What are the top rated Cottage Rentals in Windward Cay?

There are a lot of options in Windward Cay. If you plan on staying in the Windward Cay area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Windward Cay: <a href="/property/orlando-vacation-cottage-near-disney/HA-3211611059" class="class="static-page-link"">Orlando Vacation Cottage near Disney</a> <a href="/property/stunning-lakeview-townhome-w-private-pool/EP-46967029" class="class="static-page-link"">Stunning Lakeview Townhome w/Private Pool!</a> <a href="/property/modern-townhome-w-private-pool-free-water-park/EP-55442718" class="class="static-page-link"">Modern Townhome W/private Pool &amp; Free Water Park!</a> <a href="/property/serenity-lakeview-retreat-stunning-water-views-no-rear-neighbors-private-pool-game-room-star-wars-ci/EP-113092482" class="class="static-page-link"">Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room &amp; Star Wars Cinema</a> <a href="/property/upstay-6br-resort-home-w-pool-basketball-court/EP-122394145" class="class="static-page-link"">Upstay: 6BR Resort Home w Pool &amp; Basketball Court</a> <a href="/property/beautiful-and-cozy-home-at-sonoma-resort/EP-104133402" class="class="static-page-link"">Beautiful and Cozy Home at Sonoma Resort</a> <a href="/property/family-friendly-home-w-lanai-6-mi-to-disney/EP-102460198" class="class="static-page-link"">Family-friendly Home w/Lanai ~ 6 Mi to Disney</a> <a href="/property/terra-verde-swanky/EP-119350020" class="class="static-page-link"">Terra Verde Swanky</a> <a href="/property/upstay-bright-family-friendly-retreat-with-patio/EP-122394132" class="class="static-page-link"">Upstay: Bright Family-friendly Retreat With Patio</a> <a href="/property/bohemian-chic-retreat-tiny-home-near-disney/HA-3213027063" class="class="static-page-link"">Bohemian Chic Retreat - Tiny Home near Disney</a>

How much does it cost to rent a cottage in Windward Cay?

The average cost for a cottage rental in Windward Cay is $263 per night. Selectvacationvillas has a wide list of great cottages near Windward Cay that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Windward Cay that allow pets?

Yes, here are the top cottage rentals in Windward Cay that allow you to bring your pet: 5 miles from Disney & Universal! New! Family cottage near Disney-Sleep 6 Lakeview Home w/Private Pool & Free Water Park! Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee <a href="/all/usa/florida/kissimmee/windward-cay" class="class="static-page-link"">See all pet-friendly vacation rentals in Windward Cay on Selectvacationvillas</a>

Do you have any rental cottages in Windward Cay that are suitable for families?

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

Are there quality cottages in Windward Cay that have indoor swimming pools?

As of 2025, the data from Selectvacationvillas shows that there are Over 67 private swimming pools or cottages with indoor pools in the Windward Cay area along with other great amenities.

Windward Cay Cottage Rentals By Owner

From US $103

10.0 (13 Reviews)

Cottage

5 miles from Disney & Universal!

Air Conditioner
Parking
Pool

Windward Cay Cottage Rentals & Holiday Homes

Find the best cottages in Windward Cay - We found 67 exact matches

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