Holiday rentals with a pool in Owensboro

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Owensboro

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Flat in Newburgh

5 out of 5 average rating, 4 reviews

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

Guest favourite

Home in Evansville

4.83 out of 5 average rating, 18 reviews

Pool Is Open! Waterslide!Fun!Home Away From Home!

Bring the whole family to this great home! Lots of space for fun! Inground pool with water slide ,bb court & grill! Great for family reunions or to hang with friends or just away! Newly renovated bathrooms with waterfall rain massage showers in both master bath and hall bathroom which has private entrance. Soaking tub with jets in master bath. Nice spacious home perfect place for friends & family to gather! Summer is here & the pool is open! Come play! Come relax! You choose! It’s all here!

Top guest favourite

Home in Owensboro

5 out of 5 average rating, 37 reviews

Hot Tub /Pool/Fire Pit & BBQ

Hot Tub On Hill /SHORT 40 MIN DRIVE TO HOLIDAY WORLD SPLASHIN ' SAFARI . A very spacious vacation spot the whole group will enjoy! Easy access to everything and centrally located. Close to downtown, the regional airport and all major attractions the city has to offer. Unbeatable location that puts you minutes away from boutique shopping, fine dining, concerts on the river, festivals ,nightlife and sport facilities. Pool , hot tub, Fire-Pit with outdoor patio and BBQ with enough seating for 14

Top guest favourite

Castle in Cannelton

5 out of 5 average rating, 10 reviews

NYA river front 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.

Flat in Mount Vernon

5 out of 5 average rating, 4 reviews

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.

Superhost

Home in Owensboro

4.81 out of 5 average rating, 36 reviews

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**

Guest favourite

Farm stay in Evansville

5 out of 5 average rating, 5 reviews

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.

Guest favourite

Chalet in Owensboro

4.98 out of 5 average rating, 41 reviews

Woodsy Waterfront Cabin with Loft

Escape to our secluded waterfront cabin, nestled amidst natural surroundings, our cabin offers a serene retreat away from the hustle and bustle of everyday life. Wake up to the soothing sounds of nature and breathtaking views of the waterfront. Whether you're seeking a romantic getaway or a peaceful retreat with loved ones, our cabin provides the perfect setting for relaxation and rejuvenation. Experience the magic of nature at its finest in this special haven. Limited cell service at cabin

Guest favourite

Home in Owensboro

4.81 out of 5 average rating, 42 reviews

Heated Swimming Pool + Hot Tub + Event Room

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.

Top guest favourite

Cottage in Maceo

4.97 out of 5 average rating, 173 reviews

Hattie's Hill Cottage

Cottage sits behind our home (see photo). NOTE- Main house may have large groups. Pool and outside areas share spaces. Near Owensboro, Rockport, Hawesville & Lewisport. There is ONE bedroom which can be made into EITHER two California twins OR one California king -Wifi. We have a Smart TV you may use your Netflix and so on with. Kitchen is well stocked with necessities. Eating/work space is provided. Comfortable recliner chairs. Access to the grounds.

Top guest favourite

Home in Owensboro

4.98 out of 5 average rating, 65 reviews

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.

Superhost

Flat in Downtown Evansville

New place to stay

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