Kissimmee Vacation Rentals

(288 rentals)

8 BR | 5 BA | Sleeps 21 | Quick View

Distance to park: 4 miles to Major Disney Theme Parks

$758

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Free pool heating! Sleeps 21. Complimentary access to the luxurious Storey Lake clubhouse. Perfect for families and work trips, staycations and vacations. Four miles to Disney theme parks. Quick access to all of Orlando's attractions. Play Star Wars electronic pinball, pool, and foosball in the spacious ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Located in popular Sonoma Resort, our home is the perfect place to stay for a care and stress-free holiday away. Whether you are looking to spend long days lounging by the pool, exploring the parks or stretching your legs on one of the surrounding golf courses, this is the perfect location. Guests benefit ...

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Property Type

Kissimmee Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Sonoma Resort - Kissimmee, Florida is only 15 minutes to the area's main attraction... Walt Disney World. This brand new resort community sits nestled just outside of Orlando, between W. Osceola and W. Irlo Bronson Memorial Hwy and conveniently located next to "The Loop", a premier shopping ...

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Property Type

Kissimmee House

"Awesome house!"

We held our annual Married Couples Retreat. It was above and beyond all of my expectations. More than enough room for everyone that no one was on top of each other. Definitely will yes again!

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4 BR | 3 BA | Sleeps 10 | Quick View

3

Distance to park: 3 miles to Disney's Animal Kingdom

$250

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

The large, fully-equipped kitchen is complete with a microwave and dishwasher! The home’s layout is perfect for watching the fun going on in the pool area from the living room, dining area and kitchen! The fully equipped kitchen offers everything you need to feel at home; both a Kuerig coffee maker ...

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Property Type

Kissimmee House

"Excellent place to stay"

Lovely place to stay, nicely decorated and clean. Clubhouse pool is very big and was quiet in the mornings. Only thing to improve would be more loungers as there are only 2

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4 BR | 3 BA | Sleeps 8 | Quick View

2

$140

avg/night

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Key Amenities

  • Air conditioning
  • Private pool

About this property

Bella Vida - Kissimmee, Florida is an upscale gated community located just 7 miles from Walt Disney World. This luxury resort sits nestled just off Hwy 192 in Kissimmee, Florida and is one of the most desired resorts in the Orlando area. During your stay, you will enjoy this well-appointed home that has ...

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Property Type

Kissimmee Townhome

"Great home"

This was a awesome place we really enjoyed the time we spent there. My kids must have message mr. Charles a thousand times but he had a wonderful home. Nicely decorated huge kitchen, even though i forgot ...

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8 BR | 4.5 BA | Sleeps 16 | Quick View

9

Distance to park: 3 miles to Disney's Animal Kingdom

$261

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Thank you for visiting Mickey's Mansion, a resort home in the heart of all the action yet quiet and peaceful. There's nothing better than being in the Florida sunshine to relax, refresh and escape reality for awhile. Your hosts, JoAnn and Les, are ready to welcome you as their guests and give you the ...

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Property Type

Kissimmee House

"Review"

Spent part of the time with our employees and part with family. This property was accommodating to both! The owners were quick to respond and easy to work with! Great property!

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

This luxurious home will not disappoint with its 8 bedrooms and 6 bathrooms. Two masters - one on the main floor and the second master is located on the upper floor - both with en-suites.This home has a two car garage, with a South facing pool & spa overlooking the conservation area. The oversized ...

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Property Type

Kissimmee House

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7 BR | 4.5 BA | Sleeps 14 | Quick View

3

Distance to park: 3 miles to Disney World Parks

$216

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Huge Orlando vacation rental home has 7 bedrooms and 4.5 bathrooms. Great for a large Family with up to 14 guests! There are two King Master Suites, one on each floor. The master bathroom on the first floor has a walk-in shower and separate garden tub. Bedroom 3 & 4 King beds and Bedroom 5 One Queen ...

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Property Type

Kissimmee House

"Hidden Gem!"

My family and I had such an amazing stay. As we traveled to Florida from Mississippi, this beautiful home was a wonderful place to relax, kick back, and make memories. This home is located nearby numerous ...

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8 BR | 6 BA | Sleeps 20 | Quick View

3

Distance to park: 3 miles to Disney World Animal Kingdom

$454

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

You and your family can have the vacation of a lifetime in this exquisite home in a quiet neighborhood that has all the extras you could imagine and one of the largest pools in the entire area. It's in the best location - super close to all attractions as well as restaurants, shopping, golf courses, mini-golf, ...

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Property Type

Kissimmee House

"Wonderful, Beautiful, Clean, and Convenient to the Parks!"

My children and grandchildren stayed at this beautiful home for our Disney World trip. This home was so beautiful and clean and set the tone of our trip. Seeing the excitement on my 5-year-old granddaughter's ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Windsor at Westside - Kissimmee, Florida is an upscale gated community located just 10 minutes from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida and has quickly become one of the most desired locations in the Orlando area. During your stay, you will enjoy this well-appointed ...

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Property Type

Kissimmee House

"Nice sized home"

Home was what it showed online. Heat in pool worked-yay! Limited on items in the kitchen & ice maker was missing literally!! Besides that nice home for value!

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Updated with Themed Rooms!! 3 miles from Disney7 Bedrooms, 4.5 Bath, (4 KING BEDROOMS)Just minutes from Disney located in a gated community inside Emerald Island Resort, Kissimmee, Florida, this professionally decorated and spacious vacation villa offers luxurious accommodations with 7 Disney-themed ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

FIRST OPEN DATE May 15th- May 22nd. $125 A night and weekends $140Welcome to Beauty And The Cove! This is a family ran AirBnB 2 level townhome that is speckled with Disney decor and a Disney Lego Castle on display!The entire townhome will be yours to use!We strived to make our home as baby ...

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Property Type

Kissimmee Townhome

"AMAZING location"

We traveled to Disney with my daughters for the first time. The girls LOVED the Mickey Room and the home was clean, safe and exactly as pictured. Just a 5 min drive to Disney Property and everything you ...

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4 BR | 3 BA | Sleeps 8 | Quick View

14

Distance to park: 4 miles to Disney

$125

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Magical Dreams come true in our elegant private 4 bedroom villa, 3 bathroom, all located on one floor, Quiet upgraded comforts of home and luxuries of an exceptionally rated vacation resort/hotel. Newly resurfaced and freshly painted pool and spa is sure to impress. There will be no waiting in line ...

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Property Type

Kissimmee House

"Kissimmee Villa"

Lovely home, well cared for and excellent location. Quiet neighborhood which was great for walking. Park with play equipment close by for young families.

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6 BR | 5 BA | Sleeps 12 | Quick View

5

$260

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Solara Resort - Kissimmee, Florida is an upscale community currently under development just 7 miles from Walt Disney World. This gated resort community sits nestled just outside of Orlando, Florida. During your stay, you will enjoy this well-appointed home that has been designed and decorated to provide ...

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Property Type

Kissimmee House

"Perfect Family Reunion"

House was better than expected.. Excellent location. Pool was fantastic. Hope to go back next year. Close to all the attractions and restaurants.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Our beautiful 3000sq 5 Bed, 4 Bathroom home is located on a generous corner plot. With a south facing Pool and stunning views over the second tee of the Arnold Palmer Golf Course on Reunion ResortThe open plan living area is comfortably furnished and has a wood look tiled floor. Flat screen tv. ...

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Property Type

Kissimmee House

"Very Nice!"

We rented this house for 8 nights and was very pleased with it. Communication with Jackie was awesome. Always responded quickly. Definitely will rent again.

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8 BR | 6 BA | Sleeps 20 | Quick View

3

Distance to park: 11 miles to Disney Theme Parks & Water Parks

$400

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

You can Book the property by clicking on the link which you can find under " OWNER INFO "Enjoy the comforts in this spacious home located in the community of Windsor At Westside that has a water park with a lazy river, tiki bar, and spa. You will love your stay in this 8-bed x 6-bath home ...

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Property Type

Kissimmee House

"Great place great trip"

We had a wonderful time and the house with all the amenities was the perfect place to come back to after Disney world to relax and swim

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

8 Bedroom, 4.5 Bathroom pool house located within a gated community.6 bedrooms have king sized beds, 2 bedrooms have two sets of twin bunkbed, 2 Cribs. Each bedroom has a smart TV.This house boasts a private screen in pool and spa. Also a screened in, covered lanai with outdoor dining and seating ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Westgate Town Center Resort offers the perfect locale where you can reset, regroup and rejuvenate while on your family vacation to Kissimmee, Florida. This full-service resort has it all! Splash around Shipwreck Island Water Park, check out the cozy movie theater, savor made-to-order dishes at the onsite ...

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Property Type

Kissimmee Apartment

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4 BR | 2 BA | Sleeps 9 | Quick View

1

Distance to park: 5 miles to Disney World

$132

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Superb Remodeled 4 bedroom condo at 2 bedroom price! Legacy Dunes Resort. 4 bedroom/2 bathroom 1400 sq ft condo with screened balcony and children's playground & lake view. Easily accessible for the entire family so you can bring Grandma and Granddad. Or two couples each with two children, or groups ...

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Property Type

Kissimmee Condo

"Recently renovated 4 bedroom condo in a great complex, close to everything."

This is our third extended stay in this unit. We enjoy the closeness to Disny as well as the closeness to grocery shopping and most of the chain restaurants. This gated complex is set back from Route 192 ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

POOL SAFETY FENCE!!!! - Florida law requires that doors leading out to the pool have an alarm. THAT IS NOT ENOUGH!. If you are traveling with children please make sure the house you are renting has a pool safety fence.This Beautiful home is well situated, close to all major attractions and amenities, ...

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Property Type

Kissimmee House

"Great Villa for my needs"

I volunteer each year at GKTW in Kissimmee so Mark's villa for perfect for my needs. Used 3 of the 4 bedrooms with guests so we all had bathrooms as well - important for our early starts! A few things cropped ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Beautiful south facing lakeside villa with solar and electric heated pool. Great location for all the theme parks, Disney 20 mins, Seaworld 15mins, Universal 30 mins and Cocoa Beach/Kennedy Space Centre 45 mins. Local English management contact and fully inspected/licensed by the Florida Hotels Board. ...

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Property Type

Kissimmee Villa

"Cozy just right"

Everything was so accommodating. There was an issue with the pool heat in the beginning I contacted the property managers and within 24 hours there was a pool person there fixing the pool heat. It worked ...

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4 BR | 2.5 BA | Sleeps 9 | Quick View

5

Distance to park: 10 miles to Disneyworld

$149

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Our villa is modern style furnished, has everything you would expect in a holiday home, 4 bedrooms, 2 with king-size beds, 1 with single bed´s, 1 with triple bunk bed all with private TV. 2 bathrooms, 1 guest toilet, fully equipped kitchen, etc. with ceran stove, fridge, oven, microwave, coffee ...

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Property Type

Kissimmee House

"Great place"

Lots of space out of the Hustle and bustle but close enough for a small drive to get to everything needed kids love the pool

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8 BR | 4 BA | Sleeps 16 | Quick View

10

Distance to park: 6 miles to Disney

$288

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

As you step through the front door of this 2800-square-foot home, you are immediately drawn to the unique geometric wall design and mid-century modern decor throughout the house. The lighting is spectacular as you enter the great room and look through the two sliding glass doors onto the patio where the ...

