The 30 Best Holiday Rentals in San Mateo County

Ranked 1 out of 115 in the region, as well as being 1 of 6 for holiday rentals in Montara.

• “The house provided an unparalleled sense of home, wrapping...”
• “Absolutely beautiful and and amazing experience!! We had an amazing time!”
• “We thoroughly enjoyed our stay!”
• See more reviews of Montara Beach Mountain Escape

Ranked 2 out of 115 in the region, as well as being 1 of 9 for holiday rentals in Half Moon Bay.

• “We will be back and pick this cottage as our go-to place to stay while in HMB.”
• “Relaxing, lovely little gem of a place. Well done.”
• “We loved our visit. The house was very cute and welcoming. The hottub and back yard was wonderful and loved the fact tha”
• See more reviews of Charming Garden Cottage- steps to historic Old Town Half Moon Bay

Ranked 3 out of 115 in the region, as well as being 1 of 1 for holiday rentals in Oceanview.

• “”
• “”
• “Very clean and safe. It had everything we needed.”
• See more reviews of House-Canyon Dr

Ranked 4 out of 115 in the region, as well as being 3 of 11 for holiday rentals in Millbrae.

• “Great property.”
• “Fantastic, quiet stay that allowed our family to spend time with each other!”
• “Safe, clean, comfortable”
• See more reviews of 3 bedroom residential home in the lovely town near SFO San Francisco

Ranked 5 out of 115 in the region, as well as being 1 of 15 for holiday rentals in Pacifica.

• “We rented this home for my birthday with a group of friends. The house was great, views were amazing but dishes were fou”
• “It was perfect!”
• “It was a great getaway for our group.”
• See more reviews of @ Marbella Lane - Oceanfront w/ unobstructed views!!

Ranked 6 out of 115 in the region, as well as being 2 of 9 for holiday rentals in Half Moon Bay.

• “Zen Cottage”
• “It was perfect location for us because we like to walk.”
• “”
• See more reviews of Coastal Zen Cottage - Walk To Beach

Ranked 7 out of 115 in the region, as well as being 1 of 14 for holiday rentals in San Bruno.

• “Spotlessly, clean and updated.”
• “”
• “Excellent!”
• See more reviews of Lovely 3 bedroom house for 6 people Near SFO SF Bay Area Newly updated

Ranked 8 out of 115 in the region, as well as being 3 of 6 for holiday rentals in Montara.

• “Great views of the coast.”
• “Worth it if you spend most of your time outside”
• “Hidden gem with great communication by management company :)”
• See more reviews of Entire Private Coastal Retreat - Spectacular Ocean Views wHot Tub

Ranked 9 out of 115 in the region, as well as being 1 of 3 for holiday rentals in Brisbane.

• “Exceptional Home”
• “Amazing view!”
• “We had a comfortable stay. The ciew is stunning, take a descent car as it is a challenge to gonup the road”
• See more reviews of Stunning Views by the Bay 2BR

Ranked 10 out of 115 in the region, as well as being 7 of 16 for holiday rentals in Menlo Park.

• “Lovely and spacious in a quiet convenient location with highly attentive owner”
• “We love the stay and would love to book again!”
• “Very good and clean, decoration is nice, host is nice, super...”
• See more reviews of Dazzling Modern Home Close to Downtown Palo Alto and Stanford

Ranked 11 out of 115 in the region, as well as being 3 of 9 for holiday rentals in Half Moon Bay.

• “We enjoyed our stay enough that we stayed an extra day!”
• “Relaxing get away!”
• “Beautiful, dreamy experience. A perfect way to make special memeories with kids and teens.”
• See more reviews of Beach Villa Home - Walk to Beaches Trails Restaurants Activities & more

Ranked 12 out of 115 in the region, as well as being 8 of 16 for holiday rentals in Menlo Park.

• “”
• “Large, new and clean”
• “”
• See more reviews of Mint House - Menlo Park

Ranked 13 out of 115 in the region, as well as being 4 of 9 for holiday rentals in Half Moon Bay.

• “Cosy”
• “Our stay was very enjoyable!”
• “Great location. Well furnished, quite spacious, tad over priced.”
• See more reviews of Nantucket Penthouse - walk to restaurants beaches activies & so much more

Ranked 14 out of 115 in the region, as well as being 3 of 12 for holiday rentals in Daly City.

• “”
• “A warm stay for a cold city”
• “Good for people on the go to explore the city”
• See more reviews of Private Unit / Private Bathroom Near BART & SF

Ranked 15 out of 115 in the region, as well as being 4 of 15 for holiday rentals in Pacifica.

