
Luxury rentals in Santa Rosa
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Top-rated luxury holiday rentals in Santa Rosa
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Mayacama Manor - Sonoma Retreat
Mayacama Manor is a luxury retreat at the entrance to the Sonoma Valley. This newly built estate is nestled on 6 acres with downtown Sonoma and Healdsburg within 20 minutes in either direction. The 4000sf ranch style home has a beautiful open layout with a fully equipped chef’s kitchen, spacious pantry, entertainment/TV room, and 4 bedrooms. With a large swimming pool, hot tub, fire pit, outdoor dining and fireplace, this retreat is the perfect place for gathering, entertaining and wine tasting.

LUX Private Modern Villa | Pool, Spa, & Dogs OK
Welcome to your private Wine Country retreat in the hills above Calistoga! This newly remodeled luxury mountain-style home is where rustic charm meets upscale comfort. With panoramic views of Mt St. Helena, a sparkling heated pool with built-in spa, it’s the perfect escape for families or groups looking to relax, recharge, and create unforgettable memories. - 10-min drive to downtown Calistoga - 15-min drive to Castello di Amorosa - 10-min drive to Old Faithful Geyser - 10-min drive to Calistog

Private 2-Acre Sonoma & Napa Retreat + Hot Tub
Escape to a gated 2-acre private estate nestled among peaceful hills, minutes from Sonoma Valley, Napa Valley, and downtown Santa Rosa. Relax in the hot tub, enjoy expansive lawns, a children's play area, and complete privacy—a rare find in Wine Country. Explore 250+ wineries, hot springs, beaches, rivers, and redwood forests within 30 miles, with shopping, dining, and everyday conveniences just 10 minutes away. Perfect for Wine Country getaways, wedding weekends, remote work, and staycations.

Luxury Modern Home w/ Infinity Pool - 3400 sq ft
Welcome to Chestnut Knoll, a gated luxury Sonoma residence offering approximately 3,400 sq ft with 3 bedrooms and 3.5 bathrooms, featuring sweeping valley and vineyard views and a private infinity-edge pool and hot tub. Built in 2009, the home blends modern design with high-end finishes, a chef’s kitchen, open living spaces, and seamless indoor-outdoor flow. Set on a 1.24-acre lot just minutes from Sonoma Plaza and world-class wineries, the property also features expansive entertaining areas.

New! The Quails Crossing- Healdsburg Vineyard Home
Brand new modern luxury home designed to maximize the natural beauty & surrounding calm. Perched on a hill surrounded by 100 year old oak trees, this spectacular home was built facing beautiful rolling hills and vineyards with ultimate guest comfort in mind. Enjoy your AM coffee watching a family of quails roaming the vineyard and end your evening with a glass of wine on the deck watching the sun set behind the golden vineyard hills. Located approx 3.5 miles (6min) from the Healdsburg Plaza.

Year-Round Heated Pool | Hot Tub | Fire Pit | Lawn
Welcome to Sonoma Valley Villa, your one-of-a-kind wine country oasis in Kenwood. The newly built gated villa overlooking vineyards features all the luxury amenities of a five-star resort. → Year-round heated swimming pool with cover → Spacious hot tub → Cozy outdoor fire pit → Vineyard views for miles → Outdoor kitchen and dining → Chef's kitchen with everything for gourmet meals → Fast wifi → Dedicated office area → Lots of space for everyone Walking distance to Kenwood wineries.

Luxury Villa, Pool, Spa, BBQ, By Healdsburg Sonoma
Top 5% of homes, Luxe badge, and guest favorite badge by Airbnb. Welcome to Villa Montage - Brand new, luxury 4br/3.5ba Villa in the heart of Sonoma. Close to Wineries & Healdsburg. An award-winning architecture firm in SF designed the house. ☞ New & modern home ☞ Pool & Spa (Pool heated April-Oct) ☞ Outdoor & Indoor fireplaces ☞ Pool table ☞ BBQ with covered patio and dining table ☞ Chef's kitchen ☞ Baby-friendly (crib, toys, monitor) ☞ Tesla Charger ☞ IG @Villamontage.sonoma

Luxury Calistoga Retreat
Kalla Calistoga is a peaceful retreat tucked away in the hills of wine country. Thoughtfully designed with high-end finishes throughout, it offers a quiet space to relax, recharge, and enjoy the natural beauty of Calistoga. Whether you’re here to share time with friends and family, take in the surrounding nature, or simply slow down from the pace of everyday life, this home was created as a place to reconnect - with yourself, with each other, and with the land around you.

Mountain View Villa - Wine Country
Welcome to our elegant villa, where luxury furnishings complement breathtaking views from multiple decks and the gorgeous pool. Nestled on a serene property surrounded by nature, this retreat offers tranquility just 10 minutes from the Wine Country corridor. Ideal for groups, our location is perfectly situated to explore The Wine Country's best wine tasting and dynamic culinary experiences as well as Northern California's Coastline and everything else it has to offer.

The Overlook by Sonoma Stays – Modern Luxe Retreat
Set on nearly eight private acres in the hills of Santa Rosa, this spacious 5-bedroom, 4-bath home blends modern comfort with peaceful wine country living. Bright open living areas and contemporary design create an inviting atmosphere filled with natural light. Outside, enjoy a pool and spa, bocce court, and beautifully landscaped grounds. Perfect for families or groups, the home offers privacy, scenic views, and plenty of space to relax, gather, and unwind.

Luxury Retreat with Breathtaking Views
Welcome to Sunset Ridge, where the beauty of wine country unfolds before you. - Stunning interiors with soaring ceilings - Seamless indoor-outdoor living - World-class sauna, saltwater pool, and hot tub - Expansive hilltop vistas - 500 sqft gym and game room - Chef's kitchen with high-end appliances - Four luxurious bedrooms, including a Casita Suite - Complimentary 1GB Fiber Optic Internet - Heart of Wine Country, near renowned wineries

Mid-Century Secluded Oasis
Situated on over 85 acres of breathtaking views, this property, along with an adjacent home, offers ample space to host large groups, perfect for birthdays, bachelor/bachelorette parties, or wedding-related events. You can choose to rent both homes together or just one, depending on your needs. For details on the sleeping capacity and amenities of each home, feel free to reach out anytime. We’d be happy to assist!
Popular amenities for Santa Rosa luxury holiday rentals
Other great luxury holiday rentals in Santa Rosa

Modern, private Healdsburg oasis

Private Sonoma Vineyard Estate + pool, spa, views

Chalk Hill 360°

Sandstone Estate | Resort Pool & Walk to Wineries!

Wine Country Pool, Hot Tub & Views!

Kenwood Knoll

Private Villa on 4.3 Acre Estate Pool + Hot Tub +

Villa with Pool, Hot Tub and Tastings Included
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