Family-friendly vacation rentals in Los Olivos

Wine Country Cottage

Experience the tranquil ambiance of the Wine Country Cottage's serene surroundings. Bask in the breathtaking views of rolling hills and grazing cattle while savoring your favorite bottle of wine from the comfort of our deck. You will be charmed by the presence of Jack & Henry, our Mini Donkeys. As the sun sets, indulge in the magical allure of the outdoor fairy lights and cozy up by the inviting fire pit. Come and relish in the alluring tranquility that awaits you at the Wine Country Cottage.

Family · Indoor spaces · Sleep quality

Gorgeous Santa Ynez Farm House

Welcome to The Little Blooming Farm – Where Beauty is Always in Bloom! Nestled in the heart of Santa Ynez Valley, our 5-acre farm stay is a countryside retreat like no other. Unwind in our newly remodeled 4-bedroom, 3-bath home, designed for inspiration and relaxation. Stroll through vibrant rose gardens, spend time with our friendly alpacas, Nigerian dwarf goats, and wake up to the soothing sounds of mourning doves. Whether you’re here to escape or explore, The Little Blooming Farm awaits!

Indoor spaces · Family · Amenities

2 Br/ 2Ba New+Stylish Cottage Downtown Los Olivos

Welcome to "Tyler Cottage" located in the heart of Los Olivos. Park your car & you are steps from wine tasting, craft beer, great restaurants & boutique shopping. Features incl. 2 bedrooms, king mattresses, high quality linens & wifi. Each bedroom has a smart TV & attached bathroom. For the discerning guest looking for a relaxing wine country getaway, "Tyler Cottage" is perfect for you. Our Rental Agmt. is included in the listing details. Ask about the other properties we have in town!

Kitchen · Indoor spaces · Walkability

Los Olivos Vineyard Home on Winery Estate

Set on an established winery estate in the Santa Ynez Valley, Casa de Brander is a stunning two bedroom Spanish-style home overlooking the Brander Vineyard. Tastefully decorated with Mexican folk art, this is a truly unique property! Located within a five minute walk from Los Olivos Grocery, it will be easy to stock the state-of-the-art kitchen with essentials, or dine out at the many wonderful restaurants in the area. The spacious patio overlooking the vineyards offers ultimate privacy.

In the Heart of Los Olivos

Escape to this luxurious home located steps away from downtown Los Olivos. Indulge in the 50 different wine tastings and 5 great restaurants. The home is graced with a rich and tasteful decor and comfortable beds for a relaxing stay. The fully stocked kitchen with new appliances and utensils is perfect for cooking. The home is truly pet-friendly and conveniently located for playtime with your dogs. The great room offers ample space for entertainment and relaxation for you and your family.

Family · Kitchen · Wifi

Sweet King Retreat in Downtown Los Olivos

This clean, well-appointed upstairs studio at Casa Rivera is steps from the vibrant Los Olivos wine tasting scene (see the host profile for lots of 5 star reviews of our other "Sweet Queen Retreat" downstairs space on the same property). The 560 sq ft studio has a king size bed and sleeper sofa, two private decks, and a kitchenette with sink and fridge and lots of ways to make coffee. With all the other thoughtful details we are known for as Superhosts, your stay is sure to be memorable.

Kitchen · Family · Outdoor spaces

Luxurious private 2-story cottage w/free parking

Pristine and luxurious, the Grand Chalet is just steps from the downtown promenade—home to 30+ tasting rooms, restaurants, galleries, and boutiques. Located in the heart of the Santa Ynez Valley, it’s the perfect getaway for wine tasting, epicurean dining, horseback riding, hot air balloon rides, hiking, and cycling. By booking this stay, you agree to our house rules and policies, which outline simple guidelines to ensure a comfortable and respectful experience for all.

Family · Kitchen · Bathroom

Wine cellar House

Welcome to Bodega House, a restored 1920s farmhouse in the center of Los Alamos. The home features a serene queen bedroom and a separate lounge space, along with a sleeper sofa in the living area. Thoughtfully designed for two adults, the house can also comfortably host one to two children on the sleeper sofa. It’s an ideal setting for couples or small families seeking the ease and privacy of a home while being just steps away from the best of Los Alamos.

Family · Indoor spaces · Hospitality

Long Canyon Studios Nordic Hot Tub Spa Fire Pit

Long Canyon Studios - BRAND NEW NORDIC HOT TUB SPA - FIRE PIT W/ ADIRONDACK CHAIRS and BBQ. Sunrises and Sunsets - 360 Degree Endless Views and only 10 minutes to the towns of Los Olivos and Santa Ynez Gorgeous newly renovated private 1100 Square Foot 2 bedroom Mid-Century Mediterranean Adobe curated home with stunning views. Private Home on 12 Acre Property surrounded by endless views of Rolling Hills, Vineyards, Oak Trees and many Farm Animals!

Kitchen · Indoor spaces · Pets

Guesthouse in Ballard

Enjoy the serenity of Ballard in this charming neighborhood. A quiet respite from the hustle & bustle in a beautiful setting. Our home was built around 1911 & recently restored, keeping its original character in tact. A short walk to the delicious Bob's Well Bread & the Ballard Inn Restaurant. Not to mention down the road from wine tasting, delicious restaurants & shopping. Come relax & enjoy this beautiful home & great location as much as we do.

Family · Kitchen · Condition

Hillside Cottage with a View

Nestled in the quaint Santa Ynez Valley. See what our guests have to say.... ***Between the amazing sunrise, the friendly family (dog and owners!), and the wonderfully comfortable decor, this little studio is the perfect "home base" for a weekend in the area. So enjoyed being out of town, but so close to everything! Our only regret is we did not have longer to stay. ***What a wonderful studio that offers beautiful views of the mountains.

Family · Indoor spaces · Air conditioning

Los Olivos Wine Country Getaway

Wine Country living at its best! We enjoy our wine country life and would like to share it with you. Our two-bedroom, two-bath cottage has our CCOF certified organic Syrah vines as a backyard and its own private bocce ball court. Enjoy the setting of our vineyard right out the french doors or from the upstairs deck. A short stroll or ride on our complimentary bikes will take you to the heart of the historic charming town of Los Olivos.

Indoor spaces · Kitchen · View