Family-friendly holiday rentals in Ashland

4.96 out of 5 average rating, 109 reviews

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

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!

Guest house in Castro Valley

A patio area is visible near the entrance of the studio, featuring a small table and blue chairs. Potted plants line the pathway, leading to the main entrance. Sunlight filters through the surrounding trees, creating a serene outdoor space.

5 out of 5 average rating, 108 reviews

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.

4.98 out of 5 average rating, 170 reviews

An airy living space features a light-coloured sofa and a small dining table with two chairs. A coffee and tea station stands on a black cabinet. Natural light enters through the front door, complemented by indoor plants and framed wall art. A doorway leads to the bathroom.

Guest suite in Hayward

★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!

Guest house in San Lorenzo

A cozy dining and resting area features a sleek glass coffee table atop light wood flooring. A gray futon is positioned near a wall-mounted flat-screen TV, while a compact stainless steel fridge and air fryer sit on a black stand. Vertical blinds allow filtered light to enter.

4.94 out of 5 average rating, 99 reviews

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.

4.77 out of 5 average rating, 101 reviews

A spacious sleeping area is centered around a cozy queen bed adorned with decorative pillows. A statement light fixture hangs above, providing soft illumination. A dark accent wall contrasts with light walls, enhancing the warmth of the space. A dresser and small nightstand complement the room.

Guest house in Oakland

Cozy Clean Private Cottage

Welcome to this cozy private cottage in Oakland's Frick neighborhood! Enjoy a plush queen bed, full kitchen with a stove and fridge, and sleek laminate floors. Relax with high-speed internet and streaming on Netflix or Apple TV. Walking distance to Mills College, with easy access to Hwy 580, Coliseum BART (2 miles), and Oakland Airport (5 miles). Near Highland Hospital (3.7 miles), Kaiser Oakland (6 miles), and Kaiser San Leandro (7 miles). Perfect for professionals and travelers alike!

Guest house in Castro Valley

A modern kitchen is presented with sleek blue cabinetry and a white tiled backsplash. Essential appliances including a gas stove, kettle, and a cutting board set are visible. The kitchen counter is neatly arranged with cleaning supplies, contributing to an organized and functional space.

4.88 out of 5 average rating, 147 reviews

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

Guest suite in San Lorenzo

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.

4.96 out of 5 average rating, 188 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.

Guest house in San Leandro

A cozy sleeping area features a plush bed adorned with a patterned quilt, flanked by two bedside tables with lamps. Decorative wall art depicts trees, enhancing the calming atmosphere, while a throw pillow adds a touch of motivation.

4.95 out of 5 average rating, 255 reviews

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)

4.91 out of 5 average rating, 367 reviews

The image depicts a serene garden pathway leading to two adjacent cabins, framed by vibrant greenery and flowering plants. A wooden trellis is visible, providing shelter, while soft lighting from the cabins enhances the calm atmosphere. A mixture of stone and mulch surfaces directs attention toward the entrance.

Guest house in Oakland

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.

Guest house in San Lorenzo

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.

4.9 out of 5 average rating, 154 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.

4.84 out of 5 average rating, 349 reviews

A spacious bed is adorned with a navy and white checkered bedding set, complemented by a yellow decorative pillow. Three art pieces depicting city skylines are displayed above the headboard against a textured white wall.

Guest suite in Oakland

Private Master Suite + Bathroom in Oakland Hills

Spacious guest suite nestled in the beautiful Oakland Hills perfect for guests to enjoy a peaceful stay in the Bay Area This is a completely private suite offering: - Gated secured parking - Your own entrance - Full bathroom - Kitchenette - Comfortable desk space Quick access to I-580 freeway to get to Berkeley, Downtown Oakland and SF 30 min from SFO 5 min from Oakland Zoo and Leona Canyon Park 12-15 min from BART, OAK Airport and UC Berkeley

Bungalow in Castro Valley

A spacious living room is presented, featuring a black sofa, two ancient chairs, and a round coffee table. A decorative lamp stands beside the seating area, with light oak flooring and a soft area rug enhancing the inviting environment. Natural light filters through the windows.

4.96 out of 5 average rating, 212 reviews

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).

Popular amenities for Ashland family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 275 reviews

A tranquil pool surrounded by a spacious deck features lounge chairs for relaxation. The sun casts a warm glow over the water, highlighting the adjacent charming cottage and lush greenery. Tall trees provide shade, enhancing the serene atmosphere.

Guest house in Oakland

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

Guest house in North Berkeley

The room features traditional tatami mat flooring and a low wooden table surrounded by floor cushions. A wood-burning stove stands against one wall, contributing to the rustic atmosphere. Light floods in from the skylight above, illuminating the inviting space with natural warmth.

4.84 out of 5 average rating, 1,388 reviews

Traditional Japanese Tea House

Guest house in Kensington

The charming cottage exterior features natural wood siding, framed by greenery and vibrant flowers. A welcoming entrance is visible, along with a small deck furnished with two chairs and a table, offering a cozy spot for outdoor relaxation.

4.95 out of 5 average rating, 730 reviews

Secluded luxury cottage & hot tub

Guest house in Longfellow

A charming garden cabin is visible, featuring a welcoming door framed by lush greenery. Colorful landscaping and potted plants add vibrancy to the area. A patio area with wooden decking is seen in the background, suggesting an inviting outdoor space to relax.

4.79 out of 5 average rating, 272 reviews

Lovely homemade Garden Cabin + Hot Tub near Bart.

Guest house in Walnut Creek

A wooden deck is framed by palm trees, featuring a round table and an adjacent chair. The view captures a sparkling pool, surrounded by lush greenery, inviting relaxation in a serene outdoor setting.

4.91 out of 5 average rating, 607 reviews

Tropical Garden Cottage +HOT TUB &POOL by Downtown

Farm stay in Walnut Creek

The bedroom features a spacious bed with neutral bedding accompanied by vibrant accent pillows. A colorful piece of wall art adds visual interest, while two windows allow natural light to filter in. A small sitting area is present with a plant nearby, enhancing the welcoming feel.

4.99 out of 5 average rating, 579 reviews

Garden Oasis Studio with Spa and Pool Walnut Creek

4.93 out of 5 average rating, 340 reviews

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 Sheffield

Hike-in Bay Views Cabin w HotTub

4.84 out of 5 average rating, 491 reviews

A vibrant yellow wooden gate features a circular cutout, framing a view of lush greenery beyond. A fruit tree is visible through the opening, enhancing the connection to the surrounding garden.

Flat in Alameda

Secret Garden Cottage

Family- and pet-friendly home rentals

4.86 out of 5 average rating, 180 reviews

A cozy living area is displayed, featuring a grey sofa adorned with patterned cushions. A coffee table sits in front of a multi-colored area rug, with a television mounted on a wooden media console. Two pets are seen, one on the couch and the other on the floor.

Flat in Millsmont

Beautiful private 1 bedroom apartment w/ Bay views

4.99 out of 5 average rating, 149 reviews

The exterior of a spacious home is set within the Oakland Hills, featuring a paved driveway leading to an entrance. Lush greenery and natural stone landscaping flank the sides, while a gentle slope showcases the house’s elevated position.

Home in Woodminster

5 Bedroom home with bay views for large groups

Guest suite in Durant Manor

The exterior of a bright blue studio unit is shown, featuring a yellow door and white trim. Lively green plants and a lemon tree frame the entrance. A small sitting area with a patterned table and chair is positioned in front, with red umbrellas providing shade.

4.93 out of 5 average rating, 107 reviews

Modern newly built Spaceroom

Guest suite in Leona Heights

A sleeping area is furnished with a decorative metal bed frame and patterned bedding. Dark purple curtains frame the window, while a bedside table with a lamp and two framed art pieces are positioned on the wall nearby.

