Search for vacation rentals in Healdsburg.

Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Healdsburg area to find the perfect spot for your vacay.

10936 Eastside Rd

10936 Eastside Rd

Healdsburg, CA
$8,500
Vacation Rentals, Unknown
Situated on 3 acres in prime Sonoma wine country, the Chatthaveli home is a bucolic delight with multiple areas to spread out and relax. Sway on the porch swing with your morning cup of coffee,......

537 Brown St

537 Brown St

Healdsburg, CA
$4,500
Vacation Rentals, Unknown
PERFECT for NURSES THAT TRAVEL. Looking for a stylish and modern FULLY FURNISHED apartment in the heart of Healdsburg wine country? Look no further than our completely renovated 4-plex on Grant......

725 Fitch St

725 Fitch St

Healdsburg, CA
$5,500
Vacation Rentals, Unknown
This charming, 103-year-old craftsman house nestled in one of the most desirable areas has been lovingly updated to offer modern comforts while retaining its timeless appeal. Located just a few......

824 Pordon Ln

824 Pordon Ln

Healdsburg, CA
$15
Vacation Rentals, Unknown
Walk to The Plaza from this brand-new-build, three-bedroom, 2,300sf house with pool & jacuzzi located on the fifth tee of the Healdsburg/Tayman Park Golf Course. No detail left unattended in this......

332 Bridle Path

332 Bridle Path

Healdsburg, CA
$3,750
Vacation Rentals, Unknown
Beautiful 4 bedroom home with 2 1/2 baths, living room, dining room, family room, kitchen, and 2 car garage in desirable Parkland Farms area near neighborhood park in Healdsburg, Ca. Shown by......

210 Solar Way

210 Solar Way

Healdsburg, CA
$4,800
Vacation Rentals, Unknown
Welcome to 210 Solar Way, the perfect place to enjoy Healdsburg's beautiful scenery and world-renowned amenities. Centered between Mill District and North Village, this stunning home is located......

230 Zinfandel Rd

230 Zinfandel Rd

Healdsburg, CA
$8,500
Vacation Rentals, Unknown
Healdsburg Retreat: Urban Ease with Country Charm Discover a unique blend of country serenity and city amenities in this Healdsburg estate, located at the peaceful end of a cul-de-sac near the......

766 Alexander Valley Rd

766 Alexander Valley Rd

Healdsburg, CA
$3,200
Vacation Rentals, Unknown
Want country living but close to amenities? We are less than a mile from Healdsburg city limits in Alexander Valley. We have a 3-bedroom, 2 bath 1,280 ft2 flat, available from March 1st, 2024.......

1616 S Fitch Mountain Rd

1616 S Fitch Mountain Rd

Healdsburg, CA
$3,600
Vacation Rentals, Unknown
Healdsburg 3BR/2BA home on Russian River off S. Fitch Mountain Road. Main house has hardwood floors, main bedroom and guest bedroom and one full bath. A living room, dining room and kitchen with......

1702A Canyon Run

1702A Canyon Run

Healdsburg, CA
$2,500
Vacation Rentals, Unknown
This studio is truly stunning! Every aspect has been meticulously updated, featuring custom cabinets and countertops throughout. Situated in an excellent location with the Healdsburg Ridge Open......

1533 Rosewood Dr

1533 Rosewood Dr

Healdsburg, CA
$3,750
Vacation Rentals, Unknown
3 Bedroom/ 2 Bath Home - 1,588 square foot, 1.5 miles from downtown in quiet neighborhood. Close to restaurants and stores. This 3 Bedroom/2 Bath home includes a 528 Sq. Ft garage & sits on a 7,128......

558 Powell Ave

558 Powell Ave

Healdsburg, CA
$3,500
Vacation Rentals, Unknown
Healdsburg 3BR/2BA single story home with 2 car garage. Carpeted throughout. Living room, kitchen and breakfast area. Stove and dishwasher, AS IS refrigerator (this means if it needs repair or......

979 Jasmine Ct

979 Jasmine Ct

Healdsburg, CA
$5,300
Vacation Rentals, Unknown
Experience this stunning home complemented by lovely gardens. Impeccably maintained, it boasts a formal living room, dining room, and an open kitchen with a dining area and pantry. Relax in the......

