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, 114 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, 726 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, 214 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!

4.96 out of 5 average rating, 100 reviews

Farm stay in Woodside

Apartment w hot tub / forest & ocean view

Slow living at this farm (Coop d'état Farm) retreat on Kings Mountain. Set in old-growth forest with ocean views, a fire pit and a hot tub, the apartment sits on a working campsite (Kings Mountain Fancy Camp) with chickens, goats, dogs, and cats. A 10-minute walk from the Purisima Open Space trail network. It has a bedroom a living room, a bathroom and an office space. It occupies the lower floor of our home and has a private entrance and parking. With access to a shared picnic area / bbq.

4.94 out of 5 average rating, 143 reviews

The image depicts a serene coastline with gentle waves lapping at the sandy shore. Cliffs rise in the background, showcasing lush greenery and rugged terrain. Soft mist hangs in the air, blending into the horizon where the ocean meets the sky.

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

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.

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 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.

4.99 out of 5 average rating, 165 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

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.

4.94 out of 5 average rating, 103 reviews

A modern studio bedroom features a spacious queen-size bed, dressed in a light blue quilt. Two large windows allow natural light to fill the room, complemented by a small working desk and chair. Neutral tones create a calming environment.

Guest suite in Belmont

New, modern quiet private studio

New modern private studio attached to the main house with a private staircase entrance. Easy free parking in front of the entrance. Located in heart of the Bay Area: 15 minutes to SFO airport, 19 minutes to Half Moon Bay, 17 minutes to Stanford. Enjoy nice views with morning coffee. Ideal for 1-2 guests. Working desk, wifi, tv, comfortable linens, small fridge, microwave and Phillips coffee machine.

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, 225 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. *

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, 922 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.

4.98 out of 5 average rating, 321 reviews

A well-maintained backyard patio features a round table surrounded by four chairs, shaded by a large umbrella. Lush greenery and colorful flowers create a natural backdrop, while the cottage's exterior showcases a window framed by blue shutters.

Guesthouse in Burlingame

Clean&Cozy Cottage near downtown Burlingame & SFO

Our sunny backyard cottage, with outdoor private entry, is centrally located in Burlingame between Burlingame Avenue and Broadway and is a great spot suited to a business traveler in search of a home away from home while also being ideal for vacationers looking to live like a local, only miles from SF. Enjoy and unwind!

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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

5 out of 5 average rating, 14 reviews

Stowe Cottage in San Mateo Park

4.89 out of 5 average rating, 37 reviews

Large windows frame a view of the garden, featuring lush greenery and colorful flowers. Natural light filters in, enhancing the serene ambiance. Bamboo-style shades are positioned neatly above the windows, allowing for adjustable privacy.

Guest suite in Oakland

Peaceful studio w/ beautiful garden view

4.97 out of 5 average rating, 234 reviews

A wooden gate with a decorative archway frames the entrance to a charming cottage. The house is surrounded by tall trees, and natural stone accents are visible in the gate's support. Large windows can be seen, inviting light into the cozy structure.

Cottage in San Carlos

Carmelita Creek House

The iconic Golden Gate Bridge is viewed from a rocky beach, framed by gentle ocean waves. The sun sets in the background, casting a warm glow over the bridge and the surrounding landscape, highlighting the natural beauty of the area.

Guest suite in Westlake

4.76 out of 5 average rating, 37 reviews

NEW! Private | Modern | Full Kitchen | EZ Parking

Private room in Burlingame

An indoor/outdoor cat with a long, dark fur coat stands on a sandy surface near a potted plant. The cat's striking blue eyes are visible, and its fur appears soft and fluffy. Surrounding grasses add a touch of natural texture to the scene.

4.9 out of 5 average rating, 200 reviews

Relax in Old World Charm: Nurses discount

Guesthouse in Belmont

4.8 out of 5 average rating, 20 reviews

Beautiful view residence

A quaint cottage is presented, featuring a dark door accented by window details. String lights create a soft, ambient glow above a small seating area with a round table and umbrella. Nearby, a potted plant adds a touch of greenery to the cozy patio space.

Guesthouse in Belmont

4.83 out of 5 average rating, 224 reviews

Charming Cottage Studio

A modern bathroom is equipped with a glass shower featuring sleek tiles and a showerhead. A white vanity with a marble countertop holds toiletries, and neatly arranged towels are visible on a rack. A window allows natural light, while grey and white tones add to the cleanliness of the space.