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Windsor at Westside Resort Vacation Homes for Sale

8808 Macapa Drive, Kissimmee image
8808 Macapa Drive, Kissimmee $985,000

The largest floor plan on one of the best lots in Fabulous Windsor at Westside resort. This fully furnished, professionally decorated home is situated on a rare greenbelt...

  • 9 Beds
  • 6 Baths
  • Windsor/Westside Ph 2a SubDv.
  • 34747 Zip Code
1643 Lima Avenue, Kissimmee image
1643 Lima Avenue, Kissimmee $975,000

Invest in this short term rental home over 4000 square feet, Luxury vacation home has 8 bedrooms, 6 baths and is fully furnished, with a private pool and spa that is scre...

  • 8 Beds
  • 6 Baths
  • Windsor/Westside-Ph 2b SubDv.
  • 34747 Zip Code
2107 Tripoli Court, Kissimmee image
2107 Tripoli Court, Kissimmee $950,000

Newly Remodeled Turn Key Vacation Home  No need to lift a finger! This unique and trendy Star Wars themed home coined “The Stormtroopers Retreat,” is just what you are ...

  • 8 Beds
  • 6 Baths
  • Windsor/Westside Ph 1 SubDv.
  • 34747 Zip Code
1606 Lima Avenue, Kissimmee image
1606 Lima Avenue, Kissimmee $919,999

This fully furnished vacation home internet, lawn maintenance and daily trash management including in the HOA. This immaculate, professionally-designed 2-story Home with...

  • 9 Beds
  • 6 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
8895 Qin Loop, Kissimmee image
8895 Qin Loop, Kissimmee $890,000

OPPURTUNITY KNOCKS!! TAKE A LOOK AT THIS BEAUTIFUL TURN KEY, SHORT TERM RENTAL VACATION HOME Ideally located in the highly sought after Windsor by Westside community, ...

  • 8 Beds
  • 6 Baths
  • Windsor/Westside Ph 2a SubDv.
  • 34747 Zip Code
8868 Bengal Ct, Kissimmee image
8868 Bengal Ct, Kissimmee $889,000 ▼

This fantastic 8-bed, 6 bath pool home is located in the vacation resort of Windsor at Westside, one of the most popular vacation resort communities in the Disney area. T...

  • 8 Beds
  • 6 Baths
  • Windsor/Westside-Ph 2b SubDv.
  • 34747 Zip Code
8879 Menton Loop, Kissimmee image
8879 Menton Loop, Kissimmee $870,000

If you're looking for a short-term rental home in Windsor at Westside Resort, this 8-bedroom 6 bathroom property is perfect for you! With a private pool and courtyard wit...

  • 8 Beds
  • 6 Baths
  • Windsor/Westside Ph 1 SubDv.
  • 34747 Zip Code
1924 Nice Court, Kissimmee image
1924 Nice Court, Kissimmee $870,000 ▼

Don’t miss this amazing opportunity to buy this beautifully FULLY FURNISHED POOL HOME in the most desirable resort community- Windsor at Westside. 9 BEDROOM | 6 BATHROOMS...

  • 9 Beds
  • 6 Baths
  • Windsor/Westside Ph 2a SubDv.
  • 34747 Zip Code
1916 Nice Court, Kissimmee image
1916 Nice Court, Kissimmee $867,000 ▼

Welcome to this beautiful 8 Bed/ 6 Bath luxury vacation/investment nested in one of the most popular resort in Orlando: Windsor at Westside. The Windsor at Westside Resor...

  • 8 Beds
  • 6 Baths
  • Windsor/Westside-Ph 2a SubDv.
  • 34747 Zip Code
8891 Qin Loop, Kissimmee image
8891 Qin Loop, Kissimmee $859,900

Invest in this Windsor Westside Resort home that is only a few miles from Disney World, Margaritaville and other theme parks. Over 4000 square feet, this vacation home ha...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside Ph 2a SubDv.
  • 34747 Zip Code
1690 Lima Avenue, Kissimmee image
1690 Lima Avenue, Kissimmee $854,900

Exceptional attention to detail and the highest standards are evident in this 8 bedroom 6 bath Fully Furnished Pool Home! This vacation home truly has it all. Sold Turn...

