Vacation rentals in Redwood Park, San Mateo County

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Top-rated vacation rentals in Redwood Park, San Mateo County

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Guest favorite

A spacious bedroom features large windows dressed with sheer white curtains, allowing natural light to fill the space. A comfortable bed is accompanied by two elegant chairs positioned beside a small table. The warm wooden flooring complements the calming atmosphere.

Home in San Carlos

4.96 out of 5 average rating, 122 reviews

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 )

Top guest favorite

A tranquil pool area is surrounded by lush greenery and tall redwood trees. Comfortable seating is arranged on the deck alongside the pool, with planters containing vibrant plants adding a touch of nature. A spacious deck provides a peaceful spot for relaxation.

Guesthouse in Woodside

4.99 out of 5 average rating, 330 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.

Top guest favorite

A serene garden space is featured, showcasing a decorative fountain surrounded by lush greenery and colorful plants. Garden furniture, including a table and chairs, is situated beneath a shaded umbrella, creating an inviting atmosphere for relaxation or outdoor meals.

Guesthouse in San Carlos

4.99 out of 5 average rating, 724 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 favorite

A small outdoor seating area is presented, featuring two wicker chairs positioned around a round table. Potted plants are placed on the table and nearby, with a patch of artificial grass beneath them. The entrance to the cabin is visible, framed by a welcoming mat.

Cottage in Woodside

4.98 out of 5 average rating, 405 reviews

Kings Mountain Studio Cabin

Enjoy a cozy STUDIO Cabin nestled in the Redwoods up on Kings Mountain. For those who are inclined to have an active lifestyle, We are close to Purisima Creek, Huddart Park, and El Corte De Madera Hiking and Biking Trails. This space is perfect for two! (read more about the space) 20 minutes away from Half Moon Bay with beautiful beaches and 30 min. from Stanford, Palo Alto. We are adjacent to The Mountain House Restaurant. Res recommended. Short drive to local breakfast place. NO PETS!

Guest favorite

A spacious property is nestled among tall, lush trees, with a distinct white exterior. A wide driveway leads to the entrance, complemented by a covered porch area. Natural stone landscaping is visible along the side, blending harmoniously with the surrounding forest.

Guest suite in Woodside

4.88 out of 5 average rating, 385 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.

Top guest favorite

A wooden gate with a decorative archway frames the entrance to a charming cottage. The house is surrounded by tall trees, and natural stone accents are visible in the gate's support. Large windows can be seen, inviting light into the cozy structure.

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.

Top guest favorite

The guesthouse, nestled among tall redwoods, features a wooden exterior with multiple windows allowing natural light to filter in. A welcoming entrance is present, flanked by greenery, while a small raised wooden structure is visible in the foreground, blending harmoniously with the surrounding landscape.

Guesthouse in Woodside

4.97 out of 5 average rating, 273 reviews

SkyHigh Redwoods Retreat with Bay Views

Inhale. Exhale. Relax in this cozy, romantic guesthouse retreat nestled in the redwoods of the Santa Cruz Mountains, overlooking the bay and conveniently located near the famous Alice’s Restaurant on Skyline Blvd in Woodside. The 1 acre gated property has ample parking and privacy. Snuggle in with the wood burning fireplace, prepare meals in the full size kitchen and take in the views of the majestic redwoods right outside the windows with bay views peeking through the trees.

Guest favorite

The en-suite bathroom features a modern design with a glass shower enclosure and neutral-toned tiles. A floating vanity with ample storage is complemented by a large mirror. Soft lighting enhances the clean and bright atmosphere, while a towel rack and elegant fixtures are also visible.

Guest suite in Emerald Hills

4.92 out of 5 average rating, 182 reviews

Elegant retreat in Redwood City

NOW with new AC & Heating! 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. Washer/dryer and many other amenities available. This is part of a ~4000 sq ft luxury single family home with a completely separate and private entrance.

Guest favorite

A spacious loft bedroom is characterized by slanted white wooden ceilings. A large, soft white bed is centered below two windows, each flanked by stylish lamps. A plush area rug enhances the warm ambience of the room, complementing the natural light from the windows.

Home in San Carlos

4.95 out of 5 average rating, 259 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 favorite

A modern bathroom features a spacious walk-in shower enclosed by clear glass panels. The shower is adorned with stylish white and gray marble tiles, with a rainfall showerhead positioned above. A sleek toilet is situated beside the shower, contributing to the clean and contemporary design.

Home in Redwood City

4.91 out of 5 average rating, 225 reviews

The Chandelier Studio

Newly remodeled with private bathroom, kitchenette, and entry. Located in one of the most desirable areas of Redwood City known as Woodside Plaza. This is a quiet and pleasant community with tree line streets. We offer a very comfortable and spacious studio, quality linens, YoutubeTV, Netflix, Amazon Prime, Roku, Wifi. Equipped with central AC and Heater. Comfortable queen bed. Minutes away from Stanford hospital Futon converts to extra bed, bedding available.

Top guest favorite

The interior of the cabin is shown, featuring a cozy sleeping area with a trundle bed covered in striped bedding. A table with two chairs is visible, and large glass doors lead to a deck area. Natural light enters through the windows, illuminating the soft tones of the walls.

Guesthouse in La Honda

4.95 out of 5 average rating, 440 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.

Guest favorite

A wooden deck extends towards the ocean, featuring a fire pit surrounded by Adirondack chairs. The expansive view reveals the coastline and ocean, with grassy hills in the background under a clear blue sky.

Camper/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.