Vacation rentals in San Francisco Peninsula

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Top-rated vacation rentals in San Francisco Peninsula

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Guest favorite

Guesthouse in Redwood City

4.93 out of 5 average rating, 296 reviews

Soak up the Serenity on the Patio of a Charming Cottage

Light the fire pit and dress for dinner in the vine-covered garden at a peaceful retreat with a soothing waterfall. Zen beachy decor and coastal paintings set the scene indoors, with abundant natural light enhancing easy open-plan living. Pets are welcome with a small cleaning fee of a $50 (one time fee) and additional pets $25 (one time fee). The main room is 12'x17'. Closet is 6 1/2' long. Bathroom 4'x5 1/2' + shower 3'3" x 3'3". kitchen 4 1/2' x 8". Simple breakfast served. Your own private entrance, plenty of parking on the street, nice neighborhood. We are available if you have any questions or need information on the area. 2 night minimum please. The cottage is tucked away off the street in a quiet, safe neighborhood where residents walk their dogs in pleasant weather. Nearby downtown Redwood City is home to shops and groceries and freeways and public transportation are within easy reach. There is a bus that runs at the corner of our block, it would take you to downtown Redwood City or travel down the El Camino Real. There is a train depot downtown as well. Pets - 2 small dogs in the main house, 2 outdoor cats.

Mar 30 – Apr 6

G$22,714 GYD per night

Guest favorite

Guesthouse in San Carlos

4.99 out of 5 average rating, 585 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.

Jul 6 – 13

G$32,063 GYD per night

Guest favorite

Guesthouse in Belmont

4.97 out of 5 average rating, 362 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.

Mar 5 – 12

G$23,363 GYD per night

Guest favorite

Guest suite in Woodside

4.88 out of 5 average rating, 339 reviews

Stay Nestled in Ancient Redwoods in Silicon Valley

Welcome to our 6-acre home, High Ground, & have our kid and pet friendly carriage house to yourself! The large studio apt with separate entrance has stunning views of ancient redwood trees + the Bay/Mount Diablo. Immediate hiking trails, wildlife, minutes to: Alice's restaurant (5), Michelin-rated Village Pub (15) highway 280 (15) Palo Alto/Menlo Park/Half Moon Bay/Ocean (30), SFO (35) San Francisco (45). Perfect for a northern CA retreat, business in the Valley or sight-seeing in San Fran.

May 21 – 28

G$23,483 GYD per night

Guest favorite

Guest suite in Belmont

4.95 out of 5 average rating, 101 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. 🌲

Jun 14 – 21

G$26,125 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.

Feb 28 – Mar 7

G$25,793 GYD per night

Guest favorite

Home in Belmont

4.93 out of 5 average rating, 323 reviews

Hidden French Gem ~ 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

Aug 25 – Sep 1

G$31,149 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.

Oct 4 – 11

G$30,534 GYD per night

Guest favorite

Home in Redwood City

4.97 out of 5 average rating, 289 reviews

Private suite

Our home offers a private getaway perfect for business or a place to relax outside the city. Enjoy your private deck, complete with jacuzzi, and enter our large, sunny suite. Features Cal-King bed, on suite bath with heated tile flooring and bluetooth shower speaker. On site kitchenette includes mini bar, microwave, toaster oven, coffee maker & fridge/freezer. High speed WIFI connection and desk for workspace. Smart TV with blu ray, DVD, and cable.

Jul 3 – 10

G$30,472 GYD per night

Guest favorite

Guesthouse in La Honda

4.95 out of 5 average rating, 380 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 5 – 12

G$24,296 GYD per night

Guest favorite

Guesthouse in Hillsborough

4.95 out of 5 average rating, 809 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.

Oct 11 – 18

G$28,148 GYD per night

Guest favorite

Guesthouse in Redwood City

4.88 out of 5 average rating, 156 reviews

Modern Studio Cottage with Private Entrance

Beautiful modern 200 sq. ft. studio / cottage behind main house, with kitchenette, appliances, bathroom, and private entrance. Delicious fruit trees surround the property and are free for the picking! 20 miles to San Jose and 30 miles to San Francisco downtown areas. 4 miles from Stanford University. Great for couples, business travelers, and solo adventurers!

Oct 8 – 15

G$26,249 GYD per night