Search for vacation rental homes in Healdsburg

The Two of You in Healdsburg

If you’re looking for a pretty good bottle of wine, it’s no secret that Sonoma County is a smart place to start. In addition to finding a fine pour you’ll find a few other things, too, including a fabulous all-around vacation spot.


Wine sets the tone for an experience in Healdsburg but by no means does it dominate. In addition to strolling through the orchards, farms and vineyards, you’ll also find a lively downtown scene ready to sate all cultural, culinary and creative urges. Along the Russian River is a romantic vacation waiting to happen, so clear a few days from your schedule, grab your favorite person, and see what develops.


Form a solid foundation for your trip by reserving a Vacation Rental in Healdsburg. These properties are everything they should be: elegant, cozy, budget-friendly and warm. Depending on your taste and expectations you’re sure to find just what you’re looking for – most notably, plenty of privacy and a little peace and quiet.


Downtown Healdsburg has an artsy side you’ll quickly grow fond of. A Jazz Festival each June, a healthy scene of local painters, sculptors and jewelry designers, farmers markets, fine restaurants and a few surprises in between will make each journey to the city center a treat. Go back and forth between the peaceful countryside and the heart of Healdsburg in order to ensure that you don’t miss a thing.


California Wine Country could change your definition of a vacation forever. Scout out your favorite spots because a return visit is most definitely in the cards…maybe next time you’ll even bring the kids. Or not.

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  1. Villa Tranquillo -Mediterranean Resort Style Estate Pool/Spa — Property 186396

    Vacation House rental in Healdsburg area
    • House
    • 4 bedrooms , sleeps 8
    • 3 bathrooms
    • mountain, resort
    • accept credit card
    Rates (shown in USD)
    $4900 per property per week

  2. Luxury Riverside Retreat - Screened Porch, Spa, Canoe, Dock ! — Property 160768

    Vacation House rental in Healdsburg area
    • House
    • 2 bedrooms , sleeps 6
    • river, town
    • accept credit card
    Rates (shown in USD)
    $1950 per property per week

  3. Luxury Tuscan Villa- Secluded & Serene 5 Acre Vineyard Estate — Property 167873

    Vacation House rental in Healdsburg area
    • House
    • 4 bedrooms , sleeps 8
    • 3 bathrooms
    • 1 half bathroom
    • rural, town
    • air-conditioning
    Rates (shown in USD)
    $4250 per property per week

  4. Luxury wine country house in Healdsburg with pool — Property 203245

    Vacation House rental in Healdsburg area
    • House
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • near the ocean, river
    • accept credit card
    Rates (shown in USD)
    $2348 per property per week

  5. Luxury Hillside Haven with Stunning Views, Spa & Plunge Pool — Property 190651

    Vacation House rental in Healdsburg area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • 1 half bathroom
    • swimming pool
    • air-conditioning
    Rates (shown in USD)
    $3750 per property per week

  6. Beautiful bright 2- bedroom bungalow with swimming pool — Property 180500

    Vacation House rental in Healdsburg area
    • House
    • 2 bedrooms , sleeps 6
    • 1 bathroom
    • village
    • accept credit card
    Rates (shown in USD)
    $1656 - $1950 per property per week

  7. Winelover's 3br 1922 Farmhouse in a world class Merlot Vineyard — Property 190656

    Vacation House rental in Healdsburg area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • rural, town
    • accept credit card
    Rates (shown in USD)
    $2000 per property per week

  8. Healdsburg Country Gardens Vacation Homes — Property 103437

    Vacation Farmhouse rental in Healdsburg area
    • Farmhouse
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • rural, village
    • washing machine
    Rates (shown in USD)
    $2500 per property per week

  9. Fitch Mountain Lookout - Views, Hot Tub, Fireplace, Beach Access — Property 152178

    Vacation House rental in Healdsburg area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • river, village
    • accept credit card
    Rates (shown in USD)
    $2075 per property per week

  10. The Ultimate Contemporary Wine Country View Estate — Property 201489

    Vacation House rental in Healdsburg area
    • House
    • 4 bedrooms , sleeps 8
    • 4 bathrooms
    • 1 half bathroom
    • air-conditioning
    • washing machine
    Rates (shown in USD)

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