Vacation rentals with a pool in Owensboro

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

*Queen Bed *Central Location *Elevator *Free Parking Garage *Secured Building *Iron *Dishwasher *Free WiFi *Keurig Coffee Maker *Dining Room Table *Washer & Dryer *Quiet Area *Free Cable *Hair Dryer *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

Luxury 2bd 2ba Apt w/Gym, Lake & Central Location

*King Bed *Central Location *9 Min Drive to Hospital *Free Wi-Fi *Complimentary Netflix *Smart TV *Roku *Complimentary Chips *Complimentary Assorted Teas *Complimentary Assorted Coffee Pods *Complimentary Coffee Creamer and Sweeteners *Bar Cart with Ice Bucket and Glasses *Beautiful Views *Gym *Fully Stocked Kitchen *Natural Light *Stylish Experience *Less Than 5 Min Walk to Super Center *Walking distance to restaurants *Stainless Steel Appliances *Early Check-In *Late Check-Out *VERY Safe Area

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.

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!

Pet Friendly Holiday Cottage

These pet-friendly rentals come fully furnished with a queen bed in the primary bedroom, a twin-over-full bunk bed in the second bedroom, and a full-size sleeper sofa in the living room to comfortably accommodate up to 7 guests. Outside, we’ve provided a charcoal grill, picnic table, fire ring and covered porch – the perfect spot for outdoor entertaining. Pillows, pillowcases and fitted sheets are included. Please bring your own top sheets, blankets and towels.

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.

5BR Pool Home near Sports Park: Game Rm+ Fireplace

Welcome to your ultimate Evansville Get-Away! Perfectly positioned on the Northside, this spacious 5-bedroom retreat is designed for traveling sports teams, large family reunions, and groups who want the perfect balance of relaxation and fun. Minutes from the fields, yet miles away from the cramped feeling of a hotel, we offer the one thing big groups need most: Space to breathe.

Nugent House

It's rare to find a place that's both historic and one-of-a-kind. Whole house to enjoy in downtown Evansville Indiana. Walking distance to arts district , bars , restaurants, casino , ford center , Evansville museum, Evansville riverfront and much more.,, Home was built in 1915 as a mansion by the Nugent family. No lifeguard on duty, swim at your own risk