Holiday 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

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**

Lovely 2-Bedroom Apartment with Pool

This property is located in the heart of east Evansville, surrounded by hospitals. The bedrooms each have large closets and windows that face west. The bathroom features a full length tub/shower combo with single sink vanity. The kitchen features a full size fridge, dishwasher, stove, microwave, and all the kitchen essentials. Next to the kitchen is the laundry unit - washer and dryer combo. The balcony faces east, and is great for sunrises. The pool is located right outside the front door.

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+Event Area—Sleeps 23*

Forget your worries in this spacious and serene outdoor oasis! Relax in the hot tub or go for a heated swim. 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. Less than 1/2 mile from Golf Course.

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, TV, well-stocked kitchen, dining/work space, comfortable recliners, and access to the beautiful grounds.

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 .

The Pink Limozeen

Pool will be open starting April 19, 2026 - WOOHOO!🥳 🎈AS OF 7/1, our pool is currently closed due to a tear in the liner, we will update when it is back up! The home is still available for booking! 🎈 Welcome to The Pink Limozeen—Owensboro’s glam getaway for girls’ trips, bachelorettes, and birthday weekends! This 3BR, 1.5BA stay features two living spaces, a pool table room, and Insta-worthy decor. Just minutes from downtown, dining, and Green River Distillery.

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.

Poolside Cabin Heart of Camp Safe Haven.

Set among the gentle rhythms of nature, our Pool side cabin at Camp Safe Haven offers a peaceful sanctuary away from the noise of everyday life. Located just 11 miles west of Owensboro Kentucky airport, it’s the perfect place to rest wander and restore. During your stay you are welcome to wander @ the campground and explore our hiking trails, fishing holes and in season the swimming pool.