Holiday houses in South Shore

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Top-rated holiday rentals in South Shore

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Top Guest favourite
A private garden space features a white wicker seating arrangement, providing a comfortable area for relaxation. Colorful flags from various countries are strung overhead, adding a festive touch. Surrounding greenery enhances the tranquil ambiance, inviting guests to enjoy the outdoors.
Cottage in Alameda
4.9 out of 5 average rating, 421 reviews

Large Cottage Near SF, Beach, Airport w/ Backyard

Beautiful, spacious, and quiet cottage 1-bedroom 1-bath, 860sqft, with a private garden, located in the prestigious Alameda Gold Coast neighborhood, safe, 7miles to OAK Airport, 5miles to Oakland Coliseum, 9miles to UC Berkeley, walk to the beach, easy transportation to San Francisco by ferry, bart, or bus. It is walking to coffee shops, restaurants, grocery stores. Next to Crown beach with spectacular view of San Francisco. Parties are not allowed. Top speed Internet. Pet allowed, $50 per stay.

Top Guest favourite
The sleeping area is adorned with warm wood finishes, featuring a spacious bed with soft linens. Natural light filters in through circular porthole windows, enhancing the classic nautical ambiance. A wooden dresser is positioned nearby, and a doorway leads to the bathroom, which is tastefully designed.
Boat in Alameda
4.87 out of 5 average rating, 1,061 reviews

Step back in time on this beautiful classic yacht

Good Luck is a hundred-year-old classic yacht, lovingly restored and ready to transport you to another time while luxuriously spoiling you on your bay area adventure. This dockside charter gives you complete privacy and an amazing nautical experience. Alameda is a beautiful island community in the heart of the Bay, filled with beautiful homes, adorable shops, and many great restaurants. The San Francisco ferry is close by to whisk you to the big city, so why would you want to stay anywhere else?

Guest favourite
Guesthouse in Alameda
4.92 out of 5 average rating, 50 reviews

2533 - Luxury 2BR/2BA | Kitchen | Laundry | Bidet

Welcome to your home away from home! This stunning, newly and designer remodeled 2-bedroom unit is located in a safe & friendly neighborhood, offers high-end comfort with a fully equipped kitchen, perfect for cooking your favorite meals. Relax in the stylish living area, enjoy restful nights in cozy bedrooms, and take advantage of free in-suite laundry. Thoughtfully designed with luxury touches throughout, it’s ideal for couples, families, or business travelers looking for both comfort & style!

Guest favourite
A modern floating condo is shown, featuring a mix of wooden and glass exteriors. The structure is connected by a sturdy ramp leading to the water. Soft lighting from a nearby lamp enhances the tranquil evening atmosphere, with a colorful sunset reflecting off the water.
Apartment in Mill Valley
4.91 out of 5 average rating, 329 reviews

Floating condo 'A' on Sausalito's Richardson Bay.

Romantic floating condo with breathtaking water views. Relax & enjoy a tranquil escape in style and comfort. Catch the sunrise from your super comfie KING bed or lounge on the deck with occasional pelicans (or even a seaplane) coming and going. Unique and perfect for a getaway, workacation, or retreat. Golden Gate Bridge is 6 min away. Airport bus stops a block away. Walk/bike path to Sausalito & Mill Valley. Ferry/bus to SF. Free parking Read reviews of this or our 3 other floating condos!

Guest favourite
Home in Alameda
5 out of 5 average rating, 7 reviews

Alameda Island Beach House

Welcome to your home by the beach on Alameda Island where you can relax, play, and work. Tucked away on a quiet street, yet not a 5-minute walk to shops and the beach with skyline views of SF, this peaceful setting is perfect for multi-generational groups, digital nomads pursuing inspiration, couples, families, and grandparents seeking stays of 30 days or longer. A delightful ferry ride will get you to San Francisco in 15-30 minutes (or you can drive) and you can be in wine country in an hour.

Guest favourite
The exterior of a single-story home is shown, featuring a driveway leading to a two-car garage. Lush landscaping includes colorful foliage and green shrubs, while a well-maintained lawn is visible in the front yard under a clear blue sky.
Home in Alameda
4.91 out of 5 average rating, 47 reviews

Chic 3BR Home Near Beach & SF - The Alameda Snail

Welcome to your perfect Alameda retreat! This stylish and spacious 3-bedroom home invites you to slow down and unwind. Start your day with coffee in the sunny backyard, stroll to the beach, or cozy up in the inviting living room. Whether you're here to relax, explore, or both—you’ll find all you need for a comfortable stay. Just a 5-minute walk to the beach and local shops, and only 20 minutes to San Francisco via ferry. You’ll also enjoy our nearby parks, walking trails, and tennis courts.

