Oakland Holiday Rentals

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Holiday Rentals in Oakland

Cozy comfortable home near lakes, parks and downtown Sumter

10.0 out of 10, Exceptional, (43)
"This property was very central to every event We attended for homecoming.. The house all all essential needed for the stay.. It was very cozy and relaxing... I will BOOK again Next Year..... Love this spot !!!"
Cozy comfortable home near lakes, parks and downtown Sumter

Peaceful Lakeview Cabin

"We had a wonderful time in this cabin. It was so cute and relaxing and exactly like the pictures. It was about 20-30 min from any restaurants/ town but we did not mind. We planned to cook at the cabin and grill and relax and enjoy the peacefulness . It couldn’t have been better and we can’t wait to go back. "
The price is AU$834
includes taxes & fees
1 Dec - 2 Dec
Peaceful Lakeview Cabin

Sumter Vacation Rental ~ 8 Mi to Shaw AFB!

10.0 out of 10, Exceptional, (3)
"The property was amazing "
Sumter Vacation Rental ~ 8 Mi to Shaw AFB!

Remodeled home with firepit and only 9 minutes from downtown area!

10.0 out of 10, Exceptional, (12)
"The property was conveniently located right near down town on a quiet little street and Kodi was exceptionally accommodating when we did have to reach out. The house was clean, the beds were soft, and the bathrooms and kitchens were well stocked. I do wish there were curtains at the windows, especially near the back kitchen patio, but that's a very minute issue. Overall I would 100% book this property again. Clean, comfortable, and convenient. "
Remodeled home with firepit and only 9 minutes from downtown area!

Charming 3-bedroom house in wonderful Sumter

2.0 star property
10.0 out of 10, Exceptional, (3)
"The property was the right amount of space and comfort I needed after traveling. Very comfortable and clean. Definitely will stay again!"
Charming 3-bedroom house in wonderful Sumter

Peaceful Camden Vacation Rental ~ 3 Mi to Town!

9.6 out of 10, Exceptional, (5)
"Great place to stay for our trip to see the Revolutionary War reenactment to celebrate my husband’s birthday. The house was cute and welcoming."
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, (2)
"I've stayed in many properties around the world...this one was definitely Top 5. The towels smell like the towels at The Four Seasons. Close to everything and price is cheaper than a budget hotel. Bravo!"
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 AU$350
includes taxes & fees
1 Dec - 2 Dec
Carriage House near parks, walking paths, and historic downtown Sumter!

Downtown Camden Retreat

Downtown Camden Retreat

Quiet & Cozy Rembert Home ~ 9 Mi to Air Force Base

Quiet & Cozy Rembert Home ~ 9 Mi to Air Force Base

Quiet & Cozy Rembert Home ~ 9 Mi to Air Force Base

3.0 star property
Quiet & Cozy Rembert Home ~ 9 Mi to Air Force Base

Backyard Oasis w/ Pool: Sunny Sumter Studio!

Backyard Oasis w/ Pool: Sunny Sumter Studio!

Pear Tree Farm. Peaceful, Country living at its best. 12 stables. Pet Friendly

9.6 out of 10, Exceptional, (11)
"My two friends and I stayed while attending an AKC event in Camden and we couldn't have found a better location. This home is BEAUTIFUL and has so many cool features!!! It was too cold to use the pool this visit but it looked amazing and we would have used if it weren't November (my fault for travelling in cooler weather! lol) The yard was perfect for our dogs to run and play safely without fear of escape and it was so quiet and peaceful in this country setting. We didn't bring any children but...
The price is AU$418
includes taxes & fees
1 Dec - 2 Dec
Pear Tree Farm. Peaceful, Country living at its best. 12 stables. Pet Friendly

Serene Riverfront Retreat near Historic Camden Sleeps 9 with RV Hookup, WiFi, AC

2.0 star property
10.0 out of 10, Exceptional, (2)
"Absolutely loved the location, the home and the view of the river. Would definitely recommend."
The price is AU$598
includes taxes & fees
3 Dec - 4 Dec
Serene Riverfront Retreat near Historic Camden Sleeps 9 with RV Hookup, WiFi, AC

Peaceful Camden Vacation Rental ~ 3 Mi to Town!

3.0 star property
Peaceful Camden Vacation Rental ~ 3 Mi to Town!

'vibe Villa' w/ Backyard ~ 8 Mi to Shaw Afb!

3.0 star property
'vibe Villa' w/ Backyard ~ 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

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

Modern & Spacious Duplex

10.0 out of 10, Exceptional, (1)
"My family and I really enjoyed our time here. Shaun and Beth are great hosts. They were very responsive to our needs and have good accommodations. I would definitely stay here again."
Modern & Spacious Duplex
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.
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Other types of properties in Oakland you may be interested in

Baymont By Wyndham Sumter

2.5 star property
5.8 out of 10, (239)
"A bit outdated property but decent place to stay. They have an indoor pool "
The price is AU$110
includes taxes & fees
28 Nov - 29 Nov
Baymont By Wyndham Sumter

Hyatt Place Sumter / Downtown

3.0 star property
9.2 out of 10, Wonderful, (720)
"Great restaurant next to it liked downtown area"
The price is AU$207
includes taxes & fees
22 Dec - 23 Dec
Hyatt Place Sumter / Downtown

Mount Vernon Inn

2.0 star property
6.2 out of 10, (156)
"The employees are great"
The price is AU$86
includes taxes & fees
29 Nov - 30 Nov
Mount Vernon Inn
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find holiday rentals in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing stay.

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

Cozy comfortable home near lakes, parks and downtown Sumter: This holiday home rental outside Oakland is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Oakland?

With 3 Expedia holiday rentals, you're guaranteed 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, Dillion Park and Swan Lake Iris Gardens are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Shaw Air Force Base and Palmetto Tennis Center.

What’s a holiday rental in Oakland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakland. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family trips.