| *NEW* Cozy*1 Bd, Kitchen*Pets OK | 1 | 4 | Analysis |
| *NEW*1Bd Apt*Bourbon Themed*Pets Ok! | 1 | 4 | Analysis |
| 1895 House:Renovated historic home, no booking fee | 3 | 6 | Analysis |
| 2 bedroom w/free on-site parking. Near downtown | 2 | 6 | Analysis |
| 315 West 14th street | 3 | 8 | Analysis |
| 4beds3BR/30to HolidayWorld/near Conv Ctr/Fisher Pk | 3 | 6 | Analysis |
| 524 West 15th Street - Sleeps 14 | 4 | 14 | Analysis |
| A cozy place that helps you feel right at home. | 4 | 10 | Analysis |
| Adorable two bedroom two bath entire home | 2 | 4 | Analysis |
| Artistic Bohemian Bungalow | 2 | 8 | Analysis |
| Black remodeled farmhouse minutes to downtown | 3 | 8 | Analysis |
| Blue Moon Cottage: Music Room, Inground Pool | 3 | 9 | Analysis |
| Bluegrass Bliss | 3 | 7 | Analysis |
| Bluegrass Bungalow 2 Bdr/1 Bath with Large Porch | 2 | 4 | Analysis |
| Bluegrass Bungalow: Historic Charm, Modern Comfort | 2 | 6 | Analysis |
| Bluegrass Commons | 3 | 6 | Analysis |
| Brick Bungalow | 2 | 5 | Analysis |
| Bunk On Bittel Family Private Home & Big Backyard | 4 | 10 | Analysis |
| Center of city private Town Home W/fire pit &BBQ | 2 | 4 | Analysis |
| Centrally located 3 bdrm quaint house with a yard | 3 | 6 | Analysis |
| Centrally Located Apartment | 1 | 2 | Analysis |
| Charming Midtown Manor 2 Bedroom + Bonus Room | 3 | 4 | Analysis |
| Clean & comfy 3 bdrm/2 bath home; perfect location | 3 | 7 | Analysis |
| Comfortable 2 bedroom with 2 private baths, patio. | 2 | 4 | Analysis |
| Comfy! Carmel Cottage 2 BR/1BA | 2 | 2 | Analysis |
| Cottage by the River & Convention Center | 3 | 6 | Analysis |
| Cozy Retreat, modern Amenities | 3 | 6 | Analysis |
| Cozy! Corporate/Medical/Travel Pros Welcome~ | 2 | 2 | Analysis |
| Downtown - Cozy Apartment B in Heart of Owensboro | 1 | 4 | Analysis |
| Downtown - Home in the Heart of Owensboro | 2 | 6 | Analysis |
| Downtown - Large Apartment A in Heart of Owensboro | 2 | 6 | Analysis |
| Emma B's Place Close to Town and the Riverfront | 2 | 5 | Analysis |
| Fiddlewood Farm Barn Stay | 1 | 5 | Analysis |
| Granny Smith's | 1 | 2 | Analysis |
| Great house for a work or family trip. | 3 | 6 | Analysis |
| Great location! 2 Bdrm, Mthly discount | 2 | 4 | Analysis |
| Hattie's Hill Cottage | 1 | 2 | Analysis |
| Hattie's Hill Farm & Vineyard Annex | 2 | 4 | Analysis |
| Heartland Hideaway | 2 | 6 | Analysis |
| Heated Swimming Pool + Hot Tub + Event Room | 4 | 9 | Analysis |
| Hill Ave home | 3 | 7 | Analysis |
| Home away from home- long or short term studio | 1 | 1 | Analysis |
| Horse Haven at the Heartlands | 3 | 7 | Analysis |
| Hot Tub /Pool/Fire Pit & BBQ | 3 | 12 | Analysis |
| Keith's Eastside Getaway | 4 | 10 | Analysis |
| Knott Clan getaway | 4 | 15 | Analysis |
| Lost and Found | 2 | 2 | Analysis |
| Mid Town getaway | 2 | 6 | Analysis |
| Midtown Cottage- Self Check-In & Centrally Located | 3 | 6 | Analysis |
| Month+ stays - Private 1bd in central location | 1 | 3 | Analysis |