Vacation rentals in Hillsborough

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, 118 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, 742 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, 746 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.

Superhost

A cozy living area features a chaise lounge and a comfortable armchair, positioned near a vintage-style fireplace. A small desk is set against the wall, illuminated by a nearby lamp. Natural light brightens the space, highlighting the soft area rug and the neutral color palette.

Apartment in San Mateo

4.74 out of 5 average rating, 114 reviews

Gracious Flat in Downtown San Mateo

Don't miss your chance to stay in this historic mansion in downtown San Mateo- with new elegant touches placed throughout the flat, you can enjoy the old with the new. 3 blocks from San Mateo Caltrain, Philz coffee and all that lovely downtown San Mateo has to offer. Includes free parking & shared on site coin-operated laundry facilities. If you're modern urban people who accept noise from the train/other tenants & love the vibrant downtown diversity, this is the perfect place for you.

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.

4.92 out of 5 average rating, 180 reviews

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, 172 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, 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

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.

4.95 out of 5 average rating, 128 reviews

A vibrant yellow dining table is set with blue plates and silverware in a well-lit dining area. An artwork featuring blue tones is displayed on the wall above, while a softly glowing pendant light hangs overhead. A patterned sliding door adds a touch of color.

Home in San Mateo

Mid-century home w/ atrium & fire pit

Welcome to your stylish Bay Area retreat - a mid-century gem blending comfort, light, & indoor-outdoor living: • Sleeps 6 | 3 bedrooms | 3 beds | 2 baths • Private fenced backyard w/ BBQ, fire pit & 8-person dining • Enclosed atrium w/ custom mural & red maple tree • Private office w/ fast Wi-Fi - perfect for remote work • Open-concept living w/ fireplace & full kitchen • Peaceful Highlands neighborhood - 15 min to SFO, 20 min to SF

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, 230 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

A spacious room features vaulted ceilings with wooden beams. A queen-sized bed, draped in a geometric patterned blanket, sits next to a sleek fireplace. A dining table and chairs are visible, along with a large TV and two closets that provide storage options.

4.95 out of 5 average rating, 932 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, 324 reviews

A cozy sleeping space features a queen bed with white linens and colorful decorative pillows. A light fixture stands beside the bed, and a wall art piece composed of natural materials adds interest. A closet with sliding doors is visible in the background.

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

Kitchen

Wifi

Pool

Free parking on premises

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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, 18 reviews

Stowe Cottage in San Mateo Park

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, 34 reviews

Sparklingly clean guest unit with gated parking

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.

5 out of 5 average rating, 7 reviews

Charming 3BR Executive Home Minutes from SFO & SF

4.95 out of 5 average rating, 20 reviews

A compact living area features a dark gray futon with red accent pillows, paired with a black armchair. A wooden coffee table sits on a textured blue and beige area rug, with a decorative bowl on the table. A wall-mounted TV is visible across from the seating.

Cottage in San Mateo

Le Cottage Aubergine (Burlingame - San Mateo)

A spacious entryway features warm wood flooring and neutral wall colors. An elegant light fixture hangs from the ceiling, and a console table is adorned with greenery and a lamp. An archway leads into a bright living area with large windows.

4.96 out of 5 average rating, 48 reviews

Bright Spanish-style home in Burlingame

A bright living area features a comfortable dark sofa and two light-colored armchairs beside a round coffee table. A flat-screen television is mounted above a traditional fireplace. Open French doors lead to a bright adjoining room, while a patterned rug adds texture to the wooden floor.

4.99 out of 5 average rating, 67 reviews

Charming Burlingame Beauty!

Superhost

A bright living area features large floor-to-ceiling windows offering mountain views. A comfortable sofa with decorative pillows sits beside a coffee table. A dining table for four is positioned near the windows, providing a pleasant space for meals.

Apartment in San Mateo

4.84 out of 5 average rating, 31 reviews

Lovely Gorgeous View Walkable Location!