  • 8 Beds
  • 6 Baths
  • Windsor/Westside-Ph 28 SubDv.
  • 34747 Zip Code
8832 Rhodes Street, Kissimmee image
8832 Rhodes Street, Kissimmee $850,000

LOOK NO FURTHER! This Beautiful home is located in Windsor at Westside where Central Florida's major attractions are just minutes away. With it's 8 bedrooms, 6 baths thi...

  • 8 Beds
  • 6 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
8909 Bengal Court, Kissimmee image
8909 Bengal Court, Kissimmee $850,000

BEST PRICED!!! IMPECCABLE HOME! FRESH INTERNALLY PAITEND! Welcome to a short-term rental vacation home in Windsor At Westside. This ELEGANT 8-bedroom/6-bathroom, best con...

  • 8 Beds
  • 6 Baths
  • Windsor/Westside-Ph 2b SubDv.
  • 34747 Zip Code
8937 Prague Way, Kissimmee image
8937 Prague Way, Kissimmee $740,000 ▲

DAILY RENTAL VACATION HOME in WINDSOR at WESTSIDE. FULLY FURNISHED. CORNER LOT. 5 Bedrooms plus a Movie Theater Room and 4 Bathrooms. Two Story Home with Fantastic Privat...

  • 5 Beds
  • 4 Baths
  • Windsor/Westside Ph 3 SubDv.
  • 34747 Zip Code
8941 Zurich Lane, Kissimmee image
8941 Zurich Lane, Kissimmee $739,900

This is a wonderful 6-bedroom vacation home with 4 1/2 bathrooms, so there's plenty of space to spread out and relax. Entertaining is easy with an open kitchen and ample ...

  • 6 Beds
  • 4.5 Baths
  • Windsor/Westside-Ph 3a SubDv.
  • 34747 Zip Code
2436 Tangier Drive, Kissimmee image
2436 Tangier Drive, Kissimmee $739,000

Vacation Home and Fully furnished and professionally decorated, 6 Bedroom located in Windsor at Westside Resort. Windsor at Westside offers world class amenities while pr...

  • 6 Beds
  • 4.5 Baths
  • Windsor/Westside Ph 3 SubDv.
  • 34747 Zip Code
8919 Zurich Lane, Kissimmee image
8919 Zurich Lane, Kissimmee $720,000 ▼

Don't miss the opportunity to own this beautiful 7-bedroom 5,1/2-bathrooms vacation home. You are going to fall in love for this floor plan, with plenty of space to enjo...

  • 7 Beds
  • 5.5 Baths
  • Windsor/Westside-Ph 3a SubDv.
  • 34747 Zip Code
1925 Nice Court, Kissimmee image
1925 Nice Court, Kissimmee $719,000 ▼

Don't miss out on this 7 BEDROOM 5 BATH Luxury VACATION HOME. This beautiful property built by Pulte homes comes fully furnished with professionally designed decor. This ...

  • 7 Beds
  • 5.5 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
1804 Gobi Drive, Kissimmee image
1804 Gobi Drive, Kissimmee $700,000

This stunning fully furnished home with 7 bedrooms in Windsor at Westside presents an exceptional opportunity. This turnkey property boasts 2 master suites and is ideally...

  • 7 Beds
  • 5.5 Baths
  • Windsor/Westside Ph 2a SubDv.
  • 34747 Zip Code
1861 Nice Ct, Kissimmee image
1861 Nice Ct, Kissimmee $700,000 ▲

Stunning Vacation Rental home you can't miss.This gated resort community features an over 8,000 sq ft clubhouse, that comes with a fitness center, pool, waterslide, lazy ...

  • 7 Beds
  • 5.5 Baths
  • Windsor/Westside Ph 1 SubDv.
  • 34747 Zip Code
8936 Prague Way, Kissimmee image
8936 Prague Way, Kissimmee $700,000 ▼

JUST FULLY REFURNISHED AND UPDATED!!!Check out this beautiful house with 6 bedrooms & 4.5 bathrooms located at Windsor at Westside resort community. It has plenty of spac...

