Book Luxury Holiday Rentals in San Mateo County

Award-winning homes from £98

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Home spotlights in San Mateo County

Large Glass of Red

Large Glass of Red

  • 24 guests

  • 8 bedrooms

Napa County, California

Just outside of the village of Calistoga in the northernmost tip of the Napa Valley, you'll encounter this rustic yet refined retreat surrounded by acres of verdant vineyards and lush gardens. With no nearby neighbours, enjoy that all-too-rare feeling of seclusion, yet the convenience of only being a mile and a half from downtown Calistoga.

Vineyards & Verandas

Vineyards & Verandas

  • 6 guests

  • 3 bedrooms

Healdsburg, Sonoma County

Live the Dry Creek Valley dream in this magnificent modern farmhouse. Boasting unbeatable vineyard Views, a wrap-around veranda, and a private garden complete with patio, outdoor seating and barbecue station, this immaculate home is the ultimate Californian wine country destination.

If You Come Back to California

If You Come Back to California

  • 6 guests

  • 3 bedrooms

Sonoma County, California

Some places have the power to seduce you at first sight, and this exceptional home nestled in the gorgeous rural setting of Napa Valley is certainly one such place. Offering both the tranquillity of nature and close proximity to the town of Calistoga, you’ll get the best of both worlds here, and with all the exciting activities to be enjoyed in the area, you don’t have to be a wine connoisseur to have a fantastic time.

Black Walnut Cove

Black Walnut Cove

  • 2 guests

  • 1 bedrooms

Pedro Point, Pacifica

Tucked away in the serene coastal community of Pedro Point, this modern cabin offers the perfect escape to the shores of the Pacific Ocean. Located just a nine-minute walk from Pacifica State Beach and a six-minute stroll from Shelter Cove Beach – you'll be blown away by the bay's beauty, making it a popular spot for photographers.


We selected the top 3% holiday homes in San Mateo County Holiday Rentals

Explore the 122 most perfect homes in our collection

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Most popular homes in San Mateo County

Willow Cove

Willow Cove

  • 2 guests

  • 1 bedrooms

Pedro Point, Pacifica

Run Russian River Run

Run Russian River Run

  • 4 guests

  • 2 bedrooms

Guerneville, California

The Valley Stream

The Valley Stream

  • 2 guests

  • 1 bedrooms

Healdsburg, Sonoma County

Redwood Riverside

Redwood Riverside

  • 6 guests

  • 3 bedrooms

Sonoma County, California

Cabernet Cottage

Cabernet Cottage

  • 6 guests

  • 2 bedrooms

Sonoma County, California

Live Oak Cove

Live Oak Cove

  • 2 guests

  • 1 bedrooms

Pedro Point, Pacifica

Coffee Shop Soundtrack

Coffee Shop Soundtrack

  • 4 guests

  • 2 bedrooms

Menlo Park, San Mateo County

The White Cloud

The White Cloud

  • 4 guests

  • 1 bedrooms

Sonoma County, California

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in San Mateo County, California, United States. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that San Mateo County, California, United States has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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