
Vacation rentals in Oakland City
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Top-rated vacation rentals in Oakland City
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Guest favorite

Home in Owensboro
4.94 out of 5 average rating, 50 reviewsA cozy place that helps you feel right at home.
HeatherRating, 5 stars2 weeks ago
The property was exceptionally clean and well-maintained, and Patty was incredibly responsive to all of our questions. We felt very comfortable and well-cared for during our stay.
Guest favorite

Vacation home in Owensboro
4.93 out of 5 average rating, 122 reviewsThe little big cozy house
KendraRating, 5 stars1 week ago
Great place and great host! Gracious enough to let us check in early due to flooding. We definitely overpacked as everything we needed was already there, including dog food & treats!
Guest favorite

Home in Evansville
4.88 out of 5 average rating, 25 reviewsCity Cottage
IrisRating, 5 stars8 months ago
Cute little house. Very clean. Close to the car show. Will stay again. Thanks for letting us stay at your home.
Top guest favorite

Home in Dale
4.97 out of 5 average rating, 35 reviewsAmazing View Christmas Homestead
AllisonRating, 5 stars8 months ago
My family stayed here for 4 nights and it was perfect. The game room/second living room was a perfect area for the older kids to hang out at. The place is very accommodating with everything you need. The location was perfect to go to holiday world and secluded with no worries about traffic with kids outside. Would definitely recommend staying here!
Guest favorite

Home in Owensboro
4.94 out of 5 average rating, 141 reviewsCottage by the River & Convention Center
NicRating, 5 stars1 month ago
Easy, keyless entry. The listing was as described- great location, very well equipped kitchen, plenty of linens, beautiful river views and walking distance for fun in O’boro. Bettie was a friendly host and communicated well. We’d stay here again.
Guest favorite

Home in Evansville
5 out of 5 average rating, 10 reviewsHuge Home for Everyone!
JessicaRating, 5 stars1 week ago
We have stayed with Brian several times now when we are in the area. Absolutly love working with him and staying at this house of his. Super friendly, worked with the crew and I, kept line of communication open.
Top guest favorite

Home in Ferdinand
5 out of 5 average rating, 20 reviewsEagles Nest (Eagle Adventures LLC)
Austin and SylviaRating, 5 stars7 months ago
Absolutely LOVED our stay! 10/10 highly recommend to all. Do not pass this place up. It is peaceful and private, but not too far from town (less than 10 minutes) Karen and Ron have went above and beyond with the inside of the home. Everything is labeled and very easy to navigate. Karen met us to give us a quick tour upon check in and was super responsive through our stay. The pool is amazing and worth the price alone. There are games and stuffed animals for the kids and tons of water toys and floats. Next time all we will need to bring is our swimwear! There are bathroom toiletries, kitchen utensils, many coffee options, endless towels, etc. These hosts are top tier! We will be coming back for sure!
Top guest favorite

Cabin in West Salem
4.99 out of 5 average rating, 122 reviewsLake Cabin in the Woods
AngieRating, 5 stars4 months ago
House was clean and cozy. Beautiful scenery. Quiet and peaceful. Amazing hosts. couldn't ask for more. It was the perfect little weekend get away.
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