Oakland Holiday Rentals

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Our top choices for Oakland holiday rentals

Apartment in Grand Center

White House at Grand Central
4.0 star property
8.6 out of 10, Excellent, (124)
"Very clean and very friendly people "
United States
Mary
The price is AU$216
includes taxes & fees
4 Jan - 5 Jan 2026
White House at Grand Central
10.0 out of 10, Exceptional, (136)
"We loved staying here in this adorable clean house that was only 1 block off of downtown Main Street shopping. "
United States
Lisa S.
The St. Charles Guest House, lovely historic home, fun for families and groups

Aparthotel in Maryland Heights

Value Suites Extended Stay - St Louis
3.0 star property
7.0 out of 10, Good, (1110)
"We’ve stayed here twice before and have always been pleased with everything. Very good hotel close to what we need."
United States
Timothy
The price is AU$789
includes taxes & fees
15 Dec - 16 Dec
Value Suites Extended Stay - St Louis
9.8 out of 10, Exceptional, (160)
"Very clean, check in was easy, great neighborhood with lots of food close. "
United States
Laura H.
The price is AU$204
includes taxes & fees
15 Dec - 16 Dec
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

Holiday Home in St. Charles Historic District

Stunning 1890's Home - Sleeps 8!
10.0 out of 10, Exceptional, (102)
"Check-in was easy and the house was lovely "
United States
Delfino A.
The price is AU$517
includes taxes & fees
23 Dec - 24 Dec
Stunning 1890's Home - Sleeps 8!

Apartment in Downtown St. Louis

Luxury 2BEDROOM LOFT near Bush Stadium
9.4 out of 10, Exceptional, (6)
"The location was perfect to access all things Downtown! The space was clean and well furnished. Check in/out was a breeze and the included parking spot was a huge plus for us! Great place to stay! "
United States
Kelci Y.
Luxury 2BEDROOM LOFT near Bush Stadium
10.0 out of 10, Exceptional, (211)
"Nice view of the Mississippi in the morning. Just off of the main street in old town St Charles, this place was perfect for our needs."
United States
Ralph
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

Apartment in St. Charles Historic District

Cozy Clark Suite in Frenchtown Saint Charles
9.6 out of 10, Exceptional, (14)
"Awesome place to stay"
United States
paul
Cozy Clark Suite in Frenchtown Saint Charles

Holiday Home in St. Charles Historic District

St. Charles 1860's Gem - Sleeps 6!
9.8 out of 10, Exceptional, (134)
"We will be back. Nice quiet stay. "
United States
Kathe H.
The price is AU$410
includes taxes & fees
15 Dec - 16 Dec
St. Charles 1860's Gem - Sleeps 6!

Apartment in Hyde Park

Stylish City Reno Retreat!
6.4 out of 10, (15)
"We were pleased with our stay and would stay again"
United States
Nicole L.
Stylish City Reno Retreat!

Holiday Home in St. Charles Historic District

Honky Tonk Hideaway
8.8 out of 10, Excellent, (12)
"Great location close to historic district."
United States
Hugh S.
The price is AU$489
includes taxes & fees
25 Dec - 26 Dec
Honky Tonk Hideaway
9.8 out of 10, Exceptional, (26)
"The place was great! "
United States
Melissa I.
The price is AU$686
includes taxes & fees
15 Dec - 16 Dec
Home Near Main Street-Covered Patio-Hot Tub!

Holiday Home in St. Charles Historic District

Madison House 1 -Walk to Main St
8.6 out of 10, Excellent, (14)
"The house was clean and well stocked, location was great, and plenty of street parking. "
United States
Brad K.
The price is AU$361
includes taxes & fees
15 Dec - 16 Dec
Madison House 1 -Walk to Main St

Holiday Home in Dogtown

Tamm Ave 3-BR Retreat
9.6 out of 10, Exceptional, (48)
"We enjoyed are stay at this house. It was very clean and comfortable. Host was very quick to respond and easy check in. Nice neighborhood, felt very safe. Would for sure stay here again!!"
United States
Cindy A.
Tamm Ave 3-BR Retreat

Apartment in Marine Villa

Stylish South City King 1BR Apt
2.0 star property
10.0 out of 10, Exceptional, (9)
"Great location, great accommodations, great host."
United States
Scott W.
The price is AU$271
includes taxes & fees
15 Dec - 16 Dec
Stylish South City King 1BR Apt

Holiday Home in St Charles

Residence on the Roundabout
9.4 out of 10, Exceptional, (145)
"House was very nice. Pictures were good and we knew what to expect. Location was great for where we wanted to go.Owner was punctual when we had any questions!"
United States
Anne L.
Residence on the Roundabout
9.8 out of 10, Exceptional, (136)
"Very cute property in historic neighborhood. We enjoyed our stay!"
United States
Jo L.
The price is AU$242
includes taxes & fees
16 Dec - 17 Dec
Centrally located in the Tower Grove East neighborhood!

Aparthotel in St. Charles Historic District

The Otter Suite at Divine Otter
9.0 out of 10, Wonderful, (7)
"We absolutely loved this place! I would recommend this place. We had one issue but it was resolved. If you have children, I would probably stay somewhere else. There are bars all around and gets loud at night but it does get really quiet after 1:30 a.m. The property manager was absolutely amazing and is very quick to respond to your needs. "
United States
kim F.
The Otter Suite at Divine Otter
9.6 out of 10, Exceptional, (24)
"This house was beautiful and in a very nice spot in St. Louis. Close to everything and the hosts were amazing. Would definitely use again "
United States
Justin B.
The price is AU$400
includes taxes & fees
15 Dec - 16 Dec
Brand New! Soulard Charmer - Pet Friendly.

Apartment in Northampton

Spacious 2 BR Balcony Hideaway
8.0 out of 10, Very good, (15)
"Great stay! Management was easy to reach and very helpful when we couldnt find the correct wifi network. Nice place, would stay again."
United States
Bob C.
Spacious 2 BR Balcony Hideaway
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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Top Oakland Hotel Reviews

Find out more about Oakland

Everything you need to know about Oakland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Oakland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland holiday rentals we have selected for you start as low as AU$204 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oakland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Stunning 1890's Home - Sleeps 8! : This holiday home rental outside of Oakland is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

What can I see and do in Oakland?

Explore the area and family-friendly sights such as Magic House - St. Louis Children's Museum, or get out into nature at a spot like Grant's Trail - Backstopper's Park Trailhead. While in the area, you can also visit popular places such as St. Louis Union Station and Gateway Arch.

What are holiday rentals like in Oakland?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakland. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for family gatherings.