• “Easy professional”
• “Love it”
• “Lovely location”
• See more reviews of @ Marbella Lane – Home with Majestic Ocean Views

Ranked 16 out of 115 in the region, as well as being 5 of 9 for holiday rentals in Half Moon Bay.

• “Truly a home away from home!”
• “Amazing! Highly recommended.”
• “Beautiful, comfortable, home away from home. Would come back!”
• See more reviews of Half Moon Bay Vacation Rental 1 Mile to Beach!

Ranked 17 out of 115 in the region, as well as being 6 of 9 for holiday rentals in Half Moon Bay.

• “”
• “The gallery was beautiful and a really special place to stay!”
• “Beautiful!!”
• See more reviews of Seaside Art Gallery Loft Inspire Your Creativity with Breathtaking Views!

Ranked 18 out of 115 in the region, as well as being 5 of 6 for holiday rentals in Montara.

• “Quiet location away from the Hustle and bustle of San...”
• “Wonderful family break.”
• “”
• See more reviews of Oceanview Beach Home Walk to Beach Trails Food Family Activities

Ranked 19 out of 115 in the region, as well as being 6 of 15 for holiday rentals in Pacifica.

• “Spacious house. Grwat view of the ocean.”
• “Everything was as it should be. We were very happy and sad to leave.”
• See more reviews of @ Marbella Lane Top Coastline Views, Family Friendly

Ranked 20 out of 115 in the region, as well as being 4 of 12 for holiday rentals in Daly City.

• “”
• “Wouldn't book again”
• “Great location and quiet neighborhood”
• See more reviews of 靠近舊金山國際機場的民宿

Ranked 21 out of 115 in the region, as well as being 5 of 12 for holiday rentals in Daly City.

• “Very good.”
• “”
• “Our Stay in Daly City”
• See more reviews of 2 Bedroom House OR Private Studio near SF, SFSU and SFO

Ranked 22 out of 115 in the region, as well as being 7 of 9 for holiday rentals in Half Moon Bay.

• “2 nights in half moon bay”
• “It was enjoyable since we were able to spend time with family and the facilities met our needs.”
• “Overall very clean and comfy place”
• See more reviews of @ Marbella Lane Seaside Retreat, Walk to the Beach

Ranked 23 out of 115 in the region, as well as being 8 of 15 for holiday rentals in Pacifica.

• “Good value for the price and comfortable beds”
• “Decent place, slow service , near ocean”
• “Great comfortable location for group or family with short easy access to beach and easy quick drive to San Francisco.”
• See more reviews of @ Marbella Lane - Buckingham Place Laundry + P

Ranked 24 out of 115 in the region, as well as being 13 of 14 for holiday rentals in San Bruno.

• “”
• “There are good restaurants within walking distance.”
• “location & space”
• See more reviews of Luxury 5 Bedroom Home near SFO

Ranked 25 out of 115 in the region, as well as being 11 of 16 for holiday rentals in Menlo Park.

• “”
• “Very convenient and comfortable for us! Thanks”
• “Nice room in a quiet neighborhood”
• See more reviews of Menlo Park Studio about 2 Mi to Stanford University

Ranked 26 out of 115 in the region, as well as being 8 of 9 for holiday rentals in Half Moon Bay.

• “The house was ideal for our writing retreat -- perfect for shared meals, writing, beach walks”
• “The location, accommodations and host were amazing!”
• “Great place for large group.”
• See more reviews of Now Trending - Entire Beach Home Walk to Beaches Restaurants Activities

Ranked 27 out of 115 in the region, as well as being 1 of 1 for holiday rentals in East Palo Alto.

• “A nice place to stay in East Palo Alto”
• “Well Appointed and Comfortable”
• “Worth what we paid. Would stay there again.”
• See more reviews of Brand new suite, 1mi to Meta, 3mi to Stanford

Ranked 28 out of 115 in the region, as well as being 9 of 9 for holiday rentals in Half Moon Bay.

• “It was a great anniversary get away for the two of us.”
• “I couldn’t have asked for a better place to unwind and soak in the beauty of Half Moon Bay. Highly recommend for anyone”
• “Outrageous communication. Never again.”
• See more reviews of Luxury Beachfront Penthouse Walk to the Beach Restaurants Entertainment

Ranked 29 out of 115 in the region, as well as being 1 of 2 for holiday rentals in Moss Beach.

• “Heavenly house with next to open space marine reserve.”
• “Would love to come back”
• “A beautiful and restful escape.”
• See more reviews of Oceanfront Home Retreat w Breathtaking Views of Fitzgerald Marine Reserve

Ranked 30 out of 115 in the region, as well as being 10 of 17 for holiday rentals in Redwood City.

• “spacious freestanding house with great garden.”
• See more reviews of @ Marbella Lane - Modern and Sleek Home in Redwood