Holiday houses in Highlands-Baywood Park

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Top-rated holiday rentals in Highlands-Baywood Park

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Guest favourite

Home in San Mateo

4.83 out of 5 average rating, 278 reviews

❤️ Delightful 1B/1B modern with a leisure garden

This recently upgraded unit features a master bedroom with a full bathroom and two closets, along with a spacious living area. Enjoy complete privacy with a separate fence and a sunny private garden. We provide complimentary coffee and tea, and there’s free street parking available 24/7. It’s within walking distance to the Roblox office and the San Mateo Event Center, and about 10 minutes from SFO. Please note, this is not an apartment building. Self-check-in is available using the key code.

Guest favourite

Guest suite in Millbrae

4.77 out of 5 average rating, 726 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.

Guest favourite

Apartment in San Mateo

4.94 out of 5 average rating, 213 reviews

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!

Top Guest favourite

Guesthouse in San Carlos

4.99 out of 5 average rating, 729 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

Cottage in San Carlos

4.97 out of 5 average rating, 234 reviews

Carmelita Creek House

The creek house is on a beautiful tree lined street, walking distance to downtown San Carlos. The house is a spacious one bedroom cottage with designer finishes and gorgeous vaulted ceilings. You will be surrounded by mature redwoods on the peaceful balcony and one with nature at the fire pit overlooking a year round creek. Amenities include a full sized kitchen, comfortable workspace, washer/dryer, fast WiFi, cable TV and a gas fireplace. We live in the main house on the property.

Guest favourite

Guest suite in Belmont

4.94 out of 5 average rating, 142 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

Guesthouse in San Mateo

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

Guest favourite

Home in San Carlos

4.95 out of 5 average rating, 260 reviews

The Perfectly Appointed Modern English Guest House

Relax and unwind in this newly constructed guest house. Completed in 2019 it offers all the amenities of a 5-star hotel suite with the privacy and ambiance of a quaint English Tudor home. Located just 2 blocks from charming downtown San Carlos in the “City of Good Living”. We are 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).

Guest favourite

Guest suite in San Mateo

4.93 out of 5 average rating, 247 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

4.94 out of 5 average rating, 124 reviews

Mid-Century Retreat w/ Fire Pit & Private Backyard

Welcome to your stylish Bay Area retreat—where mid-century design meets modern comfort. This spacious Eichler home is perfect for families, remote workers, and weekend getaways. • 3 bedrooms, 2 full baths (sleeps 6) • Private office with fast Wi-Fi • Open-concept living, full kitchen • Enclosed atrium with custom mural • Private backyard with BBQ, fire pit, outdoor dining • Peaceful neighborhood, 20 mins to SF, 15 mins to SFO

Guest favourite

Campervan/RV in Half Moon Bay

4.98 out of 5 average rating, 128 reviews

Airstream Beach View (Dream) - New Listing

On 9 private acres overlooking the stunning Beach and Ocean from a breathtaking cliff top view. Stunning sunsets. Surf views with large windows. Fully loaded with all the amenities to make your glamping experience perfect. Fire pit, outside BBQ, outside griddle, Heat, A/C and fully stocked kitchen. Full bathroom with shower. If this one is booked, there are three other equally similar Airstreams on the property.

Guest favourite

Guest suite in Belmont

4.94 out of 5 average rating, 103 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.