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Top Holiday Rentals in Oakland City

The Family Oasis just 6 miles from Holiday World
9.0 out of 10, Wonderful, (19)
"Pefect house with fire-pit and covered picnic area. Clean and comfortable in a quiet town. Thank you!"
The price is £375
includes taxes & fees
3 Jul - 4 Jul
The Family Oasis just 6 miles from Holiday World
2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!
10.0 out of 10, Exceptional, (1)
"My family and I booked at the last minute so we could go view the Solar Eclipse. The process of booking, checking in and checking out was a breeze. Jodey was very responsive and extremely helpful in making our stay very enjoyable. We would highly recommend a stay here, and we hope to return for a Christmas visit to Santa Claus."
2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!
Rustic Guest House with acreage to explore.
9.6 out of 10, Exceptional, (34)
"Doug was awesome! The property had probably the best bed we have slept in. He was thoughtful and had some protectors for the couches knowing we had a couple dogs with us. It was nice and quiet out at his place though we didn't get to explore because of family obligations. My car decided to die on us and he was so kind offering help and not mad about the circumstance of essentially checking out a hour late due to having to run into town and back for a new battery. We greatly appreciate his...
The price is £131
includes taxes & fees
17 Jun - 18 Jun
Rustic Guest House with acreage to explore.
Cozy Bungalow in a nice friendly neighborhood
9.8 out of 10, Exceptional, (50)
"This was a the perfect fit for a short stay in Evansville. The neighborhood was quiet, and I felt very safe staying there. It is just a short 7-minute drive to downtown. The owners were very responsive and answered all of my questions."
Cozy Bungalow in a nice friendly neighborhood
Yellow Banks Log Cabin With Waterfront Views
9.6 out of 10, Exceptional, (5)
"Everything was great"
The price is £226
includes taxes & fees
18 Jun - 19 Jun
Yellow Banks Log Cabin With Waterfront Views
Yellow Banks Log Cabin With Waterfront Views
9.8 out of 10, Exceptional, (7)
"We went for our anniversary. I enjoyed the quiet and peacefulness of the area. My husband had a wonderful time fishing!"
The price is £226
includes taxes & fees
17 Jun - 18 Jun
Yellow Banks Log Cabin With Waterfront Views
Comfort and Charm Highly Recommended
9.4 out of 10, Exceptional, (8)
"Great place to host family for graduation celebration."
Comfort and Charm Highly Recommended
X Marks the Spot (Green)
X Marks the Spot (Green)
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
10.0 out of 10, Exceptional, (2)
"Clean, spacious, relaxing stay. Very kind, friendly, and accommodating host. Convenient to many southern Indiana attractions."
The price is £228
includes taxes & fees
17 Jun - 18 Jun
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Sweet Spot in the City
The price is £281
includes taxes & fees
17 Jun - 18 Jun
Sweet Spot in the City
Another Oasis just 6 miles from Holiday World
9.0 out of 10, Wonderful, (4)
"We brought our son and his wife and kids to our holiday world mini vacation. There was plenty of space for all of us and lots of space for the kids to run and play. They even had games for the kids. The place was exactly as described. The host was very easy to communicate with and promp with responses. We will definitely plan to stay there again!"
The price is £383
includes taxes & fees
30 Jun - 1 Jul
Another Oasis just 6 miles from Holiday World
X Marks the Spot(Blue)1.5 miles from Holiday World
10.0 out of 10, Exceptional, (1)
"Very nice and clean."
X Marks the Spot(Blue)1.5 miles from Holiday World
Yellow Banks Log Cabin With Waterfront Views
10.0 out of 10, Exceptional, (3)
"Contact with property manager was awesome, and super easy. He sent me recommendations for nearby food, and even found somewhere i could but fishbait at. The cabin was perfect for my family(2 adults, 5 year old and a 9 year old). My only suggestion is to add a light in the shower, as it get pretty dark inside there. But wonderful place to stay, and wonderful people for Contact. Will def stay again!"
The price is £226
includes taxes & fees
17 Jun - 18 Jun
Yellow Banks Log Cabin With Waterfront Views
Mary - H · Conveniently Located 2bd 2ba Apt w/ Pool & Wi-Fi
10.0 out of 10, Exceptional, (4)
"Easy and quick stay Easy of booking on short notice. Very clean and well maintained property. Comfortable bed. As described Thank goodness!!!"
The price is £205
includes taxes & fees
24 Jun - 25 Jun
Mary - H · Conveniently Located 2bd 2ba Apt w/ Pool & Wi-Fi
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
9.8 out of 10, Exceptional, (19)
"nice and quiet"
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
X Marks the Spot(Yellow)1.5 mi. from Holiday World
10.0 out of 10, Exceptional, (6)
"We had a very short visit at this property but would have been happy staying much longer. The kitchen was well equipped for cooking all types of meals, there was a full size washer & dryer and the beds were comfy. Great little touches, like board games and a selection of DVDs and an outdoor fire pit (bring your own wood) with seating and an outdoor grill. Nice yard for the kids to run around, play catch, etc. Even though it was on a main road, it was very quiet."
X Marks the Spot(Yellow)1.5 mi. from Holiday World
X Marks the Spot (Purple)
X Marks the Spot (Purple)
Pet friendly home in Evansville
10.0 out of 10, Exceptional, (5)
"We stayed 8 nights total, and it was great from start to finish. Very gracious and communicative hosts! Some key highlights for us: - Use of the garage for our vehicle and entry into the house. - The office room with large table to use as a desk. It was a big enough desk area for both my husband and son to share, and they both really spread out when they work. :-) - The back deck was a great place for coffee. - The dining room was my favorite place to sit and work on music for our...
Pet friendly home in Evansville
Fenced-In Yard on the East Side
10.0 out of 10, Exceptional, (2)
"Great place to stay, Very clean and comfortable home, Nice quite neighborhood."
The price is £232
includes taxes & fees
24 Jun - 25 Jun
Fenced-In Yard on the East Side
Chestnut Street Retreat
10.0 out of 10, Exceptional, (26)
"Property was great. Quiet area, clean and comfortable. Would love to come and do it again. A grill outside would be nice."
Chestnut Street Retreat
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See all available properties in Oakland City
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 City Holiday Rental Travel Info