152 Presidential Cir

152 Presidential Cir

Healdsburg, CA
$4,095
Vacation Rentals, Unknown
Nice 4br/3 full baths 1772sf two-story home on LARGE CORNER LOT in a small subdivision in beautiful Healdsburg. Walk or bike to Memorial Beach or downtown Healdsburg for great restaurants,......

566 March Ave

566 March Ave

Healdsburg, CA
$3,300
Vacation Rentals, Unknown
Healdsburg, two story 3BR/2.5BA home with 2 car attached garage. Wood look laminate floors, new kitchen appliances. 1/2 bath downstairs near entry with coat closet. Roomy living room has wet bar......

Healdsburg Ave

Healdsburg Ave

Healdsburg, CA
$5,300
Vacation Rentals, Unknown
A rural feeling retreat handy to all that Healdsburg and its surrounds offer. Thank you for checking me out. SINGLE LEVEL HOME: # Custom renovated 2020 # 3 Bedrooms # 3 bathrooms #......

316 Bridle Path

316 Bridle Path

Healdsburg, CA
$3,900
Vacation Rentals, Unknown
Fantastic property adjacent to park! Great for families with kids....

537 March Ave

537 March Ave

Healdsburg, CA
$3,300
Vacation Rentals, Unknown
Live the Wine Country lifestyle in this 3 bedroom 2.5 bath home. Located on the north end of Healdsburg, peacefully situated among trees and surrounded by a greenbelt. Features include hardwood......

242 Grant St

242 Grant St

Healdsburg, CA
$2,850
Vacation Rentals, Unknown
Healdsburg 2BR/1BA single family home with one car garage and backyard. New paint, and newly refinished hardwood floors throughout. Kitchen has modern counters, gas range. AS IS washer and dryer in......

725 Lytton Station Rd

725 Lytton Station Rd

Healdsburg, CA
$5,450
Vacation Rentals, Unknown
Newly remodeled fully furnished peaceful and safe home. Stunning location in the middle of a vineyard, with views to the mountains across the vines. We just added a beautiful new deck with hot tub......

902 Harold Ln

902 Harold Ln

Healdsburg, CA
$5,550
Vacation Rentals, Unknown
Welcome to Harold House, a lovingly renovated home in charming Healdsburg, CA. This is a furnished monthly rental with a 30 day minimum. Lease duration is flexible and determined by tenant need.......

620 Center St

620 Center St

Healdsburg, CA
$5,800
Vacation Rentals, Unknown
Newly remodeled single level home, 3 blocks from Plaza and downtown Healdsburg. Fully stocked gourmet kitchen with gas grill on the deck. 2 bedrooms, 2 full bathrooms with high-quality mattresses......

11000 Limerick Ln

11000 Limerick Ln

Healdsburg, CA
$4,500
Vacation Rentals, Unknown
NOTE: Address shown is not accurate, call for appointment. Square footage is not guaranteed. A newly remodeled country home. Healdsburg, 3BR/2.5BA only 3 miles to downtown. Wood floors throughout.......

1855 Bailhache Ave

1855 Bailhache Ave

Healdsburg, CA
$1,600
Vacation Rentals, Unknown
Stand alone rustic Healdsburg cabin near Russian River, one bedroom, fireplace, kitchen with new refrigerator, stove. Propane and electric extra. Storage room separate and included in rent. No......

5968 W Dry Creek Rd

5968 W Dry Creek Rd

Healdsburg, CA
$125
Vacation Rentals, Unknown
Furnished Dry Creek Valley home, 10 min from Central Healdsburg, 3BR/2BA with in ground pool and hot tub, fruit trees and garden beds, vineyard views and large grassy area for play. NOTE: Square......

1244 Fitch Mountain Rd

1244 Fitch Mountain Rd

Healdsburg, CA
$6,800
Vacation Rentals, Unknown
This 1,600 square foot single-level classic Healdsburg home comes fully furnished and has an additional 550 sq. ft studio. The house and separate studio have been completely remodeled with high-end......

324 Equestrian Gap

324 Equestrian Gap

Healdsburg, CA
$4,650
Vacation Rentals, Unknown
Nestled in the charming, coveted neighborhood of Healdsburg, this 4-bedroom, 2.5-bathroom gem is the perfect place to call home. Located on a peaceful cul-de-sac, 324 Equestrian Gap offers an......

