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Orlando Vacation Homes » West Hwy 192 Resort Area » Windsor at Westside Resort

  View All Windsor at Westside Properties

Windsor at Westside Resort Homes for Sale

Windsor at Westside Resort clubhouse near Disney World

Windsor at Westside is a guard-gated Pulte resort of 5-bedroom townhomes and 5- to 9-bedroom single-family pool homes in Kissimmee, about 6 miles from Walt Disney World, where short-term rentals (STR) are allowed. The large homes – villas or holiday homes, as UK buyers call them – suit big families and groups, and the resort's lazy river, water slide and poolside bar help them stand out on Airbnb and Vrbo.

 

5 to 9

bedrooms

 

Unlimited

owner usage

 

Lazy river

and water slide

  Windsor at Westside Resort Quick Facts

Short-term rentals (STR) Permitted – nightly and weekly rentals allowed
Owner usage Unlimited – use the home as much as you like (the on-site rental program may set a lower limit for units it manages)
Rental management On-site property management available, or a 3rd-party manager, or self-managed
Property type Townhomes and single-family homes, each with a private screened pool
Bedrooms 5 (townhomes) to 9 (single-family)
Size About 2,263 to 4,396 sq ft
Year built 2015 to 2020
Builder Pulte Homes
Gated Yes – 24-hour attended gate
Resort area West Hwy 192 Resort Area, Osceola County (ZIP 34747)

  View All Windsor at Westside Properties

  Can You Rent a Windsor at Westside Home on Airbnb or Vrbo?

Yes. Windsor at Westside was built as a short-term rental resort, so owners can rent their home by the night or week through Airbnb, Vrbo or a rental manager. A short-term rental, or STR, is a home rented to vacationers rather than on a long-term lease. Many Orlando-area neighborhoods do not allow it; Windsor at Westside does.

With 5 to 9 bedrooms and a private pool at every home, these rentals are aimed at large families and groups who want to stay together near Disney.

  How Much Can Owners Use Their Windsor at Westside Home?

As much as you like. There is no cap on owner usage, so you can use the home for vacations or longer stays and rent it whenever you are away. See our list of resorts by maximum owner usage to compare. If the on-site rental program manages your unit, it may set a lower limit. Contact us for current terms.

  Who Manages Rentals at Windsor at Westside?

Windsor at Westside Resort clubhouseThere is on-site property management at Windsor at Westside, and owners may also use a 3rd-party rental manager or manage bookings themselves. Fees and services vary by company. Contact us and we can introduce managers who work in the resort.

  View All Windsor at Westside Properties

  What Are Windsor at Westside Homes Like?

Windsor at Westside Resort home for salePulte Homes built Windsor at Westside in phases between 2015 and 2020. The smallest homes are 5-bedroom townhomes of about 2,263 sq ft; single-family homes run from 5 to 9 bedrooms and up to about 4,396 sq ft. Every home has a private screened pool, a full kitchen with granite counters, and a washer and dryer.

Homes are individually owned and decorated, so many have themed bedrooms, and in a lot of homes the garage has been converted into a game room or home theater.

Typical Windsor at Westside Home Features

  • Bedrooms: 5 to 9
  • Size: About 2,263 to 4,396 sq ft
  • Pool: Private screened pool at every home
  • Interior: Family room, great room, loft (larger plans), inside laundry
  • Construction: Block and concrete
  • Roof: Tile

  What Amenities Does Windsor at Westside Have?

Windsor at Westside Resort amenitiesThe large clubhouse is the center of the resort, with a restaurant and bar, fitness center, arcade and sundry shop. The main pool is a small water park, with a zero-entry pool, a lazy river, a water slide and a kids' splash area.

Windsor at Westside Amenities

  • Clubhouse with lounge
  • Zero-entry resort pool
  • Lazy river
  • Water slide
  • Kids' splash area
  • Poolside tiki bar and restaurant
  • Private cabanas (fees may apply)
  • Fitness center
  • Game room and video arcade
  • Sundry shop
  • Tennis courts
  • Basketball court
  • Volleyball court
  • Soccer field
  • Kids' play area
  • Lake pier and walking paths
  • 24-hour attended gate

Amenity access, hours and fees are set by the HOA and can change. Contact us to confirm current terms before you buy.

  Where Is Windsor at Westside?

Windsor at Westside is off Monaco Blvd, east of Westside Blvd and south of Hwy 192, in Kissimmee, Osceola County (ZIP 34747). It is part of the West Hwy 192 Resort Area. Open in Google Maps

How Far Is Windsor at Westside From the Parks?

Walt Disney World approx. 6 miles
SeaWorld Orlando approx. 13 miles
Epic Universe approx. 15 miles
Universal Orlando approx. 16 miles
Orlando International Airport (MCO) approx. 22 miles

Distances are straight-line miles from the resort.

  View All Windsor at Westside Properties

  Is Windsor at Westside a Good Fit for You?

  • A good fit if you want a large pool home for big-group rentals, resort amenities that help bookings, and no cap on personal use.
  • Consider other resorts if you want a smaller 2- to 4-bedroom property or a lower entry price.

Other Resorts Near Windsor at Westside

  • Solara Resort
  • Windsor Island Resort
  • Emerald Island Resort
  • Paradise Palms Resort
  • Windsor Palms Resort
  • All Orlando vacation homes
  • All West Hwy 192 area resorts

  Windsor at Westside Resort Video Tour

Windsor at Westside Resort video tour - click to play 

Video courtesy of Pulte Homes.

