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Vacation rentals in Woodside

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Top-rated vacation rentals in Woodside

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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A wooden picnic table and bench set are positioned on a deck area, surrounded by greenery and flowers. Steps lead up to a raised platform, with a spacious lawn visible in the background. A tall pine tree adds natural height to the setting.

Guest suite in Outer Sunset

4.89 out of 5 average rating, 163 reviews

Great Highway Oceanfront studio

LizzetteRating, 5 stars2 weeks ago

The host were amazing!!!!! Very clean perfect for 2 people! The bed was amazing felt like sleeping on clouds! About 15 min from tourist attractions and ONLY TWO MIN AWAY FROM SAN FRANCISCO ZOO!! 10/10 recommend! Beach right out front!!!

Top guest favorite

Tall redwood trees create a serene forest environment, with their textured trunks standing closely together. Lush green foliage is visible at the base, complementing the rich earth tones of the bark. A stone wall subtly outlines the natural space, adding to the peaceful atmosphere.

Guesthouse in Boulder Creek

4.99 out of 5 average rating, 218 reviews

Digital Nomad Retreat

KrishnaRating, 5 stars6 days ago

Robert was an amazing host. His place was clean and comfortable. Perfect location to explore redwoods- there are beautiful hiking trails close to his place and the drive up is beautiful as well. He gave us great recommendations for things to do in the area and food spots. Robert is a friendly, responsive host and I highly recommend his place for a great experience in the redwoods!

A bright interior space features large windows allowing natural light to fill the area. Colorful cushions in various shades are arranged on the floor, complemented by wooden accents and an open ceiling design that highlights the natural surroundings.

Treehouse in Half Moon Bay

4.98 out of 5 average rating, 103 reviews

Paradise Treehouse & Heavenly Cabin

ArmandoRating, 5 stars1 day ago

Staying here was an unforgettable experience. The treehouse itself is beautifully designed, perched among the trees with breathtaking views in every direction. It felt like stepping into a peaceful, secluded world, while still having all the comforts of home. One of the highlights was the outdoor tub — it’s large enough for two people and the water gets wonderfully hot, perfect for a long soak under the trees. It was one of the most relaxing parts of the trip. Adding to the charm, a friendly cat kept an eye on us the whole time, almost like a little guardian of the property. Their visits made the whole experience feel even more welcoming and cozy. As a heads up, you do need to walk down to the cabin to use the bathroom — a small adventure at night, but honestly part of the fun once you get used to it. Everything about the stay felt thoughtful and unique. It’s the kind of place that leaves you feeling recharged, inspired, and already dreaming about the next visit.

A verdant garden is displayed, featuring a pathway lined with stepping stones leading to the two cabins. Lush plants and vibrant flowers surround the space, complemented by raised garden beds filled with herbs and vegetables. The cabins, with large windows, are visible in the background.

Guesthouse in Oakland

4.91 out of 5 average rating, 336 reviews

Guesthouse Garden Retreat

JonahRating, 5 stars2 weeks ago

Michelle is a great host and the cottage was lovely! The garden is gorgeous and there are lots of places to relax outside. I felt very welcome and taken care of! It was not an issue for me at all, but the location is a little ways out from the action and there is not a lot close by. On the plus side, it’s relatively quiet, cozy, and relaxing! I enjoyed the hot tub both mornings I was there! Overall , a very pleasant experience!

Top guest favorite

A covered balcony features two light blue chairs with striped cushions, overlooking the neighborhood. The wooden railing offers a sense of openness, while the surrounding area includes a glimpse of greenery and residential rooftops. Natural light brightens the space.

Home in Pacifica

4.96 out of 5 average rating, 227 reviews

Brighton Beach Cottage, One Bedroom plus Loft

NaomiRating, 5 stars1 week ago

We’ve come to stay here once a year for the last 3 years and it is amazing. The home itself, the area, the 10 minute walk to the beach. I mean, we will be back again next year. We love it so much and Michael is so friendly and welcoming!

The communal lounge area features a spacious layout with a comfortable sectional sofa adorned with decorative pillows. Natural light floods in through large windows, illuminating the modern decor. A billiards table is visible in the background, along with potted plants that enhance the inviting space.

Apartment in Menlo Park

4.97 out of 5 average rating, 146 reviews

Charming 2BR Apartment near tech Giants & Stanford

AntjeRating, 5 stars2 weeks ago

Amazing home, with lots of space -more then expected- well equipped kitchen, all we could wish for making dinner, cozy beds and comfortable living area. Pool was great, calm neighbourhood, but car is necessary to shop groceries or visit restaurants. Communication was quick and easy. We will come back!

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodations and amenities

Popular amenities for Woodside vacation rentals

Laptop-friendly workspace

Stay near Woodside's top sights

Alice's Restaurant65 locals recommend

Buck’s Restaurant, Woodside49 locals recommend

The Village Pub48 locals recommend

Rosewood Sand Hill37 locals recommend

Huddart Park33 locals recommend

Lucky30 locals recommend

Other great vacation rentals in Woodside

Top guest favorite

A wooden deck is shaded by a pergola adorned with lush wisteria, offering a scenic view of the surrounding landscape. A rectangular table and several chairs provide seating for outdoor dining. Green trees frame the horizon, creating a peaceful outdoor retreat.