Norton Rd

Norton Rd

Healdsburg, CA
$3,300
Vacation Rentals, Unknown
Zen-like sanctuary. Quiet, private, romantic. Gardens and trees are your view from every window. Just 1.5 miles to Healdsburg Plaza. MasterBR has private patio. Living room has double french doors......

5091 Dry Creek Rd

5091 Dry Creek Rd

Healdsburg, CA
$3,500
Vacation Rentals, Unknown
Welcome to the tranquil escape you have been dreaming of in the heart of Dry Creek Valley, conveniently located just minutes from downtown Healdsburg. The original farmhouse is adorned with bay......

9625 Chalk Hill Rd

9625 Chalk Hill Rd

Healdsburg, CA
$9,500
Vacation Rentals, Unknown
Premium Healdsburg Vineyard Rental with heated Swimming Pool in prime Chalk Hill Location. Nestled in one of the most beautiful valleys on Chalk Hill Road, this quintessential Vintage Farmhouse......

111 Chiquita Rd

111 Chiquita Rd

Healdsburg, CA
$5,300
Vacation Rentals, Unknown
Craftsman Style Home + ADU Located just 2 miles north of Downtown Healdsburg, this recently completed home (2021) has upgraded finishes throughout. The main home features a bright and open living......

313 Greens Dr

313 Greens Dr

Healdsburg, CA
$5,000
Vacation Rentals, Unknown
This single story home is located in The Greens, a lovely neighborhood in Healdsburg, easy walking distance to downtown and close to Tayman Park golf course. Located on a corner lot, this bright......

613 Sanns Ln

613 Sanns Ln

Healdsburg, CA
$2,750
Vacation Rentals, Unknown
Fully furnished cozy cottage. WiFi. Utilities included.* Two bedroom, each with one new full size Novaform bed and, one full bath in cottage. Central Air conditioning and heat. Close to downtown,......

Sanns Ln

Sanns Ln

Healdsburg, CA
$2,650
Vacation Rentals, Unknown
Fully furnished cozy cottage. Two bedroom, each with one new full size Novaform bed and, one full bath in cottage. Central Air conditioning and heat. Close to downtown, restaurants, markets, shops......

422 Grant St

422 Grant St

Healdsburg, CA
$5,900
Vacation Rentals, Unknown
VACATION RENTAL. FULLY FURNISHED by NATIONAL DECORATOR Are you looking for a beautiful new VACATION home in Healdsburg wine country? This completely renovated house is the perfect place for you to......

1612 Winding Creek Way

1612 Winding Creek Way

Healdsburg, CA
$5,300
Vacation Rentals, Unknown
Craftsman Style Home + ADU Located just 2 miles north of Downtown Healdsburg, this recently completed home (2021) has upgraded finishes throughout. The main home features a bright and open living......

315 1st St

315 1st St

Healdsburg, CA
$4,200
Vacation Rentals, Unknown
Live the Wine Country Dream in this Healdsburg classic just 4 blocks to the downtown plaza. This beautifully and artistically appointed home is available for annual leasing. Some of the property......

315 Equestrian Gap

315 Equestrian Gap

Healdsburg, CA
$3,500
Vacation Rentals, Unknown
Available September 15 or October 1 - This 3B/2B single story home is in Parkland Farms set among the vineyards of Healdsburg with a local park and the Healdsburg Ridge Open Space Preserve just......

2745 N Fitch Mountain Rd

2745 N Fitch Mountain Rd

Healdsburg, CA
$4,700
Vacation Rentals, Unknown
Come and see this thoughtfully designed new construction river front home and enjoy the relaxing lifestyle of living on the Russian River. Enjoy cooking in the chef's kitchen and entertaining out......

6115 Dry Creek Rd

6115 Dry Creek Rd

Healdsburg, CA
$4,500
Vacation Rentals, Unknown
Welcome to the Dry Creek Valley in Healdsburg! Set on 2 acres, this charming 3-bed, 2-bath house offers 2,000 sq ft of space, with 2-car garage, and stunning vineyard views. For those seeking a......

Healdsburg, CA

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