Holiday houses in Oakland

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Top-rated holiday rentals in Oakland

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Guest favourite
A spacious living area features a green sectional sofa adorned with decorative cushions. Natural light streams through charming skylights, illuminating the wooden beams above. A small wooden side table holds stacked books, while a dining area is visible in the background.
Apartment in Oakland
4.96 out of 5 average rating, 228 reviews

El Nido—a Magnificent Victorian Home

Architectural elements like the wooden beams and whimsical shapes of the rooms inspired a Cuban approach to integrate traditional styles into the modern updates. Notice the Spanish-Moorish tiles, the charming skylights, and artisanal decor items. It's a very special home. You will feel like you are staying in a luxury spa. Every detail has been meticulously thought out; from the hangers in the bathroom to every appliance, every picture on the walls and the selection of Spanish-moorish tiles both in the bathroom and kitchen. It doesn't matter if you are staying for 3 days, for a week or for longer. The place has been purposely designed for your thorough enjoyment and extreme comfort. You have a full walking closet with capacity to hang as much clouding as you can carry and as many as 40 pairs of shoes. Of course you have top quality linens and towels as well as all the essentials for a 5-stars hotel experience. El Nido es the top unit of a former home; there are other 2 units occupied by very decent and quite families, but they have their completely separate entrances, so you will not be sharing common spaces with anyone; in fact, the entire space is at your disposal and at your disposal only, every square foot both of the apartment and of the private deck is entirely and exclusively for your use. My partner and I are avid travelers; we are AirBnB users as well; hence, we appreciate the availability of hosts as they are locals with ample knowledge of the amenities and less obvious gems of their cities. We want to let you know that we will be happy to be available as a friendly and willing source not only of problem solving, but also of information and guidance. How much interaction is for your to freely decide. Voted one of the 10 most interesting cities in the US by The Traveler magazine, Oakland is a growing area that has a wonderful selection of unique restaurants, shops, and bars. Take in the harbor views nearby and spend a fun day out on Lake Merritt. Lake Merritt Bart Station to San Francisco: Bart takes you to San Francisco (Only 2 short stops, an about 7-minutes ride, and you are in Embarcadero, the very epicenter of “the City”). It also takes you to and from both San Francisco International and Oakland International airports. While this station is only 1.2 away from the apartment, it is a good 25 minutes-walk. It is a lot easier and comfortable if you take Uber or Lift. For those of you more intrepid, there are also bikes or even those city-scooters that people leave anywhere. A major bus line runs down the Lake on Foothill Boulevard (which you catch at the intersection of 7th Ave @ Foothill, only 800 feet away). The same line brings you back one intersection over (@ E 14th). Both streets are one way, so the nearest goes down the Lake and the subsequent brings you back. Nevertheless, as we said earlier, Taxis and app-based ride services like Uber and Lyft work quite efficiently and inexpensively in our area. Nearby Stores Some popular grocery store options include: • Lucky's, a natural foods supermarket: less than half a mile • Several Chinese and Vietnamese minimarkets on International Boulevard. Less than 5 blocks away. • Trader Joe's (a specialty market): 2.3 miles Nearby Restaurants We recommend all of these restaurants: • Champa Garden (Laotian/Cambodian) 2102 8th Ave. @ 21st St. (510) 238-8819 Reservation recommended. We love every dish on the menu. • Annapurna (Indian, Himalayan, Nepalese) 948 Clay St (510) 250-9696 • Golden Lotus (Vegan Vietnamese) 1301 Franklin St (510) 893-0383 I love meat, but I don’t miss it a bit when I come to Golden Lotus. You’ll love it. • Kamdesh (Afghan) 332 14th St. (510) 286-1900 Their squash borane and bolanis are to die for • Flora Restaurant and Bar 1900 Telegraph Ave. (510) 286-0100 On the fancy/kind of expensive side, good food and outstanding drinks. • Akat Café Kally (coffee and tea) 1603 2nd. Ave. Great coffee, but the pies of the bakery next door are a piece of heaven

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, 1,000 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?

