Guesthouse vacation rentals in San Francisco Peninsula

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Top-rated guesthouse rentals in San Francisco Peninsula

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Guest favorite

Guesthouse in Redwood City

4.93 out of 5 average rating, 299 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.

Apr 6 – 13

ﺩ.ﺇ408 per night

Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 275 reviews

Rustic Cabin in the Redwoods

Tucked among the redwood trees on top of King's Mountain, this 1 bedroom cabin offers both rustic charm and modern luxury. Property owners live onsite in the main house about 30 feet away from the cabin. Located just 20 minutes off HWY 280, this cabin is the perfect weekend retreat for those looking to get away from the bay area without actually leaving. Spend time relaxing in the pool, hiking or biking one of the nearby trails, or just reading a book while sitting among the redwood trees.

Oct 24 – 31

ﺩ.ﺇ1,259 per night

Guest favorite

Guesthouse in San Carlos

4.99 out of 5 average rating, 594 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 27 – Aug 3

ﺩ.ﺇ575 per night

Guest favorite

Guesthouse in Belmont

4.97 out of 5 average rating, 365 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 11 – 18

ﺩ.ﺇ413 per night

Guest favorite

Guesthouse in San Bruno

4.96 out of 5 average rating, 55 reviews

❤️Newly remodeled SFO Guesthouse, Private entrance

Detached, and perfectly situated cute guesthouse with a private entrance. Ideal for a vacation to explore San Francisco bay area/Silicon valley while staying in a safe and quiet neighborhood. Conveniently located 8 min drive from SFO Airport! 5 min drive to BART/Caltrain station, 2 min walking distance to bus stop and 4 min to EV charging station. Close access to 101, 280 freeway. 15 mins to San Francisco and 20 mins to Silicon Valley. 10 mins to the beautiful Highway 1, Pacifica.

Jan 2 – 9

ﺩ.ﺇ425 per night

Guest favorite

Guesthouse in Pacifica

4.98 out of 5 average rating, 372 reviews

NEW Private Studio! Close to SF/SFO/Beach Sanitize

Built in 2020, our guesthouse is a perfect place for romantic getaways and road trips. It has a private entrance, smart lock, whole room UV light sanitizers, hotel-quality bedding, brand-new furniture, and the latest interior designer selection. 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!

Dec 23 – 30

ﺩ.ﺇ495 per night

Guest favorite

Guesthouse in La Honda

4.95 out of 5 average rating, 383 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.

Jan 3 – 10

ﺩ.ﺇ436 per night

Guest favorite

Guesthouse in Hillsborough

4.95 out of 5 average rating, 815 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.

Dec 28 – Jan 4

ﺩ.ﺇ488 per night

Guest favorite

Guesthouse in Redwood City

4.89 out of 5 average rating, 161 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!

Jan 15 – 22

ﺩ.ﺇ471 per night

Guest favorite

Guesthouse in Oakland

4.99 out of 5 average rating, 162 reviews

Redwood Heights Cottage with Stunning Bay Views

Quiet cottage nestled in a Redwood Heights oasis. We have lovingly renovated the detached private cottage next to our house. The whole property is half an acre with stunning views of the SF Bay and walking distance to shops and restaurants in the Laurel and Redwood Heights area.

Nov 22 – 29

ﺩ.ﺇ387 per night

Guest favorite

Guesthouse in Redwood City

4.95 out of 5 average rating, 504 reviews

Stylish Separate Loft/Cottage Walk to Redwood City

* Automated, simple, quick self check in! * Located in a quaint and desirable neighborhood in Redwood City * 15 minutes from Stanford * 5 minutes to the 101 and 280 freeways * Easy walking distance to fun and lively downtown Redwood City/Train * No pets, no pets, no pets

Oct 25 – Nov 1

ﺩ.ﺇ564 per night

Guest favorite

Guesthouse in Castro Valley

4.95 out of 5 average rating, 544 reviews

Upscale Contemporary Mediterranean Studio

This East Bay location offers a delightfully restful and well appointed living space and excellent access to BART and freeways. The Boulevard with its many amenities and Lake Chabot recreation area are both close by. We can often accommodate earlier check-in. Please inquire.

Jul 28 – Aug 4

ﺩ.ﺇ460 per night