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.

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Superhost
A spacious living area features a red leather sofa paired with a matching ottoman. A wicker chair adds additional seating, while natural light filters in, creating a bright atmosphere. A circular rug with a pattern complements the hardwood flooring.
Home in San Mateo

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
Top guest favourite
The exterior of a cozy cottage is visible, surrounded by a lush garden filled with various plants and flowers. A stone path leads to the entrance, framed by vibrant greenery. Large windows allow glimpses of the inviting interior, enhanced by a seasonal wreath on the door.
Guesthouse in San Carlos

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
Superhost
The exterior of the home displays a low-profile design with a well-maintained lawn and modest landscaping. A red-tiled roof spans across the structure, and a wooden fence outlines the front yard, providing a sense of privacy. The sky above features light clouds, allowing for ample natural light.
Home in San Mateo

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
Top guest favourite
A modern kitchen is presented, featuring a spacious island with seating for four. Sleek stainless steel appliances are complemented by white cabinetry and a stone backsplash. Natural light floods through a skylight, enhancing the vibrant blue accent wall and warm wood flooring.
Home in Foster City

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
Guest favourite
Home in San Mateo

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
Guest favourite
A cozy living area features a sectional sofa and coffee table, complemented by a 55" smart TV mounted on the wall. A standing desk with dual monitors and a small kitchenette, including a microwave and refrigerator, provide convenience. Three nature-themed artworks adorn the walls.
Guesthouse in San Mateo

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
Guest favourite
A dining area features a light wood table surrounded by four upholstered chairs. A decorative bench sits along one side of the table. Two abstract art pieces adorn the wall, and a potted plant adds a touch of greenery in the corner. Natural light enters through a large window.
Home in San Mateo

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
Superhost
Home in Woodside

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
Superhost
An outdoor seating area features a spacious table surrounded by ten chairs, complemented by a cozy texture of orange cushions on a wicker sofa. A fire pit occupies the center, with a sunshade above to provide comfort during warm days.
Home in San Mateo

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
Top guest favourite
A spacious living room features large windows allowing for ample natural light. Comfortable seating is arranged with a gray sofa and dark armchairs. A glass coffee table sits atop a plush area rug, while artwork adorns the walls, adding a touch of color to the neutral palette.
Home in San Mateo

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
Top guest favourite
Home in Foster City

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
Superhost
A scenic outdoor area is visible, featuring a trampoline alongside a grassy space. A deck extends toward the water, where a blue kayak and a boat with a cover are stationed. A shaded seating area is located nearby, with a view of the serene lake.
Place to stay in San Mateo

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 reviews

Popular amenities for Flying Cloud Isle vacation rentals