Top Guest favourite
A private patio features two chairs with cushions positioned around a small table. Lush greenery surrounds the space, complemented by vibrant flowers in a blue planter. A red awning provides shade, adding a cozy touch to the outdoor area.
Guest suite in Oakmore
4.97 out of 5 average rating, 1,048 reviews

Sunset Spa Suite w/private patio, views & parking

This private suite is a slice of heaven in a woodland setting! Accessed via a flight of garden stairs, it has a private entry, dedicated street parking, a private patio, luxurious large bath with a walk-in shower for 2, large jacuzzi tub for 2, heated floors, A.C., mini fridge, toaster oven, & microwave! The bedroom features a queen-sized bed, table for two, large screen smart TV, and strong fiber optic WIFI signal. Located in a beautiful neighborhood with wonderful hikes just outside the door.

Guest favourite
A spacious driveway leads to a well-maintained home nestled among trees. The house features a light-colored exterior and is complemented by warm lighting around the entrance. Landscaping includes bushes and flowers, enhancing the natural setting.
Guesthouse in Oakmore
4.92 out of 5 average rating, 541 reviews

Redwood Sanctuary Oakland Hills

Redwood Sanctuary is located in the idyllic Oakland Hills with beautiful vistas, hikes, and parks within a short drive. The home is situated on half an acre of land in the middle of redwood, eucalyptus, and oak trees secluded away from other homes. Montclair village is an 8 minute drive, providing lots of great food and shops. Minutes from Highway 13 and 580. It is a 1 bedroom studio with a queen bed and a pull out sofa bed. It can comfortably accommodate up to 3. We'd love to host your stay!

Top Guest favourite
A modern building with a green roof is nestled in a lush landscape, surrounded by trees. Scenic views of rolling hills and the bay are visible in the background, offering a serene and natural atmosphere. The driveway leads up to the structure, enhancing accessibility.
Bungalow in Sequoyah
4.95 out of 5 average rating, 102 reviews

Modern 2 bedroom with stunning bay views

Kick back and relax in this calm, stylish space. The Oakland Hills are filled with amazing hiking, this location is great for day trips to Napa (35 miles), San Francisco (11 miles) or Carmel (120 m). Centrally located for work or play. This open concept 2 bedroom is a peaceful break away. Given the open concept design - there is not a lot of privacy between bedrooms, just a big bookcase room divider b/w the rooms. There are a few sitting area's outside and a green roof too! And EV charging.

Top Guest favourite
Guesthouse in Oakland
4.97 out of 5 average rating, 585 reviews

Luxury Rockridge Casita in Our Sunny Garden

Featured in Sunset Magazine ✨ Tucked into our sunny Rockridge garden, this light-filled modern casita is a peaceful retreat — 3 blocks from College Avenue’s cafés, restaurants, and shops. Wake up to birds in the garden, sip coffee at the farmhouse table, and walk to BART for easy access to San Francisco, Berkeley, and downtown Oakland. A quiet space designed for those who appreciate beauty and thoughtful details. Ideal for couples exploring Rockridge, Berkeley, Oakland, and San Francisco.

Top Guest favourite
A cozy living area is presented with a rustic wooden accent wall and a flat-screen television mounted for entertainment. A spacious coffee table sits centrally with candles, accompanied by a modern yellow and blue sofa, while an armchair with a bright green cushion adds a touch of color.
Guesthouse in Oakland
4.97 out of 5 average rating, 217 reviews

The Redwood Retreat

Near Lake Temescal, Redwd Regional Prk, Bart, Hwy 13, Rockridge,Montclair, Dwntwn. We completely remodeled our guest house with a focus on short term tenants. Lots of storage within one of the most quite settings you will find. We made a thoughtful attempt to load the unit with everything u might need while away. The kitchen is functional to the point that you could actually cook a Thanksgiving dinner, multiple frying pans to crock pots a blender or chefs knives. Bathroom sundries abound!

Top Guest favourite
Guesthouse in Mosswood
4.92 out of 5 average rating, 245 reviews

Temescal Stay | Couples & Small Families | Parking

Your Private Temescal Wellness Retreat: Pet-Friendly & Walkable Escape to a cozy, pet-friendly retreat ideal for couples, small families, or travelers seeking relaxation. This charming home offers a comfortable space to unwind, and bring your furry friends along. We’ve added a wellness touch with yoga mats, pillows, and a framed QR code for a yoga and meditation guide. Whether you’re sipping coffee, exploring nearby attractions, or practicing mindfulness, this home ensures a peaceful stay.

