Windsor at Westside (Kissimmee, Florida) Vacation Rentals

(17 rentals)
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Key Amenities

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

About this property

Looking for that perfect family friendly home for your fall/winter season travels to Central Florida? Ready to create memories of holiday meals and laughter? Our spacious home offers all that with the little touches that make large family gatherings so much easier. Relax with your own private pool/space ...

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Property Type

Kissimmee Villa

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9 BR | 6 BA | Sleeps 18 | Quick View

Distance to park: 8 miles to Disney's Animal Kingdom Theme Park

$420

avg/night

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Key Amenities

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

About this property

Magic Moments is your home away from home 15 minutes from Disney. It is a five-minute walk from the family-friendly resort amenities at Windsor at Westside, including a zero-entry pool with a waterpark, free arcade games, a fully-equipped gym, a lazy river, and more! Better yet, it has just recently been ...

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Property Type

Kissimmee Villa

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5 BR | 5.5 BA | Sleeps 13 | Quick View

LAST MINUTE DEAL 9/25 - 9/30: *Weekday Special*

Distance to park: 12 miles to Disney's Magic Kingdom Park

$397

avg/night

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Key Amenities

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

About this property

This newly renovated, luxury themed villa is the perfect getaway for all ages.  Conveniently located just 15 minutes from Disney, this 5 bed, 5.5 bath villa allows 13 guests to sleep comfortably and spread out easily in the large, open-concept living/dining/kitchen area and large patio area that ...

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Property Type

Kissimmee Villa

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DEAL

Key Amenities

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

About this property

Come to Livin' Large at Windsor Westside with 100% Free Resort amenities!* Private Heated Pool & Spa * FREE Arcade! Yes, play all you want for Free! * Poolside Tiki Bar & Grill * FREE Resort w/ Heated Lazy River * Kids water playground & slides * FREE 400MB Wifi * Roku: 11 tvs ...

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Property Type

Kissimmee House

"Great home for a large group"

Let me start by saying that Laura is fantastic at communication. Our group is from Canada and we originally booked the house in 2020, but had to delay due to COVID-19 border closures. We communicated ...

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Key Amenities

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

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

"Great home"

We had a wonderful time in this rental. It is gorgeous and very clean and we will definitely be back.

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8 BR | 6 BA | Sleeps 16 | Quick View

5

Distance to park: 8 miles to Disney World

$402

avg/night

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Key Amenities

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

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 24 ...

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Property Type

Kissimmee House

"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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7 BR | 5 BA | Sleeps 14 | Quick View

2

Distance to park: 6 miles to Disney

$352

avg/night

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Key Amenities

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

About this property

Welcome to our stunning Florida holiday home where you'll find everything you could ever wish for, from our large south facing private heatable swimming pool and spa to the purpose built and well-appointed games room. Easy walking distance to the Oasis Club7 Bedrooms. 5 Full Bathrooms. Sleeps ...

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Property Type

Kissimmee House

"Amazing villa and great service"

Visited in May 2019, villa was exactly like the photos. Impeccably clean and finished to an exceptionally high standard. Everything you need for a fabulous holiday. Alison was extremely helpful and responsive. ...

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9 BR | 6 BA | Sleeps 18 | Quick View

4

Distance to park: 8 miles to Disney World

$464

avg/night

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Key Amenities

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

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 24 ...

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Property Type

Kissimmee House

"Christmas vacation"

We had a great stay. Thanks for sharing your home. Great location. Minutes away from popular attractions.

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9 BR | 6 BA | Sleeps 18 | Quick View

3

Distance to park: 8 miles to Disney World

$471

avg/night

View Details

Key Amenities

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

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 24 ...

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Property Type

Kissimmee House

"Thanksgiving"

I was a little skeptical however, Me and my family had a wonderful Thanksgiving getaway at this location. The rooms were wonderful, the pool was great and the sunrise was phenomenal. The host were responsive ...

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8 BR | 6 BA | Sleeps 16 | Quick View

7

Distance to park: 8 miles to Disney World

$408

avg/night

View Details

Key Amenities

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

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 24 ...

View all property information

Property Type

Kissimmee House

"Great Family Vacation Home"

I was pleasantly surprised when I walked into the home. It looked just like the pictures, down to the place settings on the table. The home was clean and had everything my family needed. The pool was ...

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5 BR | 5.5 BA | Sleeps 10 | Quick View

Distance to park: 8 miles to Disney

$352

avg/night

View Details

Key Amenities

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

About this property

5 Bedrooms 5 Bathrooms Family Room with large HD Cable TVAll bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 6 plus breakfast bar and outdoor dining Private screened Pool and Spa with Lanai Patio ...

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Property Type

Kissimmee House

Show less

Key Amenities

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

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 24 ...

View all property information

Property Type

Kissimmee House

"A great place to stay close to everything!"

We gave this home a 5-star review. We had 16 people staying and we had plenty of room, a great pool, a game room, and the resort has a wonderful river float, water slide, and pool. The location was excellent ...

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6 BR | 5 BA | Sleeps 13 | Quick View

1

Distance to park: 8 miles to Disney

$354

avg/night

View Details

Key Amenities

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

About this property

6 Bedrooms 5 Bathrooms Family Room with large HD Cable TV Large Upstairs Loft with HD Cable TV and Games Room with foosball. Great teen/tween or adult hang out space All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal ...

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Property Type

Kissimmee House

"Beautiful House"

I stayed at this property on vacation....this house is beautiful, exactly like the pictures....we had an awesome time and the kids were delighted that the pool was right out the back door. BEAUTIFUL PROPERTY

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7 BR | 5.5 BA | Sleeps 18 | Quick View

1

Distance to park: 4 miles to Disney

$344

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

7 Bedrooms (Sleeps 18) 51/2 Bathrooms Family Room with large HD Cable TV Huge second floor TV loft with HD Cable TV All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 8 plus breakfast bar and outdoor ...

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Property Type

Kissimmee House

"Thanksgiving vacation"

My family had such a great time. Best trip so far. No complaint. Beautiful home ,very comfortable. Just perfect

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5 BR | 5 BA | Sleeps 10 | Quick View

Distance to park: 8 miles to Disney

$344

avg/night

View Details

Key Amenities

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

About this property

5 Bedrooms 5 Bathrooms Family Room with large HD Cable TV Upstairs Loft with large HD cable TV All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 8 plus breakfast bar and outdoor dining Private screened ...

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Property Type

Kissimmee House

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9 BR | 6 BA | Sleeps 18 | Quick View

Distance to park: 6 miles to Disney

$452

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

9 Bedrooms 6 Bathrooms Family Room with large HD Cable TV Giant Upstairs Loft Large HD Cable TV and recliner seating PLUS Full Wet Bar with Beer/Wine Fridge PLUS Pool Table All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal ...

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Property Type

Kissimmee House

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6 BR | 4 BA | Sleeps 16 | Quick View

1

Distance to park: 8 miles to Disney

$343

avg/night

View Details

Key Amenities

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

About this property

6 Bedrooms 4 Bathrooms Family Room with large HD Cable TV Upstairs Cinema Room and Games Room with Pool Table and Foosball All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 8 plus breakfast bar Private ...

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Property Type

Kissimmee Villa

"Amazing house"

Me and my family loved the villa very clean and welcoming. We look forward visiting again next year.

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Windsor at Westside (Kissimmee, Florida) Vacation Rentals