Vacation rentals in Hillsborough

Guest suite in Burlingame

The Golden Gate Bridge is captured during twilight, showcasing its iconic orange-red color against a gradient of blue sky. The bridge spans across the water, with city lights twinkling in the background, providing a scenic view of the landscape.

4.87 out of 5 average rating, 112 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, 725 reviews

The kitchen area features white cabinetry and a sleek countertop with a gas cooktop. Essential appliances, including a coffee maker and microwave, are visible. A small indoor plant adds a touch of greenery, while a black refrigerator is positioned in the background.

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.

4.94 out of 5 average rating, 212 reviews

A serene beach scene is depicted, featuring gently rolling waves lapping at the shore. A sandy beach stretches into the distance, bordered by cliffs and lush coastal vegetation, with the soft glow of sunset reflecting on the water.

Apartment in San Mateo

Fabulous apartment in downtown San Mateo

Relax away from the hustle of the city in your apartment in downtown San Mateo. Located only two blocks from the San Mateo Caltrain, you can get to or from SF or SJ in 30 minutes. Our home has a separate entrance for the guest apartment on the second floor. Tuck yourself away in the California King sized bed, or explore downtown on foot. With over 100 restaurants in walking distance, you will not have a shortage of delicious dining. Eat out or enjoy a meal in the comfort of your home. Welcome!

4.99 out of 5 average rating, 723 reviews

A serene garden space is featured, showcasing a decorative fountain surrounded by lush greenery and colorful plants. Garden furniture, including a table and chairs, is situated beneath a shaded umbrella, creating an inviting atmosphere for relaxation or outdoor meals.

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.

4.99 out of 5 average rating, 164 reviews

A sleek digital lock is mounted on a white door, providing a modern entryway solution. The lock features a minimalist design and is accompanied by a simple black door handle, emphasizing convenience for guests. Glass panels with horizontal lines can be seen adjacent to the door.

Guesthouse in San Mateo

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

Guest suite in El Granada

A coastal view features gentle waves lapping against a sandy beach, bordered by rocky cliffs. In the distance, a structure is visible atop a prominent bluff, surrounded by greenery under a clear blue sky.

4.98 out of 5 average rating, 285 reviews

Cozy, creekside guest suite with private entrance

Cozy, creekside guest suite just blocks from the beach and the picturesque harbor. This one bedroom unit has been completely remodeled with a fully stocked kitchen, a separate eating/work space and a bathroom with a walk in shower. Drink your morning coffee (host provided) on the furnished deck while listening to the sounds of the running creek and the fog horn in the distance. This unit has its own private entrance and is closed off from the rest of the house.

4.94 out of 5 average rating, 124 reviews

An open-concept living area features a combination of mid-century furniture and modern design. A cozy sofa and colorful chairs surround a low table, while a dining area with a bright yellow table sits adjacent. Light filters in through large windows, highlighting the space's contemporary aesthetic.

Home in San Mateo

Modern Mid-Century Retreat • Quick Access to SFO

Close to San Francisco, SFO and the Peninsula. Step into this stunning 1956 Joseph Eichler-designed home, updated in 2017 to preserve its mid-century charm with modern touches. The enclosed atrium, featuring a custom mural and red maple tree, sets a serene tone upon entry. Inside, you'll find mid-century furniture and art, with a spacious open-concept living area, wood-burning fireplace, dining room, and a fully equipped kitchen—perfect for small gatherings.

4.93 out of 5 average rating, 247 reviews

A fabric hanging organizer with several compartments is hung on a closet rod. A fan stands on the left, providing airflow, while a heater is positioned above. The light color and vertical stripes of the organizer create a tidy appearance.

Guest suite in San Mateo

Luxury King Bed & Spa Bathroom

Our spacious guest suite has its own private entrance, comfortable pillow-top king size bed, work-friendly laptop desk, hi-speed wifi, spa bathroom with heated floor, mini fridge, microwave and a Keurig coffee maker. The guest suite is part of the main home, but there are no shared spaces and the areas are separated by a locked solid wood door & noise-dampening cushions. Our guest suite is ideal for couples visiting family in the neighborhood.

4.97 out of 5 average rating, 470 reviews

A coastal view showcases a sandy beach bordered by gentle waves. Colorful wildflowers, including vibrant orange poppies, frame the foreground, while rolling green hills rise in the background. The ocean sparkles under clear blue skies, with surfers visible in the distance.

Guesthouse in Pacifica

Elegant Guesthouse in Garden Close to SF/SFO/Beach

Built in 2020, our guesthouse is the perfect place for couples or solo travelers. It has a private entrance, smart lock, hotel-quality bedding, brand-new furniture, and the latest interior design selections. Staying in the sunbelt of beautiful Pacifica, there are a lot of fun activities nearby: spending your day on the beach, exploring the hiking trails, or road trip along Highway 1. Half Moon Bay, SF, and SFO are around 20 minutes away!

4.93 out of 5 average rating, 225 reviews

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.

Guesthouse in San Mateo

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. *

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, 918 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.

