Holiday houses in Oakland

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Top-rated holiday rentals in Oakland

Guests agree: these stays are highly rated for location, cleanliness and more.

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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
4.99 out of 5 average rating, 172 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)!

Top Guest favourite
A framed view from the unit showcases a scenic landscape of greenery and distant urban areas. The balcony railing provides an open perspective of the surrounding trees and hills, with a glimpse of the sky dotted with soft clouds.
Apartment in Woodminster
4.99 out of 5 average rating, 286 reviews

Modern retreat in the tree tops

Relax in this tranquil space nestled in Oakland Hills. Private inlaw unit furnished with modern furniture and art. Kitchen replete w/microwave-convection oven, induction cooktop, dishwasher, coffeemaker, prep tools and serving items await. Enjoy the electric fireplace, cable TV and high-speed WiFi. Stylish bathroom and comfy bed to refresh and relax. From the off-street parking spot, take the 30 well-lit and stable stairs to this quiet home away from home. No pets or smoking on premises. Enjoy!

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, 517 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, 141 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.

Top Guest favourite
The private entrance features a wooden door framed by a welcoming porch. Two teal chairs with striped cushions are positioned beside a potted plant, offering a cozy spot to relax. A patterned doormat adds a decorative touch to the entryway.
Guest suite in Bushrod
4.98 out of 5 average rating, 846 reviews

East Bay Studio Oasis - Rest, Relax, Or See It All

Cozy, clean studio apt located in the heart of North Oakland’s trendiest neighborhood. Renovated w/ kitchenette, stove/oven, fridge; large shower, cable TV, private entrance & porch. Queen size bed & small futon appropriate for a child or small adult. Walk to Temescal neighborhood for shops & foodies! Access to 3 BART stations, UC Berkeley, & the freeway. Awesome neighbors & sunny backyard for guests. Downstairs attached to main house. Located in Oakland ACROSS THE BAY from San Francisco.

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, 264 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
4.97 out of 5 average rating, 519 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
4.99 out of 5 average rating, 113 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 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.
Guesthouse in Millsmont
4.79 out of 5 average rating, 982 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
Guest suite in Redwood Heights
4.91 out of 5 average rating, 214 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.

Top Guest favourite
A modern guestroom is illuminated by natural light, showcasing a spacious bed adorned with crisp white linens and accent pillows. A small kitchenette is visible, along with a workspace featuring a desk and chair. Large windows offer a connection to the outdoors.
Guesthouse in Oakland
4.97 out of 5 average rating, 556 reviews

Luxury Rockridge Casita in Our Sunny Garden

** FEATURED in Sunset Magazine ** Our bright modern guest house with private access awaits you. Retreat from the city to our comfortable, clean casita. This lovely, light-filled space sits behind our family home, in our garden with fresh berries and lemons. Enjoy morning coffee at the wood farm table. We offer local coffee + tea, a small fridge, robes, wifi, and outdoor dining. Our quiet street is close to BART, 3 blocks from College Ave, full of great restaurants and shops.

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, 364 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.

Popular amenities for Oakland holiday rentals

When is the best time to visit Oakland?

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Avg. price$187 NZD$192 NZD$192 NZD$194 NZD$201 NZD$196 NZD$199 NZD$204 NZD$196 NZD$196 NZD$192 NZD$192 NZD
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Frequently Asked Questions

  • How is the weather in Oakland?

    Oakland has a Mediterranean climate, characterized by warm, dry summers and mild, wet winters. Temperatures typically range from 45°F (7°C) in winter to 75°F (24°C) in summer, making it a comfortable destination year-round.

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

    Visitors often enjoy exploring the Oakland Zoo, browsing the local shops and markets in Temescal Alley, or taking a kayak tour on Lake Merritt. Attending a live performance at the historic Fox Theater is also popular.

  • What is the best time of year to visit Oakland?

    Spring and fall are typically the most popular times to visit Oakland, with pleasant temperatures averaging 70°F (21°C). Events like the Oakland Art Month in May or the Eat Real Festival in September often attract visitors.

  • What are the best places to stay in Oakland?

    Popular areas to stay in Oakland include Downtown, known for its vibrant nightlife and cultural scene, Rockridge, appreciated for its charming boutiques and eateries, and Jack London District, renowned for its waterfront views.

  • What are the best places to visit in Oakland?

    Popular places to visit include Lake Merritt, a large tidal lagoon in the center of the city, the Oakland Museum of California, showcasing Oakland's art, history, and natural science, and Jack London Square, a vibrant waterfront area.

  • What are some hiking trails in Oakland?

    Oakland is home to several hiking trails. Redwood Regional Park features trails winding through majestic redwood groves, while Joaquin Miller Park has routes offering panoramic sea and city views.

  • What are some family activities to do in Oakland?

    Families can enjoy a day at the Oakland Zoo, explore interactive exhibits at the Children's Fairyland or the Chabot Space and Science Center, or take a relaxing walk in the Gardens at Lake Merritt.

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

    Day trip ideas include visiting the nearby cities of San Francisco and Berkeley, exploring the picturesque vineyards of Napa Valley, or hiking and picnicking in Muir Woods National Monument.

  • Are there vacation rentals with a dedicated workspace in Oakland?

    Yes! Work meets play with ease at over 2,870 vacation rentals in Oakland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Oakland?

    Four-legged friends are welcome in Oakland. Choose from more than 1,380 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in hotel rentals in Oakland?

    Experience the best of Oakland with our hotel rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Oakland condo rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 40 condo rentals with pools in Oakland, available on Airbnb. Make a splash and soak up the sun in style!

  • Do villa rentals in Oakland have self check-in?

    Absolutely! We offer over 10 villa rentals with self check-in in Oakland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oakland have a gym?

    Absolutely! We offer over 220 house rentals with a gym in Oakland. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Oakland have a bbq area?

    Absolutely! We offer over 10 condo rentals with a bbq area in Oakland. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly private suite rentals in Oakland?

    Oakland has more than 50 family-friendly private suite rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about holiday rentals in Oakland

  • Total holiday rentals

    Explore 5,390 holiday rentals in Oakland

  • Verified guest reviews

    Over 241,670 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,910 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 1,380 rentals that welcome pets

  • Holiday rentals with a pool

    240 properties feature pools

  • Rentals with dedicated workspaces

    2,870 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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