Vacation rentals in Hillsborough

4.97 out of 5 average rating, 184 reviews

A modern interior features a wall-mounted fireplace surrounded by a textured stone facade, creating a statement element. The open space leads to an adjacent room with large windows offering views of the outside landscape, enhancing the overall light and airiness.

Guest suite in Tiburon

Award-winning ocean view luxury master suite.

Teaberry is a private entry 1,100 sq ft master suite addition to a mid-century modern house on a 2 acre wooded lot overlooking the northern San Francisco Bay in Tiburon, CA. Featured in Dwell (Sept 2018) with a spa-like bathroom winning design awards in Architectural Record, Interior Design Magazine, Architect Magazine (Jan ‘19). With stunning ocean views from every room, the private addition includes a bridge/hall, decks, bedroom and bathroom consisting of jacuzzi tub and large walk-in shower.

5 out of 5 average rating, 112 reviews

A modern living area features a sectional sofa complemented by a glass coffee table. Large sliding doors provide natural light and a view of the outdoor space. A sleek fireplace adds warmth to the room, with a stylish area rug enhancing the comfortable setting.

Home in Half Moon Bay

Fabulous Beach Get Away - Brand New Beach House

Amazing Newly Built Beach House. Wake-up in this beautiful beach house in a tranquil neighborhood just a short stroll to the beach, walking trails, and restaurants. This beautifully decorated, two story home is perfect for your next beach get away! This house is fully equipped with TV, fireplace, new cozy beds, outdoor fire pit and BBQ, and much more. Enjoy this town which features horseback riding, fishing, boating, surfing, quaint downtown with shops, wine tasting, restaurants and much more.

4.93 out of 5 average rating, 412 reviews

A charming entrance features a light blue door and two white Adirondack chairs positioned beside potted plants and greenery. The stone path leads to a cozy patio area surrounded by lush tropical foliage.

Home in Stinson Beach

Bright and Cozy Beach Cottage

Adorable private cottage. Bright and comfortable beautifully appointed. 2 bdrm, 1 bath full kit, Lovely private garden where you can relax and enjoy after a fun day at the beach. Let the waves rock you to sleep. Our Stinson Beach Seaside Village is a special beautiful place with close proximity to some of the best hiking trails. The Dipsea and the Matt Davis Trail are steps away. Enjoy our beautiful natural surroundings, beach and gorgeous coastline. The perfect place for a memorable getaway!

5 out of 5 average rating, 106 reviews

Condo in Marina Gardens

Most Desired Vacation Spot in San Francisco.

Welcome to San Francisco, one of the most beautiful and diverse cities in the world! I would love to host you in my modern and clean home right in the middle of one of the most coveted neighborhoods in the city, the Marina District. You will only be a few steps to the Marina waterfront, beach, and Crissy Field. If you look toward your left, you can’t miss the iconic Golden Gate Bridge. You can stroll to Chestnut Street and Union Street where you will find restaurants and trendy store fronts.

4.97 out of 5 average rating, 237 reviews

Two loungers are positioned on a wooden deck, offering views of rolling hills and a soft pink sky at sunset. Tall trees frame the scene, enhancing the natural setting and providing a serene backdrop.

Guesthouse in Oakland

82 “ Pool, Jacuzzi , HOT SAUNA, VIEWS, Newer ADU!

Stunning, ADU cottage w/ higher end finishes. Endless VIEWS of mountains set on a beautiful, peaceful, upscale gated, property surrounded by redwood, pine & oak trees. 1 mile to large regional parks for hiking, mountain biking and horse stables. Nature at its best! Pool heated 82F May 1st-Oct. 31st. 16 miles to San Francisco, 5-10 minutes to many restaurants. New Jacuzzi and outdoor sauna. Large patio, pool / deck (6500 sq foot outdoor oasis shared with main house with a small family of 4)

Guesthouse in Walnut Creek

A gently sloping wooden walkway is framed by lush greenery, leading to the covered porch of the guesthouse. Soft lighting illuminates the path, enhancing the inviting appearance of the home, which is situated amid mature trees and landscaped gardens.

5 out of 5 average rating, 292 reviews

Oak Knoll Hideaway

If you're searching for one of the premier Airbnbs in Walnut Creek, your search ends here! From the moment you arrive, you'll notice the attention to detail and exceptional value of this 2-bedroom, 1-bathroom home. It comes fully equipped for a first class experience. What truly sets this guesthouse apart is the wrap-around covered porch, featuring three ceiling fans, accent lighting, a gas BBQ, a fire table, a dining table adorned with a chandelier, as well as rocking and Adirondack chairs.

Apartment in San Francisco

An outdoor seating area features a fire pit with a glass centerpiece, casting a warm glow. Comfortable cushions add to the inviting atmosphere. The distant ocean can be seen as the sun sets, creating a serene backdrop against the skyline.