  • 6 Beds
  • 4.5 Baths
  • Windsor/Westside Ph 3 SubDv.
  • 34747 Zip Code
2480 Dubai Street, Kissimmee image
2480 Dubai Street, Kissimmee $699,000 ▼

Very spacious 5 Bed , 5.5 Bath home located in Windsor at Westside Resort Community. The home is fully furnished and equipped with amazing decor. Windsor at Westside Reso...

  • 5 Beds
  • 5.5 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
2470 Dubai Street, Kissimmee image
2470 Dubai Street, Kissimmee $690,000

This vacation home is like new, only used a few times by the owners, never rented and FULLY FURNISHED. This magnificent house is located a short walk from the clubhouse, ...

  • 5 Beds
  • 4 Baths
  • Windsor At Westside Ph 3a SubDv.
  • 34747 Zip Code
8949 Zurich Lane, Kissimmee image
8949 Zurich Lane, Kissimmee $689,000 ▼

Don't miss This beautiful 7 bedroom 5 1/2 bathroom spacious pool home in the Windsor at Westside . With plenty space spread out for entertaining and relax throughout enti...

  • 7 Beds
  • 5.5 Baths
  • Windsor/Westside-Ph 3a SubDv.
  • 34747 Zip Code
1889 Nice Court, Kissimmee image
1889 Nice Court, Kissimmee $685,000

Wow! This awesome two story single family home includes 6 bedrooms, 5.5 bathrooms, and a combination living and dining room perfect for entertaining. Additional space inc...

  • 6 Beds
  • 4.5 Baths
  • Windsor/Westside-Ph 2a SubDv.
  • 34747 Zip Code
1508 Mumbai Way, Kissimmee image
1508 Mumbai Way, Kissimmee $679,900 ▼

This fully furnished, 6 bedroom, 4.5 bath, turnkey vacation home is the perfect property for those looking for a second home or a short term rental investment property in...

  • 6 Beds
  • 4.5 Baths
  • Windsor/Westside-Ph 2b SubDv.
  • 34747 Zip Code
8893 Rhodes Street, Kissimmee image
8893 Rhodes Street, Kissimmee — 1 $679,000

Beautiful fully furnished 5 bed 5/2 bath in the desirable Windsor at Westside! Luxury vacation home with private pool. Relax in your resort-style vacation home or zoned s...

  • 5 Beds
  • 5.5 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
8877 Bengal Court, Kissimmee image
8877 Bengal Court, Kissimmee $639,990 ▼

CHARMING VACATION HOME WITH 5 Suites and half bath!!! This charming and spacious home with PRIVATE POOL and deck area is located only 8 minutes away from a west Disney en...

  • 5 Beds
  • 5.5 Baths
  • Windsor/Westside-Ph 2b SubDv.
  • 34747 Zip Code
8940 Rhodes Street, Kissimmee image
8940 Rhodes Street, Kissimmee $630,000 ▼

Back on Market!Welcome to this amazing and spacious 5 Bed / 5.5 Bath home located in the Windsor at Westside Resort Community. Recently painted and with a brand new vinyl...

  • 5 Beds
  • 5.5 Baths
  • Windsor/Westside Ph 1 SubDv.
  • 34747 Zip Code
1869 Nice Court, Kissimmee image
1869 Nice Court, Kissimmee $626,000 ▼

GREAT BEGINNING! Looking for the perfect home to make your vacation and investment dreams a reality? Look no further than this beautiful five-bedroom, four-bathroom, pool...

  • 5 Beds
  • 4 Baths
  • Windsor/Westside-Ph 2a SubDv.
  • 34747 Zip Code
8921 Sydney Avenue, Kissimmee image
8921 Sydney Avenue, Kissimmee — Na $582,000

•• GREAT OPPORTUNITY FOR INVESTORS! •• Beautiful two stores home in one of the most desired condos on this area, this amazing vacation home is perfect to enjoy the hot su...

  • 5 Beds
  • 4.5 Baths
  • Windsor/Westside-Ph 3 SubDv.
  • 34747 Zip Code
2426 Dubai Street, Kissimmee image
2426 Dubai Street, Kissimmee $579,000 ▼

Amazing location, excellent investment opportunity for short-term rental and it’s being sold turnkey! This fully furnished five-bedroom, four-and-a-half-bath townhome wit...

