Holiday rentals in Oakland
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Top-rated holiday rentals in Oakland
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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!
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!
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.
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.
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.
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
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.
North Oakland / Berkeley Apartment
Welcome to our charming North Oakland apartment. Nestled on the boarder of Berkeley, close to the prestigious "Cal" Campus, vibrant Rockridge and Temescal neighborhoods. Located in the rear unit, on the 2nd floor of our family home, our delightful one bedroom, one-bathroom apartment with eat in kitchen and closed off living room with a hide-a-bed (that easily converts to a 2nd bedroom) is the perfect sanctuary for your stay whether you're on vacation, working or visiting Berkeley.
Eco-Cottage Sanctuary in Garden Oasis
Our popular cottage is like a retreat experience in the city! The cottage is an enchanting oasis nestled in the back and away from street noise. You will sleep comfortably on our new mattress topper! Our urban farm and garden offers a unique heartwarming experience-with lush gardens, frogs, chickens and 3 young goats! The cottage is perfect for guests looking for a comfortable space to relax after a busy day. Come and enjoy our beautiful and relaxing eco-friendly cottage!
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.
Private In-Law Suite Historic Crocker Highlands
🌟 Spacious suite located in one of the most scenic & safest communities in Oakland / Piedmont / Berkeley. Dog friendly. Up to 4 guests. Well suited for remote working. Nestled amongst stately homes and walkable tree-lined streets. Perfect retreat from exploring San Francisco, wine country or family. Level entrance. Suite is located on the lower story. We live above and as we are very conscientious of our guests, you may hear the pitter-patter of home life above.
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
Other great holiday rentals in Oakland
Wooded In-Law
Serene Montclair Suite-Nature Views-10 min to BART
Upper Rockridge Luxury Mid-Century Escape
Traditional Japanese Tea House
Private Mid-Century Modern W/ Secluded Yard
Newly remodeled hilltop home with stunning views
2533 - Luxury 2BR/2BA | Kitchen | Laundry | Bidet
Glenview Beauty: 1bd retreat near Piedmont
When is the best time to visit Oakland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £78 | £80 | £80 | £81 | £84 | £81 | £83 | £85 | £81 | £83 | £84 | £85 |
| Avg. temp | 10°C | 11°C | 13°C | 14°C | 16°C | 17°C | 18°C | 18°C | 18°C | 16°C | 13°C | 10°C |
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 & child-friendly amenities
Pet-friendly holiday rentals
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
Wifi availability
5,290 of Oakland holiday rentals include wifi 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
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- Moscone Center
- Stanford University
- Golden Gate Park
- Oracle Park
- Muir Woods National Monument
- Golden Gate Bridge
- SAP Center
- Pier 39
- Mission Dolores Park
- Twin Peaks
- University of California-Berkeley
- Six Flags Discovery Kingdom
- Rodeo Beach
- Palace of Fine Arts
- Levi's Stadium
- Montara Beach
- Winchester Mystery House
- Bolinas Beach
- California’S Great America
- Painted Ladies
- San Francisco Zoo
- Googleplex
- Chase Center
- University of California San Francisco
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