What are the top rated Vacation Rentals in Windward?

There are a lot of options in Windward. If you plan on staying in the Windward area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Windward: <a href="/property/ibis-landing-beach-house-directly-on-the-beach-don-pedro-palm-island/HA-32153956" class="class="static-page-link"">Ibis Landing Beach House.Directly on the Beach! Don Pedro/Palm Island</a> <a href="/property/incommunicado-a-hammock-cool-drink-whispering-pines/HA-32192733" class="class="static-page-link"">&#39;Incommunicado &#39; ~A~ Hammock, Cool Drink, Whispering Pines.</a> <a href="/property/don-pedro-s-cottage/HA-321999431" class="class="static-page-link"">Don Pedro&#39;s Cottage</a> <a href="/property/light-and-airy-beautifully-appointed-3-bed-3-bath-home-with-sunny-pool-spa/HA-6118399405" class="class="static-page-link"">Light and airy, beautifully appointed 3 bed, 3 bath home with sunny pool &amp; spa.</a> <a href="/property/private-quiet-villa-with-screened-pool-spa-on-rotonda-canal/HA-3212156170" class="class="static-page-link"">Private quiet Villa with screened Pool &amp; Spa on Rotonda Canal,</a> <a href="/property/cloud-9-on-the-beach-heavenly-views-from-beach-to-bay-come-be-on-cloud-9/HA-3211320689" class="class="static-page-link"">Cloud 9 on the beach! Heavenly views from beach to bay. Come be on Cloud 9.</a> <a href="/property/just-now-available-january-2027-is-now-available-for-rental-thank-you/HA-321880008" class="class="static-page-link"">JUST NOW AVAILABLE! - January 2027 is now available for rental. Thank you!</a> <a href="/property/island-beach-barn-charming-vacation-house-with-bay-dock-and-beach-access/HA-3212614104" class="class="static-page-link"">Island Beach Barn - charming vacation house with bay/dock and beach access</a> <a href="/property/welcome-to-boca-grande-private-luxury-home-with-pool-close-to-golf-beach/HA-1279603224" class="class="static-page-link"">Welcome to Boca Grande! Private Luxury Home With Pool, Close to Golf &amp; Beach!</a> <a href="/property/island-life-little-gasparilla-home-waterfront-on-the-bay-w-private-dock/HA-3212216396" class="class="static-page-link"">Island Life Little Gasparilla Home Waterfront on the Bay w/Private Dock</a>

Which is the best family rental in Windward?

There are many large, family-friendly vacation homes available in Windward; however, here are the most popular family rentals listed on our site: Waterfront Sleeps 8 on the bay Beach-to-Bay private land; Dock-Wildlife-Secluded Bay Watch on Little Gasparilla Island, accessible by water taxi and boat only Walk to Marina: Placida Condo w/ Community Perks! Sea La Vie - Direct Gulf Front - Amazing Sunsets - Private Island

Can we get self-catering vacation rentals in Windward?

Yes, there are 811 self-catering vacation homes in Windward that have hot tubs, swimming pools, & other amenities.

What are the best luxury vacation rentals near Windward?

There are more than 811 luxury villas and vacation homes in or near Windward. Filter by price to compare find the most expensive places to stay on Campuslegends.