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Independent vacation rentals by Florida Vacation Homes. Not the resort or HOA. Looking for resort / HOA help?

Windsor Island Resort Vacation Rentals A selection of privately owned homes offered by Florida Vacation Homes — an independent rental company

Orlando Vacation Home Rentals

Windsor Island Resort, Orlando Florida is the perfect vacation destination for families to relax and explore Orlando’s world class theme parks and attractions. Escape to the vacation rental community in the Orlando area, you will be sure to return year after year. Windsor Island is a gated community with the best resort amenities in the area. The stunning clubhouse has an arcade, fitness center, close by playground and mini golf. The zero entry resort style pool has a lazy river, dual water slides, children’s splash pad and pool side bar.

There are so many attractions to explore in the Kissimmee / Orlando area. Shop at the malls, dine out in the huge selection of restaurants and of course the world famous Disney World®, Universal Studios® and Sea World®. Windsor Island and it’s collection of vacation homes is close to all Orlando has to offer.

We, Florida Vacation Homes, offer a selection of vacation homes for rent in the resort. We do not manage any of the resort amenities. We just market professionally managed, privately owned vacation rentals.

Independent vacation rentals by Florida Vacation Homes

Find your family’s Windsor Island vacation home

Choose from a selection of privately owned Windsor Island Resort vacation rentals managed and marketed by Florida Vacation Homes. The community is home to hundreds of vacation rentals served by many independent management companies. Our local team helps you compare the homes offered on this website and plan your booking.

Located in Davenport in the Orlando area, Windsor Island offers townhomes and larger pool homes with up to 10 bedrooms. Compare each listing’s sleeping arrangements, private pool, games areas and optional extras to find the right fit for your group.

Browse our selection of Windsor Island rentals · Plan your stay and nearby outings

Property Management

Orlando

Resort Amenities

Resort Video

Your local, independent rental team

Our Florida Vacation Homes local travel experts can help you find professionally managed vacation rental homes and town homes in Windsor Island. Florida Vacation Homes is a property management company based in Davenport.

Renting a Windsor Island Resort Vacation Home is easy when you work with our local specialist team that know the Orlando area very well. We are here to assist you with the entire booking process, please call 407-633-7667 and we will do the rest. There are vacation homes and town homes in Windsor Island Resort to suit every budget and group size.

  • Amazing Amenities
  • Orlando-area Resort
  • Luxury Private Pool Homes
  • Affordable Town Homes
  • Gated Resort

Your independent rental team

Florida Vacation Homes is an independent vacation rental management and marketing company based in Davenport. We manage and market a small number of homes within Windsor Island; we do not represent every owner or rental in the community.

Our team can help you choose among the homes on this website, check availability and understand the details of a booking with us. Call 407-633-7667 for rental inquiries.

  • Privately owned townhomes and pool homes
  • Options for families and groups, with up to 10 bedrooms
  • Property-specific photos, features and booking terms
  • Local help with the rentals offered through Florida Vacation Homes

Meet your independent rental company and find the right contact for your question.

Contact Us
Call Us Today!407-633-7667

Choose a home for your Windsor Island stay

Contact our Florida Vacation Homes team that specializes in Orlando Vacation Rentals to get started on planning your vacation to Windsor Island. Blue skies and Florida sunshine await your family to relax in between enjoying family fun at the Orlando theme parks. If you have a large group of multiple families traveling together you will find large 8 to 10 bedroom villas in Windsor Island. There are also 4,5,6 & 7 bedroom vacation homes with private pools and more affordable 5 bedroom town homes.

Start with your group size, bedroom needs and travel dates. A townhome with a splash pool may suit a smaller group, while a larger detached pool home can give several families more space. Windsor Island homes have up to 10 bedrooms; occupancy and features vary by property.

Before you book

Check bed configurations, cancellation terms, the full price for your dates and any optional pool heating or equipment charges. Shared amenities are operated by the HOA and are subject to its rules, hours, fees and availability.

Who will help with my stay?

For a booking through Florida Vacation Homes, use the contact details in your confirmation for reservation or home-specific questions. If you booked through another manager, contact that company. The HOA handles shared resort facilities and services.

Read our resort amenities guide or ask Florida Vacation Homes about a rental.

Check rental availability