Family-friendly vacation rentals in Ashland

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Ashland family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
Guest suite in Mission District
4.98 out of 5 average rating, 256 reviews

Mission Private 1BR/BA Garden Suite Separate Entry

SamRating, 5 stars2 weeks ago
amazing place to stay for a visit to the Bay Area. the backyard is a beautiful secluded Oasis with its own private hot tub. easily walk to the number of spots in the Mission District and Bernal Heights for some outdoor fun. they have a picnic basket packed up with all the supplies you would need so I highly recommend taking that over to Dolores Park on a sunny day to enjoy one of the best views in the city. also highly recommend looking through their recommendation book before hitting the town so you can get an idea of some cool spots to check out. I would 100% stay here again on another trip to San Francisco
Guest favorite
Home in Half Moon Bay
4.9 out of 5 average rating, 106 reviews

TreeTops OceanView Retreat_HotTub_Month/LongTermOk

KathrynRating, 5 stars5 months ago
Had a lovely stay at Annette and Fred’s place - the location was great, the house was fully stocked and the hosts were extremely responsive when we had questions. Having a hot tub and gas fireplaces were an added bonus for spending the evenings admiring the views.
Superhost
Apartment in Muir Beach
4.89 out of 5 average rating, 255 reviews

Amazing Welcoming Unique Ocean Home

MarianneRating, 5 stars2 weeks ago
Yeshi's home is a museum of colorful artwork from her travels around the world. Wonderful to be lulled to sleep by the ocean waves.
Guest favorite
Home in North Oakland
4.84 out of 5 average rating, 284 reviews

Lovely Cottage garden oasis w/Hot Tub near BART 🌹

KeaoRating, 5 stars4 months ago
Quiet, peaceful, beautiful garden, responsive host, ample street parking. Definitely worth the price. Plus there's a hot tub you can use after the end of a long day or before the start of one like how we used. MINUTES away from bars, restaurants, and shopping in Oakland. Great location. Thank you so much for the comfortable stay!
Superhost
Guesthouse in North Berkeley
4.84 out of 5 average rating, 1,341 reviews

Traditional Japanese Tea House

SamanthaRating, 5 stars3 days ago
We had a quiet one night stay in this relaxing backyard tea house. Love North Berkeley and it was so nice to walk to our anniversary dinner at Chez Panisse.
Guest favorite
Home in Redwood City
4.97 out of 5 average rating, 297 reviews

Private suite

StaceyRating, 5 stars10 months ago
Felt like it was just lke my home accept they have a hot tub that I used almost every night during my stay also had a beautiful garden. Is very quiet and relaxing.
Guest favorite
Apartment in Mission District
4.97 out of 5 average rating, 199 reviews

Grand 1868 Victorian, Family-Friendly w/ Hot Tub

AndiRating, 5 stars1 day ago
Had a lovely stay with extended family, including 5 adults and 2 young toddlers. It was plenty spacious and very comfortable for the whole group. The location was very convenient, walking distance from great restaurants, coffee shops, and playgrounds for the kids, and just a short drive from any other sights we wanted to see. We enjoyed the fully equipped kitchen, beautiful backyard to hang out and relax in, and charming interior decor. Would not hesitate to book again!
Guest favorite
Home in Burlingame
4.97 out of 5 average rating, 165 reviews

SFO Panoramic Views 4BR/3BA near SF-Silicon Valley

EduilRating, 5 stars2 weeks ago
My family and I really enjoyed our stay. The place was exactly as described and shown in the pictures. The views, however, must be experienced firsthand. Definitely recommend!

Family- and pet-friendly home rentals

Guest favorite
Apartment in Oakland
4.87 out of 5 average rating, 279 reviews

Montclair Retreat-quiet, elevator, in unit laundry

HeatherRating, 5 stars9 months ago
Dennis & Tiiu's place was perfect for our needs. We stayed for a week while in town visiting our son, who lives only a few minutes away, so it was a perfect location for us. The location was peaceful and quite. The house was cozy and suitable for two people. It was a little smaller than it looked in the pictures but again, it worked for the two of us. The amenities were as described. We would definitely stay again.
Top guest favorite
Apartment in North Oakland
4.96 out of 5 average rating, 508 reviews

Boutique Garden Apartment-Temescal

KeelyRating, 5 stars3 weeks ago
Urban oasis is the perfect description for this residence. So quiet. Restful, verdant backyard patio (blooming Angel Trumpets were heavenly scented!), sweet dogs and comfortable and attractive furnishings. Was able to cook my breakfast every morning and easily heat up leftovers with well-outfitted kitchen and high-end appliances. Loved how eco-friendly the home is. Murphy bed in the living room was perfect. Walkable restaurants nearby - esp. Homeroom's mac & cheese! Loved everything about this place. We will definitely stay here again when visiting relatives nearby.
Top guest favorite
Home in Alameda
4.92 out of 5 average rating, 499 reviews

Historic Alameda Home Near Beach

NicoleRating, 5 stars2 weeks ago
Beautiful, well maintained historic home in a convenient location within alameda. There are plenty of coffee shops and restaurants that are walking distance. We came with our dog and 6 week old baby and felt perfectly comfortable. We’d love to stay here again!
Guest favorite
Guesthouse in Sunnyvale
4.96 out of 5 average rating, 429 reviews

Private cottage in a garden

SukuntheaRating, 5 stars1 month ago
Was a great option for close proximity to the Google campus which is where we needed to be. Neighborhood seemed to be safe and walkable. It’s evident they are very involved with the beautiful landscaping and gardening on/around the property therefore notable tree pollen/allergens during the spring time. Overall a cute, cozy, and darling stay!
Guest favorite
Apartment in Rockridge
4.87 out of 5 average rating, 211 reviews

Bright, spacious Rockridge studio with views

DeniseRating, 5 stars1 week ago
Cindy's place was perfect. Easy location and everything was as she described. She's a gracious host, and I'd stay at her place again.
Guest favorite
Guest suite in Woodside
4.88 out of 5 average rating, 385 reviews

Stay Nestled in Ancient Redwoods in Silicon Valley

SinjinRating, 5 stars1 week ago
My wife and I had a wonderful stay at Rick and Heather’s place at woodside. The place is quite spacious and quiet. It is just as described and there were no surprises . If you are looking for a peaceful mountain getaway that is within 30 min ride to Palo Alto, look no further. Things to keep in mind (these are clearly described in listing) are: 1. lack of a true kitchen despite having microwave, toaster oven and a hot plate. I do not recommend any cooking here however since there is no real place to wash dishes or drain etc. 2. The owners live there and although u get plenty of privacy you may run into to them occasionally. If this is not your thing, I recommend you find a different place.
Top guest favorite
Guest suite in Berkeley Hills
4.94 out of 5 average rating, 332 reviews

Private Guest Flat in Berkeley Hills Home

KatherineRating, 5 stars2 weeks ago
Cara's place is spacious, clean and welcoming. She has great pillows and comfy beds. We so appreciated the fresh fruit and eggs that she provided, so we didn't have to take time to go out to breakfast before heading to Muir Woods. While I didn't have time to check them out, the Berkeley Rose Garden and some of the Berkeley Paths (which take you by beautiful neighborhood gardens) are within close walking distance.
Guest favorite
Guest suite in San Ramon
4.89 out of 5 average rating, 132 reviews

Cozy suite w/ coffee, workstation, private access

DawnRating, 5 stars4 months ago
Thank you for another great stay at your beautiful place. I definitely will return.

Family-friendly home rentals with a pool

Superhost
Guesthouse in San Rafael
4.84 out of 5 average rating, 167 reviews

Farm in the city & sweeping bayview

HaleyRating, 5 stars3 weeks ago
Our stay at Lori and Mike’s place was absolutely fantastic, and Lori truly made it unforgettable. While Mike was away on a trip, Lori went above and beyond to make sure we had everything we needed—and more. From the moment we arrived, she made us feel so welcome. She was warm, thoughtful, and incredibly attentive without ever being overbearing. It’s clear she genuinely cares about her guests and takes pride in creating a comfortable, personalized experience. She checked in with us just enough to make sure we were all set and shared amazing local tips that really made our trip extra special. Her kindness, attention to detail, and friendly energy made all the difference. We couldn’t have asked for a better host. Thank you so much, Lori—you’re truly one of a kind!
Superhost
Villa in San Rafael
4.89 out of 5 average rating, 208 reviews

Waterfront Marin Retreat with Pool & Hot Tub

SethRating, 5 stars6 days ago
House is In a beautiful spot. Driveway access requires stopping on the side of the main street getting out, punching the code for the gate then making a u turn to get in to the drive way. The house was very open and spacious. Overall the family enjoyed the house.
Guest favorite
Guesthouse in Monte Sereno
4.9 out of 5 average rating, 213 reviews

Greenwood Guest House, a Peaceful Oasis

AnthonyRating, 5 stars6 days ago
I half expected to see Jay Gatsby on the balcony when I pulled in. Instead I found Lou very welcoming. The location is convenient to Santa Cruz and Los Gatos. Very peaceful.
Guest favorite
Guest suite in San Rafael
4.92 out of 5 average rating, 316 reviews

Mountaintop poolside suite, sauna, views!

ReNelleRating, 5 stars1 month ago
This place is increíble! Hosts were friendly and proactive. The pool was heated to a perfect temperature and the view is unbeatable. The recommendations for hikes and restaurants were spot on. My husband and I had an amazing little getaway and we’d recommend this place to anyone looking for a peaceful, gorgeous place to stay!
Guest favorite
Guesthouse in Walnut Creek
4.91 out of 5 average rating, 582 reviews

Tropical Garden Cottage +HOT TUB &POOL by Downtown

JustinRating, 5 stars2 weeks ago
beautiful backyard with hot tub. very quiet area. highly recommended.
Top guest favorite
Home in Portola Valley
4.93 out of 5 average rating, 155 reviews

3 BR Home on Vineyard nr Palo Alto & Stanford

GrahamRating, 5 stars1 week ago
A lovely property to relax in and enjoy. Just what we needed after doing all the sightseeing in the first part of the holiday
Guest favorite
Condo in Mountain View
4.95 out of 5 average rating, 134 reviews

Spacious Top Floor Condo Retreat

KarenaRating, 5 stars1 week ago
During my stay at Joann’s place, I felt safe and very comfortable. The whole home is bright and spotlessly clean, with greenery visible outside the windows. Parking was very convenient, and communication with her was smooth throughout. The kitchen was fully equipped, allowing me to cook and enjoy a good glass of red wine. The sofa was cozy and the bed was spacious. I was pleasantly surprised to find such a wonderful place—thank you!
Superhost
Guest suite in East San Jose
4.86 out of 5 average rating, 733 reviews

Hillside Retreat Private 2-Room Guest Unit & Pool

RavenRating, 5 stars2 days ago
overall it was a wonderful experience staying here and everything worked out great during my stay, can’t say there were any complaints as it was just the spot we needed for our trip!

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

  • Total rentals

    40 properties

  • Total number of reviews

    1K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore

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