Book Luxury Holiday Rentals in Healdsburg

Award-winning homes from £98

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Home spotlights in Healdsburg

Cabernet Cottage

Cabernet Cottage

  • 6 guests

  • 2 bedrooms

Sonoma County, California

This delightful Wine Country home is a superb choice for a family or group of friends hoping to relax, unwind, and try some of California’s finest tipples. A newly built cottage, this home sits just eight miles from Healdsburg Plaza, and a few minutes from Lake Sonoma.

Taylor Ridge Retreat

Taylor Ridge Retreat

  • 8 guests

  • 4 bedrooms

Sonoma County, California

Surrounded by acclaimed vineyards and a short drive from the rugged beauty of the Sonoma coast, this welcoming home offers a spectacular retreat for anyone looking to spend a week or so discovering everything Wine Country has to offer or simply get away from it all for the weekend. Inside, an open layout offers a wonderful flow throughout the home.

Coffee Shop Soundtrack

Coffee Shop Soundtrack

  • 4 guests

  • 2 bedrooms

Menlo Park, San Mateo County

Set in Menlo Park within the San Francisco Bay Area of California – you'll be just a fifteen-minute drive away from the world-renowned Silicon Valley, home to the iconic Meta headquarters. Blending city living with an abundance of local nature, you'll find plenty of things to do here, come day and night.

Sideways to Happiness

Sideways to Happiness

  • 4 guests

  • 2 bedrooms

Healdsburg, Sonoma County

This beautiful home situated in the centre of Healdsburg dates back to the 1880s. Beautifully restored, it offers a charming and cosy base for those visiting Wine Country and looking to make the most out of their stay.


We selected the top 3% holiday homes in Healdsburg Holiday Rentals

Explore the 90 most perfect homes in our collection

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Most popular homes in Healdsburg

Vineyards & Verandas

Vineyards & Verandas

  • 6 guests

  • 3 bedrooms

Healdsburg, Sonoma County

Black Walnut Cove

Black Walnut Cove

  • 2 guests

  • 1 bedrooms

Pedro Point, Pacifica

Large Glass of Red

Large Glass of Red

  • 24 guests

  • 8 bedrooms

Napa County, California

Cabernet & Clover

Cabernet & Clover

  • 8 guests

  • 3 bedrooms

Sonoma County, California

Fair of Face

Fair of Face

  • 4 guests

  • 2 bedrooms

Menlo Park, San Mateo County

Sonoma Sanctuary

Sonoma Sanctuary

  • 8 guests

  • 4 bedrooms

Healdsburg, Sonoma County

Utmost Taste

Utmost Taste

  • 4 guests

  • 2 bedrooms

Healdsburg, Sonoma County

Willow Cove

Willow Cove

  • 2 guests

  • 1 bedrooms

Pedro Point, Pacifica

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Healdsburg. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Healdsburg has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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