Other types of properties in Oakland City you may be interested in

La Quinta Inn & Suites by Wyndham Evansville
2.5 star property
8.4 out of 10, Very good, (1009)
"I really liked my room. Flooring is great when you know that many people travel with their dogs. "
The price is £73
includes taxes & fees
17 Jun - 18 Jun
La Quinta Inn & Suites by Wyndham Evansville
Baymont by Wyndham Evansville East
2.5 star property
8.0 out of 10, Very good, (1007)
"Room was clean and staff was friendly. Not overly nice but definitely did the job. "
The price is £68
includes taxes & fees
30 Jun - 1 Jul
Baymont by Wyndham Evansville East
Drury Inn & Suites Evansville East
3.0 star property
9.2 out of 10, Wonderful, (1003)
"Friendly, safe, good breakfast and evening snacks"
The price is £102
includes taxes & fees
23 Jun - 24 Jun
Drury Inn & Suites Evansville East
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.

Everything you need to know about Oakland City 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 City holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 City holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakland City holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland City. 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 City 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 City holiday rentals we have selected for you start as low as £131 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakland City rentals

At Expedia, we put the best Oakland City 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 City 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 City 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 City. 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 a holiday rental in Oakland City?

Yes, there are holiday rentals close to the most popular sights in Oakland City, or you can select a more secluded option if you're looking for a relaxing stay. Oakland City is known for its restaurants and university setting.

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

The Family Oasis just 6 miles from Holiday World: This holiday home rental outside of Oakland City 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 dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Oakland City?

Visit the sights while you're exploring the area such as Oakland City University and Wabash Erie Canal Park.

What are holiday rentals like in Oakland City?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oakland City. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.

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