Holiday rentals with a pool in Southern Indiana

Peaceful apartment space in beautiful farm house

Our lovely farmhouse is minutes from Lake Lemon, Griffey Lake, Indiana University & many spots in Bloomington. Conveniently not far from I-69, we're 20 minutes away from Nashville. This is a basement apartment with private bedroom, private bathroom, large living/dining area, & kitchenette. Shared front door & ~10 steps inside main floor. The ranch is 50+ acres with 8+ acres of woods for hiking, pastures with cattle, a heated pool & patio area, & a beautiful front porch looking over the ranch.

4th Street Suites - Stunning King Bed Suite

Live the best of Louisville in this sleek 1‑bed, 1‑bath downtown retreat! Perfect for couples, families, or friends, it features a cozy king bed, 2 rollaways, a fully stocked kitchen, and a bright living area. Enjoy morning coffee or evening drinks on your private balcony, stroll to nearby restaurants and bars, then relax by the pool or hot tub, play a round in the golf simulator, or unwind with a game of pool. Your launchpad for adventure—or a quiet, stylish escape when it’s time to rest!

Peppermint Cottage Norton Commons w Breakfast

Step into Peppermint Cottage ( breakfast included) and find the perfect blend of convenience and charm! Just 20 minutes from SDF airport, Churchill Downs, and downtown Louisville, this trendy east end haven offers an irresistible walkable lifestyle. Stroll or bike to 18 mouth watering restaurants, 14 unique boutiques, 3 pools and YMCA. Enjoy lakeside fishing, Sunday farmers markets, summer concerts, parks and summer Friday food trucks with live music . Your Louisville adventure awaits !

Cozy studio with private pool and firepit

Welcome to our charming studio apartment located above our detached garage with a private pool. Whether you're looking for a relaxing getaway or a convenient base to explore the city, our cozy studio has everything you need. Close to the following locations: Fayette mall 1.9 miles Bluegrass airport 4.5 miles University of Kentucky 4.6 miles Keeneland 5.1 miles Manchester Music Hall 5.7 miles Rupp Arena 6.4 miles Lexington Opera House 6.5 Please no smoking in the room.

Downtown Apt | King Bed • Heated Pool + Hot Tub

Stay in style and comfort while enjoying everything this apartment has to offer. Rest easy on a comfortable mattress, then start your morning with a complimentary cup of coffee. Work out in the gym, relax on the rooftop, or step outside to explore downtown just moments away. With dining, entertainment, and activities all around you, there’s always something to do. Wind down with a glass of wine and a movie on Hulu or Disney+. Book your stay and enjoy it all.

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.

The Treehouse - Hot Tub - Indoor Pool Get Away!

The Treehouse is a perfect retreat! It is secluded by the hills surrounding Madison. Complete privacy, yet 5 minutes from downtown, or hilltop. Year-round views of the beautiful hills of Kentucky. Winter views of the Ohio River and downtown. The house has stunning ceilings made from coastal cedar off an island near Vancouver, British Columbia and beautiful skylights in the studio and indoor pool area. This is an Adults only property. 2-night min.

Cozy 2BR Lake Monroe Golf Condo IU Bloomington

A modern coastal style and freshly renovated condo located in beautiful Bloomington Indiana less than one mile from Lake Monroe. The second story cozy condo overlooks the 18th hole of our gated community. Amenities include a king size bed, queen size bed and Ashley queen sleeper sofa, fast unlimited WiFi internet and a 50" 4K LED TV with Hulu Live. Perfect for football and basketball games, parents weekends and visits to gorgeous Lake Monroe.

King Bed - 1B/1BTH - POOL

BRAND NEW upscale one bedroom apartment with king bed. Minutes away from Downtown Fishers. Complex is conveniently located next to nature preserve, walking path & Nickel Plate Trail. Enjoy the amazing amenities: Pool, hot tub, fitness center, business center, clubhouse lounge & outdoor grilling space. 10mins away from Ruoff Music Center. Note: POOL AND HOT TUB ARE DURING SUMMER MONTHS ONLY. (FROM MEMORIAL DAY THROUGH LABOR DAY)

The Bunkhouse at Big Red Stables

There is no better way to experience Kentucky than horseback riding the rolling hills of the Bluegrass. Big Red Stables is happy to offer the Bunkhouse to visitors who want to ride horses, travel to nearby bourbon distilleries, go to the races or events at the Kentucky Horse Park, or just get away from it all on a third generation family farm. Horseback riding by appointment only as arranged with your hosts.

Captain Bill’s Lake House/seasonal swimming pool

Captain Bill’s Lake House. This majestic A-frame is at the entrance to the Cataract Lake boat ramp. The house will accommodate up to 7 guests, with three bedrooms and two full baths. All guests have full access to Captain Bill’s shared heated pool and surrounding gardens. Boat parking is provided on the property, inquire for details. Heated pool is seasonal beginning Mid May through September.

Lake Cabin in the Woods

🌲Escape to peace and nature at Lake Cabin in the Woods! Unwind in your private hot tub, enjoy the shared pool, and soak up year-round tranquility surrounded by trees and wildlife. Located between I-70 and I-64, about 60 miles from Effingham, IL and Evansville, IN, our cozy cabin offers the perfect blend of seclusion and convenience—ideal for relaxing, recharging, and reconnecting with nature.