Holiday rentals in San Mateo

Sunny Private Escape | Gated, Peaceful & Safe

Newly renovated, bright & private guesthouse with gated entry, driveway parking & sunny garden patio. Safe, quiet & central—located in the historic San Mateo Park neighborhood near downtown San Mateo, Burlingame Ave, SFO & Stanford. Completely remodeled in 2025 features queen bed,stocked kitchen & all the modern comforts including new appliances, custom kitchen & bath finishes, and a hand crafted dutch door leading out to the newly built private garden patio. Ideal for business or leisure stays.

High Ceilings! Modern Spacious Bright 4BR Home

A Hidden Gem! Spacious, tastefully designed, newly renovated modern home on a charming cul-de-sac in Foster City. Ideal open layout with 16ft vaulted ceilings, abundant natural light, expansive backyard with grill and full amenities, making for a great space to entertain and unwind in comfort & style. Centrally located between San Francisco & Silicon Valley. Close to SFO airport, caltrain, restaurants, markets, San Mateo, Stanford, Palo Alto. Perfect for business travelers or family vacations.

Modern Private Guest Suite in San Mateo

Enjoy a clean, modern, and spacious private guest suite nestled in the quiet hills of San Mateo, perfect for business travelers, couples, or solo guests. The suite is attached to the main home and does not include a kitchen, but it is equipped with a microwave and mini fridge. Free street parking is available, and the central Bay Area location offers easy access to San Francisco, San Jose, SFO, and Oakland Airport, making it ideal for both work travel and exploring the Bay Area.

Mid-century retreat - fire pit and backyard

Welcome to a beautifully renovated 1956 Eichler home in the San Mateo Highlands - a distinctive mid-century space with soaring ceilings, natural light, and a private backyard made for gathering. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & outdoor dining - Enclosed atrium w/ custom mural & red maple tree - Dedicated private office w/ door - Wood-burning fireplace & full kitchen w/ gas stove - 20 mins to SF | 15 mins to SFO | Near Caltrain

12-Min From SFO, Tastefully Designed, Work Station

Welcome to the Laurel Pad, a home away from home. You'll enjoy the convenience this house offers - fully stocked kitchen, minutes away from amazing restaurants, supermarkets, parks, 13-min to SFO, 25-min to downtown San Francisco, and easy access to major companies around Silicon Valley. This bright and sunny house is tastefully designed and updated to offer functionality and aesthetics. You'll have access to fast wifi and dedicated driveway parking for up to two cars.

Modern guest house in great location

Private 1 bedroom + 1 bathroom with your own entrance. Highlights: • self-checkin with code on digital lock • free parking + additional free street parking • professional cleaning and sanitizing • king size bed with premium mattress and linens • located at end of cul-de-sac in a safe and quiet neighborhood • standing desk with monitor and docking station • high speed WiFi • 55” smart TV • Rainfall shower, bidet toilet with heated seat, heated towel rack, makeup mirror

Delightful Hideaway in San Carlos

Fully equipped executive studio in the heart of Silicon Valley. This studio is ideal for accommodating executives, visiting doctors and nurses and other professions that might require long term stays. Visitors will enjoy the warm family-friendly environment and delightful garden setting. It is also well-suited for those on vacation who delight in visiting the nearby cities, as well as those who have families close by and want to have their own private spot.

Spacious, Remodeled 2BR Duplex Unit by Downtown SM

Enjoy a stylish, peaceful experience at this centrally located place in San Mateo! If you like to go out, an easy 15 minute walk or 4 minute drive to downtown with over 100 restaurants and dessert stops or San Mateo Central Park await you! If you like to stay in, relax in your 2024 remodeled 1400 sq ft home furnished with modern, cozy vibes. Entirely private, rear-unit of a duplex with a fully dedicated parking space, backyard space, and laundry room.

Lagoonfront Retreat: 3BR House Near SFO

Our stunning Airbnb listing offers both convenience and relaxation. 5min to multiple supermarkets and 15mins to SFO. Enjoy breathtaking views of the lagoon, modern decor, a fully-equipped kitchen, two comfortable living areas, and three cozy bedrooms with high-quality linens. We provide high-speed Wi-Fi, working desks, and heating for your comfort. We look forward to hosting you and helping you make the most of your stay in this beautiful area.

SFO 10 Min • Family 2BR + Patio Games • Baby-Ready

Two queen bedrooms, a private patio with lawn games, an in-unit washer/dryer, and a baby-and-toddler setup that covers everything from crib to high chair — this is the Bay Area family home you've been searching for. Ten minutes from SFO, a block from groceries and restaurants, and a short walk to Seal Point Park's waterfront trails, it's the kind of place where you actually unpack and settle in, not just sleep between activities

Luxury King Bed & Spa Bathroom

Our spacious guest suite has its own private entrance, comfortable pillow-top king size bed, work-friendly laptop desk, hi-speed wifi, spa bathroom with heated floor, mini fridge, and microwave. The guest suite is part of the main home, but there are no shared spaces and the areas are separated by a locked solid wood door & noise-dampening cushions. Our guest suite is ideal for couples visiting family in the neighborhood.

New modern 1 bedroom unit

New modern 1 bedroom/studio unit in beautiful residential neighborhood near the water. Separate entrance that is fully furnished with top of the line appliances and high ceilings. Full size bed. Close access to highway 101, 92 and 280. Plenty of shopping nearby, Bridgepointe Shopping Center and Hillsdale Mall. Need to relax, stroll down to Gull Park to enjoy the water. Kayak and Stand-up Paddle Board available to borrow