Holiday rentals in Flying Cloud Isle

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Top-rated holiday rentals in Flying Cloud Isle

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Superhost
Guest house in San Mateo
5 out of 5 average rating, 3 reviews

New & Spacious Studio w/Private Kitchen & Bathroom

Spacious and fully furnished 450 sqft guest house next to the main house in central San Mateo! Enjoy a private kitchen, modern bathroom, and in-unit washer/dryer. The studio features a queen size Murphy bed, workspace, fast WiFi, and smart TV. Walk to downtown shops, restaurants, and Caltrain for quick access to Downtown SF and Silicon Valley. Short 12 min. drive to SFO, easy access to Hwy 101 and 92. Min. 30-day stay required, ideal for business travelers, extended stay, or long-term visitors

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.
Guest house in San Carlos
4.99 out of 5 average rating, 783 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.

Top guest favourite
A spacious living area features a light grey couch adorned with patterned cushions, situated in front of a glass-topped table. A small succulent plant and coasters are placed on the table, with glimpses of a neat kitchen and a dedicated sleeping area visible in the background.
Guest house in Belmont
4.93 out of 5 average rating, 108 reviews

A private and quaint gateway on Belmont Hills

Welcome to our cozy Belmont studio! This charming retreat offers a comfortable stay with its stylish design, fully equipped kitchen, and a comfortable bed. Conveniently located in Belmont, CA, you'll be close to vibrant San Mateo downtown, the scenic coastline of Half Moon Bay, and the airport. This quaint studio is tucked away on a small hill, surrounded by greenery. As a delightful bonus, you'll find a lovely lemon tree in the driveway, providing complimentary lemons for your stay.

Guest favourite
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
4.89 out of 5 average rating, 74 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.

Guest favourite
A stylish deck features a sunken fire pit surrounded by smooth gravel, providing an ideal setting for outdoor relaxation. The back of the guesthouse is visible, showcasing large glass doors that open to the bright interior, inviting the natural light to flow in.
Guest house in Belmont
4.89 out of 5 average rating, 53 reviews

Newly Built Private Guesthouse, Silicon Valley

The Guesthouse is its own little residence, with direct entrance from the street. It's private, so you won't bump into host during your stay! Discover tranquility in our newly built Spanish Guesthouse nestled in Belmont Hills. The fully equipped and smartly designed 2-bed / 1-bath retreat features a state-of-the-art allergen free radiant floor heating. Enjoy the serene outdoors with a stylish deck and fire pit. Perfect for escaping and rejuvenating.

Flat in San Mateo
New place to stay

LakeFront Lavender House

Peaceful waterfront home offering beautiful lake views in a quiet, relaxing setting. Conveniently located just steps from the plaza, grocery stores, coffee shops, and a variety of restaurants. Minutes from Mills-Peninsula Hospital, San Mateo Medical Center, and only 6 minutes to Roblox HQ. This calm, lavender-themed retreat is thoughtfully designed for interns, traveling professionals, corporate guests, and families seeking comfort and convenience.

Top guest favourite
Home in Foster City
4.93 out of 5 average rating, 292 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 favourite
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
4.91 out of 5 average rating, 116 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.
Flat in Redwood City
4.66 out of 5 average rating, 352 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.

Superhost
A bright bedroom features a spacious bed with crisp white linens and an accent pillow. Natural light streams through large windows, and a modern desk with a lamp is positioned nearby. A mirrored closet reflects the room's stylish decor, enhancing the space's openness.
Guest suite in San Mateo
4.92 out of 5 average rating, 261 reviews

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.

Top guest favourite
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, 107 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, 4 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

Popular amenities for Flying Cloud Isle holiday rentals