Vacation rentals with a pool in Owensboro

Hattie's Hill Cottage

Cozy cottage located just behind the main home on the property (see photos). Relax by the pool, open seasonally, which is shared by the main house guests and host family, or enjoy an evening stroll out in the country. Conveniently located near Owensboro, Rockport, Hawesville, and Lewisport. The cottage features one flexible bedroom with either two twins or one California king, Wi-Fi, Smart TV, well-stocked kitchen, dining/work space, comfortable recliners, and access to the beautiful grounds.

NYA river front Lighthouse Castle

It's rare to find a place that's both historic and one-of-a-kind.Here you have it all, freshly renovated 4,000 sq/ft sleeps 20, in-ground summer pool and year around hot tub.Breath taking views of the Ohio River with plenty of to do inside and out. Enjoy our game room pool/pingpong table, shuffle board and darts along with a spectacular Ohio River view from each room! We are conveniently located 1 hour from Louisville,Owensboro and Evansville.Check us out NYAMillennial on ticktock and YouTube.

Third Street Retreat Modern Victorian 2BR Apt

This extraordinary 2 bedroom 3rd floor apartment offers a mix of midcentury modern decor with original trim and doors and a 14' vaulted ceiling. The apartment is accessible via stairs only and entry is through the house. Each bedroom has a desk, plenty of storage and seating. The fully furnished kitchen, dining space and large living room with a 55" TV and large bathroom with a shower is for all. The outdoor spaces are shared with other guests and hosts and are available for your enjoyment.

Bluegrass Getaway • Swim, Relax & Unwind

Welcome to **Bluegrass Getaway**, your perfect retreat for relaxation and connection. This cozy home has 2 bedrooms 1 bath and features a private pool with lounge chairs, a firepit for evening gatherings, and a beautiful, fully stocked kitchen for all your cooking needs. The warm, inviting décor creates a comfortable space to unwind and make memories. Perfect for families or small groups, this getaway combines charm and comfort for an unforgettable stay. ** Heated Pool- Closes October 17th**

Luxury Ranch in Darmstadt

Truly in "A League of Its Own"! Step into the home famously known as the residence where Tom Hanks lived during filming in Evansville. Nestled on 5 acres, just down the street from The Bauerhaus. Enjoy the private lake and walkout deck, perfect for relaxing by the water. Sonos speaker system throughout the property. Take a dip in the inground pool or watch some TV under the covered patio. This home is a true gem! Experience it for yourself and discover why it’s truly in a league of its own.

Heated Swimming Pool+ Hot Tub+Sleeps 10

Leave your worries behind! Relax in the hot tub, go for a swim, or cozy up with a book by the fireplace! There are a lot of things to do in Owensboro including “Friday After 5” event downtown, concerts, Green River Distillery, Smothers Water Park, Bluegrass Music Hall of Fame & Museum, Owensboro Museum of Science & History, Edge Ice Skating Center, Owensboro Museum of Fine Art, Malco Cinema + much more. Located only 40 minutes from Holiday World. 2 minutes from Hillcrest Golf Course!

Country Homeplace Pool/By Toyota/Sleep 14/Pets Ok

Pet friendly home w/ 4 upstairs bedrooms: This an established 5 star on another platform -1 king, 3queens & 4single beds. -one queen airbed, 2 twin airbeds, a roll away & a couch. 2 paknplay's -roll away bed - fullsize kitchen & refrigerator. Hot tub getting fixed soon so ask if it’s functional , 24ft pool and a firepit. Housekeeper lives with a small dog in an attached suite (separate entrances). You may see them outside on occasion. One acre -holds 30ppl for events .

Hot Tub on Hill Sleeps 12 | POOL|Hot Tub & Firepit

Welcome to the Hot Tub on Hill . Nestled in the center of town. This stylish group-friendly Airbnb sleeps 12 and is perfect for family reunions, wedding groups, golf trips, corporate stays, or families relocating. Enjoy two spacious living areas, upscale furnishings, and a private backyard retreat with pool, hot tub, firepit, gas grill, and full outdoor seating—designed for relaxing and entertaining. Close to downtown events , restaurants , 40 min to Holiday World .

Renovated Family Oasis • Pool • Bonus Loft • 5 BR

Bring the whole family to this beautifully renovated home with lots of space for fun! Enjoy the inground pool with water slide (seasonal), fenced yard, grill and BB court. New kitchen and updated bathrooms with modern tile showers; master bath has a soaking tub. Main level bedroom with king bed. Huge bonus room with bed, loveseat, big TV and Tetris game. TVs in every bedroom plus living and bonus room. Florida room offers a workspace. Relax or gather—it’s all here!

Blue Moon Cottage: Music Room, Inground Pool

Welcome to Blue Moon Cottage, a charming home nestled in the heart of Owensboro, that offers a lovely blend of vintage allure and modern comfort. Built in 1935 and recently remodeled, this historic home exudes both character and contemporary elegance. Relax by the pool or cozy outdoor seating area, or indulge in the beautifully decorated interiors which includes a room dedicated to bluegrass music, a musical genre that originated in this area.

Dwntwn 1bd Apt w/RooftopYoga, Cable, Wi-Fi, Office

*Queen Bed *Central Location *Elevators *Free Parking Garage *Secured Building *Free WiFi *Quiet Area *Free Cable *Complimentary Netflix *Community Courtyard *Smart TV *Walking Distance to Restaurants *Outdoor Movie Theater *Fully Stocked Kitchen *Game Room *Fitness Center *Rooftop Lounge Area *Shared Social Space *Shared Working Space *Complimentary Coffee/Tea Bar *Stylish Experience *Wine for Purchase *Early Check In *Late Check Out

Perfect for relaxation and work+100% cotton sheets

Welcome to your relaxing getaway! This beautifully decorated home combines comfort, style, and convenience — perfect for families, couples, or business travelers! Located on the east side of Owensboro, right off Highway 54 — a prime and convenient area! Just 2 miles to restaurants and shopping centers, and only 5 miles to Downtown Owensboro where you’ll find riverfront attractions, parks, and dining spots.