  Windsor at Westside Resort FAQ

Are short-term rentals allowed at Windsor at Westside?

Yes. Owners can rent their home nightly or weekly through Airbnb, Vrbo or a rental manager.

How long can owners stay in their Windsor at Westside home?

There is no limit. Owners can use the home as much as they like and rent it when they are not there.

How many bedrooms do Windsor at Westside homes have?

Townhomes have 5 bedrooms and single-family homes have 5 to 9 bedrooms, from about 2,263 to 4,396 square feet. Every home has a private pool.

Who manages rentals at Windsor at Westside?

There is on-site property management, and owners may also use a 3rd-party manager or self-manage.

Does Windsor at Westside have a lazy river?

Yes. The resort pool has a lazy river, a water slide and a kids' splash area, next to a clubhouse with a tiki bar and restaurant.

How far is Windsor at Westside from Disney World?

About 6 miles in a straight line to the center of Walt Disney World.

Rental rules, management policies and HOA fees can change. Contact us to confirm current HOA and Management Company fees before you buy.

  Buying at Windsor at Westside Resort

The latest Windsor at Westside listings appear below and update daily from the MLS – view all available Windsor at Westside homes. To schedule a showing or ask about any home, Call/Text David Myers at 407.801.3286 or send us a message.

Photos courtesy of Magical Vacation Homes.

  View All Windsor at Westside Properties Ask About Windsor at Westside Homes

Latest Windsor at Westside Listings

1940 Nice Court, Kissimmee image
1940 Nice Court, Kissimmee $749,000

Luxury Villa – “Lord of the Manor” – Minutes from Disney Experience elevated comfort and themed luxury at “Lord of the Manor,” a fully renovated 9-bedroom, 6-bathroom ...

  • 9 Beds
  • 6 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
2451 Luxor Drive, Kissimmee image
2451 Luxor Drive, Kissimmee $720,000

Welcome to this beautiful 8-bedroom, 6-bathroom vacation home in the highly desirable Windsor at Westside Resort. Perfectly located in a quiet section of the community, t...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Phase 3 SubDv.
  • 34747 Zip Code
8815 Macapa Drive, Kissimmee image
8815 Macapa Drive, Kissimmee $689,000

Enjoy breathtaking pond views and exceptional backyard privacy in this stunning 8-bedroom, 5.5-bathroom home located in the highly sought-after Windsor at Westside commun...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
8812 Macapa Drive, Kissimmee image
8812 Macapa Drive, Kissimmee $680,000

Discover an exceptional opportunity to own this beautifully furnished 8-bedroom, 6-bathroom pool home in the highly sought-after GATED resort community of Windsor at West...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
8817 Corcovado Drive, Kissimmee image
8817 Corcovado Drive, Kissimmee $678,000

Discover an exceptional blend of luxury, comfort, and investment potential in this fully furnished 9-bedroom, 6-bathroom lakefront residence. Turnkey and approved for sho...

  • 9 Beds
  • 6 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
8825 Rhodes Street, Kissimmee image
8825 Rhodes Street, Kissimmee $675,000

Welcome to 8825 Rhodes Street, 4041sqft beautifully maintained and fully furnished 8-bedroom, 6-bathroom home located within the highly sought-after gated Windsor at West...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 1 SubDv.
  • 34747 Zip Code
1941 Nice Court, Kissimmee image
1941 Nice Court, Kissimmee $670,000

Take a look at this unique amazing property at 1941 Nice Ct located in Windsor Westside, one of Disney’s most popular short term rental vacation home communities. This in...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 2a Rep SubDv.
  • 34747 Zip Code
1908 Nice Court, Kissimmee image
1908 Nice Court, Kissimmee $669,990 ▼

Welcome to this spectacular 9-bedroom, 6-bathroom fully furnished pool home located in the highly desirable Windsor at Westside Resort! Built in 2018, this spacious two-s...

  • 9 Beds
  • 6 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
2183 Tripoli Ct, Kissimmee image
2183 Tripoli Ct, Kissimmee $659,000 ▼

This spacious fully furnished 9-bedroom, 6-bathroom pool home is located in the sought-after Windsor at Westside Resort. One of the largest floor plans in the community,...

  • 9 Beds
  • 6 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
2147 Tripoli Court, Kissimmee image
2147 Tripoli Court, Kissimmee $658,000 ▼

The largest home on one of the best lots in entire Windsor at Westside resort. Equipped with brand new HVAC system for upstairs, this fully furnished/equipped home with p...

  • 9 Beds
  • 6 Baths
  • Windsor At Westside Ph 1 SubDv.
  • 34747 Zip Code
1610 Lima Avenue, Kissimmee image
1610 Lima Avenue, Kissimmee $655,000

Imagine pulling into a community where every day feels like you're on vacation. Located in the 24/7 guard-gated community of Windsor at Westside, this sprawling 8-bedroom...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 2b SubDv.
  • 34747 Zip Code
8895 Qin Loop, Kissimmee image
8895 Qin Loop, Kissimmee $649,000

Welcome to 8895 Qin Loop, an 8-bedroom, 6-bath vacation home with approximately 4,041 sq ft in the sought-after Windsor at Westside Resort in Kissimmee! The home's size a...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
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Call/Text 407.801.3286
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Ziro Realty, LLC
549B Water Street
Celebration, FL 34747
Call/Text: 407.801.3286
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