Owner Direct Vacation
Rentals in Oakland
The Best Owner Direct Vacation Rentals in Oakland. Explore thousands of vacation home rentals, large cabins, and villas near Oakland
GUESTS
Explore the Best Oakland Vacation Homes
Looking for the perfect place to stay in Oakland? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Oakland character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Oakland Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Oakland
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Popular Neighborhoods for Oakland Vacation Rentals
What are the best areas to stay in Oakland
Discover the top neighborhoods in Oakland and choose a place that suits your stay.
Thursday Jan 22
Oakland, Maryland
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Oakland vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Oakland
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How to Reserve Your Oakland Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Oakland Vacation Rental FAQs
1. What are the top vacation rentals in Oakland?
There are a lot of options in Oakland. If you plan on staying in the Oakland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Oakland:
- Sunny Escape 2 - A new era for a well loved lake front home
- 5 STAR OWNER Managed, Lake Xcess, dock, Pool, Pickle-ball, Home Theater, firepit
- Level lakefront, family-friendly, hot tub, low fees, private dock
- Timroc II, FIVE STAR REVIEWS! 15 MINUTES FROM WISP! HOT TUB! PRIVATE 2 ACRES!
- Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swingn
- Mt. Dew- AMAZING LAKE FRONT! 7 BR Home with Hot Tub, Fire Pit, Dock, Pool Table
- Fall Fun at our Centrally Located Lake View Condo that sleeps 6!
- Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip
- Unobstructed lake views from living areas. Restaurants & activities in minutes
- Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit
2. How many vacation rentals have private pools in Oakland?
There are 31 vacation rentals with private pools near Oakland. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Oakland are best for families?
If you are looking for a family-friendly vacation home in Oakland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Oakland:
4. How many vacation rentals are available in Oakland?
Currently, the total number of properties listed in 2026 is over 1080 in the Oakland area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Oakland.