Your Vacation to Windward Starts with Windward Vacation Rentals

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:

• Gulf Front on an island,kayaks,tennis/pickleball SUP, 1 pet POOL IS CLOSED
• Ibis Landing Beach House.Directly on the Beach! Don Pedro/Palm Island
• Your serene escape - Modern, cozy, and close to the beach.
• Modern Luxury Villa/Riverfront/Heated South Facing Pool/Golf Rotonda West
• Don Pedro's Cottage
• Use our kayaks to explore; your boat is in view at our dock; boardwalk to beach
• 3 bed/3 bath with Stunning Lakeview from private pool
• Light and airy, beautifully appointed 3 bed, 3 bath home with sunny pool & spa.
• Little Gasparilla Island: WATERFRONT Cabin, Boat dock at front door!
• Cloud 9 on LGI Beach! No Roads. No Cars. Just Island Life w/Beach to Bay Views.

There are many large, family-friendly vacation homes available in Windward; however, here are the most popular family rentals listed on our site:

• Bluebell Villa. Outstanding Luxury Lakeside 4 Bedroom Villa
• Quiet Rotonda Villa, 3 Br, 2.5 Ba with recent upgrades.
• 2/2 Duplex on CANAL all updated; new furniture,
• Waterfront Sleeps 8 on the bay Beach-to-Bay private land; Dock-Wildlife-Secluded

Yes, there are 1011 self-catering vacation homes in Windward that have hot tubs, swimming pools, & other amenities.

There are more than 1011 luxury villas and vacation homes in or near Windward. Filter by price to compare find the most expensive places to stay on Vacationsrental.

Yes, there are 1011 pet friendly vacation homes and places to stays that are available in or near Windward that you may consider.