Oakland Vacation Rentals

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Vacation Rentals in Oakland

Pear Tree Farm. Peaceful, Country living at its best 12 stables. Pet Friendly
10.0 out of 10, Exceptional, (1)
"Pear Tree Farm was absolute magic! The house was whimsical and beautifully furnished. Every room was a treasure trove to discover for my 4 young children. I had the sense that children were very much thoughtfully considered when opening up their home which, as a home-school mom, made our stay that much more enjoyable. And I won't give away any secrets so as to keep it fun for future guests, but there were a few intentional surprises for kids that had our children squealing with...
The price is CA $240
CA $300 total
includes taxes & fees
Jul 17 - Jul 18
Pear Tree Farm. Peaceful, Country living at its best 12 stables. Pet Friendly
3 bedroom home located within a mile from downtown
7.6 out of 10, Good, (5)
"Place was nice and very accommodating. Will definitely stay again when visiting again.It could have been alittle bit cleaner but overall a pleasant stay."
3 bedroom home located within a mile from downtown
Home Near Shaw Airforce Base Close to Major Attractions, Food, & Entertainment
8.8 out of 10, Excellent, (3)
"Very pleased"
Home Near Shaw Airforce Base Close to Major Attractions, Food, & Entertainment
Remodeled home with firepit and only 9 minutes from downtown area!
10.0 out of 10, Exceptional, (9)
"everything was great. house is clean and comfortable just a little bit far from the farm where our event was being held. but there was nearby food , shopping and a cool park called swan lake. ."
Remodeled home with firepit and only 9 minutes from downtown area!
Cozy comfortable home near lakes, parks and downtown Sumter
10.0 out of 10, Exceptional, (39)
"Needed a place for a few nights after coming in for a funeral. I didn't like any of the hotel options and this was a perfect solution. The house was immaculately clean and very cozy. Master bed was very comfortable. neighborhood was quiet. Owner was very Gracious in letting me check in just a bit early so that a could drop my bags and change before going to services. all in all, I would Highly recommend. thanks again Patricia!"
Cozy comfortable home near lakes, parks and downtown Sumter
Sumter Vacation Rental ~ 8 Mi to Shaw AFB!
10.0 out of 10, Exceptional, (2)
"Everything about the property was excellent. Look forward to staying in the property again on future business trips"
Sumter Vacation Rental ~ 8 Mi to Shaw AFB!
Peaceful Camden Vacation Rental ~ 3 Mi to Town!
10.0 out of 10, Exceptional, (4)
"Property and house was very nice. We enjoyed our stay."
Peaceful Camden Vacation Rental ~ 3 Mi to Town!
The Moise Manor, a 1934 Bungalow, centrally located in the heart of Sumter.
10.0 out of 10, Exceptional, (1)
"We loved the property. It was family friendly and baby proof. We loved the accommodations. It fit the whole family and we had plenty space. The customer service was amazing."
The Moise Manor, a 1934 Bungalow, centrally located in the heart of Sumter.
Carriage House near parks, walking paths, and historic downtown Sumter!
The price is CA $218
CA $273 total
includes taxes & fees
Jun 24 - Jun 25
Carriage House near parks, walking paths, and historic downtown Sumter!
Spacious Home 5 miles from Shaw AFB w/ Pool Table, Firepit, & Screened-In Porch!
10.0 out of 10, Exceptional, (1)
"Would stay here again! Comfortable beds and great amenities - everything we needed."
Spacious Home 5 miles from Shaw AFB w/ Pool Table, Firepit, & Screened-In Porch!
Clean & Comfortable 3 BD 1.5BA Pool Table+Gym
8.0 out of 10, Very good, (3)
"Let me start by saying that the home looks exactly as advertised. It is very cute, updated, and everything was super clean. However, it is in a sketchy part of town and surrounded by privacy fence (I’m assuming for security reasons). Also, there was a terrible marijuana smell that hit us in the face as soon as we opened the front door. After airing out the property all weekend, the smell was bearable, but still present and unpleasant. We messaged the host and they did partially refund us for the...
Clean & Comfortable 3 BD 1.5BA Pool Table+Gym
Cozy Home Minutes From Downtown
10.0 out of 10, Exceptional, (2)
"great communication. very clean and comfortable."
Cozy Home Minutes From Downtown
Beautiful 1930s brick home in historic district.
10.0 out of 10, Exceptional, (2)
"I stayed at the property for a month and couldn't have chosen a better place. The home has so much character, space and is well maintained for a historical home. John (the host) was very gracious and promptly responded to any communications prior to and during my stay. I highly recommend this property to anyone visiting/vacationing in Sumter."
Beautiful 1930s brick home in historic district.
Peaceful Camden Vacation Rental ~ 3 Mi to Town!
3.0 star property
Peaceful Camden Vacation Rental ~ 3 Mi to Town!
Sumter Vacation Rental ~ 8 Mi to Shaw Afb!
3.0 star property
Sumter Vacation Rental ~ 8 Mi to Shaw Afb!
White House on Winn
10.0 out of 10, Exceptional, (5)
"The property was very nice, clean, and quiet. We had no issues and enjoyed our stay."
White House on Winn
Stunning Sumter Home on Active 330-Acre Farm!
10.0 out of 10, Exceptional, (1)
Stunning Sumter Home on Active 330-Acre Farm!
Downtown Camden Retreat
Downtown Camden Retreat
Sumter Vacation Rental in Historic District!
3.0 star property
Sumter Vacation Rental in Historic District!
Dogs Love The Tack Room Private Cottage in Camden SC Horse Country
Dogs Love The Tack Room Private Cottage in Camden SC Horse Country
Don't see what you're looking for?
See all available properties in Oakland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Oakland Vacation Rental Travel Info

Other types of properties in Oakland you may be interested in

Hyatt Place Sumter / Downtown
3.0 star property
9.2 out of 10, Wonderful, (637)
"Great place."
The price is CA $165
CA $184 total
includes taxes & fees
Jun 23 - Jun 24
Hyatt Place Sumter / Downtown
Baymont By Wyndham Sumter
2.5 star property
5.8 out of 10, (157)
"G"
The price is CA $98
CA $108 total
includes taxes & fees
Jun 23 - Jun 24
Baymont By Wyndham Sumter
Tru by Hilton Sumter
2.5 star property
9.0 out of 10, Wonderful, (529)
"Very clean!"
The price is CA $162
CA $180 total
includes taxes & fees
Jun 27 - Jun 28
Tru by Hilton Sumter
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oakland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Oakland?

Yes, we give you a choice of vacation rentals near the most popular attractions in Oakland, or you can choose a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Oakland has to offer?

Pear Tree Farm. Peaceful, Country living at its best 12 stables. Pet Friendly : You might want to consider this vacation home rental near Oakland, which offers an outdoor pool, a fireplace, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Oakland?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Oakland stay.

What’s there to see and do in Oakland?

While you're exploring the area, Swan Lake Iris Gardens and Dillion Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Shaw Air Force Base and Sumter Mall.

What’s a vacation rental in Oakland like?

A vacation rental is a private property you can stay in for a couple of days or more in Oakland. Vacation rentals offer amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for families.

Recent reviews of Oakland properties
Expedia verified reviews