Vacation rentals in Highlands-Baywood Park

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Top-rated vacation rentals in Highlands-Baywood Park

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Guest favorite

Home in San Mateo

4.93 out of 5 average rating, 105 reviews

Lovely Mid-Century home near SF, SFO, & Peninsula

Walk through the enclosed atrium sporting a custom mural and stunning red maple in this home dating back to 1956. The spacious house boasts mid-century furniture and art with a wall of glass overlooking the deck with a backdrop of fruit trees. Spacious 2 bedrooms & den with TV converts to a sofa bed. You also have a private office if you're working from home, right off the atrium. Enjoy a lovely dinner in back garden on a cool summer night. Though we love children, our home is not childproof, and we prefer not to host children under 12 years of age, thank you for understanding. This home was built in 1956 by Joseph Eichler and completely remodeled in 2017 with the goal of staying true to its original Mid-Century design while updating the house for modern living. It features a collection of beautiful Mid-Century furniture and art made by the owner and friends. Guests enter through an enclosed atrium that sports a custom mural and stunning red maple. The back yard features a large dining area with a backdrop of fruit tree and a spacious deck overlooking thousands of acres of open space and the Coastal Range. This home has two bedrooms with queen size beds and one bedroom with a full size sofa-bed. The master bedroom has an en suite bathroom with walk-in shower, the other two rooms share a bathroom with a deep tub. There is a spacious, well lit office for your use. One of the best features of this home is it's great room with a wood-burning fireplace, dining room, and kitchen--perfect for entertaining a small group. The backyard features an 8 person outdoor dining table and 6 burner BBQ for your use, as well a large outdoor sofa surrounding a fire pit. The front atrium is another well lit modern get away where you can to sit back and enjoy nature and art. Guests will have access to the entire property including the house and gardens. There is a washer and drier for guest use in the garage. I have a co-host who will be there for you 24/7. The house is in the Highlands neighborhood, which was developed by Joseph Eichler in the mid-1950s. The community center across the street from the property features a great playground for children. San Francisco Airport is 15 minutes away. - Caltrain (Goes up and down to San Francisco and San Jose) - BART (Goes to Downtown San Francisco and East Bay) - Lyft (Use referral code JEN573431) - Uber (Use referral code jcc271ue) Parking in the drive way only (no garage use for cars). TV in one of the bedrooms, not the living room. No parties or events allowed. No curtains in two of the bedrooms, but no one can see into these room as a building wall hides them. 20 minutes to downtown San Francisco We take cleaning in this climate very seriously, we are in full compliance with the cleaning guidelines approved by WHO (Worldwide Health Organization) CDC (Center for Disease Control) and the EPA (Environmental Protection Agency)

Oct 14 – 21

G$93,749 GYD per night

Guest favorite

Guesthouse in San Carlos

4.99 out of 5 average rating, 588 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.

Jun 24 – Jul 1

G$32,012 GYD per night

Guest favorite

Guesthouse in Belmont

4.97 out of 5 average rating, 363 reviews

A Comfortable & Private Guest House

Attn: Promo Rate for Health Care Workers & First Responders on stays of ONE week, or more. Please alert us, so that we can offer you a promo rate. In light of these uncertain times, rest assured that we are doing everything to ensure the safety of our guests. Beautiful, Secluded, Safe, Fully Stocked, Comfortable, Newly Renovated, & Close to Public Transportation. In the heart of Silicon Valley with its own private entrance. It's 30 mins. N of San Jose, and 30 mins. S of San Francisco.

Feb 24 – Mar 3

G$23,358 GYD per night

Guest favorite

Guest suite in Belmont

4.95 out of 5 average rating, 102 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. 🌲

Sep 25 – Oct 2

G$23,018 GYD per night

Guest favorite

Home in Burlingame

4.91 out of 5 average rating, 149 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.

Dec 28 – Jan 4

G$31,541 GYD per night

Guest favorite

Guest suite in Emerald Hills

4.92 out of 5 average rating, 146 reviews

Elegant retreat in Redwood City

Gorgeous one bedroom apartment with en-suite bathroom, a spacious walk-in closet, ample light, and stunning views. Private fully equipped kitchen and sitting area allow for very comfortable living. Bedroom and sitting area/kitchen are separated by a door to allow for 2 separate work spaces. All furnishings are selected by a professional decorator and routinely upgraded. This is part of a ~4000 sq ft luxury single family home with 2 completely separate and private entrances.

Sep 9 – 16

G$25,752 GYD per night

Guest favorite

Cottage in San Mateo

4.95 out of 5 average rating, 465 reviews

Entire Private Studio by SFO, AC/Heat/Free Parking

Entire cottage with private entrance. * self check-in with codes * free parking on driveway * AC & heating * 1 queen bed, 1 sofa (converts into twin bed) * fiber speed WiFi * kitchenette with sink, dishes & utensils, microwave, oven, mini fridge, keurig coffee maker, water boiler, NO STOVE * 15 min drive to SFO * 10 min walk to Caltrain * walking distances to restaurants, bars & groceries * located at end of cul de sac in a safe & quiet neighborhood * TV with Chromecast

Sep 30 – Oct 7

G$31,646 GYD per night

Guest favorite

Guest suite in El Granada

4.97 out of 5 average rating, 213 reviews

Cozy, creekside guest suite with private entrance

Cozy, creekside guest suite just blocks from the beach and the picturesque harbor. This one bedroom unit has been completely remodeled with a fully stocked kitchen, a separate eating/work space and a bathroom with a walk in shower. Drink your morning coffee (host provided) on the furnished deck while listening to the sounds of the running creek and the fog horn in the distance. This unit has its own private entrance and is closed off from the rest of the house.

Sep 9 – 16

G$30,486 GYD per night

Guest favorite

Guest suite in San Mateo

4.94 out of 5 average rating, 206 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.

Jul 5 – 12

G$39,841 GYD per night

Guest favorite

Guesthouse in La Honda

4.95 out of 5 average rating, 382 reviews

Bicycle Shack @ La Honda Pottery

My place is close to miles of hiking and biking trails in county parks and openspace, great views, the beach and not far from the Peninsula, S.F. and Santa Cruz. You’ll love my place because of the location, the people, the ambiance, the outdoors space and that it is a self contained small cabin with a tiny deck.. My place is good for couples, solo adventurers, and furry friends (pets). Perfect for hikers and bikers.

Nov 14 – 21

G$24,257 GYD per night

Guest favorite

Guesthouse in San Mateo

4.93 out of 5 average rating, 193 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. *

Nov 29 – Dec 6

G$28,342 GYD per night

Guest favorite

Guesthouse in Hillsborough

4.95 out of 5 average rating, 810 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.

Nov 28 – Dec 5

G$28,818 GYD per night