4.97 out of 5 average rating, 101 reviews

Beautiful sweet retreat

4.83 out of 5 average rating, 305 reviews

A spacious bed with crisp white linens is centered in the room, complemented by decorative yellow pillows. A simple desk is positioned nearby, featuring a wall-mounted TV above it. A potted plant adds a touch of greenery, enhancing the cozy atmosphere.

Flat in Merritt

Cozy & Chic Farmhouse Studio: Walk to Lake Merritt

4.97 out of 5 average rating, 217 reviews

The living area is defined by a cozy couch with decorative pillows, positioned across from a wall-mounted TV. Natural light filters through a skylight and window, illuminating the room adorned with soft curtains. A small coffee table rests on a neutral area rug, contributing to a relaxed atmosphere.

Home in Millsmont

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

Guest suite in Maxwell Park

A modern kitchen area is seen, equipped with stainless steel appliances, including a refrigerator and gas stove. A round white dining table sits on decorative tile flooring. A cozy sleeping area is visible, featuring a queen bed with a deep blue comforter against a contrasting wall.

4.91 out of 5 average rating, 113 reviews

The Suite on Camden Street! Pet friendly.

4.92 out of 5 average rating, 273 reviews

A serene outdoor space is illuminated by string lights, creating a cozy atmosphere. Potted flowers add color to the area, while a shaded dining table and seating invite relaxation. The patio features stone paths and lush greenery, offering a peaceful retreat.

Guest suite in Oakland

New convenient comfortable studio

Family-friendly home rentals with a pool

4.92 out of 5 average rating, 168 reviews

A charming tiny house is nestled among towering redwood trees, featuring a red door and a large window. Potted plants line the front steps, and a small patio area with red chairs and a table invites outdoor relaxation.

Tiny home in La Honda

Delightful Tiny Home in the Redwoods !

Apartment in Civic Center

A modern living space presents a deep-seated couch paired with a stylish coffee table, set against a backdrop of vibrant artwork. Natural light filters in through a window, while a door leads to the outside. A dining area is visible in the corner.

4.91 out of 5 average rating, 304 reviews

Lakeside Retreat (w/ private parking)

4.87 out of 5 average rating, 263 reviews

A cozy cottage is surrounded by lush greenery and a variety of shrubs. Stairs made of bricks lead up to a welcoming entrance with multiple windows that allow natural light to fill the interior. The setting is serene, with trees enhancing the tranquil atmosphere.

Guest house in Belmont

Private Garden Cottage in Belmont Hills

Guest suite in San Rafael

A spacious guest studio features large windows that provide natural light and panoramic views. The room includes a comfortable queen bed with premium linens, a small dining table with two chairs, and a minimalist wooden dresser. A warm color palette enhances the cabin-like feel.

4.9 out of 5 average rating, 467 reviews

Romantic Mtn Studio - Pool, Sauna, Views!

4.99 out of 5 average rating, 344 reviews

A rustic cabin is situated among tall redwood trees. A wooden deck extends towards a tranquil pool, which is surrounded by greenery and flower beds. The warm tones of the cabin's exterior complement the natural surroundings, enhancing the serene atmosphere.

Guest house in Woodside

Rustic Cabin in the Redwoods

Guest suite in Indian Valley

A framed black and white photograph depicts six individuals arranged casually in a natural setting under a large tree. Instruments such as a guitar are visible, while varied chairs and a rustic box add to the composition.

4.88 out of 5 average rating, 112 reviews

1 BR suite in Rock & Roll History

4.94 out of 5 average rating, 150 reviews

The interior of the converted school bus features rustic wooden cabinetry and appliances. A spacious teak countertop extends over the cooking area, complemented by a red refrigerator. Sunlight illuminates the living area, showcasing a cozy seating arrangement and large windows with views of the surrounding nature.

Bus in San Jose

Cozy BUS on Farm Animal Rescue with CITY VIEW