Top Guest favourite
A bright and airy hallway is displayed, leading to a modern kitchen and private deck. The space features warm wooden flooring and natural light. Art pieces adorn the walls, while a dining table with wooden chairs is positioned beside a potted plant, creating an inviting atmosphere.
Apartment in Piedmont Avenue
4.99 out of 5 average rating, 135 reviews

Sunlit Oakland Retreat w/ Designer Touches & Deck

Sunlight + greenery + indoor-outdoor flow to the deck. Perfect for remote workers, couples, or friends looking for a calm, design-forward retreat. Not suitable for toddlers. Located in the heart of sought-after Piedmont Avenue district. Why you’ll love it: • Premier Walk Score of 96 – enjoy cafés, boutiques just steps away • Michelin 2-star dining around the corner, along with many local favorites • Gourmet kitchen – fully equipped and stocked • Private deck nestled among mature trees

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 Sheffield
4.94 out of 5 average rating, 375 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.

Guest favourite
A bright living room features large windows allowing natural light, framed with sheer white curtains. The space includes a comfortable white sofa, a round coffee table, and decorative accents like a geometric art piece and sunflowers placed on the table.
Guesthouse in West Oakland
4.94 out of 5 average rating, 116 reviews

Charming Victorian Retreat | Minutes to SF

Welcome to your Victorian retreat in the heart of West Oakland! 4 BD - 2 BT - 1 off-street parking, uniquely blend of historic charm and modern comfort, has everything you need for a home base for your vacation or work trip. Located in the West Oakland neighborhood, just few short blocks from BART station & nearby freeways access offer quick and easy commute options to San Francisco and downtown Oakland, greater East Bay and South Bay

Top Guest favourite
A bright and modern kitchen area features dark cabinetry and a coffee station, accompanied by a patterned rug on the floor. A breakfast bar with two stools is visible, and the open layout connects to a cozy living space that showcases colorful furnishings and artwork.
Apartment in Longfellow
4.99 out of 5 average rating, 185 reviews

The Cozy Casita 2

Welcome to the Cozy Casita, you’re home away from home. The central location makes it the perfect jumping off point for all your Bay Area adventures with close proximity to MacArthur BART station, Multiple bus stops, Bay Wheels bike rental, shops and restaurants in Emeryville and Temescal, Access to 4 major highways within 1/4 mile, Lake Merritt, Uptown/Downtown Oakland, San Francisco, Berkeley, and many more Bay Area hotspots.

Popular amenities for Oakland holiday rentals

When is the best time to visit Oakland?

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Frequently Asked Questions

  • What are the best places to stay in Oakland?

    Many travelers stay around the Downtown, Jack London Square, and Lake Merritt neighborhoods, known for lively arts, dining, and waterfront scenes. Areas like Rockridge and Temescal are also often recommended for their local shops, markets, and easy access to parks.

  • What are the best things to do in Oakland with kids?

    Families frequently suggest exploring the Oakland Zoo, Lake Merritt, and Children's Fairyland for hands-on activities and nature encounters. Many parks, museums, and weekend farmers markets also create engaging spaces for kids around the city.

  • What are some of the best things to do in Oakland?

    Explore Oakland’s vibrant arts scene at the Oakland Museum of California, stroll the gardens around Lake Merritt, or wander the shops and galleries in the Temescal and Uptown neighborhoods. Jack London Square is frequently suggested for waterfront dining and community events.

  • How is the weather in Oakland?

    Oakland has mild weather, with winter temperatures generally between 42–58°F (6–14°C) and drier, warmer summers around 56–74°F (13–23°C). Rainfall peaks in the winter, while summer days are usually sunny and pleasant.

  • When is the best time to visit Oakland?

    Late spring through early fall is often recommended for clear skies and outdoor events, with summer featuring sunny weather around 56–74°F (13–23°C). Many visitors also enjoy the region’s festivals and outdoor markets held throughout these months.