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Property Type

Kissimmee Villa

"Mad Men Vacation Rentals Magic Kingdom Kissimmee Fl"

€ Mad Men Magic Kingdom House Post We stayed at Mad Men Vacations Magic Kingdom Home In Kissimmee from December 26, 2021 to January 10, 2022. There were nine of us in our party plus 2 small dogs. ...

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4 BR | 3.5 BA | Sleeps 10 | Quick View

5

Distance to park: 5 miles to Animal Kingdom

$109

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Enjoy Orlando, Florida, home to Disney World, Sea World, Universal Studios, and Islands of Adventure, in style. Our home is within minutes of all the Orlando attractions, golf courses, shopping, and exciting night life. Our richly appointed vacation Townhouse will give you luxurious living and a vacation ...

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Property Type

Kissimmee Townhome

"We loved this house"

We really liked this beautiful house! Nice beds and good kitchen. It has got everything we needed. Great location and great neighbourhood.

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4 BR | 2 BA | Sleeps 8 | Quick View

4

Distance to park: 7 miles to Walt Disney World

$202

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Welcome to our Florida villa, the Lake House at Sunset Lakes. The Lake House at Sunset Lakes is an upscale rental villa in the greater Orlando Florida area, minutes away from Disney’s Magic Kingdom and theme parks, your choice of fine golf courses and many other attractions. This four bedroom house ...

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Property Type

Kissimmee Villa

"6 Stars"

If I could give 6 stars I would!We stayed for 16 nights and it was such a great time!Gorgeous house in a great location with stunning views, Jane is a fantastic host who responds to any queries ...

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5 BR | 4 BA | Sleeps 10 | Quick View

1

Distance to park: 5 miles to Disney World

$247

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Situated on one of the largest corner lots at the resort, there's plenty of privacy in the rear of the villa. The rear facing pool means you'll always have sunshine and warmth no matter what season of the year. You'll love spending time at the pool area featuring an over-sized deck, large swimming pool ...

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Property Type

Kissimmee Villa

"Great Place"

The house was very comfortable, beautiful heated pool and spa but should have had railings to get in and out of. Not far from Disney although a little far from the magic kingdom (leave early for that park).The ...

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3 BR | 2.5 BA | Sleeps 8 | Quick View

1

$118

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

You have arrived in the "Vacation Capital of the World" and you're going to love staying in our luxury, 3 bedroom, 2.5 bath, fully equipped vacation townhouse rental situated near DisneyWorld and all other theme park attractions. The property rental is located within the resort community at ...

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Property Type

Kissimmee Townhome

"Beautiful Condo! Exactly as shown!"

We are a retired couple who stayed for 3 months from Jan to March. Beautiful Condo, exactly as pictured. Furniture is very comfy. Close to all attractions. We felt very safe. Publix and Walmart are ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Built in 2002, Windsor Palms Resort is a gated community approximately five miles from Disney. This luxury complex has a 7500 square foot clubhouse, basket ball courts, volleyball courts, children's play area, large swimming pool, splash pad, hot tub, picnic and barbecue area, outdoor bar, convenience ...

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Property Type

Kissimmee Condo

"Location, location, location!"

Well, this main floor condo was a great place to stay. It is close to the pool, easy access for parking and luggage/groceries and had all the amenities we could think of. Five minutes to Walmart for all ...

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3 BR | 2 BA | Sleeps 8 | Quick View

1

Distance to park: 5 miles to Disneyworld and Disney Springs

$95

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

You have arrived in the "Vacation Capital of the World" and you're going to love staying in our luxury, three bedroom, two bath, fully equipped vacation condo rental situated near DisneyWorld and all other theme park attractions. The property rental is located within the resort community of ...

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Property Type

Kissimmee Condo

"nice place"

nice place, the location was great the golf course was not far away. The condo had a nice pool and hot tub will come back

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4 BR | 3 BA | Sleeps 8 | Quick View

8

Distance to park: 3 miles to Mgm

$119

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Beautiful 4 bedroom /3 bath private villa only 3 miles to Disney and other parks. Including heated pool/jacuzzi and game room. Free wifi and phone use in USA and Canada and PR. Fully furnished with all kitchen needs . Greatest location to shopping , all major restaurants and stores including supermarkets ...

