Orlando Vacation Homes » West Hwy 192 Resort Area » Windsor at Westside Resort
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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
| 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) |
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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.
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.
There 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.
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Pulte 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.
The 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.
Amenity access, hours and fees are set by the HOA and can change. Contact us to confirm current terms before you buy.
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
| 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.
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Video courtesy of Pulte Homes.
Yes. Owners can rent their home nightly or weekly through Airbnb, Vrbo or a rental manager.
There is no limit. Owners can use the home as much as they like and rent it when they are not there.
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.
There is on-site property management, and owners may also use a 3rd-party manager or self-manage.
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.
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.
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.
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David Myers
Call/Text 407.801.3286
Your Orlando Vacation Home Expert