  • What are the best places to visit in Oakland?

    Lake Merritt, the Oakland Museum of California, and Jack London Square are frequently suggested for first-time visitors. The Redwood Regional Park and Temescal neighborhood are also known for their natural beauty, scenic trails, and local eateries.

  • What are some hiking trails in Oakland?

    Oakland has scenic trails in Reinhardt Redwood Regional Park, Joaquin Miller Park, and Sibley Volcanic Regional Preserve, where you can walk among redwoods or explore volcanic landscapes. Many paths are suitable for gentle walks, wildlife watching, or longer hikes.

  • What are some family activities we can do in Oakland?

    Families can enjoy the Oakland Zoo, Children’s Fairyland, and interactive exhibits at Chabot Space & Science Center. Walking or biking around Lake Merritt is another popular choice for group activities.

  • What are some of the best day trip ideas from Oakland?

    Explore scenic trails and picnic areas in nearby regional parks, or discover the rich art, culinary, and coastal experiences in neighboring cities like Berkeley and San Francisco. Wine enthusiasts often head to the vineyards of Alameda County for tastings and vineyard tours.

  • Are there any pet friendly accommodations available in Oakland?

    Many accommodations in neighborhoods like Temescal, Rockridge, and around Lake Merritt welcome pets. Oakland has several parks and trails where you can enjoy the outdoors with your dog.

  • What are some local tips for visiting Oakland?

    Explore Oakland’s murals and public art, and check out independent coffee shops and local food markets for a taste of neighborhood vibes. Biking is popular on city trails; carrying a light jacket is helpful, as evenings can cool down even in summer.

  • What is Oakland known for?

    Oakland is known for its vibrant arts scene, diverse food culture, and deep-rooted histories reflected in music, activism, and community festivals. The city’s natural spaces, including redwood forests, and local sports culture are also widely recognized.

  • What are the best hidden gems to explore in Oakland?

    Oakland has lesser-known spots like the Bonsai Garden at Lake Merritt, unique independent galleries found in the Jingletown arts district, and small neighborhood bakeries and vintage shops. These places highlight Oakland’s creative spirit and locally rooted makers.

  • What are the best foods to try in Oakland?

    Oakland’s diverse food scene includes locally rooted dishes like barbecued meats, fresh seafood, and Vietnamese banh mi. The city is also known for innovative vegan cuisine, specialty coffee, and sweet potato pies found at neighborhood bakeries.

  • What should I bring for a trip to Oakland?

    Pack comfortable shoes for exploring neighborhoods and parks, a light jacket for cooler mornings or evenings, and a reusable water bottle. A sun hat or sunglasses may be handy for sunny afternoons, even outside of summer.

  • What is the nightlife in Oakland like?

    Nightlife centers around Uptown and Downtown, where you can explore music venues, dance clubs, and late-night eateries. Oakland’s scene is known for live jazz, local DJs, and inclusive community events drawing diverse crowds.

  • What are the most popular events or festivals in Oakland?

    The Oakland Art & Soul Festival, First Fridays in Uptown, and Chinatown StreetFest are often recommended annual events celebrating music, food, and culture. Summer and early fall feature outdoor community gatherings and street fairs throughout the city.

  • Are there family friendly vacation rentals in Oakland?

    Many vacation rentals in Oakland are family friendly, especially in the Rockridge, Grand Lake, and Temescal neighborhoods. These areas have nearby parks, local markets, and easy access to family activities.

Quick stats about holiday rentals in Oakland

  • Total holiday rentals

    Explore 5,340 holiday rentals in Oakland

  • Verified guest reviews

    Over 245,230 verified reviews to help you choose

  • Family-friendly holiday rentals

    2,020 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 1,350 rentals that welcome pets

  • Holiday rentals with a pool

    230 properties feature pools

  • Rentals with dedicated workspaces

    2,880 properties have a dedicated workspace

  • Wi-Fi availability

    5,290 of Oakland holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Oakland rentals

  • 4.8 Average rating

    Oakland stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Oakland's top spots, include Oakland Zoo, Jack London Square, and Oakland Museum of California

Destinations to explore

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