What are the top rated Cottage Rentals in Windsor Hills?

There are a lot of options in Windsor Hills. If you plan on staying in the Windsor Hills area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Windsor Hills: <a href="/property/windsor-poolside-escape-with-stunning-pool-view-perfect-for-families/HA-3214196468" class="class="static-page-link"">Windsor Poolside Escape with Stunning Pool View-Perfect for Families!</a> <a href="/property/our-disneydreamvilla-minutes-to-disneyworld/HA-32198669" class="class="static-page-link"">Our DisneyDreamVilla - minutes to DisneyWorld!</a> <a href="/property/mickeys-magical-villa-disney-five-star-pool-villa-home-at-windsor-hills/HA-321211474" class="class="static-page-link"">Mickeys Magical Villa Disney Five Star Pool Villa Home at Windsor Hills</a> <a href="/property/steps-from-waterpark-pool-next-to-disney-w-frozen-aladdin-beauty-beast-theme/HA-3213232320" class="class="static-page-link"">Steps from Waterpark/Pool. Next to Disney w/Frozen, Aladdin, Beauty&amp;Beast theme</a> <a href="/property/villa-sonrisa-5-bedroom-5-bath-luxury-minutes-to-disney-in-windsor-hills/HA-1213832338" class="class="static-page-link"">Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills</a> <a href="/property/luxury-for-you-fun-for-the-kids-3br-3ba-2-miles-from-disney/HA-321426326" class="class="static-page-link"">Luxury for You, Fun for the Kids! 3BR/3BA 2 Miles from Disney</a> <a href="/property/wonderful-vacation-villa-close-to-disney-epcot-wide-world-of-sports-and-golf/HA-1214792351" class="class="static-page-link"">Wonderful Vacation Villa/Close to Disney, Epcot, Wide World of Sports and Golf</a> <a href="/property/minutes-away-from-theme-parks-3-bed-townhome-6-minutes-to-disney-world/HA-3211855566" class="class="static-page-link"">Minutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!</a> <a href="/property/beautiful-disney-retreat-3-bed-2-bath/HA-3211428655" class="class="static-page-link"">Beautiful Disney Retreat - 3 Bed/2 Bath</a> <a href="/property/last-minute-special-updated-pool-home-w-3-kings-princess-suite-near-disney/HA-1214469704" class="class="static-page-link"">Last-Minute Special! Updated Pool Home w/3 Kings + Princess Suite Near Disney</a>

How much does it cost to rent a cottage in Windsor Hills?

The average cost for a cottage rental in Windsor Hills is $348 per night. Selloffcruises has a wide list of great cottages near Windsor Hills that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Windsor Hills that allow pets?

Yes, here are the top cottage rentals in Windsor Hills that allow you to bring your pet: Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills Dream Villa Spacious Home W/private Pool/spa & Free Waterpark! WINNER:TOP VACATION RENTAL , CERTIFICATE OF EXCELLENCE <a href="/all/usa/florida/kissimmee/windsor-hills" class="class="static-page-link"">See all pet-friendly vacation rentals in Windsor Hills on Selloffcruises</a>

Do you have any rental cottages in Windsor Hills that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Windsor Hills to find one that works for you.

Are there quality cottages in Windsor Hills that have indoor swimming pools?

As of 2026, the data from Selloffcruises shows that there are Over 2293 private swimming pools or cottages with indoor pools in the Windsor Hills area along with other great amenities.

Windsor Hills Cottage Rentals By Owner

Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills

From US $397

10.0 (190 Reviews)

Villa

Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills

Air Conditioner
Parking
Pool

Windsor Hills Cottage Rentals & Holiday Homes

Find the best cottages in Windsor Hills - We found 2293 exact matches

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