Holiday rentals in Oakland
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Top-rated holiday rentals in Oakland
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Urban Retreat In Art, Spa & Garden - Villa Jade
Villa Jade is a beautiful space to immerse into art & Beauty. Artist commissioned oil painting & wall mural, it is newly renovated with luxurious amenities. Huge Spa-like bath. It's a stand alone little house with a sweet garden tucked in from street, private & secluded. A sweet home away from home, a romantic getaway; a centrally located convenient base for your Bay Area travel. Fiber Optic 10G Wifi Dedicated work Space 12 ft high ceiling Skylight Romantic Fireplace Private Garden Washer/Dryer
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.
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.
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!
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.
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.
A Midcentury's Night Dream- Oakland
Welcome to Fabulous Lake Merritt and the Haddon Hill/Cleveland Heights neighborhood, your gateway to Oakland, Berkeley, SF and beyond. This sunny one bedroom, one bathroom duplex apartment was built in 1955 and is mid-century modern in style with modern conveniences. Here you can enjoy vintage decor that doesn't take itself too seriously; think Don Draper meets Howdy Doody. A vibrant, yet relaxing, place to stay!
Bright Modern Secluded Oakland Hills Retreat
Bright, secluded, cozy and modern detached studio in Montclair / Oakland Hills. Just across the bay from San Francisco. Queen bed, full bath and open kitchen w/ appliances + dining bar w/ bay vista views. Hike/bike trails 5 min. away. Your oasis is up the hill past trees, the occasional deer and a few turns through a friendly neighborhood. Car is essential to reach your private getaway!
Private Cabin by Lake Merritt
Backyard cabin steps away from Lake Merritt and Grand Avenue restaurants and businesses. Very quiet and cozy space for singles and couples, the cabin can work for 3 or 4 close friends who are very comfortable with sharing space .Convenient to public transportation, easy commute to San Francisco or Berkeley. Located behind our home . 400 square foot cabin with sleeping loft.
Architectural Gem Mid Century Modern in the Trees
ABSOLUTELY NO PARTIES and no more than 10 people in the home at any time. This is my person home & I will be staying on the lot in another structure. anyone who is looking for a relaxing quiet time in a unique home that feels like you’re living in the trees, then this home is for you. Please note there are stairs to get to the front door (approx 12) but they are wide
Studio Palace
Nice Spacious studio with the view of city lights. Located in the heart of downtown oakland. Convenient for business travels, vacationing and sight seeing. A lot of great food places, lake merit, close to San Francisco. Make your visit most memorable ! Enjoy
Popular amenities for Oakland holiday rentals
Other great holiday rentals in Oakland
Bright Apt • King Bed • Near UC Berkeley & SF
Upper Rockridge Luxury Mid-Century Escape
Villeta Pastena - Rockridge guest house w/patio
Artsy 2BD Loft, Pool & H/tub
Charming spacious two bedroom with an awesome view
Cozy private apartment
2533 - Luxury 2BR/2BA | Kitchen | Laundry | Bidet
Rockridge Studio
When is the best time to visit Oakland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $134 SGD | $138 SGD | $138 SGD | $139 SGD | $144 SGD | $140 SGD | $143 SGD | $147 SGD | $140 SGD | $143 SGD | $145 SGD | $147 SGD |
| 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 5,380 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 & child-friendly amenities
Pet-friendly holiday rentals
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
Wifi availability
5,270 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 Alameda Beach
Destinations to explore
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- Moscone Center
- Stanford University
- Golden Gate Park
- Oracle Park
- Muir Woods National Monument
- Golden Gate Bridge
- SAP Center
- Mission Dolores Park
- Pier 39
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- Bolinas Beach
- California’S Great America
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- Rodeo Beach
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- Googleplex
- Duboce Park
- California Academy of Sciences
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