
Vacation rentals in Oakland City
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Oakland City
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Oakland City vacation rentals
Other great vacation rentals in Oakland City
Guest favorite

Home in Loogootee
4.86 out of 5 average rating, 95 reviewsCovel’s Cottage 3br easy checkin great location
ChristianRating, 5 stars3 weeks ago
nice place to stay! clean and comfort . recommended!
Guest favorite

Vacation home in Owensboro
4.93 out of 5 average rating, 127 reviewsThe little big cozy house
KatherineRating, 5 stars3 weeks ago
We enjoyed our stay at Francisco’s place! It was so clean and homey. Both us and our pets felt at home. It’s close to anything you need but still private and enough to provife quiet comfort. We could not be happier with our stay! And we will definitely stay again!
Superhost

Cabin in Falls of Rough
4.87 out of 5 average rating, 134 reviewsWaterfront Cabin with Hot Tub
BaileyRating, 5 stars2 weeks ago
We loved this cabin!! Perfect for a little getaway time. I couldn't make any phone calls due to zero service. But I was able to text via the Wi-Fi that is available. I had no problem with this, as I wanted to be off-grid as much as possible! The cabin has that nice "woody" smell immediately upon entering. The hot tub was ready to go when we arrived and was awesome! The neighboring cabins didn't bother us at all. We forgot they were even there. Everything we needed was provided. (Besides groceries, obviously!) I highly recommend this place if you're looking for some peace and quiet. It was so relaxing and gave me the recharge I desperately needed! It is the perfect spot for some tranquility. Thanks again, James!!!!
Guest favorite

Cottage in Birdseye
4.95 out of 5 average rating, 105 reviewsEagles Nest
BrianRating, 5 stars1 month ago
Everything was just as advertised. Cabin is well stocked. Area was quiet as we had hoped for. Hot Tub is a nice added feature.
Guest favorite

Home in Paoli
4.97 out of 5 average rating, 34 reviewsPrivate Wooded Getaway
CarolRating, 5 stars5 months ago
Wooded getaway is very accurate. Accommodations were perfect for our needs. The outdoor area is so pretty and Ron had turned the strings of lights on for our arrival. So very thoughtful for us Texans who were tired from a day of travel. There is ample outdoor seating and firewood available for an outdoor camp fire. We all rested well. The price is really good for everything you get. This area of Indiana is stunning. I would like to come back and stay longer! Thank you Ron!
Superhost

Townhouse in Newburgh
4.91 out of 5 average rating, 32 reviewsQuiet home on the water downstairs duplex A
MaryRating, 5 stars6 months ago
Kaci and Chuck’s place is exactly what we needed for the week we visited family. The location was perfect and we really enjoyed how peaceful it was. We even brought our chihuahua and she loved it! It felt like a French lakeside cottage, very clean and well stocked for everything we needed. We’ve found a home away from home for when we visit family and will be back!
Top guest favorite

Home in Ferdinand
5 out of 5 average rating, 22 reviewsEagles Nest (Eagle Adventures LLC)
DustinRating, 5 stars1 week ago
I wish I could write two reviews, because that's honestly how many stars Eagle Adventures deserves! The pictures did not do the home justice. The pool was amazing and the landscaping was immaculate. The host provided all the necessary items including things we didn't think of. The house had a warm cozy "home" feel. The home was beautifully decorated and spotless. Everything had its own place and was appropriately labeled. The host was responsive and courteous. There are some delightful fur friends that are sure to steal your heart. Overall, this was the best experience we have ever had in an Airbnb. If ever there was an award for Host of the Year, Karen would win it hands down.
Top guest favorite

Cottage in Owensboro
4.97 out of 5 average rating, 139 reviewsThe Woodford Retreat Cottage
DavidRating, 5 stars4 weeks ago
wonderful stay. we were in Owensboro for 4 days. Had 3 couples in the house. Had a vintage show car that we got to keep and work on in the detached garage. Since it rained nearly everyday, this was a blessing. Great comfortable house..
Destinations to explore
- Louisville Vacation rentals
- Southern Indiana Vacation rentals
- Bloomington Vacation rentals
- Nashville Vacation rentals
- Evansville Vacation rentals
- Terre Haute Vacation rentals
- Jeffersonville Vacation rentals
- Owensboro Vacation rentals
- French Lick Vacation rentals
- Nashville Vacation rentals
- Gatlinburg Vacation rentals
- Chicago Vacation rentals
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes