Elevating Life

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Luxury Vacation Rentals

Immerse yourself in the tranquility of your own luxury vacation rental — a place to de-stress, soothe your spirit, indulge your soul. The Wine Stay provides beautiful surroundings, and so much more. We curate vacation experiences tailored just for you. Let our sommelier personalize a boutique wine tour. Enjoy dinner al fresco prepared by a 5-star chef at your luxury vacation home. Cycle through the back roads with a local guide. We inspire an unforgettable wine experience that elevates the quality of your luxury vacation, and your life!

Healdsburg Vacation Rentals & Visitors Guide

Rent your 2nd home — hassle-free!

The Wine Stay makes renting a second home simple for homeowners because we handle all the bookings, paperwork, permits, maintenance, repairs, 24/7 guest services — everything. This way you reap only the benefits of your vacation property. You get to enjoy your second home in the wine country whenever you want and earn a nice income from your investment. And we offer you options. You can take advantage of our TrueRent Guarantee for a reliable monthly income regardless of occupancy or try our Variable Monthly Rent, with fluctuating pricing that is always top dollar. Either way, our bottom line is always to create win/win relationships, where both homeowners and guests enjoy an elevated vacation experience.

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