Vacation Rentals & House Rentals in Healdsburg

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Healdsburg, 4BR/3BA, Hot tub, Fire pit, Vineyard views

Healdsburg house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Fireplace

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Price per night from

$1,031

Healdsburg, 4BR/4BA, Pool, Internet, Fireplace

Healdsburg house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Fireplace

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Price per night from

$1,603

Healdsburg, 4BR/2.5BA, hot tub, Fire pit, Bocce Ball, BBQ

Healdsburg house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,031

Kenya's Kastle

Healdsburg house

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 8

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Price per night from

$210

Healdsburg, Jimtown, 3BR/2BA, hot tub, Internet, BBQ, Gardens

Healdsburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Difficult to reserve, but beautiful property” We recently stayed at the Jimtown house with 2 other couples. We had a great time enjoying the lovely house. The hard work came before when trying to make the reservations. We found the property management to be polite, but irritating. They sent a 12 page contract with an ridiculous amount to signatures required. They didn't answer repeated questions and the payment process was very unprofessional. They asked for my credit card information through email. They require you to open a special account to pay for the security deposit. It has been 2 weeks and I haven't seen my deposit returned yet. They require you to pay a cleaning fee of $200 and then ask you to clean the house before you leave. We had to empty waste baskets, sweep and remove linens from the bed. The house itself is beautifully furnished and very clean. It is close to the road so there is road noise, but we loved the surrounding and the gardens. The irrigation to the garden in back was out of order so we hand watered the trees and veggies because they were literally dying. Hopefully the owners were alerted and fixed it because the garden is great If the management company were different, I would have given 5 stars, but they need to revamp their system to make it easier for their clients to rent the house!

Match: Fireplace

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Price per night from

$745

Great rentals within 20 miles that match your search

Deja Blu-Magical Ocean Front Property (Beach View)

Bodega Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$912

Cabin Compound on the Creek in the Redwoods

Cazadero log cabin

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Fireplace

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Price per night from

$132

The Ranch Above St Helena ~ 5 bedroom 8 1/2 bath Overlooking St. Helena

St. Helena house

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 12

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Price per night from

$6,880

The TreeHouse- Charming Cabin in the Redwoods

Monte Rio house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$213

Downtown B&B close to Arts, Food, Wine great beer

Santa Rosa house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$480

Superbowl 50; February 3-10

Windsor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$574

Sonoma Wine Nest - Location! Location! Location!

Windsor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$373

Alexander Valley Lodge on 54 acres with Pool and Hot Tub

Geyserville house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$1,032

Grand Riverfront Estate with Dock, Minutes from the Beach

Monte Rio house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$258

Wine Country Getaway in Napa/Sonoma, Hot Tub, Redwoods and Creek Views

Santa Rosa house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Fireplace

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Price per night from

$516

Wine Country Luxury Home-Pool, Hot Tub, Brush Creek

Santa Rosa house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,376

A Perfect Getaway in The Wine Country

Santa Rosa house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$366

Bright Modern Wine Country Hilltop Home w/ Office!

Santa Rosa house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$286

Cool & Calm Wine Country Home w/ Panoramic Views

Santa Rosa house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$250

Peaceful Modern Sta Rosa Home w/ Vineyard Views!

Santa Rosa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$230

Lily Pad: Perfect Riverfront Family Resort/Hot Tub/On River/Game Room/Pup OK!

Guerneville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“The Lily Pad Exceeded Our Expectations!” One word: wow. My family & I were incredibly excited to stay at The Lily Pad after looking at the lovely photos of the property online. But wow, when we arrived it was even better than it looked in the pictures. I've never stayed at a property that is as thoroughly maintained as this place. Clean from wall to wall, with every ammenity you could possibly want & need. Great family vacation home!! This will be a staple home away from home from now for myself & my family. Thank you Lily Pad!

Match: Fireplace

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Price per night from

$1,263

Mi Corazon-5 STAR Upscale Bungalow Compound! Hot Tub/Walk to River/Pup OK

Guerneville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Fireplace

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Price per night from

$652

Happy Days-Large,Fun Home/DowntownGuerneville!WalktoEverything/PingPong/Darts

Guerneville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Fireplace

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Price per night from

$628

Perfect Friend/Family Tree House-Vibe Cabin! HotTub/Golf/PupOK/Near Wineries

Guerneville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

“Wonderful Cabin in the Redwoods” The cabin worked perfectly for our week in the Russian River area. Clean, quiet and very convenient to the numerous things to do in the Russian River Valley. Thank you Stace!

Match: Fireplace

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Price per night from

$582

Vino Velo-Enchanting Forest Escape! Wineries/HotTub/PupOK/GameRoom

Rio Nido log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Fireplace

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Price per night from

$472

RedwoodRetreat-Sweet Remodeled Cabin! Great location! HotTub! Walk to River!

Guerneville log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Fireplace

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Price per night from

$576

River Oasis- Chic Romantic Personal Resort! Pool/ Sauna/ Hot Tub/Bikes/

Guerneville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Fireplace

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Price per night from

$845

Match: Fireplace

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Price per night from

$1,027

Guerneville Escape: Fabulous Redwoods Retreat! Brand New Hot Tub! Pup OK!

Guerneville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Fireplace

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Price per night from

$448

Guerneville Cottage - Relax, Rekindle and Rejuvenate! HotTub/Decks/FireTable

Guerneville cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Adorable Cottage in the Redwoods” We loved the little cottage in the redwoods. It was clean, comfortable, and lovely. The stove heated up the place quickly and you could open the windows to cool the place down quickly. The kitchen had everything we needed to cook, and there was a wonderful stereo if we wanted music, or a tv and dvd player when we wanted to watch a movie. The only difficulty with the property is the location. It's in a neighborhood of cottages/cabins on a very very steep hillside. We took our car that is a manual transmission and it was no fun navigating the small streets at very steep angles. Just bring your small automatic car! Otherwise, a beautiful location and place to relax.

Match: Fireplace

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Price per night from

$649

Dhyana- Playful 5-Star Cabin by Russian River/Guerneville/HOT TUB/Arcade!

Guerneville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Fireplace

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Price per night from

$1,016

Wine Country Retreat! Craftsman style meets Modern chic! Decks/Hot Tub

Forestville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Fireplace

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Price per night from

$695

Wood Chalet: Dazzling, bright & Upscale! Huge windows/HotTub/Near Wineries

Guerneville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Fireplace

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Price per night from

$487

Guerneville Getaway: Craftsman Retreat! Fun! Game Room / Hot Tub / Wineries!

Guerneville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Fireplace

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Price per night from

$687

Little Red House: COZY Cabin Vibe! Wineries/Ocean/Hot Tub/Golf Course/Pup OK

Guerneville house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

“Little Red House” We had an awesome experience. We would pick this cabin again. It's very nice, cozy and clean. It's a great location, close to the River and BodegaBay. This home is very well taken care of. Property mgmt team are professional and very helpful. Thank you everyone!

Match: Fireplace

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Price per night from

$381

Super Charming Remodeled Retreat! PoolTable/PupOK/Great Location-Absolute Zen

Guerneville house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Fireplace

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Price per night from

$426

Match: Fireplace

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Price per night from

$344

Secluded Hillside Hideaway Offers Elegance/Comfort

Forestville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Fireplace

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Price per night from

$257

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