Family-friendly holiday rentals in Los Olivos

Walk to Wine Country from Floribunda Garden

We offer a peaceful respite from everyday life. Park your car for the weekend, and enjoy yourself. The bed is big and luscious. The bathroom is ample. There's a private dressing area, a zoom room, a courtyard for dining, and an additional dedicated seating area in a sun-spangled exotic garden. We are in walking distance from 47 wine tasting rooms, 5 good restaurants, and 2 vineyards. FYI: We use unscented cleaning products and the suite is always pet-free ( our sensitive guests need to know).

Kitchen · Family · TV

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!

Kitchen · Indoor spaces · Walkability

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!

Indoor spaces · Family · Parking

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.

Family · Kitchen · Checkout

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.

Kitchen · Family · Accuracy

Heated pool, hot tub, arcade, walk to town

Welcome to Seven Palms in Los Alamos, CA! This 3BR/3 full bath urban wine country retreat offers space to relax and play. Enjoy the year-round heated pool (82°), hot tub, bocce, horseshoes, and gas fire pit for s’mores with the kids. Fill your days lounging poolside, unwinding with happy hour in the Adirondacks and strolling into town (10 min walk) to the famous Bob’s Bakery for fresh croissants and espresso or try one of the many restaurants or tasting rooms. You may never want to leave!

Kitchen · Indoor spaces · Comfort

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 · Getting around

Hilltop Vineyard and Agave Field with View

Keep it simple at this peaceful and centrally-located home. Set on an established winery estate in the Santa Ynez Valley, Casa de Azul y Oro is a stunning recently remodeled 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 kitchen with essentials, or dine out at the many wonderful restaurants in the area and bring back and star gaze.

Family · Kitchen · Heating

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.

Indoor spaces · Kitchen · Nearby

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.

Kitchen · Indoor spaces · Laundry

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 · Family · 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.

Indoor spaces · Kitchen · Pets