Windsor at Westside (Kissimmee, Florida) Vacation Rentals

(26 rentals)
6 Bedroom Pool Home, minutes from Disneyworld

$200

per night

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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

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Westside Escape

5 BR | 4 BA | Sleeps 10 | Quick View

$175

per night

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Key Amenities

  • Air Conditioning
  • Private Pool

About this property

New in 2016, Windsor at Westside is a gated vacation rental community close to Disney featuring an 8,000 sq.ft. clubhouse with the Tu Casa Bar & lounge, market & deli, video arcade, sundries shop & fitness center. Other fantastic amenities such as a playground, volleyball court & multi-purpose ...

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Property Type

Kissimmee Townhome

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April Specials!! 8 bedroom Luxury Pool Villa!!

$345

per night

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Key Amenities

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

About this property

Come and enjoy our home away from home that offers peace & relaxation while only being 6 miles from all the action at Disney. Our home is furnished with the most luxurious items for your comfort & enjoyment and we have tried to think of every possible thing you would need to have the most relaxing ...

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Property Type

Kissimmee Villa

"Beautiful Villa"
Reviewed January 19, 2019

Thank you for letting us stay at your beautiful villa. My four children and their families and myself enjoyed everything from the great stocked kitchen to the comfy mattresses. Plenty of room for all of ...

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New 9 Br/6 Ba luxurious Pool House from $300/nt, Close To Disney

9 BR | 6 BA | Sleeps 20 | Quick View

1
Owner special: Last minutes deal for $290/NT

Distance to park: 8 miles to Disney World

$300

per 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 ...

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Property Type

Kissimmee House

"tripl A stay"
Reviewed March 6, 2019

nice house nice place clean we will come back next time. good price good location. triple AAA stay. :)

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New Opening 8br/6ba pool villa from $259/nt ,Close to Disney

8 BR | 6 BA | Sleeps 18 | Quick View

3
Owner special: Last minutes deal for $250/NT

Distance to park: 8 miles to Disney World

$257

per 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 ...

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Property Type

Kissimmee House

"Beautiful home located in a great area."
Reviewed February 9, 2019

This home was beautifully appointed and very spacious! Everyone enjoyed the hot tub and swimming pool. The clubhouse has plenty of amentities and the lazy river was a nice bonus. Close to shopping and ...

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Brand new 8br/6ba pool villa , Close to Disney

8 BR | 6 BA | Sleeps 18 | Quick View

4
Owner special: Last minutes deal for $260/NT

Distance to park: 8 miles to Disney World

$257

per 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

"Everything was perfect"
Reviewed October 16, 2018

This property was everything we were hoping for. It was very clean upon arrival and came with all the appliances and dishes that one would need when living in such a house. The pool and hot tub were very ...

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New 9Br/6Ba Pool Villa from $300/nt, Close To Disney

9 BR | 6 BA | Sleeps 20 | Quick View

1
Owner special: Last minutes deal for $290/NT

Distance to park: 8 miles to Disney World

$300

per 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 ...

View all property information

Property Type

Kissimmee House

"Wonderful"
Reviewed April 26, 2018

Beyond expectation. Spacious , great kitchen, lots of bathrooms. Pool was lovely. The resort pool area is great for all ages.

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

$289

per 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 Grill * FREE 200MB Wifi * ...

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Property Type

Kissimmee House

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New Opening 9 Br/6 Ba luxurious Pool House

9 BR | 6 BA | Sleeps 20 | Quick View

3
Owner special: Last minutes deal for $290/NT

$300

per 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 ...

View all property information

Property Type

Kissimmee House

"Amazing stay"
Reviewed July 18, 2018

My family and I at first didn't know what to expect with our stay at this particular home. Usually pictures looks better than vacation homes look in person; so we was hoping for the best and expecting the ...

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Modern 5BD 5BA Windsor at Westside Sleeps 14 Pool/Spa Games Room TV Loft

$185

per night

View Details

Key Amenities

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

About this property

5 Bedrooms 5 Bathrooms SLEEPS UP TO 14 Family Room with large HD Cable TV Upstairs TV Loft/Den is a great kids hang out space 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 ...

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Property Type

Kissimmee House

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New 2019 Beautiful 5BD/4BA Very Private Pool/Spa Games Room Free Resort Use!

