Family-friendly vacation rentals in Ashland

Find and book unique family-friendly homes on Airbnb

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 favorite

Cabin in Oakland

4.97 out of 5 average rating, 185 reviews

Spa style cottage! Jacuzzi, Sauna, Pool, Views!

POOL HEATED MAY 1st! Stunning, detached cottage w/ higher end finishes. Endless views of mountains set on beautiful, peaceful, upscale property. Very close to regional parks for hiking. Quiet & set amongst over an acre of land with redwood, pine, & oak trees. Pool heated 81F May 1st-October 31st. 16 miles to San Francisco, 5-10 minutes to many restaurants. New Jacuzzi and outdoor sauna. Large patio, pool / deck (4000 sq ft) is shared with main house (small family of 4). Secured driveway gate.

Nov 18 – 25

G$50,597 GYD per night

Guest favorite

Cabin in Oakland

4.91 out of 5 average rating, 173 reviews

Hike-in Bay Views Cabin w HotTub

Hike up to an amazing view and a well designed, small-but-mighty modern cabin with fast WiFi, your own hot tub and BBQ. A panoramic view spans across the bay from the Golden Gate to the San Mateo bridge. Sunsets are glorious here. 15 min from OAK and city life, but a world away. 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! The Aerie is a special spot just for one or two, so leave the posse behind. Registered guests only.

Aug 1 – 8

G$46,298 GYD per night

Superhost

Guesthouse in Oakland

4.85 out of 5 average rating, 250 reviews

Beautiful Modern ADU Apt With Private Entrance

Beautiful modern home, quiet, peaceful & has beautiful views of the trees and hillside. You’ll love my place because of the large king size bed, large open spaces & private balcony. My place is perfect for everyone whether on vacation or business. You will have your own private entrance to the first fl. of the apartment, full bathroom, private balcony, large open kitchen & large living room, w/ NO shared spaces. Oakland Airport (10 min) & BART are few miles away w/ freeway access close by.

Jul 2 – 9

G$24,261 GYD per night

Guest favorite

Home in Alameda

4.93 out of 5 average rating, 267 reviews

“Alameda Island Hideaway”- Clean, Safe, Modern

Welcome to our Airbnb in the heart of the San Fransisco Bay! Located on the beautiful island of Alameda! “ALAMEDA ISLAND HIDEAWAY” -Spacious, Private, Quiet and Safe -Fully Renovated, Tastefully Decorated Duplex -Non-smoking -2 Bedroom, 1.5 Bath -Pull out Sofa for an extra (5th) person -Fully enclosed backyard patio with BBQ -In-Suite Laundry -Convenient location for business & holiday guests -Central to SF, Napa, and other Bay Area attractions -Crib & high chair available upon request

May 31 – Jun 7

G$26,420 GYD per night

Guest favorite

Guesthouse in Oakland

4.98 out of 5 average rating, 160 reviews

The Redwood Retreat

Near Lake Temescal, Redwd Regional Prk, Bart, Hwy 13, Rockridge,Montclair, Dwntwn. We completely remodeled our guest house with a focus on short term tenants. Lots of storage within one of the most quite settings you will find. We made a thoughtful attempt to load the unit with everything u might need while away. The kitchen is functional to the point that you could actually cook a Thanksgiving dinner, multiple frying pans to crock pots a blender or chefs knives. Bathroom sundries abound!

Jul 15 – 22

G$26,664 GYD per night

Guest favorite

Guesthouse in Alameda

4.94 out of 5 average rating, 178 reviews

Cute, backyard Cottage close to All!

Great space for a lovely trip to the Bay Area! Located in a very safe & quiet neighborhood of Alameda. The cottage has a private bathroom with shower (no tub), a kitchenette with microwave, and the most comfortable queen bed. Close to Oakland Coliseum, BART, SF, Oakland Airport, and ferry to SF. Great access to Bay Farm Trail and just a short walk to restaurants and shopping. ** Please note that the bed is against the wall, so if you are a group of two, one person will be against the wall.

Oct 5 – 12

G$24,850 GYD per night

Guest favorite

Guest suite in Lafayette

4.97 out of 5 average rating, 877 reviews

Mt. Diablo view 2 Bedroom/ King & Queen Suite

Our private 2 bedroom suite with amazing views of Mt. Diablo is located in a suburb of San Francisco and Berkeley called Lafayette in the East Bay. We neighbor Walnut Creek and are close to Hwys. 24/680. We are a 5-8 minute drive to the Lafayette BART station. San Francisco is a 25 minute train ride and when there is no traffic a quick 30 minute drive to downtown SF (with traffic add another 15-20 minutes). CAL or St. Mary's College bound? We are about 15-20 minutes away.

Oct 2 – 9

G$24,149 GYD per night

Guest favorite

Guesthouse in Oakland

4.96 out of 5 average rating, 182 reviews

Charming Cozy Cottage in Eco-Garden Oasis

Our charming cottage is a relaxing retreat in the city! Our sweet cabin is small and cozy set in an expansive garden oasis. We offer a unique experience for those interested in a beautiful and tranquil escape in the heart of city. The cottage is at the back of our large garden with views of our beautiful urban farm with a pond with croaking frogs, chickens and goats! Couples and families with up to 2 children are best suited for this space. No more than 2 adults please.

Sep 30 – Oct 7

G$21,205 GYD per night

Guest favorite

Guesthouse in Oakland

4.98 out of 5 average rating, 429 reviews

Garden cottage in convenient Oakland location.

You’ll love my place because of the good location, convenience to public transport, the friendly neighborhood, the ambiance.. My place is good for couples, solo adventurers, business travelers, and families (with kids). Although there is just one bedroom, the couch folds down for extra sleeping space. Please be aware that the property is in a hilly area and that there are stairs to navigate which can be challenging if you have large luggage or mobility issues.

Nov 22 – 29

G$16,368 GYD per night

Guest favorite

Home in Oakland

4.98 out of 5 average rating, 534 reviews

Private Casita with Stunning View

Relax in a private, fully equipped Casita with stunning views of East Oakland and the Bay. This newly constructed one-bedroom guest house in the quiet Eastmont Hills neighborhood has everything you need to work and play. Enjoy lounging in a hammock on the deck or on the couch streaming movies to a 32" television. Brand new stainless steel gas range and full-sized fridge make cooking a breeze, or you can partake in booming Oakland's restaurant scene.

Nov 29 – Dec 6

G$17,104 GYD per night

Guest favorite

Guesthouse in Oakland

4.96 out of 5 average rating, 490 reviews

Lakeshore Cottage

Our quiet studio cottage is located in the Lakeshore/Grand Ave area of Oakland. The neighborhood is safe and beautiful and the cottage is neat and easily accessible. There is a large bright main room and a spacious bathroom that was recently updated. The cottage includes a mini kitchen. The location is close to downtown Oakland, Berkeley and San Francisco.

Sep 2 – 9

G$20,763 GYD per night

Guest favorite

Guesthouse in San Leandro

4.92 out of 5 average rating, 118 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.

Oct 12 – 19

G$27,100 GYD per night