Windsor at Westside (Kissimmee, Florida) Vacation Rentals

(14 rentals)
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Kissimmee House
8 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 6 bathrooms
2 reviews

$260

avg/night

$260
avg per night
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Key Amenities

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

About this property

Enjoy a whimsical getaway when you book a stay at this sleek, refreshing, 8-bedroom, 6-bathroom vacation rental home. Take a dip in the private pool, fix up something tasty in the fully equipped kitchen, play a game of pool in the game room, or head to the community fitness center for a quick workout. ...

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Property Type

Kissimmee House

Featured review

"Kissimmee Home/Windsor"

My family & I enjoyed our stay at this lovely home during the summer time. This house gave us an enjoyable experience that we will all remember. We didnt have any problems with the house and we hope to ...

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Kissimmee House
5 BR | 4.5 BA | Sleeps 15 | Quick View
Sleeps 15, 5 bedrooms, 4.5 bathrooms

$236

avg/night

$236
avg per night
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Key Amenities

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

About this property

Welcome to our luxurious and spacious vacation home situated in the stunning gated community of Windsor at Westside. This magnificent 5-bedroom, 4.5-bathroom villa boasts everything you need for an unforgettable vacation with your family and friends, Close to theme parks, shopping mall outlets, restaurants ...

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Property Type

Kissimmee House

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Kissimmee Villa
8 BR | 6 BA | Sleeps 17 | Quick View
Sleeps 17, 8 bedrooms, 6 bathrooms
1 review
owner special
Owner special: November, December, January and February book 7 night one free and free pool heat and BBQ including

$219

avg/night

$219
avg per night
Owner special:
November, December, January and February book 7 night one free and free pool heat and BBQ including

View Details

Key Amenities

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

About this property

Disney Wood Wonderland*** 7 miles from Disney popular attractions Disney's Animal Kingdom Theme Park and Epcot. Walt Disney World and Magic Kingdom Park.

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Property Type

Kissimmee Villa

Featured review

"Couples retreat"

The house was well accommodated for the amount of guests. It was very specious, well maintained. We were satisfied with our stay.

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Kissimmee Villa
8 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 6 bathrooms

$392

avg/night

$392
avg per night
View Details

Key Amenities

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

About this property

Escape to a magical 8-bed 6-bath retreat for up to 16 guests at the Windsor at the Westside resort community. This is an entire home rental. Super Mario game room, Beauty and the Beast dining, Paris-themed kitchen, Guardians of the Galaxy primary bedroom. Upstairs: Hollywood, Pirates, Mickey Mouse, Princesses, ...

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Property Type

Kissimmee Villa

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Kissimmee House
8 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 6 bathrooms
8 reviews

$349

avg/night

$349
avg per night
View Details

Key Amenities

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

About this property

5 star Property!Welcome to Sunset Magic Villa!Delightful Windsor at Westside Resort home villa8 bedrooms (2 Downstairs/6 Upstairs) and 6 full bathrooms. Space for up to 16 guests, (stretch out and relax with all the comforts of home) WEST facing private pool ensuring stunning sunset ...

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Property Type

Kissimmee House

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Kissimmee House
6 BR | 4.5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 4.5 bathrooms
3 reviews

$301

avg/night

$301
avg per night
View Details

Key Amenities

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

About this property

Welcome to your dream vacation home located in Windsor at Westside! This 6 bedroom, 4.5 bathroom sleeps 12 perfectly and is pure luxury. This home has 3 king bedrooms, 2 rooms with a twin and double and then one room with twin bunkbeds. The bedrooms are really fun for the kids with a Harry Potter theme ...

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Property Type

Kissimmee House

Featured review

"Disney vacay"

Mickeys mansion was wonderful. Very clean. Everything you may need in kitchen. We paid extra for heated pool and the adult kids and grandchildren loved it. We would definetly go back and rent this again.

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Kissimmee House
8 BR | 6 BA | Sleeps 18 | Quick View
Sleeps 18, 8 bedrooms, 6 bathrooms
4 reviews

$517

avg/night

$517
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Private pool
  • WiFi

About this property

Check out this amazing home! The sparkling pool basks in sunlight all day, while the lanai offers refreshing shade. It's the perfect setting for complete relaxation and enjoyment.This spacious family retreat comfortably accommodates up to 16 adults. If there is a mix of children and adults, the ...

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Property Type

Kissimmee House

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Kissimmee House
9 BR | 6 BA | Sleeps 18 | Quick View
Sleeps 18, 9 bedrooms, 6 bathrooms
8 reviews

$389

avg/night

$389
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • 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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Property Type

Kissimmee House

Featured review

"Great View"

Fantastic time. Pool overlooks the lake. We had an issue with a burner on the stove the first day and the owner had a brand new stove delivered the next day. The owner has similar properties also. We have ...

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Kissimmee Villa
5 BR | 3 BA | Sleeps 14 | Quick View
Sleeps 14, 5 bedrooms, 3 bathrooms

$157

avg/night

$157
avg per night
View Details

Key Amenities

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

About this property

Welcome to our magical Disney-themed retreat! Nestled in the heart of the Westside at Windsor Resort, our cozy and charming home is the perfect place for you and your loved ones to experience all the wonders of the happiest place on earth. Whether you're planning a family vacation or a romantic getaway, ...

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Property Type

Kissimmee Villa

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Kissimmee House
9 BR | 6 BA | Sleeps 18 | Quick View
Sleeps 18, 9 bedrooms, 6 bathrooms
6 reviews

Distance to park: 8 miles to Disney World

$398

avg/night

$398
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • 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 ...

View all property information

Property Type

Kissimmee House

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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Kissimmee House
8 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 6 bathrooms
5 reviews

Distance to park: 8 miles to Disney World

$354

avg/night

$354
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • 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 ...

View all property information

Property Type

Kissimmee House

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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Kissimmee House
8 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 6 bathrooms
8 reviews

Distance to park: 8 miles to Disney World

$350

avg/night

$350
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • 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 ...

View all property information

Property Type

Kissimmee House

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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Kissimmee House
8 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 6 bathrooms
4 reviews

Distance to park: 8 miles to Disney Animal Kingdom

$351

avg/night

$351
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • 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 ...

View all property information

Property Type

Kissimmee House

Featured review

"Quite and comfortable"

Nice area, quite and convenient to many attractions many restaurants close by.nice pool and hot tub and gym in clubhouse.

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Kissimmee House
9 BR | 6 BA | Sleeps 18 | Quick View
Sleeps 18, 9 bedrooms, 6 bathrooms
4 reviews

Distance to park: 8 miles to Disney World

$366

avg/night

$366
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • 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 ...

View all property information

Property Type

Kissimmee House

Featured review

"Great for large family"

Very spacious, 9 bedrooms, for my family vacation of 12 people. Had some issues with the spa heat, but Iverson was very responsive.

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Windsor at Westside (Kissimmee, Florida) Vacation Rentals