
Vacation rentals in Flying Cloud Isle
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Top-rated vacation rentals in Flying Cloud Isle
Guests agree: these stays are highly rated for location, cleanliness, and more.

Quiet 3ba/2ba HOUSE with backyard orchard. 🏡
For Business or Leisure. Comfortable place with easy check in with a team, smart choice over hotel. Beautiful 3 bedrooms home in nice neighborhood of San Mateo in the heart of Silicon Valley. 10 mins to SFO, 7 mins to Cal Trains, 11mins to BART train. A convenient location just a short hop to San Francisco and Palo Alto. Walk to the beach, running trail with breathtaking bay view, tennis court. Open to long term furnished rental. All 3 bedrooms with premium queen beds and mattresses. New Sofa
ValueFamilyKitchen
4.83 out of 5 average rating, 227 reviews
Private Garden Cottage
Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.
ValueFamilyBathroom
4.99 out of 5 average rating, 856 reviews
3 Bed 2 bath San Mateo Home
Mid-Peninsula home, close to major companies: Oracle, Gilead, Visa, and San Mateo Expo Center. 15 min to the coast, 25 min to SF, 35 min to SJ, 10 min to SFO. Several shopping centers within 5 min drive, so many shopping and food options. 1. No parties . 2. Flexible on price Mid-Nov to Mid- Feb. 3. Due to City single use soap/ shampoo ban guest will need to bring their own (hand and dish soap is provide). 4. Max number of guest overnight guests is 2 per room or 6 total. See house rules
LocationValueNearby
4.74 out of 5 average rating, 73 reviews
Lavish Modern Home 4BR near SFO/Palo Alto/Stanford
Experience a luxurious modern home in Foster City featuring an open floor plan, high ceilings with ample natural light, stylish decor, and top-tier appliances. The house also offers a beautiful outdoor living area with a contemporary patio, grill, outdoor dining table, along with a dedicated children's sandbox and play area. Situated in the heart of Silicon Valley, it's just a 20-minute drive to SFO, Stanford, Palo Alto, Meta, making it an ideal choice for families and business travelers!
FamilyLocationAccess
5.0 out of 5 average rating, 85 reviews
SFO 10 min, Stylish Suite, Walk to Grocery
Ten minutes to SFO, a short walk to Caltrain, and one block from cafés and restaurants— this private San Mateo suite is the ideal Bay Area base for business travelers, airport transits and couples exploring the peninsula. Settle into a comfortable queen bed with room-darkening shades, pull up a dedicated workspace with 789 Mbps WiFi, and unwind with Netflix, HBO Max, Disney+, Hulu, or Amazon Prime on the smart TV. Everything is taken care of so you can focus on why you're here.
FamilyValueAir conditioning
4.93 out of 5 average rating, 126 reviews
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
LocationValueCheck-in
4.98 out of 5 average rating, 254 reviews
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.
FamilyLocationAccess
4.88 out of 5 average rating, 247 reviews
Redwood Forest A-Frame Retreat in the Bay Area
Live in this Redwood Forest estate where fresh air and nature is abundant. Unique A frame architecture and wrap around deck offers a serene escape from the bay area bustle. Fully remodeled kitchen and bathrooms with sauna. Just 15 minutes to San Mateo and Half Moon Bay and Woodside town center and 10 minutes to Alice's. Off Skyline Blvd without the main road noise and nestled within the giant sequoias and wander inside the redwoods through endless trails.
LocationBathroomIndoor spaces
5.0 out of 5 average rating, 8 reviews
Relaxing Backyard Retreat -Spacious + Bright Home
Escape, relax, and recharge at our beautiful 3-bedroom, 2-bath retreat in San Mateo, perfectly designed for families, friends, and remote workers seeking comfort and convenience. Featuring a modern open-concept layout, this spacious home is ideal for gathering, entertaining, or unwinding in style. Step outside to your private backyard oasis with lush greenery, a cozy patio, and glowing string lights,the perfect spot to enjoy peaceful Bay Area evenings.
FamilyLocationComfort
4.83 out of 5 average rating, 122 reviews
Serene Modern Home with Yard & Parking
This spacious, tastefully decorated and full of natural light large house is a perfect combination of comfort and style. The house is recently renovated and has got everything to accommodate all your needs for a perfect stay. Convenient strategic location and easy commute to SF, Silicon Valley, BART and Airport, full amenities, parking, safe and quiet neighborhood, professionally managed, immaculately clean and more. Book now before someone else does!
ValueFamilyAccuracy
4.92 out of 5 average rating, 319 reviews
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.
FamilyLocationLayout
4.93 out of 5 average rating, 326 reviews
Cottage on the Water -SUP,Kayaking,Canoeing
Private Club House Water Front. Free use of stand-up paddle board, kayak, and canoe. Private entrance with Smartlock and wifi. Modern studio with full bathroom. and the kitchenette area is fully furnished for light cooking. Conveniently located near grocery, Target, Trader Joes, and restaurants. 5 minutes from Downtown San Mateo, and 10 minutes from SF Airport. Looking to get away from the bay area without actually leaving, nice escape.
ValueFamilyQuiet
4.88 out of 5 average rating, 135 reviewsPopular amenities for Flying Cloud Isle vacation rentals
Other great vacation rentals in Flying Cloud Isle

1725 - Modern & Cozy 2B2B at Heart of San Mateo
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4.94 out of 5 average rating, 53 reviews
Tesla EV Charger Basketball Pool Table Hot Tub Spa
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5.0 out of 5 average rating, 76 reviews
Panoramic Bay View • Single-Level • 1Gbps WiFi
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5.0 out of 5 average rating, 27 reviews
Renovated 3b1.5b San Mateo hill near SFO/Stanford
LocationFamilyGetting around
4.98 out of 5 average rating, 51 reviews
3B AC | EV charging| Jacuzzi| Fence yard| WiFi
FamilyLocationGrill
4.82 out of 5 average rating, 62 reviews
High Ceilings! Modern Spacious Bright 4BR Home
FamilyLocationCleanliness
4.97 out of 5 average rating, 125 reviews
Dandy retreat convenient location
FamilyLocationBeach
4.81 out of 5 average rating, 181 reviews
Jane's Home (LA) | Remodeled 2b2b +Backyard
ValueFamilyLong stay
4.88 out of 5 average rating, 52 reviewsDestinations to explore
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