Windsor at Westside (Kissimmee, Florida) Vacation Rentals

(18 rentals)
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New 9Br/6Ba Pool Villa from $330/nt, Close To Disney

9 BR | 6 BA | Sleeps 20 | Quick View

3

Distance to park: 8 miles to Disney World

$414

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid 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

"Thanksgiving 2020"
Reviewed December 5, 2020

My family and I decided to do Thanksgiving in Florida this year. This house was amazing!!! We were in the pool and hot tub everyday!!! It was very spacious and nice, we truly enjoyed!!! Will be booking ...

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New 9Br/6Ba luxurious Pool House from $330/NT,,Close to Disney

$415

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid 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

"Great Escape"
Reviewed November 14, 2019

This was a nice home with great location on top of a hill with the backyard overlooking the water/fountains. The house was very clean . The entertainment room upstairs was enjoyable. I could not have chosen ...

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6 Bedroom Pool Home, minutes from Disneyworld

$241

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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"
Reviewed October 10, 2020

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

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Luxury Sunset View 8 bed pool home, water views, game room, pet friendly

8 BR | 6 BA | Sleeps 16 | Quick View

2

Distance to park: 4 miles to Animal Kingdom

$332

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool

About this property

This is the one you've been looking for! Your holiday home from home - our fabulous luxury villa with private pool and spa is situated in the gated resort community of Windsor at Westside, conveniently situated approximately 10-15 mins from Disney and close to Golf at Champions Gate. Up to 16 people can ...

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Property Type

Kissimmee Villa

"Spring Break Retreat"
Reviewed March 12, 2021

We were looking for a place to spread out, have a heated pool, and be close to the parks. This place delivered all that and more. When we arrived, the place was clean and ready for our visit. We cooked ...

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Tropical Oasis - Windsor at Westside

7 BR | 5.5 BA | Sleeps 18 | Quick View

1

Distance to park: 8 miles to Disney

$199

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

This remarkable seven bedroom pool and spa home located in the popular Windsor Westside Resort - ideally located for a memorable family or pool of friends. It is a beautifully designed Tropical Oasis getaway to the theme parks and attractions of Orlando, including Walt Disney World®,Universal Studios, ...

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Property Type

Kissimmee Villa

"BEAUTIFUL HOUSE 2127 TRIPOLI CT"
Reviewed May 3, 2021

WE ALL FIT JUST RIGHT.. NO ONE WAS ON TOP OF ONE ANOTHER..THE POOL AND JACUZZI WAS JUST RIGHT.. THE ONLY THING I DIDNT LIKE WAS WE HAD TO PURCHASE ANOTHER PRPANE TANK TO COOK ON THE GRILL WHEN WE ALREADY ...

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"Livin' Large"♦️9 BR Free Windsor Resort - 8 mi Disney/ESPN-Great Family/Corp

$330

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"Everything I expected!"
Reviewed March 25, 2021

I was very pleased with the homes cleanliness it was exactly as it shows in the pictures. I had no problems while being there as the instructions were very clear for our checkin and checkout. The home was ...

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Livin' the Life❤️NEW Clean 9BR/5 King/FREE Resort/WDW/ESPN

9 BR | 6 BA | Sleeps 24 | Quick View

3

Distance to park: 8 miles to Disney

$315

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

This is truly one of the best 9 BR homes close to Disney/ESPN!It's just been completely repainted and deep cleaned top to bottom. Our cleaners are top notch - always 5 STAR REVIEW - kitchen, baths and linens are bleached every clean.* We have a second 9 BR 2 doors down! * Private Heated Pool ...

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Property Type

Kissimmee House

"Family Fun!"
Reviewed June 15, 2021

Me and my family had an awesome stay. Management was readily available to attend to our needs. The kids had fun in the pool and the adults enjoyed the hot tub. Plenty of room for our family of 16.

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Windsor at Westside-8956CEZLJGIL

7 BR | 5 BA | Sleeps 14 | Quick View

1

$272

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

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 Villa

"Windsor at Westside"
Reviewed April 10, 2021

Beautiful house and pool. Kitchen could use a few more utensils and a pizza pan or cookie sheet. Very comfortable beds. Good location. The pool areas of this house and other neighboring house back up to ...

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6BD/4BA Designer Home Modern Affordable. private Pool/Spa Cinema Room. Game Room

6 BR | 4 BA | Sleeps 16 | Quick View

1

Distance to park: 8 miles to Disney

$255

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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"
Reviewed March 28, 2021

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

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New 8br/6ba pool villa from $290/NT , Close to Disney

8 BR | 6 BA | Sleeps 18 | Quick View

5

Distance to park: 8 miles to Disney World

$355

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid 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

"Wonderful Family Vacation"
Reviewed July 14, 2019

My family vacation was wonderful and the house was amazing! I definitely look forward to renting a home for my family's next vacation trip!⭐⭐⭐⭐⭐

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New 9Br/6Ba luxurious Pool House from $330/NT, Close To Disney

9 BR | 6 BA | Sleeps 20 | Quick View

3

Distance to park: 8 miles to Disney World

$419

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid 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"
Reviewed December 2, 2020

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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New 8br/6ba pool villa from $290/NT,Close to Disney

8 BR | 6 BA | Sleeps 18 | Quick View

4

Distance to park: 8 miles to Disney World

$356

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid 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

"Amazing !!!!!"
Reviewed January 4, 2020

Loved,loved,,,,,, we were 13 persons ,,,,what you see is what you get ,,,, everything was perfect ,,,

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5BD 5BA Private Pool/Spa Gamesroom Free use of Resort Facilities

5 BR | 5 BA | Sleeps 10 | Quick View

Distance to park: 8 miles to Disney

$230

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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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Wonderful Home. Close to Disney. Great Value. Amazing Games Room. Pool /Spa

7 BR | 5.5 BA | Sleeps 18 | Quick View

1

Distance to park: 4 miles to Disney

$255

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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"
Reviewed December 5, 2019

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

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7 Bed 5 Bath Windsor at Westside. Cinema. Games Room. Affordable.

7 BR | 5 BA | Sleeps 14 | Quick View

2

Distance to park: 6 miles to Disney

$255

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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"
Reviewed May 21, 2019

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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Beautiful 6BD 5BA Very Private Pool/Spa Games Room Free use Resort Facilities

6 BR | 5 BA | Sleeps 13 | Quick View

1

Distance to park: 8 miles to Disney

$230

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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"
Reviewed August 18, 2019

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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Affordable 5Bath/5Bath. Private Pool. Games Room Free Use of Resort Facilities.

5 BR | 5.5 BA | Sleeps 10 | Quick View

Distance to park: 8 miles to Disney

$255

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

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Lake Views! Summer Kitchen with Grill! Modern Design! Resort Facilities!

9 BR | 6 BA | Sleeps 18 | Quick View

Distance to park: 6 miles to Disney

$344

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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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Windsor at Westside (Kissimmee, Florida) Vacation Rentals