Oakland Holiday Rentals

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Holiday Rentals in Oakland

Apartment in Grand Center

4.0 star property
8.6 out of 10, Excellent, (124)
"Very clean and very friendly people "
United States
Mary
The price is NZ$276
includes taxes & fees
2 Dec - 3 Dec
White House at Grand Central

Holiday Home in St. Charles Historic District

10.0 out of 10, Exceptional, (135)
"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

Holiday Home in St. Charles Historic District

10.0 out of 10, Exceptional, (94)
"Check-in was easy and the house was lovely "
United States
Delfino A.
The price is NZ$519
includes taxes & fees
3 Dec - 4 Dec
Stunning 1890's Home - Sleeps 8!

Cottage in St. Charles Historic District

10.0 out of 10, Exceptional, (210)
"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!

Holiday Home in St. Charles Historic District

9.2 out of 10, Wonderful, (10)
"Great location close to historic district."
United States
Hugh S.
The price is NZ$602
includes taxes & fees
25 Dec - 26 Dec
Honky Tonk Hideaway

Holiday Home in The Hill

9.8 out of 10, Exceptional, (156)
"Clean, very nice host, cute little building. It was a little warm in there with the window unit but other wise it was amazing "
United States
Lindsay
The price is NZ$255
includes taxes & fees
1 Dec - 2 Dec
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

Aparthotel in Maryland Heights

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 NZ$936
includes taxes & fees
29 Nov - 30 Nov
Value Suites Extended Stay - St Louis

Holiday Home in Saint Charles

9.8 out of 10, Exceptional, (25)
"The place was great! "
United States
Melissa I.
The price is NZ$859
includes taxes & fees
2 Dec - 3 Dec
Home Near Main Street-Covered Patio-Hot Tub!

Apartment in St. Charles Historic District

9.6 out of 10, Exceptional, (12)
"Awesome place to stay"
United States
paul
Cozy Clark Suite in Frenchtown Saint Charles

Apartment in Hyde Park

6.4 out of 10, (13)
"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

9.8 out of 10, Exceptional, (132)
"This was such a cute historical home and was perfect for our weekend in St Charles!"
United States
Isabelle C.
The price is NZ$480
includes taxes & fees
30 Nov - 1 Dec
St. Charles 1860's Gem - Sleeps 6!

Holiday Home in Tower Grove East

9.8 out of 10, Exceptional, (136)
"Our stay was exactly what we needed and that was a quick getaway. Thank you for your hospitality!"
United States
Johnathon F.
The price is NZ$298
includes taxes & fees
30 Nov - 1 Dec
Centrally located in the Tower Grove East neighborhood!

Holiday Home in St. Charles Historic District

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 NZ$429
includes taxes & fees
2 Dec - 3 Dec
Madison House 1 -Walk to Main St

Apartment in Downtown West

6.0 out of 10, (12)
"Very cool spot, everything was easy! Would for stay here again if I pass through STL again. "
United States
Hunter J.
The price is NZ$324
includes taxes & fees
29 Nov - 30 Nov
Downtown STL Lovely Loft w/Pool/ Free Breakfast/Free Parking

Holiday Home in St. Charles Historic District

9.0 out of 10, Wonderful, (19)
"Excellent location and a great space for 4 couples. The beds were exceptionally comfortable! "
United States
Kimberly C.
The price is NZ$717
includes taxes & fees
4 Dec - 5 Dec
The Lewis & Clark Hangout

Apartment in St. Charles Historic District

9.8 out of 10, Exceptional, (99)
"The loft was very nice, very clean, well appointed, and in a perfect location. I highly recommend this property!"
United States
Mary ann S.
The price is NZ$466
includes taxes & fees
7 Dec - 8 Dec
Prime Loft of Main Street

Apartment in Skinker DeBaliviere

2.0 star property
10.0 out of 10, Exceptional, (8)
"My friends and I really enjoyed how close it was to the loop and how clean the place is."
United States
David M.
The price is NZ$594
includes taxes & fees
7 Dec - 8 Dec
TOP RATED! FANTASTIC LOCATION! 3 bedroom near WASHU, LOOP, Pageant, Forest Park

Aparthotel in St. Charles Historic District

9.4 out of 10, Exceptional, (12)
"We really enjoyed our stay! The Hare was an amazing suite & the location was great!"
United States
Angela R.
The Hare Suite at Divine Otter

Apartment in Marine Villa

9.6 out of 10, Exceptional, (117)
"Host was fantastic with communication. "
United States
Patrice B.
Spacious 2 bedroom apartment with 3 queen beds and 2 full baths

Holiday Home in St Charles

9.4 out of 10, Exceptional, (142)
"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
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 favorite 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 depends 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 NZ$255 per night. Entering your travel dates in the search wizard you might find 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.