Superhost

A modern bathroom features a glass-enclosed shower over a white soaking tub. Two deep burgundy towels hang neatly on a silver bar, adding a touch of color to the neutral tiled walls. A small window allows natural light into the space.

Guest suite in Burlingame

4.95 out of 5 average rating, 209 reviews

2 Bedroom Home Away from Home

Apartment above garage (up one flight of stairs) with a separate entrance. Recently renovated and fully furnished with queen-size beds in both bedrooms. Easy access to Highway 101 for easy access to San Francisco and South Bay as well as SFO Airport (7 min). Very walkable to Broadway (2 blocks) and Burlingame Ave (about 15 min).

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Popular amenities for Hillsborough vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Hillsborough

4.95 out of 5 average rating, 19 reviews

A modern bathroom is presented with a spacious shower enclosed in glass. Large frosted windows allow for natural light while ensuring privacy. The stone walls and floor add a luxurious touch, complemented by a wooden bench placed thoughtfully within the space.

Home in Hillsborough

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

RickRating, 5 stars1 month ago

Heather was an exceptional host from start to finish. The communication was clear, friendly, and fast—she responded immediately when we realized we’d accidentally booked the wrong dates and helped us adjust the reservation without any hassle. The home was exactly as described: clean, comfortable, and well-stocked, with plenty of space for our group of five. The check-in instructions were easy to follow, and she checked in to make sure we had everything we needed during the stay. Heather also provided thoughtful checkout guidance and made everything seamless. We really appreciated her attentiveness and kindness, and wouldn’t hesitate to stay here again. Highly recommend!

Superhost

The exterior of the Spanish-style home features a welcoming facade with a terracotta tiled roof and arched windows. A curved pathway leads to the front entrance, surrounded by well-maintained gardens and greenery, enhancing the home's charm in its tranquil setting.

4.96 out of 5 average rating, 45 reviews

Bright Spanish-style home in Burlingame

EricRating, 5 stars4 weeks ago

Lauren’s place is fantastic. The remodel does a great job of matching the original architecture with updated appliances (the six burner Wolf stove, for example) and the decoration was just perfect for our taste. The location is fantastic — a short 3-4 block walk to downtown Burlingame and a Caltrain stop, close to 101 and 2-3 blocks from a nice park with tennis and pickleball courts. The only slight negative is there is some noise from planes landing at the airport nearby but it was most noticeable in the night when it could easily be blocked out with the fans in the bedrooms. The backyard is very large and the deck set up nicely for bar-b-queuing or enjoying a drink or meal outside. This is a very comfortable house and would come back without hesitation.

An outdoor seating area is presented, featuring a light-colored, cushioned sofa and two matching armchairs, arranged around a small black table. The space is enclosed by lush green hedges, providing a sense of privacy, with a stone patio surface beneath.

5 out of 5 average rating, 58 reviews

Charming Burlingame Beauty!

KarenRating, 5 stars3 weeks ago

We stayed at Carla’s place for two nights and loved everything - the convenience of the location, the cleanliness of the cottage and how it was organised and the communication with Carla. The beds were super comfy and I enjoyed my coffee each morning. We had just arrived in the Bay Area from New Zealand and it was a wonderful space for two weary travellers. We wouldn’t hesitate to stay again and recommend to others.

4.95 out of 5 average rating, 259 reviews

A spacious loft bedroom is characterized by slanted white wooden ceilings. A large, soft white bed is centered below two windows, each flanked by stylish lamps. A plush area rug enhances the warm ambience of the room, complementing the natural light from the windows.

Home in San Carlos

The Perfectly Appointed Modern English Guest House

FlorianRating, 5 stars1 week ago

We had such a great time, the place is perfect for two. Fully equipped kitchen, everything was there. Very quiet neighborhood. San Francisco, Palo Alto and SFO are all easy to reach. Groceries are also close by. Would definitely book again! Thanks for everything!

4.97 out of 5 average rating, 165 reviews

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

EduilRating, 5 stars6 days 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!

A fire pit is centrally located on the outdoor patio, featuring glowing flames surrounded by sparkling glass stones. The background includes wooden fencing and potted plants, while soft lighting enhances the cozy outdoor ambiance.

4.92 out of 5 average rating, 178 reviews

Cozy Modern Craftsman Retreat

RaedRating, 5 stars4 months ago

John was a great great host and very responsive. This location is perfect, way better than staying in the heart of San Francisco. Very close to the airport and restaurants and close to San Fran. The place was extremely clean and very affordable. Definitely worth it and would stay again if John would have us.

Superhost

A charming entryway is showcased with red double doors featuring glass panels, adorned with a straw hat. A white rocking chair with red and white striped fabric is positioned nearby, inviting relaxation. Natural light enhances the warmth of the space.

4.92 out of 5 average rating, 168 reviews

Lovely Craftsman Bungalow

HollisRating, 5 stars2 weeks ago

This was a lovely place to stay. Nicely furnished. The kitchen was huge and had all kinds of things to make cooking easy - if we had been interested in cooking.