Vacation rentals in Highlands-Baywood Park

4.96 out of 5 average rating, 122 reviews

Home in San Carlos

Serene Oasis in the Midst of Silicon Valley

Gaze out at the beautiful green canyon while having a morning coffee in bed. Head to the fully equipped kitchen to prepare breakfast and enjoy it outside on the balcony, surrounded by the sights and sounds of this stunning hilltop location. Close to 280. Centrally located in Silicon Valley for easy access to both San Jose and San Francisco. Deck/BBQ Lounge Area. Minimal. Enjoy life in the San Carlos hills. Drive about 5 minutes to lively San Carlos downtown for several restaurants and bars. Go hiking in Edgewood, Crestview, or Big Canyon. For a taste of big city life, adventure a bit further to San Francisco. Driving is the best option, I280 and 101 are easily accessible. Cal Train station down the hill - connects all the way from San Francisco to San Jose. Very spacious unit ( approximately 1200 sq.ft )

Camper/RV in Half Moon Bay

4.98 out of 5 average rating, 250 reviews

Airstream Coastal Hideaway (Sunset)

On 9 private acres overlooking the stunning Beach and Ocean from a breathtaking cliff top view. Stunning sunsets. Famous 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. Within 10 mins of Half Moon Bay shopping. Beach access short walk or drive. If this one is booked, there are three other equally similar Airstreams on the property.

4.77 out of 5 average rating, 725 reviews

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

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!

4.97 out of 5 average rating, 234 reviews

Cottage in San Carlos

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.

4.94 out of 5 average rating, 142 reviews

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, 365 reviews

Home in Belmont

Hidden French Gem for Fam/Biz~near Caltrain,SFO

Highly welcome respectful travelers to step through the 750ft super quiet European-style private studio with secluded bay view. Curl up in front of the 4K TV for movie nights at this stylish, soundproofed nest with a luxury mattress, washer and dryer! — welcome infant & kids. — Read everything to avoid surprises. — 5 min walks to park, Caltrain/restaurants; 10~13 min drive to SFO/Stanford; 20-25 min SF. — No pets, no smoking/vaping, no party! — book for 3 if need single bed

4.99 out of 5 average rating, 164 reviews

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

4.93 out of 5 average rating, 247 reviews

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

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!

4.94 out of 5 average rating, 103 reviews

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.

4.93 out of 5 average rating, 225 reviews

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. *

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Other great vacation rentals in Highlands-Baywood Park

4.88 out of 5 average rating, 51 reviews

Guesthouse in Belmont

Newly Built Private Guesthouse, Silicon Valley

CatherineRating, 5 stars3 days ago

We really enjoyed our stay here! The guest house was bright and clean and had amazingly comfortable beds. The location was perfect for toggling between San Francisco and Stanford University (and for a quick trip over the hills to visit Half Moon Bay for a day). There is even a park with hiking trails close by. San Carlos and Belmont, with numerous restaurants and shops, are an easy 5-10 drive away. Sohui was a fabulous host! I would happily stay here again.

Superhost

Private room in San Bruno

4.81 out of 5 average rating, 231 reviews

Near SF Airport 1-bedroom home

直尚Rating, 5 stars3 weeks ago

I think it's a great place to stay near the airport!Thank you!

4.97 out of 5 average rating, 265 reviews

Baytree Bungalow.

LaurenRating, 5 stars3 days ago

Booked this as my first solo AirBnB trip for 4 nights and absolutely loved it! The location was perfect, walkable to downtown and close to my family nearby! I highly recommend checking out the San Carlos Sunday Farmers market, it’s a nice walk from the house and has lots of local treasures to enjoy! Christopher was very welcoming and attentive to making my stay the best it could be - he made sure to ask if I needed anything each day. The room was very clean, had plenty of storage, and the remodeled bathroom is amazing! The shower’s pressure is perfect and the heated floors in the AM and PM were a nice addition! The room and bathroom attachment made it extra private and convenient. I also enjoyed the sitting area to across from the room. Christopher did well to make his place feel safe, friendly and a welcoming home!

4.94 out of 5 average rating, 110 reviews

Beautiful, Spacious Private Master Suite

MichaelRating, 5 stars1 week ago

The space was immaculate and the both the house and neighborhood were very quiet

Superhost

4.89 out of 5 average rating, 103 reviews

Master Bedroom at Silicon Valley, private bathroom

ScottRating, 5 stars1 month ago

Exactly what I needed to decompress after work each day. Clean place. Peaceful area in the hills and trees, yet 10 minute drive to many many (many) neat restaurants. This place is a gem in this area!

4.89 out of 5 average rating, 183 reviews

Studio Rm-Priv Bath & Entrance-10 min walk 2 train

MichaelRating, 5 stars2 weeks ago

Allison’s studio is perfect for both short and extended stays. The space is thoughtfully equipped with everything you need for a comfortable visit, and the bed is especially cozy. While the private bathroom isn’t directly connected to the room, it’s just next door and fully stocked with all the essentials. Allison is a warm and attentive host who clearly cares about making her guests feel welcome and at ease. I would definitely stay here again in the future.

4.9 out of 5 average rating, 40 reviews

Guest suite in San Mateo

Luxury guesthouse close to SFO/Parking/waterfront

PhanRating, 5 stars2 days ago

The location was perfect for our visit, putting us close to SF as well as South Bay cities. We walked the shore trail every morning during our stay. Pam was a wonderful host, anticipating our needs and brought extra towels and water even without us asking. We will definitely stay with Pam again on future visits.