  • 5 Beds
  • 4.5 Baths
  • Windsor/Westside-Ph 3 SubDv.
  • 34747 Zip Code
8919 Sydney Avenue, Kissimmee image
8919 Sydney Avenue, Kissimmee — . $578,000 ▼

Welcome to this beautiful 5Bed/4.5 Bath fully furnished short term rental vacation home in Windsor At Westside. This townhouse features open kitchen with granite countert...

  • 5 Beds
  • 4.5 Baths
  • Windsor/Westside-Ph 3 SubDv.
  • 34747 Zip Code
2098 Rome Drive, Kissimmee image
2098 Rome Drive, Kissimmee — 2098 $575,000

Newly Remodeled Turn Key 5 bedroom 4.5 bathroom Vacation Home No need to lift a finger! This ready to market Windsor at Westside vacation rental home has all you could ...

  • 5 Beds
  • 4.5 Baths
  • Windsor/Westside-Ph 1 SubDv.
  • 34747 Zip Code
8831 Geneve Court, Kissimmee image
8831 Geneve Court, Kissimmee — X $560,000

Fantastic, fully-furnished townhouse in gated, resort-style! Close to shopping, Wall-Mart, restaurants, and theme parks! Walk through the quaint entryway and into the ope...

  • 5 Beds
  • 4.5 Baths
  • Windsor/Westside-Ph 2b SubDv.
  • 34747 Zip Code
8890 Geneve Court, Kissimmee image
8890 Geneve Court, Kissimmee — Na $555,000

Great townhouse near Walt Disney. This property is a fully furnished 5 bedroom / 4.5 bathroom townhome located in one of the most renowned short term communities in the O...

  • 5 Beds
  • 4.5 Baths
  • Windsor/Westside Ph 2b SubDv.
  • 34747 Zip Code
8810 Geneve Court, Kissimmee image
8810 Geneve Court, Kissimmee — 8810 $550,000 ▼

Don't miss this amazing Windsor at Westside Townhome. It has it all, private location, large south facing backyard, culdesac for low street traffic. This 5 bedroom 4.5 B...

  • 5 Beds
  • 4.5 Baths
  • Windsor/Westside-Ph 2b SubDv.
  • 34747 Zip Code
8907 Sydney Avenue, Kissimmee image
8907 Sydney Avenue, Kissimmee — 8907 $549,900 ▼

A GREAT OPPORTUNITY FOR INVESTORS, Short Term Rental Vacation Home. A beautiful 5 bedrooms, 4 and a half bath townhome with a full bedroom downstairs, located in one of O...

  • 5 Beds
  • 4.5 Baths
  • Windsor At Westside-Ph 3 SubDv.
  • 34747 Zip Code
8906 Sydney Avenue, Kissimmee image
8906 Sydney Avenue, Kissimmee — Na $540,000

Amazing house in the desired Windsor at Westside near DISNEY! Future bookings can be conveyed to buyer! 24 hour guarded gate short term rental/VACATION community. Turn-ke...

  • 5 Beds
  • 4.5 Baths
  • Windsor At Westside SubDv.
  • 34747 Zip Code
2003 Majorca Drive, Kissimmee image
2003 Majorca Drive, Kissimmee — Na $519,900 ▼

PRICED TO SELL!! CORNER LOT! Three extra-large windows that really bring in the natural light! A FEW STEPS FROM THE GORGEOUS CLUBHOUSE! GREAT BOOKING HISTORY AND FUTURE R...

  • 5 Beds
  • 4.5 Baths
  • Windsor/Westside SubDv.
  • 34747 Zip Code
1921 Majorca Drive, Kissimmee image
1921 Majorca Drive, Kissimmee $509,000 ▼

WALK DISTANCE TO THE CLUBHOUSE! This immaculate 4-bedroom, 3-bathroom townhouse is nestled in a quiet place in the community but close to the clubhouse. There is a street...

  • 4 Beds
  • 3.5 Baths
  • Windsor At Westside Ph 1 SubDv.
  • 34747 Zip Code

Windsor at Westside Resort - West Hwy 192

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

Owning a Vacation Home at Windsor at Westside Resort

Windsor at Westside Resort near Disney WorldWindsor at Westside Resort is a gated resort of Single/Multi Family Homes and Townhomes in the West Hwy 192 Resort Area of Orlando. Windsor at Westside is a medium sized townhome and single/multi family resort with BIG amenities.

