
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.

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.

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.

Charming Redwood Heights Garden Studio
Private studio in a family home with separate entrance and dedicated parking spot. We are located in the Redwood Heights neighborhood of Oakland California with easy access to freeways, shopping, sights, and restaurants. This is the perfect home base for national and inter-national travelers visiting the Bay Area. The studio has a small kitchenette, bathroom, and a comfortable queen size bed. There’s a flatscreen TV , wifi, and a shared garden patio right outside the door.

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.

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.

STAR WARS: Cozy, Kid & Pet Friendly, Private Entry
Welcome to San Francisco! Star Wars fans, enjoy our newly remodeled, galaxy-themed space. Located in San Leandro, perfectly between SF and Silicon Valley, with easy access to BART and a shopping mall. Kids love the ball pit! Well-behaved dogs are welcome for a $100 pet fee, so enjoy a cozy stay with your furry friend.

A Home Away From Home
You can just grab your bag and come to stay in my place just feel like home. A cozy, relax and private place in a blind alley with well-stocked amenities. It’s located near 3 busy HWY 880,238 & 580. And also close to the Bayfair BART station, SF International airport, SF Downtown, Oakland airport, & Coliseum.
Popular amenities for Ashland family-friendly rentals
Family-friendly home rentals with a hot tub

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

Modern Designer Home w Hot Tub - Villa Pearl

Traditional Japanese Tea House

Tropical Garden Cottage +HOT TUB &POOL by Downtown

Relax and Rejuvenate. Cave Spa, Incredible Views

Garden Oasis Studio with Spa and Pool Walnut Creek

Secret Garden Cottage

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

Beautiful private 1 bedroom apartment w/ Bay views

Cozy & Chic Farmhouse Studio: Walk to Lake Merritt

Caboose in the redwoods just outside of Cupertino

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

Private cottage in a garden

SkyHigh Redwoods Retreat with Bay Views

Step back in time on this beautiful classic yacht

New convenient comfortable studio
Family-friendly home rentals with a pool

Lakeside Retreat (w/ private parking)

Delightful Tiny Home in the Redwoods !

Rustic Cabin in the Redwoods

Mountaintop poolside suite, sauna, views!

Private Queen Suite-Pool & Hot Tub, private entry

Cozy BUS on Farm Animal Rescue with CITY VIEW

Pool, Hot tub, Sauna I Your Silicon Valley Luxury

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 | $178 CAD | $170 CAD | $168 CAD | $173 CAD | $188 CAD | $196 CAD | $187 CAD | $184 CAD | $180 CAD | $191 CAD | $182 CAD | $192 CAD |
| 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 vacation rentals that are family-friendly in Ashland

Total vacation rentals
Explore 40 vacation rentals in Ashland

Nightly prices starting at
Ashland vacation rentals start at $112 CAD per night before taxes and fees

Verified guest reviews
Over 1,210 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
40 of Ashland vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Ashland rentals

4.6 Average rating
Ashland stays receive an average rating of 4.6 out of 5 from guests
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