Holiday houses in Oakland

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Top-rated holiday rentals in Oakland

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Top Guest favourite
A dining area is shown, featuring a light wooden table set for two with plates and glasses. Two gray chairs are neatly arranged around the table. A potted plant adds a touch of greenery, positioned near a bright window with a light-filtering shade.
Guesthouse in Eastmont Hills
4.98 out of 5 average rating, 181 reviews

Serene foothills Garden Suite, private parking +EV

Have the entire Bay Area at your fingertips... & right outside your window! This private studio tucked into the Oakland Foothills is the perfect base for adventures. A 9min drive & you can be on the train into San Francisco. Coliseum & redwoods are minutes away, as are many other attractions*. You’ll be welcomed home to a comfy Cal King bed & a serene garden view. Enjoy coffee/tea as you settle in at the table, & our high speed wifi has you covered. Have an EV? Charge Level 2 overnight (J1772)!

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, 524 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!

Guest favourite
The spacious room features vaulted ceilings and natural light streaming through large sliding glass doors. A queen bed is positioned with a light-colored quilt and decorative pillows. A small seating area includes a chair and a television set, while an air conditioning unit is visible to the side.
Guesthouse in Grand Lake
4.9 out of 5 average rating, 150 reviews

Quiet space, great location!

Spacious single room ADU with vaulted ceilings, queen bed, and natural light. Access to a large yard with beautiful views. A new private bathroom is just outside, steps away in the main house. Located in a quiet, safe neighborhood near Grand Lake Theater, Lake Merritt, Morcom Rose Garden, restaurants, and shopping. Minutes to Berkeley, Piedmont, downtown Oakland, and public transport to SF. Dedicated entrance to room. No kitchen - mini fridge, coffee pot, kettle included for your convenience.

Guest favourite
A cozy living area features a blue sofa, accompanied by dark throw pillows. A modern coffee table is placed on a textured rug, with candles and decorative items atop it. The kitchenette showcases sleek cabinetry and appliances, illuminated by natural light through large windows.
Guest suite in Oakland
4.97 out of 5 average rating, 282 reviews

Curated Studio w/ Hot Tub & Outdoor Bath

Stay in a modern space curated by Oakland artists! This spacious studio features reclaimed barn wood throughout with eclectic modern furnishings. Snuggle up in the queen sized Casper mattress with luxurious spa quality sheets. Working while traveling? We've got gigabit wi-fi. Couples will enjoy the garden hot tub & outdoor bath with dual shower heads. Just looking to relax? Take a dip in our private outdoor bathing tub. Gated off-street parking & anytime contactless checkin are included too!

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 Oakmore
4.98 out of 5 average rating, 544 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
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
4.98 out of 5 average rating, 116 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

Top Guest favourite
A compact bedroom featuring a foldable bed with a light blue comforter. Natural light enters through two windows adorned with blinds. A bedside lamp and small shelf are present on either side, with a tall fan situated nearby. The walls are decorated in a subtle beige wood finish.
Guesthouse in Oakland
4.98 out of 5 average rating, 317 reviews

Modern, bright Rockridge studio with patio.

Recently renovated modern studio apartment, with lots of light and an open layout featuring full kitchen, dishwasher, and washer/dryer in the unit. Designed as a luxury cottage for family visits, this cozy space feels very open, with skylights and French doors that open onto a patio with seating and gas grill. Quiet and private - the entrance is at the end of a long driveway - and ideally located within easy walking distance of BART, bus routes, College Ave and 24 to the Bay Bridge.

Top Guest favourite
Guest suite in Redwood Heights
4.91 out of 5 average rating, 220 reviews

Charming Redwood Heights Garden Studio

Private studio in a family home with separate entrance and dedicated parking spot. We are located in the Redwood Heights neighborhood of Oakland California with easy access to freeways, shopping, sights, and restaurants. This is the perfect home base for national and inter-national travelers visiting the Bay Area. The studio has a small kitchenette, bathroom, and a comfortable queen size bed. There’s a flatscreen TV , wifi, and a shared garden patio right outside the door.

Guest favourite
The image depicts a serene garden pathway leading to two adjacent cabins, framed by vibrant greenery and flowering plants. A wooden trellis is visible, providing shelter, while soft lighting from the cabins enhances the calm atmosphere. A mixture of stone and mulch surfaces directs attention toward the entrance.
Guesthouse in Oakland
4.91 out of 5 average rating, 376 reviews

Guesthouse Garden Retreat

Our 'sister guesthouses' consist of two small side-by-side cabins (you get both) located behind our home, nestled in a verdant hillside garden that our friends and family lovingly call ‘Little Tuscany’. Cabin 1 - living room with a well-stocked kitchenette, pull-out couch, table and chairs Cabin 2 - bedroom with a queen-size bed, full bathroom and a private deck Accessed by a private entrance, the cabins are luminous and efficient, designed to meet all your needs.

Guest favourite
A cozy interior of a cabin is showcased, featuring a lofted sleeping area accessed by a wooden ladder. Below, a spacious bed is positioned near windows that invite natural light. A small dining table with chairs and bookshelves add functionality to the warm wooden space.
Guesthouse in Redwood Heights
4.95 out of 5 average rating, 243 reviews

Charming Cozy Cottage in Eco-Garden Oasis

Our charming cottage is a relaxing retreat in the city! Our sweet cabin is small and cozy set in an expansive garden oasis. We offer a unique experience for those interested in a beautiful and tranquil escape in the heart of the city. The cottage is at the back of our large garden with views of our beautiful urban farm with a pond, chickens and goats! Families with up to 2 children are best suited for the loft because of the low ceiling. No more than 2 adults please.

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, 174 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.

Top Guest favourite
A spacious yard is encircled by lush greenery and mature trees, creating a private outdoor setting. A stone fireplace is visible near a charming garden shed. Patio furniture, including chairs and a table, is arranged invitingly on the grass, ideal for outdoor meals.
Guesthouse in Crocker Highlands
4.96 out of 5 average rating, 590 reviews

Lakeshore Cottage

Our quiet studio cottage is located in the Lakeshore/Grand Ave area of Oakland. The neighborhood is safe and beautiful and the cottage is neat and easily accessible. There is a large bright main room and a spacious bathroom that was recently updated. The cottage includes a mini kitchen. The location is close to downtown Oakland, Berkeley and San Francisco.

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 5,380 holiday rentals in Oakland

  • Verified guest reviews

    Over 245,360 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,920 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 1,400 rentals that welcome pets

  • Holiday rentals with a pool

    250 properties feature pools

  • Rentals with dedicated workspaces

    2,910 properties have a dedicated workspace

  • Wi-Fi availability

    5,270 of Oakland holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Monthly stays, Self check-in and Gym 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 Joaquin Miller Park

Destinations to explore

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