Guest favourite
The studio apartment features a spacious layout with a queen-size bed, a cozy sofa, and a glass dining table. A desk with a TV is positioned nearby, providing an inviting space for relaxation. Natural light enters through window treatments, illuminating the area.
Guest suite in Alameda
4.94 out of 5 average rating, 455 reviews

Fully-equipped studio in victorian home

Fully-equipped studio apartment in Alameda victorian home. Spacious, with modern amenities (WiFi, Netflix), free coffee and tea, queen-size bed, and big yard, shared with the main house. Separate entrance through the backyard. Young kids live in the upstairs house part-time (see “other notes”) and can be loud until 9:30pm. We’re a dog-friendly space and love hosting pups (maximum of 2, house trained)! Please note that we’re not able to accommodate cats at this time. Lab lives in property.

Top Guest favourite
A spacious studio is showcased with a large bed and a serene wall mural of trees. Natural light fills the room through sliding glass doors, which lead to the outside garden. A comfortable chair and side table create a cozy seating area.
Guesthouse in Alameda
4.93 out of 5 average rating, 149 reviews

Detached Cozy Studio w/ private patio garden & BBQ

Renovated 100 yr old backyard studio in the heart of the Alameda island. Private fenced garden with bbq. 7 mins from Oakland Int. Airport. 20 mins to SF city by ferry. Convenient location to UC Berkeley. Close to BART, beach, parks, local markets and restaurants in walking distance. • Fully-equipped, self contained studio, with cooking basics, microwave, airfrier/oven, induction cooktop, coffee machine, electric water boiler, BBQ, patio. Private entrance. No share ventilation.

Top Guest favourite
A vibrant sunset paints the sky in shades of orange and pink. The silhouette of the Bay and Golden Gate Bridges is visible in the distance, framed by rolling hills that contrast with the serene water below.
Guest suite in Oakland
4.97 out of 5 average rating, 617 reviews

BridgesView Spa & Couples Retreat, Easy Parking

This luxurious suite with kitchenette features a beautiful view towards the Bay and Golden Gate Bridges, designed especially for a romantic getaway or anyone needing a relaxing space. Soak and play in the two-person jetted tub, enjoy the gorgeous large bathroom. Easy street parking is always available, and garden lined exterior stairs take you to the private entry and patio. A laundry is provided for guest use only. Hikes into the canyon below or neighborhood above are a special treat.

Top Guest favourite
An expansive living room features a leather sectional sofa, a circular coffee table, and a stone fireplace. Large glass windows provide views of the surrounding greenery, while wooden beams and a rustic stone wall create a natural ambiance. A television is positioned near the sofa.
Home in Mill Valley
4.99 out of 5 average rating, 135 reviews

Two Creeks Treehouse

Looking for a healthy dose of tranquility and adventure at your doorstep? Over 100 steps from the road below, this 'treehouse' is perched above it all and horizontally oriented on a steep lot between two creeks. The all glass façade creates dramatic views of the redwoods, Mt. Tam and across downtown Mill Valley to Blithedale Ridge. Anchored to granite the house sits on handmade stone walls from rock harvested on the property during construction in the 1960s. Truly a one of a kind stay.

Top Guest favourite
A modern studio space features a queen-size bed with a wooden headboard, flanked by nightstands. A cozy sofa sits opposite the bed. A smart TV is mounted on the wall, and kitchen amenities including a microwave and small fridge are visible in the corner.
Apartment in Alameda
4.97 out of 5 average rating, 115 reviews

Sunny Garden Studio with Parking

This is a fully-equipped, self contained studio with off-street parking in a private driveway, located in central Alameda. Walking distance to stores, less than a mile from the beach, & easy access to transportation to San Francisco by bus or ferry. The studio has everything you need for your stay - microwave, smart TV, induction cooktop, fridge, airfryer, and more. Shared access to the backyard. Perfect for weekend getaways or visiting the sights of San Francisco. LGBT+ friendly.

Guest favourite
A private hot tub is shown in the foreground, with soft bubbles visible on the surface. In the background, a modern cabin facade features large glass doors reflecting warm sunset hues, framed by a wooden deck with seating.
Cabin in Oakland
4.94 out of 5 average rating, 397 reviews

Hike-in Bay Views Cabin w HotTub

Hike up to a well designed, small-but-mighty modern cabin with fast WiFi, your own hot tub and a panoramic view spanning across the bay from the Golden Gate to the San Mateo bridge. 108 stairs lead up to the Aerie, so if you don’t want to get your steps in, this is probably not the space for you! 15 min from OAK and city life, but a world away. Sunsets are glorious here. The Aerie is a special spot just for 1 or 2, so leave the posse behind. Registered guests only.

Popular amenities for South Shore holiday rentals