5 BR | 4 BA | Sleeps 1 | Quick View

Distance to park: 8 miles to Disney

$184

per night

View Details

Key Amenities

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

About this property

5 Bedrooms 4 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 8 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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New opening 8bd/6ba from $260/nt close to disney

8 BR | 6 BA | Sleeps 18 | Quick View

1

Distance to park: 8 miles to Disney World

$257

per 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

"Awesome spacious home"
Reviewed April 15, 2019

Awesome spacious home with 4 comfortable suit bedrooms, great amenities and hospitality! super clean and large pool & hot tub! Well worth the price,

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Modern 8BD 5BA Windsor at Westside Pool/Spa Game Room Free use Resort Facilities

$290

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Kissimmee Villa

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Amazing 7BD 5BA Windsor at Westside. Game Room. Cinema Room. Pool & Spa

$310

per night

View Details

Key Amenities

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

About this property

7 Bedrooms 5 Bathrooms Family Room with large HD Cable TV Upstairs Loft with Cinema Screen All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 10 plus breakfast bar and outdoor dining Private screened ...

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Property Type

Kissimmee House

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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

$184

per 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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Fantastic 5BD 4BA Private pool/spa PLUS Windsor at Westside Resort Facilities!

$188

per night

View Details

Key Amenities

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

About this property

5 Bedrooms 4 Bathrooms Family Room 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 and outdoor dining Very Private screened Pool and Spa with Lanai with ...

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Property Type

Kissimmee House

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Fantastic Pool/Spa 5BD 4BA Windsor at Westide. Free use of Resort Facilities.

$188

per night

View Details

Key Amenities

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

About this property

5 Bedrooms 4 Bathrooms Family Room 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 10 plus breakfast bar and outdoor dining Private screened Pool and Spa with Lanai and conservation ...

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Property Type

Kissimmee House

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Beautiful 8BD 5BA Windsor at Westside. Private Pool/Spa. Games Room. Cinema Loft

$290

per night

View Details

Key Amenities

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

About this property

8 Bedrooms 5 Bathrooms Family Room with large HD Cable TV Upstairs Loft with Cinema Projection Screen 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 and outdoor dining Private ...

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Property Type

Kissimmee Villa

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Designer 7BD 5BA Windsor at Westside Private Pool Spa TV Den/Loft Games Room

$310

per night

View Details

Key Amenities

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

About this property

7 Bedrooms 5 Bathrooms Family Room with large HD Cable TV Upstairs TV Loft/Den 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 dining Private ...

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Property Type

Kissimmee Villa

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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

$290

per 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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Modern 5BD 4BA Windsor at Westside Private Pool & Spa Games Room

$185

per night

View Details

Key Amenities

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

About this property

5 Bedrooms 4 Bathrooms Family Room with large HD Cable TV Upstairs Loft 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 Pool ...

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Property Type

Kissimmee Villa

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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

Distance to park: 8 miles to Disney

$184

per 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

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Stylish Affordable. Private South Pool. Free use of Resort Facilities 5BD/4.5BA

5 BR | 4.5 BA | Sleeps 11 | Quick View

Distance to park: 8 miles to Disney

$185

per night

View Details

Key Amenities

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

About this property

5 Bedrooms 4.5 Bathrooms Family Room with large HD Cable TV Upstairs Loft with HD Cable TV. Ideal teen/tween or second family hang out space All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 6 plus ...

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Property Type

Kissimmee Townhome

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Wonderful Family Home. Close to Disney. Great Value. Summer Kitchen.

6 BR | 5 BA | Sleeps 13 | Quick View

Distance to park: 4 miles to Disney

$184

per night

View Details

Key Amenities

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

About this property

6 Bedrooms 5 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 6 plus breakfast bar with seating for 4 and ...

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Property Type

Kissimmee House

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Fantastic 9BD 6BA Sleeps 20 Home Cinema, Game Room, Pool Spa Free use of Resort

$290

per night

View Details

Key Amenities

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

About this property

9 Bedrooms 6 Bathrooms Sleeps 20 Family Room with large HD Cable TV Upstairs Movie Loft with Projection Cinema Screen All bedrooms with Flat Screen TVs Fully Equipped Chefs Gourmet Kitchen with Granite Counters and Stainless Steel Appliances Formal Dining Room seating 18 plus breakfast bar and ...

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Property Type

Kissimmee House

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Tropical Oasis - Windsor at Westside

7 BR | 5.5 BA | Sleeps 18 | Quick View

Distance to park: 8 miles to Disney

$226

per 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

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Windsor at Westside (Kissimmee, Florida) Vacation Rentals