Oakland holiday lettings

We found 19 holiday rentals — enter your dates for availability

Discover a selection of 6 cabins and other holiday rentals in Oakland that are perfect for your trip. Holiday rentals offer the amenities that you expect for your stay with friends, family or just your pet, such as Wi-Fi and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Oakland getaway

The parks and other outdoor surroundings create an inviting atmosphere in Oakland. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Oakland

Do you want to discover attractions to see in the area? Venture out of your cosy holiday rental and experience everything that makes Oakland a one-of-a-kind holiday spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Dogwoods Golf Course (20.5 mi / 33 km)
  • Panola Country Club (17.4 mi / 27.9 km)

Exploring the natural landscape of Oakland

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Oakland is a great place to get outside. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • George Payne Cossar State Park (5.8 mi / 9.4 km)
  • Enid Lake (10.5 mi / 17 km)
  • Hugh White State Park (20.1 mi / 32.3 km)
  • Batesville Mounds (20.2 mi / 32.4 km)
  • Lakeview Public Use Area (20.3 mi / 32.7 km)
  • Grenada Lake (20.6 mi / 33.2 km)

Transport options to and around Oakland

Fly into University, MS (UOX-University - Oxford), the closest airport, located 31.2 mi (50.2 km) from the city centre.

Frequently asked questions

How much does it cost to rent a holiday home in Oakland?
Prices for holiday rentals in Oakland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oakland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Oakland holiday house rentals?
You can find great discounts on house rentals in Oakland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Oakland?
In Oakland, the most popular types of holiday rentals are cabins and holiday houses, with several options available in the area. These properties often provide a rustic charm, featuring amenities such as fully equipped kitchens, comfortable living spaces, and outdoor areas ideal for enjoying the scenic surroundings. Many cabins come with features like fireplaces and porches, great for relaxing after a day of exploring. Holiday houses typically offer more space, making them suitable for families or groups, with multiple bedrooms and a backyard for gatherings.
Are there any family house rentals in Oakland?
In Oakland, Mississippi, there are several family-friendly house rentals available, making it a suitable destination for those travelling with children. The area features spacious homes that often come equipped with full kitchens, allowing families to prepare their own meals together. Many properties also boast generous living areas, where families can gather and enjoy quality time.

Visitors can explore the nearby attractions, including the charming local parks that offer playgrounds and picnic areas, ideal for outdoor activities. The surrounding landscapes provide opportunities for nature walks and appreciating the serene environment, contributing to a relaxed family getaway.
Can I find long-stay holiday rentals in Oakland?
A long-stay holiday rental in Oakland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Oakland?
In Oakland, Mississippi, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these holiday homes feature amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy some fresh air. The rentals typically cater to families or groups, offering comfortable accommodations with easy access to local attractions.

While the area is primarily residential, Oakland's close-knit community and surrounding natural beauty make it a pleasant destination for those looking to unwind. Nearby parks and recreational areas provide opportunities for outdoor activities with pets, ensuring that both guests and their furry companions have a memorable stay.
Are there any remote work holiday rentals in Oakland?
In Oakland, Mississippi, there are several remote work holiday rentals available that cater to the needs of those looking to balance work and leisure. Many of these properties offer essential amenities such as free Wi-Fi, ensuring a reliable internet connection for remote working. Guests can expect comfortable living spaces with dedicated work areas, allowing for productivity in a relaxed setting.

The town itself is characterised by its charming Southern atmosphere, and visitors will find local attractions and amenities within easy reach. Whether it's enjoying the local cuisine at nearby eateries or exploring the natural beauty of the surrounding area during breaks, Oakland provides a conducive environment for remote workers seeking both comfort and convenience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Oakland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Oakland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Oakland?
In Oakland, Mississippi, popular holiday rental amenities typically include kitchens, allowing guests to prepare their own meals, and comfortable living spaces that often feature a fireplace for cosy evenings. Many rentals also provide a deck or patio, superb for enjoying the pleasant Mississippi weather, as well as porches or lanais where visitors can relax outdoors. Additionally, coffee and tea makers are common, ensuring that guests can enjoy their favourite hot beverages during their stay.
When is the best time to visit Oakland for a holiday rental?
September is the most popular time to visit Oakland, Mississippi, as the warm summer days begin to transition into the more temperate autumn weather. The peak season runs from July to September, drawing visitors eager to enjoy the vibrant local culture, outdoor festivals, and recreational activities. This period is ideal for those who appreciate lively events and gatherings, with plenty of opportunities for sightseeing and exploring the beautiful Mississippi landscape.

During September, temperatures typically range from the mid-teens to low 30s Celsius, making it superb for outdoor activities. Visitors can explore scenic parks, enjoy leisurely strolls along the waterfront, or participate in local events that showcase the region's history and charm. The atmosphere is welcoming, and the community spirit is palpable, offering a comfortable environment for travellers seeking both adventure and relaxation.

For those looking to save on accommodation costs, December presents a wonderful opportunity. While it falls within the low season, visitors can enjoy a quieter experience, superb for exploring the town's unique shops and enjoying the festive decorations without the hustle and bustle of peak tourist crowds.
How early should I book a Oakland holiday rental?
Book your Oakland holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Oakland?
In Oakland, Mississippi, visitors can explore several interesting attractions that reflect the local culture and history. The area is known for its proximity to the legendary blues music scene, and a trip to the nearby town of Clarksdale is a must for music enthusiasts, featuring the Delta Blues Museum and live music venues.

The surrounding countryside offers beautiful landscapes, making it ideal for those looking to enjoy the outdoors. The nearby Tallahatchie River provides opportunities for fishing and leisurely walks along its banks.

For a taste of local history, the nearby city of Batesville features the Panola County Historical Society Museum, showcasing the region's rich heritage, while the quaint downtown area is dotted with charming shops and restaurants.
Can I change or cancel my Oakland home rental booking on Vrbo?
To find Oakland holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Oakland holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More holiday ideas