Vacation rentals in Hillsborough

4.78 out of 5 average rating, 1,206 reviews

A well-lit kitchen area features light-colored cabinetry and a spacious counter. Large windows provide a view of the outside greenery. The sink is positioned next to various kitchen appliances, including a coffee maker and microwave. A small dining table with a stool is set against the wall.

Guest suite in Millbrae

Charming Private Studio Near SFO

Private studio overlooks a beautiful garden is minutes away from the Bart Station and SFO Airport! Enjoy a bathroom, wi-fi, outdoor garden area, parking for a perfect little getaway/vacation. Queen bed and couch. Please note this listing only accommodates for two people and we do not accommodate additional guests. We hope you respect this rule as the neighborhood is quiet and would like to respect our neighbors. Infants and children are considered as guests. Note: No Kitchen, 3 night max stay

4.94 out of 5 average rating, 125 reviews

A spacious living area features mid-century furniture, including a sofa with colorful cushions and wooden armchairs. A wood-burning fireplace is positioned within a textured white wall. Large glass doors provide natural light and an inviting view of the outdoors, enhancing the open layout.

Home in San Mateo

Elegant 3-BR Escape w/ Backyard near Western Hills

Welcome to your Bay Area retreat in this stylish 3-bedroom, 2-bath Eichler home. - Designed for ease and comfort, it features an open living space filled with natural light and a private office with high-speed Wi-Fi. - Cook in the full kitchen or relax in the atrium with its custom mural. - Step into the private backyard with a BBQ, fire pit, and outdoor dining area. - Located in a peaceful neighborhood just 20 minutes from San Francisco and 15 minutes from SFO, it’s perfect for work or rest.

4.88 out of 5 average rating, 246 reviews

The guest suite features a spacious bed with neutral bedding, accompanied by two light pillows. A modern desk and chair sit beside a large window, which allows natural light to fill the room. A ceiling fan and wall-mounted television enhance the contemporary design.

Guest suite in Millbrae

Boutique Hotel Feel - Private Luxury Master Suite

Private luxury guest suite in newly built architectural gem in Mills Estate. Boutique hotel feel, spacious guest room and bathroom suite. This two room suite has a private entry and smart lock for self check-in. The suite is attached to the main house, but closed off from the rest of the house. No amenities are shared. Super fast internet, 1000 mbps. Prime location, located in a quiet residential neighborhood, just 15 mins from SFO, 10 mins from Bart/Caltrain station, 20 mins to San Francisco.

Guest suite in Burlingame

The bedroom features a spacious bed with white bedding, complemented by decorative pillows. A blue accent chair sits nearby, next to a decorative bedside table with a lamp. Natural light filters in through a window with white shutters, illuminating the light-colored walls and geometric rug.

4.87 out of 5 average rating, 115 reviews

Gorgeous Suite close to SFO Airport, Self Check-In

Enjoy a peaceful stay at this newly appointed luxury suite. Burlingame is a suburb of San Francisco, known for it's tree-lined streets. Close to downtown San Mateo and Silicon Valley. This suite is part of a beautiful Spanish style house with a private entrance. Minutes from shops and restaurants Broadway Burlingame and Burlingame Avenue. Perfect for business travelers, couples or solo adventures! Features queen size bed, smart TV, refrigerator, microwave, Light and Bright! Wi-Fi, Parking.

4.77 out of 5 average rating, 731 reviews

A cozy living area features a grey sofa adorned with colorful cushions. A sleek black coffee table sits in front of a modern television, with a decorative plant nearby. Bright yellow curtains covered in floral patterns frame the window, allowing natural light to illuminate the space.

Guest suite in Millbrae

Private 1 bedroom suite for quick SFO trip withA/C

1 bedroom 1 bathroom guest suite with private entrance. Good for a short SFO trip. But be aware it might not fit family vacation need! Newly remodeled kitchen, full bathroom, Wi-Fi, gas cooktop, coffee maker, toaster, microwave. Soft foam topper queen bed. Convenient for Bay Area commuter, 15 mins driving to SFO airport. Close to 101, 280 freeway. 30 mins driving to San Francisco or 50 mins to San Jose. 15 mins walk to grocery store, Starbucks and restaurants. Easy and free street parking.

4.99 out of 5 average rating, 734 reviews

The exterior of a cozy cottage is visible, surrounded by a lush garden filled with various plants and flowers. A stone path leads to the entrance, framed by vibrant greenery. Large windows allow glimpses of the inviting interior, enhanced by a seasonal wreath on the door.

Guesthouse in San Carlos

Private Garden Cottage

Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.

4.94 out of 5 average rating, 145 reviews

A spacious sleeping area features a queen-sized bed with a neutral-toned blanket, accompanied by bedside lights. A desk with a chair is positioned near a window, allowing natural light to brighten the room. A lounge chair and wall-mounted TV are visible in the corner.

Guest suite in Belmont

Cozy private in-law suite, close to SFO, fast WiFi

Newly renovated, spacious in-law unit in the Belmont hills with a private entrance and Bay views. This adorable space is cozy and great for a weekend respite or remote work. SFO airport is just 15 mins away. Close by Stanford and San Carlos. Short drive to hiking trails and 30 mins away from the Pacific ocean. Easy access to San Francisco and San Jose, via freeway 101, 280, and 92. 🌞 Solar-powered through the day with battery 🔋 back-up at night. No outages and eco-friendly. 🌲

4.92 out of 5 average rating, 178 reviews

The studio space features a kitchenette with modern appliances, including a stainless steel refrigerator. A cozy sofa and a dining table for two are positioned near the window, while a comfortable queen bed with light bedding is visible in the background.

