Windsor at Westside (Kissimmee, Florida) Vacation Rentals

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

$334

avg/night

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

$216

avg/night

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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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10 Bed 6 Bath Windsor at Westside. Private Pool Spa. Cinema Room. Game Room.

$394

avg/night

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Key Amenities

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

About this property

10 Bedrooms 6 Bathrooms Family Room with large HD Cable TV Upstairs TV Loft/Den with HD Cable TV Cinema / Movie Theater Room 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 ...

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Property Type

Kissimmee Villa

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

$216

avg/night

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

$334

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

$196

avg/night

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

$334

avg/night

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

$196

avg/night

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

$346

avg/night

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

8 BR | 6 BA | Sleeps 16 | Quick View

1

Distance to park: 4 miles to Animal Kingdom

$334

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

"Relaxing!"
Reviewed January 9, 2021

We enjoyed our stay at your home very much. Would definitely stay again! The pool area was our favorite.

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

9 BR | 6 BA | Sleeps 22 | Quick View

2
LAST MINUTE DEAL 2/20 - 2/27: A week in the SUN!!! $285/night 9 bed home with pond view!

$388

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

"Excellent pet-friendly house for the whole family!"
Reviewed January 31, 2021

We stayed here for our post-wedding vacation with 16 people. It had plenty of space, great amenities, and a dining room table to fit the whole family!It was great having access to the community water ...

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DEAL
6 Bedroom Pool Home, minutes from Disneyworld

$291

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

9 BR | 6 BA | Sleeps 24 | Quick View

2

Distance to park: 8 miles to Disney

$463

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

"Nice place to stay"
Reviewed September 16, 2020

Very clean place, close to restaurants and stores Short drive to attractions. Close to Orlando international airport.

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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

$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

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New 9Br/6Ba Pool Villa from $280/nt, Close To Disney

9 BR | 6 BA | Sleeps 20 | Quick View

3

Distance to park: 8 miles to Disney World

$346

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

"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 Opening 9Br/6Ba luxurious Pool House from $280/NT,,Close to Disney

$348

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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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

$252

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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New 9Br/6Ba luxurious Pool House from $270/NT, Close To Disney

9 BR | 6 BA | Sleeps 20 | Quick View

3

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 ...

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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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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

$252

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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Brand new 8br/6ba pool villa from $230/nt , Close to Disney

8 BR | 6 BA | Sleeps 18 | Quick View

5

Distance to park: 8 miles to Disney World

$295

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

6 BR | 4 BA | Sleeps 16 | Quick View

Distance to park: 8 miles to Disney

$252

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

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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

$215

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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New 8br/6ba pool villa from $230/nt ,Close to Disney

8 BR | 6 BA | Sleeps 18 | Quick View

4

Distance to park: 8 miles to Disney World

$292

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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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

$321

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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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

$252

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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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

$215

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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Windsor at Westside (Kissimmee, Florida) Vacation Rentals