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Property Type

Kissimmee Villa

"An Excellent Choice for both you and your pet!"

We waited a bit late to find and rent a home for 3 months this winter, and happened to find this one was still available in March of 2021. Our hopes were for our children and grandchildren to possibly ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Our luxury Kissimmee vacation villa will comfortably sleep 10 people. It is fully air-conditioned for your comfort, and has a very roomy and spacious floor plan. It has 2 lounge areas (one with 2 full sofas, and a ceiling fan, the other with a love seat and a sofa bed), both have cable T.V. The kitchen ...

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Property Type

Kissimmee Villa

"We are Home"

Enjoyed my stay at this property it was very homey for me and my family. Only one question if the filters was changed in the home all of our sinuses went haywire even down to the babies. It could be the ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Private 2 story home with 4 Bedroom/3 Bathroom with private pool which has all of the spacious and convenient accommodations for your entire family vacation. Storey Lake is near to all of the major parks & attractions of Disney World, Epcot, Animal Kingdom, Disney Water Parks, Universal Studios and ...

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Property Type

Kissimmee Townhome

"Escaping to Kissimmee for the winter."

Nice location (close to all the attractions). The resort amenities were wonderful and within walking distance (we did take advantage of the free golf cart shuttle service on a few occasions to avoid the ...

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5 BR | 3 BA | Sleeps 12 | Quick View

2

Distance to park: 3 miles to Disney

$158

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

5 bedrooms, 3 bathrooms, sleeps 10 - 12.Spacious, 5 bed, 3 bath, luxury villa with Private Pool, Spa +Games Room (pool, air hockey and football tables) Guests have full use of all facilities of the Prestigious Emerald Island Resort, including Club House with pool, spa & licensed Tiki Hut Bar, ...

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Property Type

Kissimmee Villa

"Great experience"

We had a great experience dealing with Ian he is professional and responded right away if we needed anything , the house was clean and organized when we got there. Everything worked out as planned. Would ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

MAGIC HOUSE, is a beautifully furnished 4 bedrooms, 3 bathrooms home with a 26ft x 14ft swimming pool and Spa,. covered lanai. It is only a 3 mile drive to Walt Disney World Resort. It's in easy reach of all other major attractions.MAGIC HOUSE is a luxury villa located in the quiet friendly neighborhood ...

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Property Type

Kissimmee House

"Great Home owner, Great Home!!"

When we first arrived the hot tub and pool were not heated when we paid extra for the heat, With a quick email to the owner he had the issue resolved by morning. House was clean, and in a very seemingly ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Welcome to Sunshine Memories Villa, where you will have an amazing vacation enjoying all that the Orlando area has to offer. Our 5-bedroom 5-bathroom villa is located less than 10 minutes away from Disney in the beautiful gated resort of Windsor Hills. As you step inside the foyer of your vacation home ...

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Property Type

Kissimmee Villa

"Don’t worry, be happy"

Even with all that’s going on, this was a blessing in disguise. Really needed this and everything was perfect. You can’t live your life in fear, just be cautious in all you do. No complaints whatsoever. ...

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4 BR | 2.5 BA | Sleeps 11 | Quick View

Distance to park: 14 miles to Disney

$250

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Enjoy Orlando, Florida, home to Disney World, Sea World, Universal Studios, and Islands of Adventure, in style. Conveniently located on Crescent Lakes. The house is spacious where family can enjoy being together and also have some alone time. Our home is within 11 miles approximately of all the Orlando ...

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Property Type

Kissimmee House

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4 BR | 2 BA | Sleeps 8 | Quick View

Distance to park: 3 miles to Walt Disney World

$190

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

4 Bedrooms| 2 Baths| Sleeps 8|Private Pool|Games Room|Disney-Themed Kids Rooms| Updated Decor|If you’re looking for the perfect home away from home for your family’s perfect Disney vacation, look no further. Our bright, airy house in the desirable 5-star Emerald Island Resort means that ...

