Windsor at Westside (Kissimmee, Florida) Vacation Rentals

(25 rentals)
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8 BR | 6 BA | Sleeps 16 | Quick View

4.8 rating on other travel sites

$588

avg/night

View Details

Key Amenities

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

About this property

"One word - FUN!! Incredible movie theater inside. Awesome movie theater poolside. And, a really cool Star Wars themed game room with LED lighting. The home is professionally decorated. It's beautiful, yet very comfortable." Cindy C.LOOKING for an incredibly fun vacation home to rent? This ...

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Property Type

Kissimmee House

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8 BR | 6 BA | Sleeps 16 | Quick View

4.5 rating on other travel sites

$577

avg/night

View Details

Key Amenities

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

About this property

"Kids and adults love the game room. Really cool. Movie theater in the converted garage is incredible - better than being at a regular movie theater. And, maybe your biggest treat will be the poolside theater. Very pretty and comfortable home and full of fun." Keith C.LOOKING for an incredibly ...

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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

Make unforgettable family memories that will last a lifetime on your next stay at our massive and luxurious home, Tranquility Retreat! Located near the attractions, shopping and theme parks, you'll have access to 2 themed game rooms and all the bells & whistles - think gourmet kitchen, huge living ...

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Property Type

Kissimmee Villa

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Key Amenities

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

About this property

"Kids and adults will love the Star Wars movie theater and huge Harry Potter game room. The virtual reality room is really cool. The pool, spa and lanai offer a lot of fun as well plus it's a perfect area to relax. The home has something for everyone." Chris S.Looking for a fun and very ...

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Property Type

Kissimmee House

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8 BR | 6 BA | Sleeps 16 | Quick View

5.0 rating on other travel sites

$628

avg/night

View Details

Key Amenities

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

About this property

"Professionally decorated, classy and full of fun vacation home with a beautiful waterfront view from the pool area. The inside movie theater and game room have a Jurassic Park theme - both of which make you feel like you are in Jurassic Park. You will find the poolside to be a huge hit at night ...

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Property Type

Kissimmee House

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8 BR | 6 BA | Sleeps 16 | Quick View

4.9 rating on other travel sites

$588

avg/night

View Details

Key Amenities

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

About this property

"Private, peaceful, comfortable, and FUN!! Incredible movie theater inside. Awesome movie theater poolside. And, a really cool Star Wars themed game room. The pool and spa are very private. The home is beautiful, and it is a very short walk to the clubhouse and water park." Keith C.LOOKING ...

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Property Type

Kissimmee House

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8 BR | 6 BA | Sleeps 16 | Quick View

4.9 rating on other travel sites

$625

avg/night

View Details

Key Amenities

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

About this property

"This was our first time renting a home for a vacation. This vacation rental has changed our future vacation options forever. Everything about the home and community was A+. The kids didn't want to leave and the grown ups enjoyed the amenities more than the kids. I would recommend this home for rental ...

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Property Type

Kissimmee House

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8 BR | 6 BA | Sleeps 16 | Quick View

4.8 rating on other travel sites

$581

avg/night

View Details

Key Amenities

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

About this property

"Great house, even better than the listing indicated. Great pool and hot tub, huge living area and plenty of space for a group of 14. The movie room was great, with a highlight of watching Space X launch a rocket on the big screen, then walking to back yard to watch it in the sky. The upstairs is ...

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Property Type

Kissimmee House

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5 BR | 5.5 BA | Sleeps 13 | Quick View

4.9 rating on other travel sites

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

$373

avg/night

View Details

Key Amenities

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

About this property

This newly renovated, luxury themed villa is the perfect getaway for all ages. Located just 20 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 area and large patio area that overlooks the PRIVATE POOL (heat included). ...

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Property Type

Kissimmee House

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9 BR | 6 BA | Sleeps 22 | Quick View

6
Owner special: SPRING BREAK IS STILL OPEN!!! 5 Star Customer Service & Cleaning. BOOK WITH US NOW!!!

$508

avg/night

View Details

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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9 BR | 6 BA | Sleeps 18 | Quick View

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

$514

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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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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5 BR | 4.5 BA | Sleeps 12 | Quick View

Distance to park: 8 miles to Disney

$212

avg/night

View Details

Key Amenities

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

About this property

5 Bedrooms 4.5 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 6 plus breakfast bar seating 4 and outdoor dining ...

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Property Type

Kissimmee Townhome

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7 BR | 5.5 BA | Sleeps 18 | Quick View

1

Distance to park: 4 miles to Disney

$356

avg/night

View Details

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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7 BR | 5 BA | Sleeps 14 | Quick View

2

Distance to park: 6 miles to Disney

$356

avg/night

View Details

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

$493

avg/night

View Details

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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Excellent luxurious home"

First class all the way and we will do it again!! It was a beautiful home and everything that was advertised was true.

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8 BR | 6 BA | Sleeps 16 | Quick View

5.0 rating on other travel sites

$380

avg/night

View Details

Key Amenities

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

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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8 BR | 6 BA | Sleeps 19 | Quick View

Distance to park: 6 miles to Disney

$456

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

8 Bedrooms 6 Bathrooms Family Room with large HD Cable TV Giant Upstairs Loft 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 14 plus breakfast bar seating 4 and outdoor dining Private ...

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Property Type

Kissimmee House

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7 BR | 5 BA | Sleeps 17 | Quick View

1

Distance to park: 8 miles to Disney

$356

avg/night

View Details

Key Amenities

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

About this property

7 Bedrooms 5 Bathrooms Family Room with large HD Cable TV Large Upstairs 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 seating 3 and outdoor dining ...

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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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8 BR | 6 BA | Sleeps 16 | Quick View

5

Distance to park: 8 miles to Disney World

$441

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

"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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9 BR | 6 BA | Sleeps 18 | Quick View

3

Distance to park: 8 miles to Disney World

$495

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

"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

$502

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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6 BR | 4 BA | Sleeps 16 | Quick View

1

Distance to park: 8 miles to Disney

$356

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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5 BR | 4.5 BA | Sleeps 10 | Quick View

Distance to park: 8 miles to Disney

$223

avg/night

View Details

Key Amenities

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

About this property

5 Bedrooms 4.5 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 seating 4 outdoor dining for 6 Private screened Pool Patio with ...

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Property Type

Kissimmee Townhome

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Windsor at Westside (Kissimmee, Florida) Vacation Rentals