Family-friendly holiday rentals in Ashland

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Ashland

Total holiday rentals
Explore 40 holiday rentals in Ashland
Verified guest reviews
Over 1,590 verified reviews to help you choose
Pet-friendly accommodation
Find 10 rentals that welcome pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wi-Fi availability
40 of Ashland holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Ashland rentals
4.7 Average rating
Ashland stays receive an average rating of 4.7 out of 5 from guests

Top-rated family-friendly rentals in Ashland

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

A modern kitchen features high-end stainless steel appliances and a spacious island with slick bar stool seating. The well-lit area is complemented by contemporary pendant lights. Double french doors open to a backyard, enhancing the connection between indoor and outdoor living.

Home in Castro Valley

4.95 out of 5 average rating, 150 reviews

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!

KitchenFamilyNearby

Guest favourite

The exterior of the charming single-unit showcases a light-colored facade with a sloping roof. A white picket fence frames the entrance, where a small garden of pink roses and greenery adds a touch of color. The sky above is bright with wispy clouds.

Apartment in San Leandro

4.83 out of 5 average rating, 114 reviews

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!

KitchenFamilyGetting around

Guest favourite

A modern living area features a dark sectional sofa and a glass-topped coffee table. A small dining table with two chairs is located beside a window. Decorative wall art is displayed above the furniture, and a portable air conditioner is positioned in a corner.

Guest suite in San Lorenzo

4.95 out of 5 average rating, 211 reviews

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.

KitchenFamilyBackyard

Top Guest favourite

Guest suite in San Lorenzo

4.97 out of 5 average rating, 388 reviews

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.

FamilyKitchenSleep quality

Guest favourite

A cozy studio interior features a spacious bed with a light-colored blanket and a soft grey tufted bench. A smart TV is mounted on the wall, and a kitchenette area with essential appliances is visible in the background. Natural light filters through blinds enhancing the warm ambiance.

Guesthouse in Hayward

4.81 out of 5 average rating, 141 reviews

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.

FamilyIndoor spacesBathroom

Guest favourite

A bright studio space features a king-size bed with soft blue accents, near a window that allows natural light to fill the room. A small dining table sits adjacent to the bed, and a wall-mounted TV is positioned above. Decorative artwork adds a touch of color.

Guest suite in Castro Valley

4.93 out of 5 average rating, 174 reviews

Cozy in Law Studio - Castro Valley

Cozy and centrally-located studio. It is a 300 Sq. Ft In law Studio with its own entrance. Fast Smart Lock self check-in. Very Safe Neighborhood close to all the bay area has to offer. The bedroom has a king size bed. You will have the basics in the kitchen, and bathroom. Plenty Street parking, and fast WiFi. 4 min walking distance to local cafe. 7 min drive to Eden Medical Center 5 min drive to Bart 35 min to San Francisco or San Jose! 15 min to Oakland airport

Indoor spacesKitchenAccess

Guest favourite

Guest suite in Hayward

4.94 out of 5 average rating, 263 reviews

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.

KitchenFamilyOutdoor spaces

Guest favourite

A private hot tub is shown in the foreground, with soft bubbles visible on the surface. In the background, a modern cabin facade features large glass doors reflecting warm sunset hues, framed by a wooden deck with seating.

Cabin in Oakland

4.94 out of 5 average rating, 398 reviews

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.

FamilyIndoor spacesQuiet

Guest favourite

An open living space features dark tiled flooring and natural wood cabinets in the kitchen area. A round dining table with four chairs is positioned near a flat-screen TV. Two bedrooms can be seen through two doors, providing a layout that emphasizes accessibility.

Guesthouse in San Lorenzo

4.9 out of 5 average rating, 183 reviews

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

Indoor spacesFamilyTV

Top Guest favourite

A bright living area features a comfortable gray sectional sofa and a stylish armchair, surrounded by natural light from large windows. A decorative electric fireplace is positioned below a wall-mounted TV, with two patterned chairs and a small end table completing the space.

Home in Castro Valley

4.98 out of 5 average rating, 225 reviews

Cheerful 2-bedroom near San Francisco &FW580/238AC

Welcome to Tom & Melissa's a cheerful 2-bedroom 1-bath in a single family house, It is a spacious 1016 sq feet house. Centrally located in the East Bay, and very close to freeway 580 and 238! You're within 30 minutes of San Francisco or 40 minutes of San Jose. Enjoy this spacious residential home with a large private patio, two separate bedrooms, a bright and comfortable living space, and a kitchen, making it a great place for family or couples.

KitchenFamilyLocation

Guest favourite

A modern living area features a gray sofa positioned across from a large wall-mounted smart TV. A glass coffee table sits in the center, while light wood flooring complements the neutral color scheme. A dining area is visible in the background.

Home in San Lorenzo

4.78 out of 5 average rating, 212 reviews

15A-Modern & Cheerful Comfy 3B2B Front Unit

This is a modern and stylist, newly remodeled 3-bedroom 2-bath front unit of a single family house, with full kitchen and shared free laundry. - 2 mins drive to stores & restaurants (Walmart, Target, Grocery Outlet) - 3 mins drive to Bayfair BART station - 15 mins drive to Oakland Airport - 25-min drive to San Francisco Our place is perfect for a big group of up to 6 guests who want a private relaxing stay and want to explore the Bay Area.

FamilyIndoor spacesWalkability

Top Guest favourite

A wooden staircase leads upward through a landscaped yard, flanked by palm trees and vibrant vegetation. A stone pathway connects various garden elements. In the background, a koi pond is visible, while a decorative lantern stands at the base of the stairs.

Guesthouse in San Leandro

4.93 out of 5 average rating, 164 reviews

Charming Backyard Guest House with Koi Pond

Charming and cozy, this cottage has beautiful back yard with koi pond and bridge is ideal for both weekend getaways as well as longer stays. Centrally located in the bay area, clean, modern accommodation. Only 3 miles from Bart, 10 miles from OAK and 30 miles from SFO. Relax in your own room in a completely updated home.

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