
Luxury rentals in San Mateo County
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Top-rated luxury holiday rentals in San Mateo County
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5BR Designer Home w/ SunDeck Near Stanford & 280
Welcome to your modern oasis in Menlo Park — just minutes from Stanford University, Palo Alto, and Sand Hill Road. Whether visiting for work, or a gathering, this spacious 5-bedroom home offers stylish comfort, thoughtful design, and a peaceful outdoor terrace with a sunlit curved sundeck. Bedrooms: 5 spacious bedrooms | 7 beds total -1 King bed -5 Queen beds (2 Queens in one bedroom) -1 Twin bed (in a cozy area with piano & desk) Perfect for families, teams, or groups seeking an elegant stay.

Montebello Views Villa
Set in the Santa Cruz Mountain Foothills, one mile below the world famous Ridge Vineyards, this luxurious vineyard villa is decorated with soaring mountain views, lush greenery, and mature trees. The lagoon-style pool and hot tub feels like a truly private oasis; kids will love playing under the waterfalls and on the slide. Enjoy dining alfresco with the outdoor kitchen while taking in the sunset on one of the many decks. Inside you'll have various spaces to gather including a media/game room

Stunning California Resort + Infinity Pool
Ready to be WOWed!? We can't wait to welcome you to this California Getaway! It's perfect for your relaxing and fun-filled stay! The property is located in Woodside and is extremely secluded with breathtaking views. The house is just what you need to escape the hustle and bustle of daily life. The home has received a number of improvements over the year: a pool heater, new movie theater chairs, desks & chairs for the bedrooms, Peloton Tread & Mirror Workout Studio in the gym!

Distinguished Oceanfront Point Estate with Iconic
Perched above Montara State Beach, Point Estate is a gated coastal estate with sweeping Pacific vistas and unmatched privacy. Just 20 minutes from San Francisco and Silicon Valley, it offers a main residence, private guest residences, expansive decks, and wellness amenities—perfect for retreats, events, and unforgettable stays.

The Pacific Dream
Your ocean dream manifests here. Resting on the very edge of the Pacific, this exquisite villa has been designed and constructed from the ground up to unite you with the beauty and peace of the surrounding waters. All-new construction completed in 2020 and professionally curated decor encompasses every corner of the villa.
Popular amenities for San Mateo County luxury holiday rentals
Other great luxury holiday rentals in San Mateo County

Distinguished Oceanfront Point Estate with Iconic

The Pacific Dream

Montebello Views Villa

Stunning California Resort + Infinity Pool

5BR Designer Home w/ SunDeck Near Stanford & 280
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