Windward Bay

Booking Now for Summer 2027! Booked for January-June 30, 2027. Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January 2027! Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets directly across the street, with three beach access points — including private deeded beach access. Appreciate the convenience of pulling directly into your private carport with no steps or elevators and relish the peace and privacy of having no neighbors above or below during your stay. This beautifully appointed coastal villa features two bedrooms, two bathrooms, a spacious open concept living area, and an opulent interior design that is soaked in sunlight. The brand new remodeled and fully equipped kitchen is ideal for preparing meals with fresh local ingredients from nearby farmers' markets or head out to dine at one of the delectable nearby restaurants. Windward Bay is a low-density, wildlife-rich community nestled mid-Longboat Key on 26 acres, offering resort-style amenities including two heated pools, two tennis/pickleball courts, two marinas, kayak racks, shuffleboard, a clubhouse with kitchen, library, fitness room, two saunas, and multiple fire pits and barbecue areas throughout the property. Enjoy half a mile of scenic waterfront trails and direct access to the Gulf or Bay for boating, fishing, or simply soaking up the sun. Located just minutes from Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez Fishing Village, championship golf courses, shopping, dining, and vibrant cultural attractions. This is a rare opportunity to create lasting memories in a home that guests return to year after year. This villa is more than a vacation rental — it’s a tradition. One couple has returned every March and April for over a decade, drawn by the comfort, beauty, and unbeatable location.

Est. Mortgage

$35

HOA Fee

$0

Est. Property Tax

$0

Est. Insurance

$2

* Estimates are for illustration purposes only and do not constitute an offer of financial advice. Actual rates, payments, insurance, and taxes will vary based on credit, location, and other factors. Contact a licensed mortgage professional for a personalized quote. Homeowners insurance estimate based on Florida averages.