, while the average drive to SeaWorld takes 25 minutes.

Are there Kissimmee communities that offer shuttle services to the theme parks?

Yes. Encore Resort Condo, Wyndham Bonnet Creek Resort Condo, and Champions Gate Condo are some of Kissimmee’s vacation rentals offering shuttle service to Walt Disney World, Universal Studios, SeaWorld, and other attractions.

How bad is the traffic on US-192 or I-4 when driving from Kissimmee to the parks?

Both US-192 and I-4 are busy roadways leading to the parks. Traffic is heavier or lighter depending on the day of the week and the time of day. Weekday mornings, early evenings, and Saturdays are especially crowded.

Property Type & Communities

What are the most popular resort communities in Kissimmee (e.g., Reunion, ChampionsGate, Windsor Hills)?

Champions Gate, Reunion, Emerald Island, Windsor Hills, and Indian Creek are all popular resort communities in Kissimmee.

What kind of exclusive amenities do these large resort communities offer?

Some exclusive amenities include a clubhouse, tennis courts, a fitness center, a movie theater, a sauna, and a marketplace to purchase food.

Is it better to stay in a large resort or a smaller, non-gated community in Kissimmee?

The answer depends on your preferences. A smaller, non-gated community in Kissimmee offers fewer amenities than a large resort but still has a collection of fun activities nearby.

What are the main differences between staying in Kissimmee versus staying in Orlando?

Orlando is a large, bustling city full of restaurants, shops, and attractions, while Kissimmee is less crowded with a more family-friendly atmosphere. Though both cities are close to the major parks, Kissimmee is closer to Disney World, whereas Orlando is closer to Universal Studios.

Amenities & Features

What size homes are typically available for rent in Kissimmee?

The typical Kissimmee vacation home has four bedrooms and ranges from 1,980 to 2,000 square feet.

Do most house rentals come with a private, screened-in pool and lanai?

Though most house rentals come with a private, screened-in swimming pool, not all of them have a lanai.

Are multi-generational homes with multiple master suites common?

Yes, multiple master suites are common in Kissimmee vacation homes for rent.

What are some unique amenities to look for in Kissimmee homes, like private movie theaters or elaborate game rooms?

Check listings for unique amenities in Kissimmee house rentals such as EV chargers, gardens, balconies, ping pong tables, pool tables, game rooms, and heated pools.

Booking & Cost

Is it generally more affordable to rent a large house in Kissimmee compared to a similar one in Orlando?

Yes, when comparing similar homes in these two Florida cities, Kissimmee house rentals are the more affordable option.

What are the typical resort fees or community access fees I should budget for?

The typical resort fee is around $40 per day.

Are there any "hidden costs" associated with Kissimmee rentals, like pool heating or BBQ grill rental?

Studying the “Fees” section of a Kissimmee rental’s listing can help you avoid any surprise costs. Some owners list fees for services like pool heating, damage protection, and pets.

What is the best time of year to find deals on Kissimmee vacation homes?

September and October are the best times to find deals on Kissimmee vacation homes because fewer people are booking rentals.

Kissimmee Specifics

What attractions are there to see in Kissimmee itself, outside of the major theme parks?

Boggy Creek Airboat Adventures, Gatorland, Shingle Creek Regional Park, Congo River Golf, and Lake Tohopekaliga (Lake Taho) are all unique attractions in Kissimmee.

What are the best places for shopping and dining in the Kissimmee area?

The Promenade at Sunset Walk, The Crosslands, and Universal CityWalk are some of the best places for shopping, dining, or both.

How does the vibe of Kissimmee differ from the International Drive area in Orlando?

Orlando’s International Drive has a high-energy vibe with dozens of shops, restaurants, shows, spas, and other attractions. While Kissimmee has its own collection of shops, eateries, and attractions, the city’s vibe is more laid-back.

Are there any good nature-based activities, like airboat tours, that are easily accessible from Kissimmee?

Yes. Wild Florida Adventure Park, Gatorland Bird Rookery, and horseback riding sessions at Lazy H Ranch give visitors the opportunity to admire Kissimmee’s natural environment.