Oakland Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Oakland vacation rentals

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

Vacation Home in Rembert

Pear Tree Farm. Peaceful, Country living at its best. 12 stables. Pet Friendly
9.6 out of 10, Exceptional, (24)
"Would definitely stay here again! This property is very reasonably priced. Host was great in communication. It was just a lovely, peaceful, and safe place to stay! Wish we would have stayed longer! Thank you so very much."
United States
Josh M.
The price is ￥18,928
￥33,764 total
includes taxes & fees
Dec 15 - Dec 16
Pear Tree Farm. Peaceful, Country living at its best. 12 stables. Pet Friendly
Property grounds
Serene Riverfront Retreat near Historic Camden Sleeps 9 with RV Hookup, WiFi, AC

Vacation Home in Camden

Serene Riverfront Retreat near Historic Camden Sleeps 9 with RV Hookup, WiFi, AC
2.0 star property
10.0 out of 10, Exceptional, (11)
"Loved staying here again! This place is nice and quiet and a wonderful place to unwind after a race day at CMP. We all look forward to staying here again in the fall!"
United States
Zach W.
Serene Riverfront Retreat near Historic Camden Sleeps 9 with RV Hookup, WiFi, AC
Fridge, microwave, oven, stovetop
Charming 3-bedroom house in wonderful Sumter

Vacation Home in Sumter

Charming 3-bedroom house in wonderful Sumter
2.0 star property
8.6 out of 10, Excellent, (20)
"Cozy home in a very quiet neighborhood close to shopping great location "
United States
John J.
Charming 3-bedroom house in wonderful Sumter
Fridge, microwave, oven, stovetop
Cozy comfortable home near lakes, parks and downtown Sumter

Vacation Home in Sumter

Cozy comfortable home near lakes, parks and downtown Sumter
10.0 out of 10, Exceptional, (51)
"The property is excellently kept. Comfortable, inviting, and spacious We very much enjoyed our time there. "
United States
Carmen B.
Cozy comfortable home near lakes, parks and downtown Sumter
Smart TV
3 bedroom home located within a mile from downtown

Vacation Home in Sumter

3 bedroom home located within a mile from downtown
8.0 out of 10, Very Good, (11)
"I booked the property then second guessed it but I was surprised when I checked in. I will definitely book again when visiting family "
United States
Dwayne
3 bedroom home located within a mile from downtown
Fridge, microwave, oven, stovetop
Remodeled home with firepit and only 9 minutes from downtown area!

Vacation Home in Sumter

Remodeled home with firepit and only 9 minutes from downtown area!
9.6 out of 10, Exceptional, (17)
"Will definitely stay again"
United States
James H.
Remodeled home with firepit and only 9 minutes from downtown area!
House (3 Bedrooms) | Interior
Peaceful Camden Vacation Rental ~ 3 Mi to Town!

Cottage in Camden

Peaceful Camden Vacation Rental ~ 3 Mi to Town!
3.0 star property
8.0 out of 10, Very Good, (1)
"Location was perfect for us. Very cozy, and clean. Hadn't been modernized, but it was in great shape. Nasolgic; felt like I was visiting my grandparents! Only having one bathroom was a bit challenging, but we made it work!"
United States
David
Peaceful Camden Vacation Rental ~ 3 Mi to Town!
Fridge, microwave, oven, stovetop
Charming 4-bedroom house with WiFi near Shaw Airforce and Downtown Sumter

Vacation Home in Sumter

Charming 4-bedroom house with WiFi near Shaw Airforce and Downtown Sumter
10.0 out of 10, Exceptional, (1)
"Clean, beautiful home in a safe neighborhood. Beds were comfy and kitchen and bathrooms were properly equipped. We would definitely book again."
United States
Sonya J.
Charming 4-bedroom house with WiFi near Shaw Airforce and Downtown Sumter
Private kitchen
The Farm House on Adams

Vacation Home in Sumter

The Farm House on Adams
The price is ￥28,042
￥54,788 total
includes taxes & fees
Jan 2 - Jan 3, 2026
The Farm House on Adams
House (3 Bedrooms) | Interior
Quiet & Cozy Rembert Home ~ 9 Mi to Air Force Base

Cottage in Rembert

Quiet & Cozy Rembert Home ~ 9 Mi to Air Force Base
3.0 star property
Quiet & Cozy Rembert Home ~ 9 Mi to Air Force Base
Exterior
The Moise Manor, a 1934 Bungalow, centrally located in the heart of Sumter.

