Vacation rentals in Simi

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Simi

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Guesthouse in Healdsburg

4.98 out of 5 average rating, 183 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)

Guest favorite

Home in Healdsburg

4.95 out of 5 average rating, 437 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.

Guest favorite

Guesthouse in Healdsburg

4.98 out of 5 average rating, 257 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

Guest favorite

Home in Healdsburg

4.98 out of 5 average rating, 105 reviews

Beautiful, Spacious, ArtHaus!

Welcome to ArtHaus! Tree is up for the holidays and ready to host your friends and family. 3 Bed, 3 Bath on 1.5 Acres. Includes 2 Bed 2 Bath 1,600 Ft2 main house _ ++Completely separate and set back 558 Ft2 1 Bed 1 Bath with an outdoor shower. Super spacious living room opening onto an outdoor deck. Modern and fully equipped kitchen w/ glass and dining ware so you can stylishly host an entire dinner party. We do. Home feature beautiful art pieces created by the homes designer Sargam Griffin.

Guest favorite

Cottage in Healdsburg

4.96 out of 5 average rating, 120 reviews

❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤

❤New! Welcome to the "The Elegant Barn", our newly built stylish Barn Cottage in the HEART of wine country! Our *INSTAWORTHY* barn cottage boasts a HOT TUB, panoramic vineyard VIEWS, comfy furnishings & convertible glass indoor/outdoor doors to bring the outdoors inside! LOCATION, LOCATION, LOCATION! Set on a historic vineyard property on Dry Creek Road, the location of Healdsburg's most famous wineries, and an easy walk, bike ride or drive to many of the best wineries in the area! PETS OK!❤

Guest favorite

Guest suite in Windsor

4.98 out of 5 average rating, 371 reviews

Private Entrance Suite in Heart of Wine Country

Situated in an upscale neighborhood, this exquisite guest suite boasts a private entrance on a safe, quiet cul-de-sac in the heart of the wine country. The en-suite is perfect for a romantic getaway, comfortable for an infant or small child, and ideal for the business traveler. We are 5 miles from Healdsburg and 3 from the Sonoma Co. Airport. Three parks within 4 miles encompass over 20 miles of hiking/biking. The Russian River, Redwoods, and Sonoma Coast are only a short, panoramic drive away.

Guest favorite

Home in Healdsburg

4.97 out of 5 average rating, 153 reviews

Secluded Healdsburg Sanctuary on 10 Private Acres

This stunning, modern home sits on a picturesque 10-acre property, complete with a thriving vineyard that provides a serene and secluded backdrop for your getaway. As you enter the home you'll be struck by its elegant and refined design and large picture windows that look out on breathtaking vistas of vine, olive & oak dotted hills. Whether you are seeking a romantic getaway, a family vacation or a peaceful respite from city life, this exceptional retreat has everything you need & more.

Guest favorite

Home in Healdsburg

4.98 out of 5 average rating, 409 reviews

Vineyard Modern Barn House - Dry Creek Valley

Stylish house on a 9 acre vineyard. Beautifully crafted, the property features high end furnishings, professionally laundered/ironed sheets, original art, and 2 master bedroom suites separated by a great room w/full kitchen. Close-in location up a gated road, 5 min. to the Plaza. Amazing view from the 45 foot covered porch overlooking vineyards and Dry Creek Valley. Perfect for two couples; not suitable for infants or children under 8, max 2 daytime guests. No parties or pets allowed.

Superhost

Villa in Healdsburg

4.94 out of 5 average rating, 124 reviews

Hilltop Vista Villa

Set on an Acre by Fitch Mountain Park and Open Space Preserve, Hilltop Vista Villa offers a quiet private setting, spectacular views of world class vineyards, private access to hiking trails and proximity to the Russian River beach. This inviting single level retreat has an open floor plan with lots of sunshine. The open kitchen features stainless steel appliances, custom cabinetry, and a granite topped island. The Master Suite includes a custom soaking tub.

Guest favorite

Guest suite in Healdsburg

4.92 out of 5 average rating, 419 reviews

Pony Ranch Vineyard Estate with Pool

Guest House with private entrance on gorgeous gated Vineyard Estate. Overlooks pool and vineyards with views to Mount St. Helena. Gas fireplace, refrigerator, microwave, Keurig coffee maker, queen bed. Toilet and sink separate from shower. 8 minutes to the Healdsburg Plaza. Less than a mile from 3 wineries, very close to dozens more. Agricultural Education Programs available. Sonoma County TOT Certificate 1362N

Guest favorite

Home in Healdsburg

4.91 out of 5 average rating, 129 reviews

Dry Creek w/Hot Tub, Bocce, Vineyard Views

Ideally located 5 minutes from the Healdsburg Square on Dry Creek Road, this home has it all! Cozy home has spectacular vineyard views on a magical 1/2 acre lot, a hot tub, Bocce ball court, large deck, and a fully stocked kitchen. We pride ourselves on keeping the house fully stocked with everything our guests may need & spotlessly clean! World class food, wine, cycling, and nature are at your fingertips here!

Guest favorite

Cottage in Healdsburg

4.99 out of 5 average rating, 248 reviews

Luxurious, Private, Healdsburg Guest Cottage

1083 Guest House is a Healdsburg find; comfortable luxury in a spacious private cottage with terrific amenities within walking distance of four-star restaurants, wineries, fabulous boutique shopping, and the Russian River. Your secluded cottage is nestled in the trees with views of a wooded area and is the perfect destination for your personal romantic getaway to enjoy all that the Wine Country has to offer.