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Property Type

Kissimmee House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Luxury Reunion Villa By Disneyhis 8 bedrooms 7 bathrooms Contemporary Villa is located very close to Disney, a perfect choice for family and friends wanting an Orlando vacation. Sleeping up to 18 guests, this home has 3 owner suites with bathroom also 2 additional queen bedroom with en suite bathroom. ...

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Property Type

Kissimmee House

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9 BR | 5 BA | Sleeps 18 | Quick View

1

$509

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comThe Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. ...

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Property Type

Kissimmee House

"Great family vacation home!"

We really enjoyed our time in this house! The few little glitches were handled immediately by the villatel staff. There was so much to do on our "house day" while we rested between long days at the parks. ...

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9 BR | 5 BA | Sleeps 18 | Quick View

$509

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comThe Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. ...

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 8 | Quick View

1

$188

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comStorey Lake - Kissimmee is a brand new vacation community located just 4 miles from the magical world of Disney and just minutes to Universal, ...

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Property Type

Kissimmee House

"Great town home with wonderful amenities"

The location was a short trip from the airport. Large town home to accommodate space for all. Loved having our own pool and we all loved the community pool area. We will be back.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

6 bedrooms 6 bathrooms Villa by Disney. 5 ensuite rooms and the 6 th bedroom downstairs has a bathroom right outside the door. 1 Themed room, nice pool with hot tub. Smart TVs in all rooms.Nice full kitchen for those who miss home cooked meals. Close all the parks, malls and restaurants.The ...

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Property Type

Kissimmee House

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10 BR | 5 BA | Sleeps 20 | Quick View

$551

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comThe Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. ...

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Property Type

Kissimmee House

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9 BR | 5 BA | Sleeps 18 | Quick View

$509

avg/night

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About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comStorey Lake - Kissimmee is a brand new vacation community located just 4 miles from the magical world of Disney and just minutes to Universal, ...

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Property Type

Kissimmee House

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6 BR | 4 BA | Sleeps 12 | Quick View

1

$330

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

Guests: 12 / Bedrooms: 6 / Bathrooms: 4 / Community: Indian Creek / Type: Villa6 LARGE BEDROOMS, 4 FULL BATHS A King Size Master Bedroom with TV, walk-in closet, a private pool/spa access door, a large en-suite master bathroom consisting of a large walk in shower and separate tub,his & hers ...

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Property Type

Kissimmee Villa

"Fantastic trip!! Wonderful property management."

My family and I had a great Christmas vacation. We were very close to Disney and the house was clean, quiet and well cared for. We were very pleased with the communication from the property management team ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Welcome to VIPvilla Johanna and Stephen thank you for visiting our website of hand-picked 5 Star quality villas. We manage the bookings for 50 private villa owners on this website and we can personally assure you that you will be delighted with any of the villas offered to you. We have many repeat ...

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Property Type

Kissimmee Villa

"Spring break vacation"

The communication was a 100% and the place is nice and accessible. The villa comes fully equipped. Thank you

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6 BR | 5 BA | Sleeps 12 | Quick View

Distance to park: 5 miles to Old Town, food,shops and rides

$190

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Spacious air conditioned home on large plot and not overlooked! Living area with 3 sofas and huge TV with cable triple play included and doors to pool deck. Dining tables and chairs enough for all guests and seating at breakfast bar. Refurbished kitchen with granite work tops, stove, microwave, dishwasher, ...

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Property Type

Kissimmee House

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4 BR | 3 BA | Sleeps 8 | Quick View

14

Distance to park: 10 miles to Disney Theme Parks

$121

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

A brilliant family home for a Florida holidayQuiet and peaceful, Stylishly furnished with granite countertops in kitchen and bathrooms, the open-plan accommodation offers both formal and informal dining inside, as well as al fresco dining in the lanai by the sparkling, South-facing private pool. The ...

