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

Guesthouse in San Carlos

4.99 out of 5 average rating, 588 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.

Jun 24 – Jul 1

G$31,986 GYD per night

Guest favorite

Guesthouse in Belmont

4.97 out of 5 average rating, 363 reviews

A Comfortable & Private Guest House

Attn: Promo Rate for Health Care Workers & First Responders on stays of ONE week, or more. Please alert us, so that we can offer you a promo rate. In light of these uncertain times, rest assured that we are doing everything to ensure the safety of our guests. Beautiful, Secluded, Safe, Fully Stocked, Comfortable, Newly Renovated, & Close to Public Transportation. In the heart of Silicon Valley with its own private entrance. It's 30 mins. N of San Jose, and 30 mins. S of San Francisco.

Mar 13 – 20

G$22,661 GYD per night

Guest favorite

Guest suite in Belmont

4.95 out of 5 average rating, 101 reviews

Cozy private in-law suite, close to SFO, fast WiFi

Newly renovated, spacious in-law unit in the Belmont hills with a private entrance and Bay views. This adorable space is cozy and great for a weekend respite or remote work. SFO airport is just 15 mins away. Close by Stanford and San Carlos. Short drive to hiking trails and 30 mins away from the Pacific ocean. Easy access to San Francisco and San Jose, via freeway 101, 280, and 92. 🌞 Solar-powered through the day with battery 🔋 back-up at night. No outages and eco-friendly. 🌲

Aug 21 – 28

G$23,028 GYD per night

Guest favorite

Home in Belmont

4.93 out of 5 average rating, 323 reviews

Hidden French Gem ~ near Caltrain, SFO

Highly welcome respectful travelers to step through the 750ft super quiet European-style private studio with secluded bay view. Curl up in front of the 4K TV for movie nights at this stylish, soundproofed nest with a luxury mattress, washer and dryer! — welcome infant & kids. — Read everything to avoid surprises. — 5 min walks to park, Caltrain/restaurants; 10~13 min drive to SFO/Stanford; 20-25 min SF. — No pets, no smoking/vaping, no party! — book for 3 if need single bed

Aug 22 – 29

G$31,074 GYD per night

Superhost

Guesthouse in San Mateo

4.92 out of 5 average rating, 145 reviews

Cozy Studio 1B/1B w A/C No Pet in San Mateo

This cozy studio is good for a couple vacation. It is also suitable for business trip with high speed WIFI. It is well equipped with all the amenities you need to enjoy your stay! 15 minutes walk to San Mateo Downtown. 11 minutes walk to Cal Train Station, which takes you to San Francisco in 30 min, and San Jose 45 min. If you have a car, you can reach those popular destinations easily: Hwy 101: 3 min San Francisco Airport: 9 min Apple Palo Alto: 12 miles Stanford: 17 miles

Oct 5 – 12

G$22,374 GYD per night

Guest favorite

Cottage in San Mateo

4.95 out of 5 average rating, 465 reviews

Entire Private Studio by SFO, AC/Heat/Free Parking

Entire cottage with private entrance. * self check-in with codes * free parking on driveway * AC & heating * 1 queen bed, 1 sofa (converts into twin bed) * fiber speed WiFi * kitchenette with sink, dishes & utensils, microwave, oven, mini fridge, keurig coffee maker, water boiler, NO STOVE * 15 min drive to SFO * 10 min walk to Caltrain * walking distances to restaurants, bars & groceries * located at end of cul de sac in a safe & quiet neighborhood * TV with Chromecast

Oct 1 – 8

G$31,619 GYD per night

Guest favorite

Home in Oakland

4.98 out of 5 average rating, 532 reviews

Private Casita with Stunning View

Relax in a private, fully equipped Casita with stunning views of East Oakland and the Bay. This newly constructed one-bedroom guest house in the quiet Eastmont Hills neighborhood has everything you need to work and play. Enjoy lounging in a hammock on the deck or on the couch streaming movies to a 32" television. Brand new stainless steel gas range and full-sized fridge make cooking a breeze, or you can partake in booming Oakland's restaurant scene.

Dec 8 – 15

G$17,105 GYD per night

Guest favorite

Home in Foster City

4.93 out of 5 average rating, 203 reviews

Tranquil Lagoon View 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.

Sep 28 – Oct 5

G$70,374 GYD per night

Guest favorite

Guest suite in San Mateo

4.94 out of 5 average rating, 206 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, microwave and a Keurig coffee maker. 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.

May 22 – 29

G$29,515 GYD per night

Guest favorite

Guesthouse in La Honda

4.95 out of 5 average rating, 382 reviews

Bicycle Shack @ La Honda Pottery

My place is close to miles of hiking and biking trails in county parks and openspace, great views, the beach and not far from the Peninsula, S.F. and Santa Cruz. You’ll love my place because of the location, the people, the ambiance, the outdoors space and that it is a self contained small cabin with a tiny deck.. My place is good for couples, solo adventurers, and furry friends (pets). Perfect for hikers and bikers.

Apr 14 – 21

G$24,237 GYD per night

Guest favorite

Guesthouse in San Mateo

4.93 out of 5 average rating, 193 reviews

Charming Private Quiet Backyard Studio

This charming, sunny, secluded backyard studio is located in the heart of San Mateo, near public transportation, freeways, restaurants, shopping, and 15 minutes to SFO. Private entrance, quiet backyard setting, plenty of street parking. Less than a 5-min walk to Safeway, CVS, Starbucks and restaurants. * To my regular guests, the rate increase is due to SM County increasing the tax rate. *

Nov 29 – Dec 6

G$28,318 GYD per night

Guest favorite

Guesthouse in Hillsborough

4.95 out of 5 average rating, 809 reviews

Little Cottage on the Hill

Enjoy a peaceful stay at this charming, secluded detached garden cottage great for a stay-cation or as a work-from-home alternative. Due to the coronavirus, we are taking extra care to disinfect frequently touched surfaces between reservations. The cottage features a queen-sized bed, a fireplace, private bathroom and kitchenette. Perfect for both leisure and Business travelers.

Oct 25 – Nov 1

G$28,013 GYD per night