Holiday rentals in South Shore

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Top-rated holiday rentals in South Shore

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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, 1,039 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
A cozy living room features a gray sofa paired with colorful ottomans on a soft area rug. Two windows allow natural light to brighten the space, supplemented by a floor lamp and a desk in the corner, along with a small side table for convenience.
Home in Alameda
4.92 out of 5 average rating, 124 reviews

Peaceful 2-BR Bungalow w/Parking and Patio Deck

Welcome to our peaceful cottage style home in Alameda! This location is perfect for those visiting the area, with easy access to San Francisco and Oakland via convenient bus access just a short walk away. The waterfront, restaurants, and USS Hornet are a short distance from our home. Our patio is a great spot to relax and enjoy the sunshine. We are dedicated to making your stay comfortable. Pet fee: $150/pet. We also have an electric charger on property which can be used for $0.40/kWh. Welcome!

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.
Guest house in Alameda
4.92 out of 5 average rating, 137 reviews

Detached Cozy Studio w/ private patio garden & BBQ

Newly 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.

Guest favourite
Guest house in Alameda
4.94 out of 5 average rating, 48 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
Home in Alameda
5 out of 5 average rating, 5 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 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, 449 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 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, 601 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.

Guest favourite
A private garden area is framed by wooden fencing, featuring various plants and greenery. A door with a purple frame leads into the guesthouse. The wooden deck enhances the natural setting, contributing to a sense of tranquility and seclusion.
Guest house in Oakland
4.8 out of 5 average rating, 1,040 reviews

The Purple Door, Private Sanctuary, Epic View

Private guesthouse located in the Oakland Hills with stunning views of the bay. We recognize the importance of privacy, this guesthouse will allow you to have everything you need all while never having to be bothered. The sunset views can be taken in from your bed or the deck. There is a bus stop about 150 yards away if you need, the airport is about a 7 minute ride away, rail (BART) is about 5 minutes and the house is near a freeway for quick access to everywhere in the Bay Area.

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.
Flat in Alameda
4.96 out of 5 average rating, 109 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.

Top guest favourite
The Victorian-style house features a distinctive turret and ornate detailing, with large windows reflecting the evening light. The inviting front porch is framed by greenery, while the sky is painted in hues of purple and orange, enhancing the house's architectural charm.
Home in Alameda
4.98 out of 5 average rating, 104 reviews

Historic Victorian in a Great Location

Welcome to the Brehaut House. Built in 1893, the home is a local landmark in a city known for Victorians. It is not uncommon to see an artist across the street painting the house, or to be enjoying an afternoon on the front porch and having someone walking by stop to say hello and ask bout it. Enjoy the house, or get out and explore. The beach, Park St, and South Shore are a short walk. The ferry is a quick drive/bike, and can take you to San Francisco, Angel Island, etc.

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, 394 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.

Top guest favourite
A charming cottage exterior features a brown wooden façade and white trim. Two sets of windows allow natural light to illuminate the interior. A flight of stairs leads to the front door, flanked by vibrant greenery and flowering shrubs, creating an inviting entrance.
Home in Alameda
4.87 out of 5 average rating, 121 reviews

Downtown Dream Cottage

Cozy cottage, close to the best restaurants in town, walking distance to beach and public transport. Private entrance, this is your own building without shared hallways or walls. Quiet neighborhood in the heart of the city. Alameda is a beautiful historic city if you're visiting San Francisco Bay Area, Ferry access to San Francisco attractions and business district and to Oakland. Conveniently located close to Oakland airport and major highways.

Popular amenities for South Shore holiday rentals

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