Vacation Home in Sumter

The Moise Manor, a 1934 Bungalow, centrally located in the heart of Sumter.
10.0 out of 10, Exceptional, (3)
"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."
United States
Melissa P.
The Moise Manor, a 1934 Bungalow, centrally located in the heart of Sumter.
Fridge, microwave, oven, dishwasher
Modern & Spacious Duplex

Vacation Home in Sumter

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."
United States
Elronzo W.
Modern & Spacious Duplex
Smart TV
Carriage House near parks, walking paths, and historic downtown Sumter!

Apartment in Sumter

Carriage House near parks, walking paths, and historic downtown Sumter!
2.0 out of 10, (1)
"Stood in 100 degree heat just to check in"
United States
pat W.
Carriage House near parks, walking paths, and historic downtown Sumter!
Exterior detail
Charming home in downtown Camden

Vacation Home in Camden

Charming home in downtown Camden
Charming home in downtown Camden
Fridge, microwave, oven, stovetop
Home away from home

Vacation Home in Dalzell

Home away from home
9.0 out of 10, Wonderful, (2)
"This property is exactly as described. It was immaculate, spacious and comfortable. The kitchen is well stocked with everything you could need. Great water pressure in the showers and updated appliances. The owner was immediately responsive to any questions. 10/10 would recommend and rent again. "
United States
Stacy G.
Home away from home
Living area
Lakefront log cabin

Cabin in Eastover

Lakefront log cabin
Lakefront log cabin
House (3 Bedrooms) | Interior
Sumter Vacation Rental in Historic District!

Cottage in Sumter

Sumter Vacation Rental in Historic District!
3.0 star property
Sumter Vacation Rental in Historic District!
House (4 Bedrooms) | Interior
Near Rev & Civil War History Museums! Camden Home

Cottage in Camden

Near Rev & Civil War History Museums! Camden Home
3.0 star property
Near Rev & Civil War History Museums! Camden Home
House (4 Bedrooms) | Interior
'vibe Villa' w/ Backyard ~ 8 Mi to Shaw Afb!

Cottage in Sumter

'vibe Villa' w/ Backyard ~ 8 Mi to Shaw Afb!
3.0 star property
'vibe Villa' w/ Backyard ~ 8 Mi to Shaw Afb!
House (3 Bedrooms) | Interior
4 Mi to Weston Lake: Eastover Gem w/ Grill

Cottage in Eastover

4 Mi to Weston Lake: Eastover Gem w/ Grill
3.0 star property
4 Mi to Weston Lake: Eastover Gem w/ Grill
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oakland Hotel Reviews

Tru by Hilton Sumter

Tru by Hilton Sumter

10/10 Excellent
"Good"
Shayna 2-night trip
Posted 2 days ago
Tru by Hilton Sumter

Find out more about Oakland

Search for holiday rentals in Oakland on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakland using one of the methods below:

  • View our selection of featured holiday rentals in Oakland
  • Use the map to find apartments and other holiday homes in the Oakland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland while they last

Look no further and take a look at our great range of rental properties in Oakland!

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?

3 bedroom home located within a mile from downtown: Visitors like this Oakland vacation home rental. It is located in the city center and has a patio, a barbecue grill, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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, Palmetto Park and Swan Lake Iris Gardens are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Shaw Air Force Base and Palmetto Tennis Center.

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.