Holiday rentals in Ashland

★UNIQUE STAY in the middle of the BAY★ Wifi+MORE!

Comfortable in-law suite located in the “Heart of the Bay.” Just a 5-minute drive to downtown Hayward and BART, 25 min. from OAK Airport, and 35 min. from SFO Airport. In-N-Out, Sprouts, Raising Cane’s, Starbucks and much more are conveniently located just 4 minutes away. Our space is ideal for couples, travelers, and guests looking for a well-located home base. Enjoy easy access to nearby cities, dining, transportation, and experience the Bay Area’s energy and diversity from a central location.

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!

Modern 2 bedroom with stunning bay views

Kick back and relax in this calm, stylish space. The Oakland Hills are filled with amazing hiking, this location is great for day trips to Napa (35 miles), San Francisco (11 miles) or Carmel (120 m). Centrally located for work or play. This open concept 2 bedroom is a peaceful break away. Given the open concept design - there is not a lot of privacy between bedrooms, just a big bookcase room divider b/w the rooms. There are a few sitting area's outside and a green roof too! And EV charging.

15B - Cozy & Comfortable 1B1B Back Unit

This is a newly remodeled back unit of a single family house. It has a Queen bedroom, a nice dining/resting room with smart TV (no local channels), air fryer, fridge, coffee basic utensils, and free laundry. - 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.

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

***UPDATE: Just finished a full kitchen renovation May 2026, fresh cabinets, new countertops. We think you'll love it! Welcome to our lovely 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, BART, supermarkets, and 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!

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.

Tiny Casita/Studio | Near Oakland, SF & SJ

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

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.

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.