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Property Type

Kissimmee Villa

"Great Stay and Close to Disney!"

The house was exactly what we were looking for. It was set in a quiet gated community and just minutes from several shopping centers and a Walmart.The house was fully furnished, dishes/plates, pots, ...

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6 BR | 6 BA | Sleeps 12 | Quick View

$334

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

Be sure to visit our website to check availability on all our homes! Save our page for future vacations to the Orlando area!Visit us at lostinthemagic . comThe Retreat at Champions Gate - Kissimmee, Florida is a new upscale gated resort community located just 12 miles from Walt Disney World. ...

View all property information

Property Type

Kissimmee House

Show less

Key Amenities

  • Air conditioning

About this property

DREAM!! 3 BEDROOM 2 BATHROOM CONDO WITH BALCONY AT AMAZING STOREY LAKE RESORT!*Property sanitized and professionally cleaned following all CDC guidelines*Condo Amenities:Free High Speed Wifi Telephone with FREE Local Calls Iron and Iron Board Hairdryers Central air conditioning and heating Linens ...

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Property Type

Kissimmee Apartment

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Kissimmee Vacation Rentals

Kissimmee Weather

 | 

7222°  489°
JANUARY
7323°  499°
FEBRUARY
7725°  5312°
MARCH
8228°  5814°
APRIL
8731°  6418°
MAY
9032°  7021°
JUNE
9233°  7222°
JULY
9233°  7222°
AUGUST
9032°  7122°
SEPTEMBER
8429°  6518°
OCTOBER
7926°  5714°
NOVEMBER
7323°  5010°
DECEMBER

Soak up the Sun on Your Next Trip to Kissimmee Vacation Rentals

There’s nothing quite like a vacation to sunny Florida, a unique and inviting state with a huge variety of distinctive cities and natural areas to explore. One popular vacation destination in Florida is Kissimmee, a charming city with plenty to see and do just south of the Orlando metropolitan area. 

Kissimmee has a lot more to offer visitors than just excellent weather year-round. With a huge variety of scenic nature, shopping opportunities, and outdoor activities, Kissimmee itself has lots to offer every member of the family, not to mention its extremely close proximity to some of Orlando’s biggest amusement parks. 

You could stay in a busy hotel during your trip to Kissimmee, but then you wouldn’t be able to get a truly immersive experience of local city life. Kissimmee vacation rentals allow you to enjoy Kissimmee from inside its authentic residential neighborhoods. Additionally, having your own home to live in rather than a jam-packed hotel will provide some much-needed peace and quiet during your vacation. It will also offer plenty of space for the whole family to spread out.  

Top Tips for Traveling to Kissimmee Rentals

Like most other Florida cities, Kissimmee enjoys sunshine and clear skies throughout the majority of the year. However, the tropical climate of the state means that bouts of rain can occur throughout the seasons, particularly during the summer months, peaking in August. 

In addition to a higher likelihood of rain, the summer season in Kissimmee tends to be the most humid time of year. That’s why most vacationers choose mid to late spring or early autumn to make their trip to the city. At those times of the year, vacationers can enjoy great weather and lots of outdoor activities. 

Though the Kissimmee Gateway Airport is located centrally within the city, most vacationers taking commercial flights will fly into Orlando International Airport. It is located roughly 17 miles northeast of the city center, about halfway between Kissimmee and Orlando. Vacationers coming in from elsewhere in Florida can access Kissimmee by road using U.S. Route 192 and U.S. Route 441.