Home in Oakland

4.99 out of 5 average rating, 123 reviews

Beautiful Home. Gorgeous Views. Five Bedrooms.

JohnathonRating, 5 stars5 days ago

This home was perfect. the view from the porch was breathtaking. everything was great. safe quite location.

Camper/RV in Half Moon Bay

4.94 out of 5 average rating, 16 reviews

Breathtaking CA Coast Airstream - Beachfront (NEW)

FleourdelisRating, 5 stars1 week ago

we had an amazing stay here! view was breathtaking! campfire was a plus!!! we’ll be back!

A modern bathroom features a glass-enclosed shower with a sleek showerhead and contemporary fixtures. The walls are adorned with textured tile, and a vanity with a mirror is seen in the background. Soft lighting from multiple sconces enhances the clean aesthetic.

Apartment in South San Francisco

4.92 out of 5 average rating, 37 reviews

Sparkling Clean Newly Remodeled 1BR near SF/SFO+EV

AlyssaRating, 5 stars1 month ago

We found George's place last minute on our way into San Francisco and it was the perfect place for a restful night after a long day of flying. In the morning it was a nice 10 minute for some delicious breakfast, would definitely book again!

An open kitchen and dining area feature a large kitchen island with modern appliances and dark cabinetry. A dining table with white tablecloths is surrounded by various chairs, while a small desk with a monitor is positioned near a window, allowing natural light to fill the space.

Home in Campbell

5 out of 5 average rating, 25 reviews

3 bdrm 2bath bright renovated private deck

NathanRating, 5 stars5 months ago

I always choose to stay at Emrehans when I need a place near San Jose. Very beautiful, clean home/yard, great location. Emrehan communicates well and has been very accommodating to me. Very good price for the stay. Would recommend.

Home in Castro Valley

5 out of 5 average rating, 3 reviews

2BR House with Canyon & Hillside Views

MercedesRating, 5 stars2 months ago

Our stay was absolutely wonderful! The home was peaceful and located in a quiet, friendly neighborhood with beautiful views. One of the biggest highlights was how welcoming they were to our pups. It made our stay even more enjoyable. Communication was excellent; they were always quick to respond to any questions we had. Overall, a fantastic experience, and we would definitely stay here again!

The image showcases a panoramic view of a residential neighborhood with a clear ocean view in the background. Several houses with varied architectural styles are visible, surrounded by greenery and open spaces. The blue sky is dotted with a few clouds, enhancing the serene coastal atmosphere.

Home in Half Moon Bay

4.97 out of 5 average rating, 150 reviews

Entire house：Steps to beach and ample space

DarleneRating, 5 stars1 week ago

Loved the home. Very comfortable and great location for us. Beds comfortable. Kitchen well equipped. Would definitely return

A view of the ocean and pier is framed by sliding glass doors, which open onto a private terrace. The calm water reflects the colors of the sky, while a comfortable seating area is positioned nearby, providing an inviting spot to enjoy the scenery.

Condo in Pacifica

4.98 out of 5 average rating, 240 reviews

Luxury Beachfront Condo Near SF (Blue Wave 1)

MonikaRating, 5 stars1 week ago

It's a beautiful place! The ocean view is spectacular. The lights on the Pacifica Pier light up the ocean at night so it feels like you have an ocean view 24/7.

A panoramic view of the San Francisco neighborhood is showcased, with rolling hills and homes visible in the distance. The foreground features tall trees and an elevated street, while a glimpse of the bay and distant hills can be seen under a clear blue sky.

Home in Noe Valley

4.91 out of 5 average rating, 172 reviews

Noe Valley entire guest suite overlooking downtown

IsmailRating, 5 stars5 days ago

Very comfortable apartment, Veronica was available and responded quick for all queries

Quick stats about vacation rentals in Woodside

Total rentals
130 properties
Total number of reviews
6.4K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
80 properties have a dedicated workspace

Frequently Asked Questions

Where should I stay in Woodside?
Make yourself at home in Woodside by choosing from our most frequently booked neighborhoods. We have over 940 vacation rentals in Woodside Plaza, over 940 vacation rentals in Woodside Hills, and over 1,050 vacation rentals in Farm Hill.
Are there vacation rentals with a dedicated workspace in Woodside?
Yes! Work meets play with ease at over 80 vacation rentals in Woodside featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in private suite rentals in Woodside?
Experience the best of Woodside with our private suite rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Woodside?
Four-legged friends are welcome in Woodside. Choose from more than 40 vacation rentals for guests traveling with pets.
Are there Woodside vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Woodside, available on Airbnb. Make a splash and soak up the sun in style!
What are the most popular amenities for House Rentals in Woodside?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with self check-in, over 10 homes with a bbq area, over 50 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Woodside have self check-in?
Absolutely! We offer over 10 house rentals with self check-in in Woodside. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Woodside have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Woodside. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Woodside have wifi?
Absolutely! We offer over 50 house rentals with wifi in Woodside. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Woodside?
Woodside has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore