Holiday houses in Hillsborough

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Top-rated holiday rentals in Hillsborough

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Top Guest favourite

Home in San Mateo

4.87 out of 5 average rating, 105 reviews

10-Min SFO *A/C* Modern Comfort 2BR Family Retreat

Welcome to our beautifully remodeled 2-bedroom home, just minutes from Downtown San Mateo! Whether you’re a couple, a family, or a business traveler, this is the perfect spot for you. Enjoy a fully equipped kitchen, comfortable living space, and kids-friendly amenities. Explore San Mateo's vibrant neighborhoods or take a short drive to San Francisco. We've thought of everything to make your stay comfortable, including fast WiFi and plush bedding. Book now and experience the best of the Bay Area!

Top Guest favourite

Guest suite in Burlingame Hills

4.88 out of 5 average rating, 123 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.

Guest favourite

Guest suite in Millbrae

4.77 out of 5 average rating, 752 reviews

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.

Top Guest favourite

Guesthouse in San Carlos

4.99 out of 5 average rating, 756 reviews

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.

Top Guest favourite

Guest suite in Belmont

4.95 out of 5 average rating, 148 reviews

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. 🌲

Guest favourite

Guest suite in San Mateo

4.93 out of 5 average rating, 252 reviews

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.

Guest favourite

Home in San Mateo

4.95 out of 5 average rating, 130 reviews

Single-level retreat w/ fire pit & patio

Welcome to your Bay Area retreat in San Mateo’s tranquil Highlands neighborhood - perfect for families & friends to relax indoors & out: - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Enclosed atrium w/ custom mural & red maple tree - Pvt backyard w/ fire pit, BBQ & 8-person dining - Fully equipped kitchen w/ stainless appliances - Wood-burning fireplace & spacious living area - 15 min to SFO, 20 min to San Francisco

Guest favourite

Guest suite in Belmont

4.94 out of 5 average rating, 106 reviews

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.

Top Guest favourite

Apartment in Burlingame

4.97 out of 5 average rating, 451 reviews

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.

Top Guest favourite

Guesthouse in Hillsborough

4.95 out of 5 average rating, 945 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.

Guest favourite

Guest suite in Burlingame Terrace

4.95 out of 5 average rating, 212 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).

Top Guest favourite

Guesthouse in Burlingame

4.98 out of 5 average rating, 329 reviews

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!