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
    Villa Tranquillo for 2 -3 Nights
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $4900 per property per week

  2. 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

  3. 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

  4. Alexander Valley Lodge - Pool, Spa, Tiki Bar, Waterfall w/Great Views — Property 182065

    Vacation Lodge rental in Healdsburg area
    • Lodge
    • 5 bedrooms , sleeps 14
    • 5 bathrooms
    • rural, town
    • accept credit card
    Rates (shown in USD)
    $3500 - $5200 per property per week

  5. Healdsburg 4 bedroom Vacation Home with Pool and Spa — Property 191424

    Vacation House rental in Healdsburg area
    • House
    • 4 bedrooms , sleeps 10
    • 3 bathrooms
    • 1 half bathroom
    • rural
    • accept credit card
    Rates (shown in USD)
    $3225 - $3975 per property per week

  6. Bright and Cozy 2-Bedroom Bungalow — 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. Two Wine Country Homes on 7 acres Russian River — Property 115595

    Vacation House rental in Healdsburg area
    • House
    • 6 bedrooms , sleeps 16
    • 6 bathrooms
    • rural, waterfront
    • internet access
    Rates (shown in USD)

  8. Luxury Gated 3 BR Estate Home with Spectacular Views — Property 186540

    Vacation rental in Healdsburg area
    • 3 bedrooms , sleeps 6
    • 3 bathrooms
    • town
    • air-conditioning
    Rates (shown in USD)
    $3000 per property per week

  9. July Special! Riverhouse in the Redwoods Deck, Spa, Beach,Kayak — Property 193217

    Vacation Cottage rental in Healdsburg area
    • Cottage
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • air-conditioning
    • washing machine
    Rates (shown in USD)
    $1950 per property per week

  10. 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)
    $1550 per property per week

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