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.

Utmost Taste

Utmost Taste

  • 4 guests

  • 2 bedrooms

Healdsburg, Sonoma County

Sitting in the middle of California's Wine Country, you might picture homes here to lie on the rustic side of things, but that couldn't be further from the truth at this address. Behind the sliding glass doors, guests will find an interior that is exquisitely put together – whitewashed walls are adorned with tasteful artwork, the furnishings hark back to mid-century trends, and the glossy bathrooms wouldn't look out of place in a spa.

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.

Live Oak Cove

Live Oak Cove

  • 2 guests

  • 1 bedrooms

Pedro Point, Pacifica

Compact yet strikingly chic, this bright studio in Pacifica is an ideal base for those looking to be within walking distance of the beach in a quiet, residential community. You’ll immediately be drawn to the home’s stylish architecture – from its wood panelling to its cool wraparound balcony.


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

Explore the 130 most perfect homes in our collection

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Most popular homes in San Mateo County

Black Walnut Cove

Black Walnut Cove

  • 2 guests

  • 1 bedrooms

Pedro Point, Pacifica

The Northstar

The Northstar

  • 6 guests

  • 3 bedrooms

Placer County, California

Amidst The Vines

Amidst The Vines

  • 6 guests

  • 3 bedrooms

Sonoma County, California

Wine Country Rhapsody

Wine Country Rhapsody

  • 12 guests

  • 6 bedrooms

Sonoma County, California

If You Come Back to California

If You Come Back to California

  • 6 guests

  • 3 bedrooms

Sonoma County, California

Fair of Face

Fair of Face

  • 4 guests

  • 2 bedrooms

Menlo Park, San Mateo County

Willow Cove

Willow Cove

  • 2 guests

  • 1 bedrooms

Pedro Point, Pacifica

The Viticulturalist

The Viticulturalist

  • 4 guests

  • 2 bedrooms

Paso Robles, San Luis Obispo County

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Check upcoming rates & availability for San Mateo County Holiday Rentals


Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in San Mateo County. 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 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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