Oakland City Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Oakland City

2BR/2Bth, walking to Holiday World. Outdoor grilling area. Family Friendly!!
Aerial view
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!!
The Family Oasis just 6 miles from Holiday World
Property grounds
The Family Oasis just 6 miles from Holiday World
8.8 out of 10, Excellent, (18)
"Excellent location, quiet, clean with nice thoughtful touches to make a welcoming stay. Perfect place to have a weekend getaway."
The price is ￥45,315
￥72,705 total
includes taxes & fees
Jun 8 - Jun 9
The Family Oasis just 6 miles from Holiday World
Rustic Guest House with acreage to explore.
Property grounds
Rustic Guest House with acreage to explore.
9.6 out of 10, Exceptional, (33)
"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 ￥19,664
￥25,547 total
includes taxes & fees
Jun 2 - Jun 3
Rustic Guest House with acreage to explore.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Cozy Bungalow in a nice friendly neighborhood
Fridge, microwave, oven, stovetop
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
Another Oasis just 6 miles from Holiday World
Exterior
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!"
Another Oasis just 6 miles from Holiday World
Comfort and Charm Highly Recommended
Exterior
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
Sweet Spot in the City
Private kitchen
Sweet Spot in the City
The price is ￥31,360
￥54,968 total
includes taxes & fees
Jun 4 - Jun 5
Sweet Spot in the City
X Marks the Spot (Green)
Fridge, microwave, oven, stovetop
X Marks the Spot (Green)
X Marks the Spot (Green)
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Private kitchen
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
10.0 out of 10, Exceptional, (1)
"A great fully finished basement with ample room for a group. Wonderful location to stay to enjoy all that Dubois County has to offer."
The price is ￥20,854
￥33,542 total
includes taxes & fees
Jun 4 - Jun 5
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Yellow Banks Log Cabin With Waterfront Views
Smart TV
Yellow Banks Log Cabin With Waterfront Views
9.6 out of 10, Exceptional, (5)
"Everything was great"
The price is ￥24,383
￥44,223 total
includes taxes & fees
Jun 3 - Jun 4
Yellow Banks Log Cabin With Waterfront Views
Yellow Banks Log Cabin With Waterfront Views
Property grounds
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 ￥24,383
￥44,223 total
includes taxes & fees
Jun 3 - Jun 4
Yellow Banks Log Cabin With Waterfront Views
X Marks the Spot(Blue)1.5 miles from Holiday World
Fridge, microwave, oven, stovetop
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
Interior
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 ￥24,383
￥44,223 total
includes taxes & fees
Jun 3 - Jun 4
Yellow Banks Log Cabin With Waterfront Views
Mary - H · Conveniently Located 2bd 2ba Apt w/ Pool & Wi-Fi
Fridge, microwave, oven, stovetop
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 ￥15,731
￥39,485 total
includes taxes & fees
Jun 5 - Jun 6
Mary - H · Conveniently Located 2bd 2ba Apt w/ Pool & Wi-Fi
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Smart TV, books
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 (Purple)
Fridge, microwave, oven, stovetop
X Marks the Spot (Purple)
X Marks the Spot (Purple)
Chestnut Street Retreat
3 bedrooms, iron/ironing board, travel crib, free WiFi
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
Fenced-In Yard on the East Side
Fridge, microwave, oven, stovetop
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 ￥22,540
￥45,215 total
includes taxes & fees
Jun 9 - Jun 10
Fenced-In Yard on the East Side
X Marks the Spot(Yellow)1.5 mi. from Holiday World
3 bedrooms, iron/ironing board, cribs/infant beds, travel crib
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
New Construction | New Furnishings | Luxury Unit
Smart TV
New Construction | New Furnishings | Luxury Unit
10.0 out of 10, Exceptional, (1)
"This unit is absolutely spotless and comfortable. Keith was an incredibly gracious host, and the whole experience was pleasant and easy. I highly recommend this property and host to anyone looking for a comfortable place to stay in Evansville."
The price is ￥27,440
￥62,066 total
includes taxes & fees
Jun 9 - Jun 10
New Construction | New Furnishings | Luxury Unit
Don't see what you're looking for?
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.

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

Baymont by Wyndham Evansville East
Lobby
Baymont by Wyndham Evansville East
2.5 star property
8.0 out of 10, Very Good, (1008)
"Clean, safe and comfortable bed. "
The price is ￥10,431
￥11,996 total
includes taxes & fees
Jun 9 - Jun 10
Baymont by Wyndham Evansville East
La Quinta Inn & Suites by Wyndham Evansville
Premium bedding, desk, iron/ironing board, free cribs/infant beds
La Quinta Inn & Suites by Wyndham Evansville
2.5 star property
8.4 out of 10, Very Good, (1009)
"Staff was friendly & room was clean and comfortable "
The price is ￥11,901
￥13,686 total
includes taxes & fees
Jun 3 - Jun 4
La Quinta Inn & Suites by Wyndham Evansville
Drury Inn & Suites Evansville East
Lobby
Drury Inn & Suites Evansville East
3.0 star property
9.2 out of 10, Wonderful, (1002)
"Aĺl conditions as expected. Staff was great for the most part. Rooms and beds were comfortable. I do wish another blanket was provided. Wife likes it cool, and i prefer warm and toasty. Didn't request one, but would be nice to have available. "
The price is ￥17,696
￥20,350 total
includes taxes & fees
Jun 9 - Jun 10
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.

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

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

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

Frequently asked questions

Can I find a vacation rental in Oakland City?

Yes, you can find vacation rentals close to well known sights in Oakland City, or you can go with a more remote option if you're looking for relaxation. Oakland City is known for its restaurants and university setting.

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

The Family Oasis just 6 miles from Holiday World: Located near Oakland City, this vacation home rental is equipped with a barbecue grill, 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 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 vacation rentals like in Oakland City?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Oakland City. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for families.

Recent reviews of Oakland City properties
Expedia verified reviews

La Quinta Inn & Suites by Wyndham Evansville

La Quinta Inn & Suites by Wyndham Evansville

5/5 Excellent
"Staff was friendly & room was clean and comfortable "
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Evansville
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Evansville