Vacation rentals in Simi

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Top-rated vacation rentals in Simi

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Guesthouse in Healdsburg

4.98 out of 5 average rating, 177 reviews

Healdsburg Contemporary Cottage With Lush Backyard Patio

Stay in shape in the fully equipped Pilates studio, Afterwards, freshen up in the skylighted shower room with heated stone floor. Later, enjoy a glass of wine and a good book in the outdoor lounge and dine alfresco in the landscaped garden. The perfect home away from home. Makes this your personal sanctuary wether you are staying for the weekend or for the whole month while looking for the perfect home to buy. Well appointed, decorated with international contemporary art with just enough touches that take you beyond the hotel luxury suite. A great modern getaway with Garden, al fresco dining with BBQ, garden lounge area and fully equipped Pilates Studio. Park right in front of your guest house with private gated entry to your personal cottage. I am happy to help you plan your Healdsburg and Wine country excursions. From restaurants and wineries along with the perfect biking routes, top classical dressage lessons on Lusitanos or private Art Studio Tour, Pilates training at the on site studio, massage in the Guest house, Culinary Tour, Farmers Market to Picnic at Music on the Square on Tuesdays.... Head out for an easy stroll to downtown and the Plaza area, with boutiques, galleries, and antique shops to browse. Stock up at the farmers' market, sample local vintages in wine-tasting rooms, and dine at a wide choice of chic restaurants. Within easy walking distance to downtown Restaurants, Wine Tasting Rooms, Galleries, Antique Shops, Spas, Boutiques and Farmers Market. Healdsburg Contemporary Cottages is registered with the City of Healdsburg and is collecting TOT Taxes of 16% for the City of Healdsburg which are included in the pricing. The Business License Number is: (PHONE NUMBER HIDDEN)

Oct 17 – 24

$630 per night
Guest favorite

Home in Healdsburg

4.96 out of 5 average rating, 429 reviews

Dry Creek Valley Cottage

Enjoy your stay in beautiful Dry Creek Valley, a pastoral rural setting surrounded by vineyards and local wineries, minutes from Healdsburg's historic quaint downtown plaza. The cottage is 480 square feet with big windows, high ceilings and its own private entrance. There is parking right in front. It has kitchen amenities (coffee and tea pot, mini refrigerator, toaster and microwave), living room and bathroom with a mosaic tile shower. Right across the way you can take a lovely walk or run alongside the vineyards or you can rent a bike to explore the beauty of the valley. If you enjoy hiking, seasonal kayaking or canoeing there are opportunities all around us to explore as well. Our property has multiple fruit trees and we will be happy to share whatever bounty is in season when you arrive. The water here is also clean spring fed and very tasty and the sky at night is full of stars! You can enjoy sitting in the front yard which is bordered by a dozen Redwood trees or you can picnic in our big back yard among the fruit trees. We also have 2 female dogs who are quite friendly if you'd like to meet them. We would be happy to welcome you to Sonoma County and insure that your stay here is enjoyable.

Mar 26 – Apr 2

$172 per night
Guest favorite

Guesthouse in Healdsburg

4.98 out of 5 average rating, 246 reviews

Alexander Valley: Wine Lover and Cycling Paradise

The Finca Guest House is a beautiful modern & private unit, which offers country seclusion just a short hop into Healdsburg. Three private outdoor spaces for your use! Coffee patio, wine patio, goat patio--your choice! World-class biking out the door. Guest House will be thoroughly cleaned per Airbnb guidelines! *This property has farm animals so no outside animals allowed. See Rules and Policies notes Gas grill w/burner is available for outdoor cooking. NO full kitchen. Sonoma Co. TOT#3191N

Sep 2 – 9

$164 per night

Popular amenities for Simi vacation rentals

Other great vacation rentals in Simi

Guest favorite

Home in Healdsburg

4.93 out of 5 average rating, 522 reviews

Healdsburg Garden House

Nov 25 – Dec 2

$197 per night
Guest favorite

Loft in Windsor

4.81 out of 5 average rating, 499 reviews

The Loft Under The Oaks

Nov 21 – 28

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Guest favorite

Guest suite in Forestville

4.97 out of 5 average rating, 152 reviews

Forest Gem: peaceful retreat hot tub and firepit

May 15 – 22

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Guest favorite

Cabin in Healdsburg

4.99 out of 5 average rating, 145 reviews

Updated Russian River Cabin (beach/river access!)

Feb 5 – 12

$345 per night
Guest favorite

Guesthouse in Healdsburg

4.94 out of 5 average rating, 285 reviews

Th Roost - Sun Room

Mar 3 – 10

$261 per night
Guest favorite

Guest suite in Windsor

4.98 out of 5 average rating, 356 reviews

Private Entrance Suite in Heart of Wine Country

Aug 12 – 19

$111 per night
Guest favorite

Guesthouse in Healdsburg

4.93 out of 5 average rating, 299 reviews

Healdsburg Cottage-Workspace, Walk to Plaza

Oct 16 – 23

$282 per night
Guest favorite

Cottage in Healdsburg

5.0 out of 5 average rating, 13 reviews

Casa Campo

Aug 11 – 18

$294 per night
Guest favorite

Home in Healdsburg

5.0 out of 5 average rating, 49 reviews

10 Acre Vineyard Cottage w/Hot Tub + Bocce Court

Nov 17 – 24

$290 per night
Guest favorite

Home in Geyserville

4.97 out of 5 average rating, 29 reviews

Healdsburg Wine Country Oasis, Hot Tub & Bocce

Nov 2 – 9

$297 per night
Guest favorite

Home in Healdsburg

5.0 out of 5 average rating, 16 reviews

Creekside Cottage

Oct 26 – Nov 2

$282 per night
Guest favorite

Home in Healdsburg

5.0 out of 5 average rating, 36 reviews

Vineyard views, stunning house & deck

Oct 2 – 9

$517 per night

Destinations to explore

  1. Airbnb
  2. United States
  3. California
  4. Sonoma County
  5. Simi