Book Luxury Short Stay Rentals in San Mateo County

We selected the 118 homes worth renting in this location

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Home spotlights in San Mateo County

Climb the Vine

Climb the Vine

  • 4 guests

  • 2 bedrooms

Sonoma County, California

Escape to the (wine) country with a stay at this stunning single-storey home, complete with its own vineyard. Vast floor-to-ceiling sliding doors reflect that life here is best lived outside, while its single-storey layout and open living spaces encourage you to spend time together inside and out.

Cabernet Cottage

Cabernet Cottage

  • 6 guests

  • 2 bedrooms

Sonoma County, California

This delightful Wine Country home is a superb choice for a family or group of friends hoping to relax, unwind, and try some of California’s finest tipples. A newly built cottage, this home sits just eight miles from Healdsburg Plaza, and a few minutes from Lake Sonoma.

Academic Pursuits

Academic Pursuits

  • 8 guests

  • 4 bedrooms

College Terrace, Palo Alto

This home might be close to Stanford University, but it's a million miles away from your average student house. In fact, parts of it feel more like a learned professor's seminar room, from the shelves packed full of books and the grand piano, to the historic paintings hanging on the walls.

The Curve of the Moon

The Curve of the Moon

  • 10 guests

  • 4 bedrooms

El Granada, San Mateo County

With the magic of the sea, sun, and stars surrounding you at Half Moon Bay, this incredible home is the perfect weekend retreat for a family, only twenty minutes away from San Fransisco. Charge the Tesla at the EV charging station and then explore the trails of the National Forest backing the house or pack your beach bag and stop by the Pacific Ocean, a fifteen-minute stroll away.


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

Explore the 118 most perfect homes in our collection

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Most popular homes in San Mateo County

The Northstar

The Northstar

  • 6 guests

  • 3 bedrooms

Placer County, California

Run Russian River Run

Run Russian River Run

  • 4 guests

  • 2 bedrooms

Guerneville, California

The Circle Of Light

The Circle Of Light

  • 10 guests

  • 4 bedrooms

Incline Village, Washoe County

The Smiling Poet

The Smiling Poet

  • 4 guests

  • 2 bedrooms

Golden Rectangle, Carmel-by-the-Sea

Redwood & Palm

Redwood & Palm

  • 6 guests

  • 3 bedrooms

Santa Cruz County, California

Silicon Cypress

Silicon Cypress

  • 4 guests

  • 3 bedrooms

Shoreline West, Mountain View

Amidst The Vines

Amidst The Vines

  • 6 guests

  • 3 bedrooms

Sonoma County, California

Crow's Nest

Crow's Nest

  • 6 guests

  • 3 bedrooms

Cambria, San Luis Obispo County

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Frequently asked questions

Browse our curated collection of Short Stay Rentals in San Mateo County, California, United States. From impeccable interior design and chef-worthy kitchens, to fully furnished bathrooms and the inclusion of all linens, the homes in our collection come complete with everything you need. Each of the San Mateo County luxury short stay apartments in our collection has been expertly reviewed to ensure the quality standards you can trust, so book today to enjoy a getaway to remember. And should you need any assistance, our friendly team of experts are here to help you find the perfect home.

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