4.88 out of 5 average rating, 367 reviews

Beautiful 1 bdrm Apt with Ocean Views and Hot Tub

Super safe neighborhood in San Francisco. It is residential and quiet. Gate to get in. Beautifully remodeled inlaw suite with private keypad entrance, one block from famous tile steps and blocks to dining options and Golden Gate Park. Bedroom has stunning ocean views. Unit is equipped with streaming enabled TVs, microwave/convection oven, electric stove, nest heat, towel warmers, washer/dryer, writing desk and chair, and more! Hot tub and fire pit! * “Not suitable for parties/events”

4.94 out of 5 average rating, 139 reviews

A tranquil outdoor space is shown, with a pergola providing shade amidst lush greenery and purple flowers. Stone pathways weave through the garden, leading to seating areas surrounded by native plants and mature trees with a peaceful landscape in the background.

Home in Ben Lomond

Central Coast; Meadow, Hot Tub, Polite Pets Welcom

VR#111596 Seemingly remote & private yet so close to everything, single level home with massive deck on 2 1/2 acres backs to park and trails. The cook’s kitchen & herb garden overlook our meadow. The hot tub, outdoor living room & garden shower are just a few of the surprises you will uncover. The 350 heritage oak tree with 10,000 sq ft canopy is a magnet for wildlife. Ask about detached office if you need to work from home; the internet is great. Polite well trained pets OK.

Tiny home in Half Moon Bay

A view into the loft studio is presented, showcasing a cozy living space. The staircase leads to the upper loft area, while a spacious bed is positioned in the lower section, complemented by warm wood floors and soft natural light filtering through the windows.

4.85 out of 5 average rating, 650 reviews

Small Beach Cottage Near the Coastal Trail

This is the perfect place for a getaway near the beach. Tiny House provides you and your dog comfort and privacy in a quiet neighborhood close to the dog friendly Poplar Beach. We provide the basics to prepare small meals in our kitchenette. You have close access to miles of coastal trails, great shopping and dining in downtown (1 mile away). Ritz Carlton is just 2 miles South of us. The Harbor also has great options for dining. Many trails for hiking and biking very close by.

Apartment in Stinson Beach

A coastal building is visible, featuring large windows that offer views of the surrounding landscape. Wooden fencing enhances the property’s boundary, while a sandy path leads towards the entrance. Lush greenery and mountains rise in the background under a soft, cloudy sky.

4.96 out of 5 average rating, 273 reviews

Oceanfront at La Paz in Stinson Beach

Feel at home on the beach...Fantastic views of sand, surf & mountains. 1 BR apt located upstairs in 3 unit building. Max 2 guests. Fully furnished w/full kitchen, patio BBQ, WiFi, Smart TV, queen bed w/heated mattress pads. 1 dog welcome..$75 fee-charged separately once booking is confirmed & accepted by the host. (no cats please). Cleaning fee, AirBnb Service Fee & hotel occupancy tax charged at the time of booking. No occupancy tax: 30+ days stays.

4.96 out of 5 average rating, 227 reviews

A covered balcony features two light blue chairs with striped cushions, overlooking the neighborhood. The wooden railing offers a sense of openness, while the surrounding area includes a glimpse of greenery and residential rooftops. Natural light brightens the space.

Home in Pacifica

Brighton Beach Cottage, One Bedroom plus Loft

Just a short stroll from Sharp Park beach and hiking trails our large private spacious 1 bedroom plus loft is perfect for your next beach and hiking getaway. Centrally located in the desirable Sharp Park neighborhood of Pacifica, you can get to San Francisco, Half Moon Bay, hiking trails, golf, and beaches quickly and easily. A few minutes drive to Linda Mar beach, one of the best surf spots in Northern California. The cottage is a single-family home.

4.93 out of 5 average rating, 296 reviews

The entrance features a wooden trellis gate leading into a private yard. A light-colored dog stands on a gravel path, framed by the wooden fence and lush greenery. The home's architecture is visible in the background, with skylights and a sloped roof.

Home in Stinson Beach

Luxury and Design- 200 ft or 1 min walk to beach

Enjoy nature & great design in one gorgeous location. We are 200 ft from beach. Rentals usually have 4 nt min stay (except for holidays). High season (Sept thru Mid Oct) has 5 nt min stay with check in days on Fridays (but ask if you want Thurs check-in) . Longer stays possible, just ask. Occasionally, we have a last minute deal (LMD) with shorter stays. Let us know if you want to be added to the LMD list.

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What guests are saying

Lighthouse Holiday Home in Discovery Bay

5 out of 5 average rating, 79 reviews3 months ago

This home was perfect for our group! Every year we book a place large enough for 5-13 people and spend a week together to ring in the new year. This was easily one of the best places we've stayed in! Lots of kitchen supplies, fun activities, clean towels and blankets, amazing instructions and manual made everything super easy, and Jules was incredibly responsive!! Couldn't ask for a better host or a better house!