Home in Burlingame

Cozy Modern Craftsman Retreat

Private studio with a large outdoor patio. Just a short walk to the dinning and shopping on Burlingame Avenue and also on historic Broadway. Caltrain and Bart are minutes away to get take you to wherever you need to go. Fast wifi and espresso maker provided. Enjoy fresh fruit from our orange tree, and a rosemary bush for those that enjoy cooking. Relax with our large queen bed, recessed dimmable lighting and a large flat panel 4K smart TV w/apps for Netflix, Amazon Video, etc.

A cozy living area features a sectional sofa and coffee table, complemented by a 55" smart TV mounted on the wall. A standing desk with dual monitors and a small kitchenette, including a microwave and refrigerator, provide convenience. Three nature-themed artworks adorn the walls.

4.99 out of 5 average rating, 166 reviews

Modern guest house in great location

Private 1 bedroom + 1 bathroom with your own entrance. Highlights: • self-checkin with code on digital lock • free parking + additional free street parking • professional cleaning and sanitizing • king size bed with premium mattress and linens • located at end of cul-de-sac in a safe and quiet neighborhood • standing desk with monitor and docking station • high speed WiFi • 55” smart TV • Rainfall shower, bidet toilet with heated seat, heated towel rack, makeup mirror

The entrance to the studio features double glass doors framed by potted plants and flowers in various sizes. A welcome mat is positioned at the threshold, and small wall-mounted lights provide illumination. Natural light can be seen streaming through the doors.

4.93 out of 5 average rating, 227 reviews

Charming Private Quiet Backyard Studio

This charming, sunny, secluded backyard studio is located in the heart of San Mateo, near public transportation, freeways, restaurants, shopping, and 15 minutes to SFO. Private entrance, quiet backyard setting, plenty of street parking. Less than a 5-min walk to Safeway, CVS, Starbucks and restaurants. * To my regular guests, the rate increase is due to SM County increasing the tax rate. *

4.97 out of 5 average rating, 444 reviews

A private deck area is surrounded by lush greenery and colorful shrubs. A large umbrella provides shade over the wooden table and chairs, inviting relaxation outdoors. The deck is accessible from the yard, enhancing the tranquil outdoor experience.

Apartment in Burlingame

Home away from home in wonderful Burlingame

It's my honor to be your host and I will try to make your stay really great. I provide suggestions of things to do but feel free to ask for advice! Our city requires their hosts obtain a 12% transient occupancy tax, therefore the price has been increased to reflect that tax. *** Please see House Rules and the complete description of the property to ensure our apartment will work for you.

Guesthouse in Hillsborough

The cottage entrance is shown, featuring a green door framed by a screen door. A small outdoor seating area with two chairs and a table is visible on a gravel path, surrounded by lush greenery and trees.

4.95 out of 5 average rating, 923 reviews

Little Cottage on the Hill

Enjoy a peaceful stay at this charming, secluded detached garden cottage great for a stay-cation or as a work-from-home alternative. Due to the coronavirus, we are taking extra care to disinfect frequently touched surfaces between reservations. The cottage features a queen-sized bed, a fireplace, private bathroom and kitchenette. Perfect for both leisure and Business travelers.

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Popular amenities for Hillsborough vacation rentals

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Other great vacation rentals in Hillsborough

The exterior of the cottage is shown, featuring a dark front door framed by two large windows. Potted plants with colorful blossoms sit on either side of the entrance, adding a touch of greenery to the facade, which is painted in a soft gray tone.

5 out of 5 average rating, 15 reviews

Stowe Cottage in San Mateo Park, California

4.93 out of 5 average rating, 249 reviews

A bright bedroom features a spacious bed with crisp white linens and an accent pillow. Natural light streams through large windows, and a modern desk with a lamp is positioned nearby. A mirrored closet reflects the room's stylish decor, enhancing the space's openness.

Guest suite in San Mateo

Luxury King Bed & Spa Bathroom

4.81 out of 5 average rating, 21 reviews

A spacious living area features a light-colored sectional sofa alongside two brown armchairs. A coffee table sits in the center, complemented by a decorative plant. A flat-screen TV is mounted on the wall, and natural light brightens the space through ceiling lights and nearby greenery.

Apartment in Burlingame

Charming 2BR/1BA Apt in Burlingame, Close to SFO

A modern kitchen is shown with light-colored cabinetry and stainless steel appliances. A wooden dining table with two chairs is positioned nearby. Soft lighting creates a functional space, and a window offers natural light, complemented by warm-toned walls.

4.94 out of 5 average rating, 33 reviews

Sparklingly clean guest unit with gated parking

4.95 out of 5 average rating, 19 reviews

A spacious living area is filled with natural light from large windows, showcasing views of the lush garden. A cream-colored sectional sofa and a tufted bench provide comfortable seating, while modern pendant lights hang above. A glass coffee table is positioned at the center.

Home in Hillsborough

Modern San Francisco Bay Area home, 4bed/2bath

5 out of 5 average rating, 6 reviews

A circular wooden dining table is surrounded by six upholstered chairs, creating a cozy dining space. A chandelier hangs from the ceiling, softly illuminating the area. The open kitchen can be seen in the background, featuring elegant cabinetry and modern appliances.

Home in Burlingame

Charming 3BR Executive Home Minutes from SFO & SF

Guest suite in Burlingame

A bright kitchen space is highlighted by two windows that provide natural light. A circular table with two chairs is positioned near the windows. Cream-colored cabinetry and dark countertops complement the stainless steel appliances, creating a functional and inviting area.

4.95 out of 5 average rating, 211 reviews

2 Bedroom Home Away from Home