Things to Do Nearby Kissimmee House Rentals

Some of the most popular natural areas around Kissimmee are the swamps, which are located in major local bodies of water like Lake Tohopekaliga (known around town as Lake Toho). At Boggy Creek Airboat Adventures, you can experience the swamps from the water and get the thrill of a lifetime on an airboat driven by a local wetlands expert. Get up-close views of gator ponds, discover precious gemstones, and then grab a delicious lunch with the family at Boggy Bottom BBQ! 
Looking to explore a piece of history during your trip to Kissimmee? Medieval Times Dinner & Tournament allows visitors to step into the 11th century for an evening of authentic feasting, jousting, and sword fighting in true medieval style! Enjoy a delicious four-course meal, incredible performances, and a truly unforgettable experience for the entire family. 
Any vacation to Kissimmee isn’t complete without a trip or two to Old Town, a popular outdoor attraction with opportunities for shopping, dining, and family fun. Old Town is made up of an 18-acre stretch of classic city attractions, including the Old Town Ferris Wheel, the Great Magic Hall, and Mortem Manor, a year-round haunted house that is open for visitors to explore.
Kissimmee Annual Events

Kissimmee is a vibrant area with lots of annual festivals and events to enjoy in and around the city throughout the year. Kissimmee locals and visitors alike flock to the Ford Cuban Sandwich Festival each May near downtown Kissimmee, which celebrates the colorful history of Cuban cuisine in the area. Watch as local dining professionals attempt to build the world’s biggest Cuban sandwich during the event! 
The Ford Taste of Latino Festival is another local opportunity to celebrate and experience the best in authentic Latin cuisines in Kissimmee. The event features a contest to find the Top Latino Chef as well as plenty of live music and dance performances to enjoy as you taste a variety of Latin dishes. 
Not sure if you’ll be in town for any of Kissimmee’s larger annual events? You can enjoy Show Car Saturday Nights every Saturday night in the city on Margaritaville Boulevard. Check out the city’s best classic cars from a variety of eras and enjoy the plethora of delicious eateries and exciting shops located along the boulevard.

Wining and Dining in Kissimmee  

Between your outdoor activities and trips to local amusement parks while in Kissimmee, you’re sure to need some satisfying food and refreshing drinks to complete your perfect day. Luckily, Kissimmee is home to some of the best restaurants that Florida has to offer, combining authentic local flavors with worldly cuisine. 

To start your day off right with a delicious and hearty breakfast, look no further than Woodsby’s Countryside Café. This spot has authentic, cozy diner vibes to spare, not to mention a stacked menu of classic breakfast favorites, coffee bar items, and unique dishes you won’t want to miss out on. 

Tarantino’s Italian Restaurant is a great choice for a vacation date night or simply a nice dinner out with the family. A hearty Italian meal is a great way to finish a fun day of activities, and you’re sure to get that and more at Tarantino’s. If you bring the family along, you can take advantage of the takeout dinner special, which feeds four and includes a massive entrée, salad, and garlic bread.


FAQ

How many vacation rentals are there in/around Kissimmee?

There are 288 Kissimmee vacation rentals available on FloridaRentals.com. From house rentals to cottage rentals to beach condos and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Kissimmee?

There are vacation rentals available in Kissimmee for as low as $85 per night with an average price per night of $206.

Can I rent a house in Kissimmee?

Yes, you can find house rentals in Kissimmee close to Lakefront Park, Monument of States, and Old Town. Don't forget to stop in to Shingle Creek Park or the nearby theme parks!

Do any vacation rentals in Kissimmee have a pool?

Yes, there are 241 vacation rentals in Kissimmee with a pool on FloridaRentals.com. Search using our filters and book one for your next vacation!

What are the best vacation rentals in Kissimmee?

Visitors give great reviews to these top-rated Kissimmee vacation rentals available on FloridaRentals.com:
Indian Creek Retreat: Well maintained home in the Indian Creek subdivision which is literally on Disney's doorstep and your home away from home.
Casa Bonita: 'Casa Bonita' which means 'Beautiful Home' is a beautifully furnished four bedroom, three bathroom home with a 26 ft x 14 ft swimming pool.
Mickey's Villa: This beautiful 5-Bed 4-Bath home located in the very popular community of Indian Creek is one of only three homes in the development with a Mickey Pool.