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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Guest favorite

A bright living area features a round table with a floral centerpiece and two cushioned chairs. The backdrop displays an open kitchen with cabinetry, leading to a warmly painted bedroom door. A small plant and modern decor enhance the welcoming atmosphere, illuminated by natural light.

Home in San Mateo

4.83 out of 5 average rating, 281 reviews

❤️ Delightful 1B/1B modern with a leisure garden

This recently upgraded unit features a master bedroom with a full bathroom and two closets, along with a spacious living area. Enjoy complete privacy with a separate fence and a sunny private garden. We provide complimentary coffee and tea, and there’s free street parking available 24/7. It’s within walking distance to the Roblox office and the San Mateo Event Center, and about 10 minutes from SFO. Please note, this is not an apartment or condo building. Self check-in o& Check out with code.

Top guest favorite

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

4.99 out of 5 average rating, 777 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.

Guest favorite

Guest suite in San Mateo

4.86 out of 5 average rating, 7 reviews

Cozy Studio w/ Kitchen + Laundry | Self Check-in

Welcome to Your Private Studio in San Mateo! Enjoy a cozy, stylish, and studio attached to our family home. With its own back entrance, full kitchen, and in-unit laundry, it’s the perfect home-away-from-home for solo travelers, couples, or small families. 🌟 Location Highlights • few minutes to SFO Airport for easy travel. • Walk to the scenic Coyotes Point Bayfront trail for jogging, biking, or sunsets. • 5 minutes to downtown San Mateo or Burlingame for dining, shopping, and coffee

A modern living room features a black leather sofa facing a large flat-screen TV mounted on the wall. Natural light is allowed through large windows dressed with sheer curtains. A coffee table is centered on a textured area rug, with a plant placed near the fireplace.

Home in Foster City

4.89 out of 5 average rating, 45 reviews

Jane's Home (LA) | Remodeled 2b2b +Backyard

Discover a Secluded Treasure! Experience the elegance of this spacious, newly updated modern residence nestled in a quaint cul-de-sac in Foster City. Boasting a perfect open floor plan with impressive 16ft vaulted ceilings and plentiful natural light, this home offers an extensive backyard for ultimate relaxation. Situated at the heart of convenience, halfway between San Francisco & Silicon Valley, and near SFO airport, Caltrain, dining, shopping, San Mateo, Stanford, and Palo Alto.

The living and dining area features a cozy love seat, a circular dining table with two chairs, and large windows allowing natural light to fill the space. A stylish area rug adds warmth to the hardwood floor, complementing the modern kitchen appliances visible in the background.

Guesthouse in Belmont

4.63 out of 5 average rating, 32 reviews

Sunny 1BR Oasis | A+ Kitchen | Walk 2Town, Parking

100% Private, Sunny 2nd-story Guest House * A+ Downtown Belmont location: walk 3 blocks to dining, parks & CalTrain to SF & SJ * Cozy living/dining area w/love seat, 65" Smart TV and 2-person dining area * New listing. Host has 500+ 5-star reviews * ASK us about 60+ day discounts! * Remodeled kitchen w/gas stove, granite countertops, full fridge, dishwasher * Comfy bedroom w/Full 10" thick memory foam bed, 100% cotton sheets & spa towels * Remodeled bathroom * Laundry * Parking

Guest favorite

An outdoor breakfast bar is featured, constructed of natural wood with a polished countertop. Several decorative items are placed on the bar, while four metal chairs with intricate designs are arranged nearby. Sunlight highlights the wooden textures and accents of the surrounding greenery.

Guest suite in San Mateo

4.91 out of 5 average rating, 70 reviews

Luxury guesthouse close to SFO/Parking/waterfront

Recently remodel, modern & luxurious guesthouse, private entrance. Perfect for the business traveler in search of a home away from home while also being ideal for vacationers. Solo traveler or couple. 10 minutes from SFO & 2 mins walk from the amazing scenic bay trail. 15 minutes away from shopping, dining, and entertainment. Book your stay now for a relaxing and enjoyable experience! Whether business or pleasure, our location will meet all your needs and more.

Top guest favorite

Home in Foster City

4.93 out of 5 average rating, 285 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.

Guest favorite

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

4.9 out of 5 average rating, 115 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.

A contemporary sleeping area features a full-size bed with crisp white linens positioned against a geometric accent wall. A wall-mounted smart TV is framed by natural wood, while a large mirror reflects the space. Natural light filters in through a window with a minimalistic treatment.

Apartment in Redwood City

4.65 out of 5 average rating, 339 reviews

Kasa the Niche Redwood City | Micro-pod Full Bed

Nestled in the heart of Downtown Redwood City, this renovated hotel offers an array of essential amenities within its thoughtfully designed micro units. Walk restaurants, shopping, or to the nearby Caltrain station, which offers direct service into San Francisco and Silicon Valley. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

Top guest favorite

A neat outdoor space features three tall planters filled with greenery and colorful flowers, positioned on a pathway of square stone pavers. Dark pebbles line the edges, contrasting with the lush green artificial grass beside the residence.

Guest suite in Foster City

4.99 out of 5 average rating, 105 reviews

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

Home in Foster City

5 out of 5 average rating, 3 reviews

115 -Waterfront Oasis, Dock & Sunroom, Grand Piano

Welcome to this stunning waterfront retreat in Foster City featuring spacious living areas, and stylish décor. Perfect for families, business travelers or a group of friends looking for a memorable stay. ✔ 4 spacious bedrooms and 2 bathrooms ✔ Expansive living room with Smart TV ✔ Large sunroom facing water ✔ Fully equipped kitchen ✔ Washer & Dryer in unit ✔ Central heating ✔ Sleeps up to 8 guests ✔ Grand piano

A cozy studio space is shown featuring a spacious bed with multiple pillows. A compact kitchenette area is visible next to the bed. Natural light enters through a window with blinds, while a bathroom doorway with organized towels is at the back, enhancing functionality.

Guesthouse in San Mateo

4.81 out of 5 average rating, 195 reviews

Charming cozy studio King-sized bed

Hi there! Welcome to our cozy studio in the heart of the bay area. You'll find yourself conveniently located to downtown San Mateo and all the transportation. This is a shared walkway, private studio. The unit has 1 king sized bed with ample pillows. Included are fast wifi, 43" TV, Netflix, coffee, full kitchenette for light cooking. Self-check in. No central heat, no AC unit. Equipped with space heater