Family-friendly holiday rentals in Ashland

The Blue Door Retreat

This hotel-like home has been professionally renovated and designed to maximize the comfort, convenience and enjoyment of your stay. The kitchen has a huge WOW factor w/ stainless high-end appliances, fully stocked, ideal for cooking, entertaining, or baking. Indoor/outdoor living w/ double french doors that both open up to the beautiful backyard space complete with patio furniture, BBQ and firetable, ideal for enjoying our amazing CA weather. Smart TV's in every room for those Netflix nights!

15min walk to Bart/New remodel/Private entrance

Private access to the entire guest suite. Front door parking for 1 vehicle. Nice, quiet, peaceful, children friendly, convenient and centrally-located place. The unit is brand new remodel, washer and dryer in the unit! Walking distance to public transportation, including BART train, within 15mins to OAk, within 30mins to SFO. Major car rental is nearby. - queen size bed - twin size bed - computer desk - independent Central AC/ Heating - Full kitchen & eating utensils - Fast wifi

570 - Cozy & Comfortable 1B1B guesthouse w/parking

This is a newly remodeled adjacent unit of a single family house. It has a Queen bedroom, a nice living room with portable AC, a futon, smart TV, fridge, airfryer, microwave, coffee, basic utensils - 3 mins drive to Bayfair BART station - 15 mins drive to Oakland Airport - 25-min drive to San Francisco - Min away to Hwy 880, 238 & 580 -Mins walk to Walmart, Starbucks, Grocery outlet, restaurants and many more. Our place is perfect for 1-2 guests who want a private relaxing stay.

Adorable Private Garden Studio

Centrally located, cozy, fully furnished studio with all of the amenities needed for a relaxing stay! Just bring your luggage! Conveniently located in a Hayward garden oasis near freeways leading to San Francisco, San Jose, and Palo Alto. You will be pleasantly surprised once you enter the property by how well hidden this gem is away from the busy bustle of Hayward. Enjoy your morning coffee in the sunny courtyard or perhaps share a glass of wine by the fire-pit in the evening.

East Bay Cozy Cottage

Your lovely cottage is ready and perfectly located to explore the Bay Area or catch a flight in or out. This peaceful space has a plush, comfy queen size bed and a fold down sofa-futon (best utilized for a child or teenager). There is a well-stocked kitchenette. BBQ grill too. We are conveniently located near the two main highways linking all East Bay destinations. Oakland's Oracle Arena (15 min), Jack London Sqr (25 min), San Francisco-downtown (40 min), Lake Chabot (10 min)

Spacious 3BR Home Near San Francisco

Spacious 3-Bedroom Home Near San Francisco Welcome to our comfortable 3-bedroom, 2-bath home in Castro Valley, ideal for families visits, business travelers, tech professionals, traveling nurses and extended stays. This 1,300 sq ft home features central A/C, fast WiFi, a fully equipped kitchen and comfortable beds. Located in a quiet, safe neighborhood. We maintain a peaceful, respectful environment. Parties, events, loud music, smoking, and drug use are not permitted.

Private Guest Suites | Fast Wifi & Parking

Enjoy a comfortable and private guest suite perfect for business travelers, couples, or anyone visiting the Bay Area. The space is clean, quiet, and thoughtfully set up so you can relax, work, or explore with ease. The suite features a private entrance, cozy sleeping area, comfortable living space, and convenient amenities to make your stay feel like home. Whether you’re here for work or a quick getaway, you’ll have everything you need for a smooth and restful stay.

Hike-in Bay Views Cabin w HotTub

Hike up to a well designed, small-but-mighty modern cabin with fast WiFi, your own hot tub and a panoramic view spanning across the bay from the Golden Gate to the San Mateo bridge. 108 stairs lead up to the Aerie, so if you don’t want to get your steps in, this is probably not the space for you! 15 min from OAK and city life, but a world away. Sunsets are glorious here. The Aerie is a special spot just for 1 or 2, so leave the posse behind. Registered guests only.

Tiny Casita/Studio | Near Oakland, SF & SJ

Welcome to our <b>Cozy Casita Studio</b> ✨ This charming casita-style studio is a peaceful stay for up to two guests. Enjoy a private entrance, queen bed, kitchenette with mini fridge and microwave, and a full bathroom with standing shower. 🐾 Pet-friendly! The casita is fully private but attached to our home, so occasional household sounds may be heard. Conveniently located minutes from San Francisco, Oakland Airport, and just 30 minutes from San Jose Airport.

Peaceful Retreat w/ Views + Gated Parking

This romantic retreat is perched on a sunny ridge with sweeping views of the bay, surrounding hills, and spectacular sunsets. Farm vibes with California natives, fruit trees, redwoods, and outdoor space to enjoy. No shared walls, behind our family home inside a secure gate with door-side parking. Super quiet in a safe, residential neighborhood. Convenient to everything in the Bay. Perfect home base for visiting family, work trips and extended stays.

16017-Private 2BR Guest Unit near HWY, BART & Mall

This is a detached 2-bedroom 1-bath guest unit with full kitchen and laundry at the back of my house. It has a private entrance which is accessed from our driveway and backyard. It is conveniently located near freeway 580, 880 and 238, and Bay Fair Bart Station. It's also close to Costco, Walmart, Target and many restaurants and shops, as well as everything you need. It is 13-min drive to Oakland Airport, 16 mins to Coliseum, 30 mins to Downtown SF.

2BR ｜King Bed ｜Exclusive Parking｜Walk to Grocery

Welcome to our newly renovated 2BR, 1BA unit in San Leandro. Enjoy a cozy King-size bed in one room and a comfortable Queen-size bed in the other. Minutes from Oakland Airport, with a nearby BART station, supermarkets, and a shopping plaza. Relax in the bright living room and make use of the fully equipped kitchen. Perfect for a family or friends’ getaway. Book now for a memorable stay!