
Family-friendly holiday 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.

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!

Private and serene studio with full kitchen
Lovely studio is light and bright with a vaulted ceiling and sky light, and the property is in a country setting. It is close to hiking trails, Redwood Canyon Golf Course, Lake Chabot, shopping and restaurants, Bart, and easy access to the freeway. The outside view is a meadow, hiking trail, and rolling hills. The studio has a full kitchen so if you decide to cook, we have all the tools you’d need for you to prepare a meal. We’d love to host you for stays of two days up to 28 days at a time.

★COZY & Unique Guest Suite★ (Wifi, Netflix & MORE)
Located in the “Heart of the Bay” is our cozy & private guest suite (SUITE A). Just a 5 minute drive to downtown Hayward & BART, 20 minutes from Oakland International Airport and 35 minutes from SFO. You'll have ONE dedicated parking space on our driveway for your vehicle & SEPARATE entrance. Complimentary coffee, tea, and snacks provided. Perfect for couples or professionals coming to CA for an extended stay. Enjoy the Bay Area's beauty and excitement from your stay in the middle of it all!

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.

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.

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)

Guesthouse Garden Retreat
Our 'sister guesthouses' consist of two small side-by-side cabins (you get both) located behind our home, nestled in a verdant hillside garden that our friends and family lovingly call ‘Little Tuscany’. Cabin 1 - living room with a well-stocked kitchenette, pull-out couch, table and chairs Cabin 2 - bedroom with a queen-size bed, full bathroom and a private deck Accessed by a private entrance, the cabins are luminous and efficient, designed to meet all your needs.

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.

10% off for Weekly Stay Studio in Downtown
Welcome to our cozy and newly remodeled studio in Downtown San Leandro. It offers 1 queen bed & 1 futon sofa bed, modern kitchenette and washer & dryer in unit. Located in downtown San Leandro, offers easy access to bart, I-880 & I-580. Secured gated lot. Our team is dedicated to making your experience memorable, and we are available to assist you with any inquiries.

Cozy Bungalow near Bart to SF, SJ, & Hwy 238 & 580
Welcome to this charming Bungalow 2-bedroom 1-bath single family home that offers you a fully equipped nice stay with comfort in the neighborhood of Castro Valley, conveniently commute to many central locations, and minutes to Bart station to S.F., S.J., Oakland, and other destinations. (Station map and location details available inside the house).

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.
Popular amenities for Ashland family-friendly rentals
Family-friendly home rentals with a hot tub

Pool, Jacuzzi, Sauna, Huge Views, gated, ADU

Country Cottage w private parking & Rose Garden

Garden Oasis Suite with Spa and Pool, Walnut Creek

Traditional Japanese Tea House

Tropical Garden Cottage +HOT TUB &POOL by Downtown

Pool, Hot tub, Sauna I Your Silicon Valley Luxury

Secret Garden Cottage

Sunset Spa Suite w/private patio, views & parking
Family- and pet-friendly home rentals

New, Secluded Tiny Home on a creek with a fire pit

Beautiful private 1 bedroom apartment w/ Bay views

Modern newly built Spaceroom

Beautiful sweet retreat

Cozy & Chic Farmhouse Studio: Walk to Lake Merritt

The not so tiny, tiny house (with private laundry)

SkyHigh Redwoods Retreat with Bay Views

Step back in time on this beautiful classic yacht
Family-friendly home rentals with a pool

Lakeside Retreat (w/ private parking)

Delightful Tiny Home in the Redwoods !

Romantic Mtn Studio - Pool, Sauna, Views!

Rustic Cabin in the Redwoods

Private Queen Suite-Pool & Hot Tub, private entry

Cozy BUS on Farm Animal Rescue with CITY VIEW

3 BR Home on Vineyard nr Palo Alto & Stanford

Private Oasis Btwn SF, Napa. Big Views + Pool!
When is the best time to visit Ashland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $226 NZD | $215 NZD | $213 NZD | $219 NZD | $238 NZD | $249 NZD | $267 NZD | $260 NZD | $222 NZD | $242 NZD | $231 NZD | $244 NZD |
| Avg. temp | 11°C | 12°C | 13°C | 15°C | 16°C | 18°C | 19°C | 20°C | 20°C | 18°C | 13°C | 11°C |
Quick stats about holiday rentals that are family-friendly in Ashland

Total holiday rentals
Explore 40 holiday rentals in Ashland

Nightly prices starting at
Ashland holiday rentals start at $142 NZD per night before taxes and fees

Verified guest reviews
Over 1,210 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, Wi-Fi and Pool across Ashland rentals

4.6 Average rating
Ashland stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
- Northern California Holiday rentals
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- Golden Gate Park
- Stanford University
- Oracle Park
- Muir Woods National Monument
- Twin Peaks
- Alcatraz Island
- Golden Gate Bridge
- SAP Center
- Mission Dolores Park
- Bolinas Beach
- Montara State Beach
- Henry Cowell Redwoods State Park
- Davenport Beach
- Pier 39
- Six Flags Discovery Kingdom
- Pescadero State Beach
- Palace of Fine Arts'`
- California’S Great America
- Winchester Mystery House
- Rodeo Beach
- Painted Ladies
- San Francisco Zoo
- Santa Maria Beach
- Half Moon Bay State Beach