Home in Discovery Bay

What guests are saying

Seaside Home Modern Retreat with Breathtaking

4.93 out of 5 average rating, 60 reviews1 week ago

We came here to celebrate a milestone birthday in the family and the house exceeded expectations. You can’t beat the neighborhood, the 2 block walk to the beach, waking up to birds and coastal fog in the morning, all the great local markets and convenience despite this being a more remote and quiet part of town. The house itself was exactly as shown in the pictures and was such a lovely stay. If anything it was way bigger than we thought it’d be. 10/10 would book this again and again.

Home in Half Moon Bay

What guests are saying

Canyon View Casita

5 out of 5 average rating, 66 reviews3 weeks ago

I've been to countless Airbnbs, and I was very impressed by this listing. Abril's home was absolutely perfect for my family and I + She was able to accommodate us very last minute. Her home was cozy, clean and perfect if you have small kids. She was very responsive throughout our time there. Thank you, Abril! We very much enjoyed our stay.

Guesthouse in Castro Valley

What guests are saying

Guesthouse Garden Retreat

4.91 out of 5 average rating, 336 reviews1 week ago

Michelle is a great host and the cottage was lovely! The garden is gorgeous and there are lots of places to relax outside. I felt very welcome and taken care of! It was not an issue for me at all, but the location is a little ways out from the action and there is not a lot close by. On the plus side, it’s relatively quiet, cozy, and relaxing! I enjoyed the hot tub both mornings I was there! Overall , a very pleasant experience!

Guesthouse in Oakland

What guests are saying

Enchanting cottage in charming Bolinas

4.98 out of 5 average rating, 209 reviews3 weeks ago

Our stay in Bolinas was fantastic, and we couldn't recommend Francesca's casita more highly. What a peaceful, beautiful setting for exploring Bolinas and the surrounding area. The casita was the perfect size for a long weekend stay for two adults and a toddler, and the large yard and treehouse were a huge hit with the toddler. The kitchen was extremely well-stocked for its size with everything you could need to cook meals, which was very helpful given that dining options in Bolinas are pretty limited. We would definitely return!

Cottage in Bolinas

What guests are saying

Modern Rustic Retreat Home w/cedar hot tub

4.87 out of 5 average rating, 69 reviews3 weeks ago

This place is a gem! It feels like you are in a tree house with almost 360 views. I stayed here during my wedding and it was amazing. It made my wedding that much more special. The house is a bit older but nothing that took away from the beauty of this home.

Home in Kentfield

What guests are saying

Redwood Cottage & Hot Tub

4.96 out of 5 average rating, 181 reviews1 day ago

We had such a beautiful getaway! Shannon and Nick were so helpful and very helpful with instructions. Their space is gorgeous, clean, and just as described! I could lay in the hammock all day :) I would definitely recommend and I would love to come back and stay again!

Guesthouse in Felton

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Popular amenities for Hillsborough vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Hillsborough's top sights

Safeway148 locals recommend

Century 12 San Mateo68 locals recommend

Draeger's Market66 locals recommend

Curry Up Now63 locals recommend

Sawyer Camp Trail54 locals recommend

Pizza My Heart53 locals recommend

Other great vacation rentals in Hillsborough

4.99 out of 5 average rating, 122 reviews

A wooden deck is shaded by a pergola adorned with lush wisteria, offering a scenic view of the surrounding landscape. A rectangular table and several chairs provide seating for outdoor dining. Green trees frame the horizon, creating a peaceful outdoor retreat.

Home in Oakland

Beautiful Home. Gorgeous Views. Five Bedrooms.

4.96 out of 5 average rating, 52 reviews

Home in Discovery Bay

Remodeled in 2020-Large deck w/ spa & ping pong!

Apartment in South San Francisco

A modern bathroom features a glass-enclosed shower with a sleek showerhead and contemporary fixtures. The walls are adorned with textured tile, and a vanity with a mirror is seen in the background. Soft lighting from multiple sconces enhances the clean aesthetic.

4.92 out of 5 average rating, 37 reviews

Sparkling Clean Newly Remodeled 1BR near SF/SFO+EV

5 out of 5 average rating, 25 reviews

An open kitchen and dining area feature a large kitchen island with modern appliances and dark cabinetry. A dining table with white tablecloths is surrounded by various chairs, while a small desk with a monitor is positioned near a window, allowing natural light to fill the space.

Home in Campbell

3 bdrm 2bath bright renovated private deck

5 out of 5 average rating, 3 reviews

Home in Castro Valley

2BR House with Canyon & Hillside Views

4.97 out of 5 average rating, 149 reviews

The image showcases a panoramic view of a residential neighborhood with a clear ocean view in the background. Several houses with varied architectural styles are visible, surrounded by greenery and open spaces. The blue sky is dotted with a few clouds, enhancing the serene coastal atmosphere.

Home in Half Moon Bay

Entire house：Steps to beach and ample space

4.91 out of 5 average rating, 170 reviews

A panoramic view of the San Francisco neighborhood is showcased, with rolling hills and homes visible in the distance. The foreground features tall trees and an elevated street, while a glimpse of the bay and distant hills can be seen under a clear blue sky.

Home in Noe Valley

Noe Valley entire guest suite overlooking downtown