Vacation rentals with a pool in Orange County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Orange County

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

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Guest favorite

Cabin in Paoli

4.94 out of 5 average rating, 18 reviews

Quiet, Cozy Paoli Cabin Overlooking a Nice Pond

The Cabin is less than 20 minutes from French Lick & Paoli and only 15 minutes from Patoka Lake and Hoosier National Forest. You will love the view of the Pond from all three decks as you eat your meals, sit around the fire pit, or swim in the pool. Very quiet and you have it all to yourself. From time to time, you may see deer, turkey or quail around the property. On clear nights the stars are amazing, and at times the sunrises can be spectacular. It is hard to get any better than this.

Cottage in Paoli

4.78 out of 5 average rating, 67 reviews

Private and Cozy Cottage with Views Seasonal Pool

Private and cozy cottage located on 100 acres with spectacular views & pool. Are you ready to get away from the city lights and enjoy the peaceful countryside? Grab your special someone or get some alone time by yourself. Wait til you see the views perched from top of this hilltop. Great for catching up on a good book, outdoor campfires and star gazers alike. This small but efficient cottage has vaulted ceilings, ambient lighting and a small kitchenette. See more pics at BlueberryHillEstate.com.

Cabin in Eckerty

4.75 out of 5 average rating, 4 reviews

Deluxe w/Jacuzzi #8 on Patoka Lake

This home sleeps 5 people. Upstairs in an open loft area is a Queen and Twin bed and a TV with Satellite. The downstairs bedroom has a Queen bed and a TV with Satellite. The living area has a couch, loveseat and a TV with Satellite and DVD player. The full-size kitchen comes equipped with the basic utensils. The bathroom has a Jacuzzi and a shower and includes towels and basic toiletries. Smoking is not allowed in any of the buildings, but we do supply ashtrays outside. Dog-Friendly with a fee.

Guest favorite

Cabin in Ferdinand

5 out of 5 average rating, 65 reviews

Eagle Pines Cabin (Eagle Adventures LLC)

Relax w/us at our beautiful, comfortable, and private Eagle Pines CABIN!! We sold our campers & the cabin was delivered in the spring of 2024. We are 12 miles from Holiday World. Cabin rental includes the pool May-Sept & the hot tub year round. Pool & tub are shared spaces with Eagles Nest guests. Private fire pit, we supply the firewood. Cabin is stocked with everything you’ll need. Hosts are on site, but out of sight. In 2025, pool & hot tub are not available June 2-14, 25-29 & July 25-30.

Guest favorite

Cabin in Birdseye

4.9 out of 5 average rating, 97 reviews

Swim Spa Hot All Winter Shaded Woods Log Cabin

Newly remodeled Log Cabin with new pillows, sheets, towels. Wooded property next to creek. Enjoy the screened in front porch or the back deck with 14 foot Swimspa, fire pit & grill with quiet wooded setting. Free State Park pass save $7 day. Downstairs Master bedroom with king bed. Matching queen beds in loft bedroom. NEW Electric fireplace w/5 settings, new AC/heat, New grill. High speed wifi/internet, SMART TV with Bluetooth sound bar, Direct TV, Washer/dryer. Ice maker NO BOATS/TRAILERS

Vacation home in West Baden Springs

4.88 out of 5 average rating, 25 reviews

Gorgeous estate formerly owned by NBA legend

The Nest is a spacious oasis offering a secluded mini-resort feel. The large 6 suite home sleeps 22 and sits on 11 acres of picturesque rolling Indiana hills with a private swimming pool, tennis court, hot tub, and poker room. Previous home of local NBA legend, it offers a unique experience with themed rooms and memorabilia. This perfect getaway is located only 2 miles from downtown French Lick and French Lick Casino, 10 minutes from Paoli Peaks Ski Resort, and 9 miles from Patoka Lake.

Cabin in Eckerty

4.8 out of 5 average rating, 5 reviews

Deluxe w/Jacuzzi #10 on Patoka Lake

*FIREPLACE UNDER MAINTENANCE* This home sleeps 8 people. Upstairs in the open loft area is a queen and two twin beds and a half bath. The downstairs bedroom has 2 queens. The bedrooms and living room have a TV with Satellite. The living room has a couch, loveseat and a wood-burning fireplace. The kitchen comes fully supplied with basic cooking utensils. The full bathroom has a Jacuzzi tub and a standalone shower. Linens and basic toiletries are included. This is a non-pet friendly home.

Cabin in Paoli

4.64 out of 5 average rating, 39 reviews

Dream Getaway Cottage w/ Hilltop Views and Pool

Beautiful New Hilltop Cottage with Spectacular Views with Seasonal Pool & Hot Tub. Master bedroom has a private door to deck. Additional bed located off adjoining living room. 65" TV and WiFi. This property comes with some of the best views in southern Indiana that you can enjoy from your private deck or the 2,000 s.f. concrete patio w/ yard games. Rain or shine, you'll love this exclusive getaway. More pics at BlueberryHillEstate.com. 10 m - French Lick Casino, 4 m- Paoli Peaks

Guest favorite

Home in Ferdinand

5 out of 5 average rating, 20 reviews

Eagles Nest (Eagle Adventures LLC)

Spacious 3 BR, 2.5 bath, LR w/six recliners, baby bed, kitchen, dining, laundry, pool, hot tub, & outdoor patio with seating, TV, & pellet grill. Space is set up for up to three families traveling together. No neighbors in sight. We also rent a cabin on our property. The pool & hot tub are shared w/cabin guests. If you need something bigger check out Eagles Nest Plus which includes the master bedroom & bathroom and sleeps 12. For more info see our website visiteagleadventures.

Guest favorite

Home in Ferdinand

5 out of 5 average rating, 9 reviews

Eagles Nest Plus/Eagle Adventures LLC

Eagles Nest Plus is our Eagles Nest rental PLUS the master BR & bath. This sleeps 12, has 3.5 bathrooms plus a baby bed. It’s perfect for four families traveling together. We also have one cabin on our property that sleeps four. The pool & hot tub are shared with the cabin guests. For reviews, see Eagles Nest or Eagle Pines Cabin. For more info check out our FB page Eagle Adventures or our website visiteagleadventures. We provide everything you'll need for a great vacation.

Guest favorite

Home in Paoli

4.97 out of 5 average rating, 33 reviews

Majestic Cabin | POOL & HOT TUB

Majestic timber home on 20 private acres with swimming pond, heated indoor pool, hot tub, rec room with pool table, ping pong, foosball and free weights, extensive gardens and walking paths on property. Cows, sheep, goats & donkeys in fully fenced pasture land/barnyard. Sleeps 12+ 8 min to Paoli Peaks 15 minutes to French Lick 35 minutes to Patoka Lake (boating, fishing, hiking) One hour to Bloomington One hour to Louisville (SDF airport)