Holiday houses in Oakland

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Top-rated holiday rentals near Oakland

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

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Top Guest favourite

A peaceful garden pathway is framed by lush greenery and colorful flowering plants, leading to a welcoming guest house. The exterior of the guest house is visible, featuring large windows that allow natural light to enter, surrounded by a variety of vibrant landscaping.

Guesthouse in Oakland

4.99 out of 5 average rating, 263 reviews

Private Studio & Office-Bay Views, Oakland Hills

Enjoy this wonderfully appointed, 550-sq-ft Private Guest House in one of Oakland's nicest and quietest neighborhoods – the Piedmont Pines section of Montclair. Gaze at ever-changing SF Bay views, while relaxing on the private deck. Explore outstanding hiking trails, just minutes away. Visit Montclair Village, with grocery stores, boutiques, lots of services, great restaurants, and a fantastic farmer's Market on Sundays! Make full use of the separate office space, complete with desk and WiFi!

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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 Oakland

4.97 out of 5 average rating, 1,089 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.

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Top Guest favourite

The exterior of a spacious home is set within the Oakland Hills, featuring a paved driveway leading to an entrance. Lush greenery and natural stone landscaping flank the sides, while a gentle slope showcases the house’s elevated position.

Home in Oakland

4.99 out of 5 average rating, 169 reviews

5 Bedroom home with bay views for large groups

Spanish-style home in the Oakland hills , a quiet neighborhood Spacious, open layout with fantastic views of the San Francisco Bay Area. Great location: Close to Montclair village and quick access to San Francisco. Half-mile walk to the best open space parks in the east bay: Joaquin Miller Park! Features one acre of attractive gardens, patios, and a large deck with bay views. Great for family reunions, get-togethers or larger families. Plenty of parking, 4 cars+, in huge private driveway

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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 Oakland

4.99 out of 5 average rating, 315 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!

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Top Guest favourite

An outdoor lounge area features a sectional sofa arranged around a fire pit, illuminated by warm flames. The pool glistens in the background, surrounded by lush greenery and gently lit by the evening sky. The setting offers a tranquil atmosphere for relaxation.

Guesthouse in Oakland

4.96 out of 5 average rating, 311 reviews

Heated Pool, Jacuzzi, Sauna, Huge Views, Chic ADU!

Tucked between pine, oak, & redwood trees is a 4 year old, high end cottage nestled with amazing views of the mountains. Peaceful, upscale gated, property. 1 mile to large regional parks for hiking, mountain biking & horse stables. Nature at its best! Pool heated to 82F 4/1-10-31. 16 miles to San Francisco, 5-10 minutes to many restaurants. Jacuzzi & barrel sauna, grill. Large patio, pool /new deck (6500 sq foot outdoor oasis shared with main house small family of 4). Own spot in driveway.

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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 Oakland

4.91 out of 5 average rating, 562 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!

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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 Oakland

4.96 out of 5 average rating, 113 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.

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Guest favourite

An outdoor deck is surrounded by lush greenery, featuring sturdy wooden railings. Steps lead down from the deck, adorned with the shade of towering trees. The tranquil setting invites the sights and sounds of nature, with bright sunlight filtering through the foliage.

Guest suite in Oakland

4.8 out of 5 average rating, 238 reviews

Treetop Refuge in Oakland Hills

Escape to this cozy in-law studio in the Oakland Hills. Perched on a steep hill, this lower-level retreat offers a private entrance and expansive outdoor deck space. Perfect for solo travelers or couples with a child. Enjoy peaceful forest views amongst towering redwoods. Wake up to chirping birds. Unwind with a book, a drink or movie on Roku TV. Just minutes from Montclair Village, Redwood Regional Park and Joaquin Miller Park, enjoy easy access to Oakland, Berkeley, and San Francisco.

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Superhost

A cozy seating area features a white sofa adorned with soft cushions, complemented by a wooden side table and a woven chair. Warm lighting is provided by a pendant lamp, creating a serene atmosphere. Natural decor, including a branch with leaves, adds a touch of tranquility.

Guest suite in Montclair

4.88 out of 5 average rating, 139 reviews

Designer Wabi Sabi Retreat with Private Hot tub

Take it easy at this unique and tranquil retreat at our wabi sabi inspired guest suite with private access and an outdoor jacuzzi. This clean, comfortable and tastefully decorated one bedroom suite is located in our family home's ground floor, connected to our deck with pine, the aroma of mint and eucalyptus and luscious forest views . We offer a variety of coffee, tea and snacks, a mini fridge, high speed wifi, free parking, spa like bathroom and an outdoor jacuzzi. A truly unique retreat!

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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 Oakland

4.99 out of 5 average rating, 152 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

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Top Guest favourite

A wooden deck features two comfortable chairs positioned for relaxation. Lush greenery surrounds the area, providing a sense of privacy. Bright blue skies with scattered clouds create a serene backdrop, enhancing the peaceful ambiance of the outdoor space.

Guest suite in Oakland

4.98 out of 5 average rating, 129 reviews

Urban Hillside Retreat - 1 Bedroom Suite

Take it easy at this peaceful, wooded garden-level suite. Freshly remodeled with all new furnishings and a comfy king sized bed. Kick back on the lower level of a split-level house & take in the spacious back yard. Saddle up at the bar or lounge at the outdoor patio under the Redwoods. The perfect basecamp for your Bay Area adventure, nestled in the Oakland Hills with easy freeway access and proximity to BART. 15 mi from SF 6 mi from Cal Berkeley 3 mi from nearest Bart station

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Guest favourite

A well-lit kitchenette is featured with wooden cabinetry and a white refrigerator. A large potted plant adds greenery to the space, while a small wooden chair is positioned to the right. Natural light streams in through the window, enhancing the neutral-colored walls.

Apartment in Oakland

4.92 out of 5 average rating, 115 reviews

Hills Hideaway - Steps from Redwood Forest

Bike, hike, run or ride through our 2,500 acre wonderland, Redwood Regional Park, right outside your door. Come home to a quiet, comfortable sanctuary with everything you need: fast WiFi, dedicated workspace, free parking, kitchen, and a cozy bedroom with views of the trees. Whether you're here to explore the trails, work remotely, or simply recharge, this is your peaceful escape. 15 min from downtown Oakland, 25 min from SF.

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