Owners and guests enjoy a clubhouse packed with amenities including tiki bar and grill, fitness center, arcade, sundry and gift shop, resort pool with splash zone, lazy river and much more. Homes range from 2102 sq ft townhomes to 4391 sq ft 9 bedroom homes with private pools.

Where is Windsor at Westside Resort?

Windsor at Westside Resort is located off Monaco Blvd in the West Hwy 192 resort area near Disney World.

The resort is East of Westside Blvd and South of Hwy 192 and is found in the 34747 zip code in Osceola County.

How Far from Windsor at Westside Resort to...

  • Walt Disney World: 7 miles
  • Universal Studios:20 miles
  • Sea World: 17 miles
  • Busch Gardens Tampa: 62 miles
  • Kennedy Space Center: 70 miles
  • Cocoa Beach: 78 miles
  • Daytona Beach: 82 miles
  • Clearwater Beach: 87 miles
  • Orlando International Airport: 28 miles
  • Port Canaveral Cruise Ships: 72 miles

Windsor at Westside Resort Owner Usage & Property Management

Windsor at Westside Resort ClubhouseWindsor at Westside Resort owners my use their property up to 365 days per year if they so choose. Owners may also rent their unit out for any length of time when not in use to generate income and/or to cover part or all of the owner fees.

There is on site property management at Windsor at Westside Resort. Owners may use 3rd Party rental management or self manage. to handle to reservations and management of their unit at Windsor at Westside Resort.

Windsor at Westside Resort AmenitiesWindsor at Westside Resort Amenities

The 10,000 sq ft clubhouse is the heart of the resort. An on site concierge greets you upon entry and within the clubhouse you have an arcade, state of the art fitness center, sundry shop and kids club. The main pool is more of a miniature water park with a zero entry beach style pool with splash zone on one side and lazy river on the other. The Tu Casa Tiki Bar and Fireplace Lounge offers poolside food and drinks daily and will also have the big game on the TV.

Other amenities include sand volleyball court, tennis court, playground and fishing pier. There is a secondary "quiet" pool overlooking a lake in the newer phase of the resort.

Windsor at Westside Resort Amenities in Orlando near Disney

Windsor at Westside Resort Amenities include:

  • Fishing
  • Fitness Center
  • Playground
  • Park
  • Clubhouse
  • Security
  • Spa/Hot Tub
  • Tennis Courts
  • Basketball Court
  • Waterfront Resort Pool Area with Water-slide
  • Lazy River
  • Restaurant
  • Bar
  • Marketplace
  • Game Room
  • Sand Volleyball Court

Vacation Homes Available in Windsor at Westside Resort

Windsor at Westside Resort Homes for SaleThe majority of the homes in Windsor at Westside Resort were built 2015-2019 by Pulte Homes. There are 3 to 10 bedrooms, a similar number of bathrooms, and between 2500 to 5000 square feet of living space in each of the houses.

All townhomes and homes come with full size kitchens with granite counter-tops in the kitchen and bathrooms, laundry rooms or closets with washer and dryer as well as private, screen pools.

All homes are individually owned, so owners may decorate their home in any style they like. Many of the bedrooms are decorated in a unique theme and most of the garages have been converted to either game rooms or movie theaters.

Windsor at Westside Resort Homes

Typical Windsor at Westside Resort Home Features Include:

  • Architectural Style(s): Florida
  • Number of Bedrooms: 3 to 10
  • Garage Spaces: 2
  • Approx Sq Ft under AC: 2500 to 5000
  • Interior Rooms: Family Room, Great Room, Inside Utility, Loft and Screened Pool
  • Construction Material: Block, Concrete
  • Roof: Tile

Windsor at Westside Resort Video Tour Courtesy of Pulte Homes

Call Us Now at 407-801-3286 and schedule your viewing of vacation homes for sale in Windsor at Westside Resort today!

Photo Credit: Above images by Magical Vacation Homes.

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Realtor David MyersDavid Myers 407-801-3286
Your Orlando Vacation Home Expert

Orlando Vacation Properties Buyers Guide

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