Holiday 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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Top guest favourite

Cabin in Paoli

4.95 out of 5 average rating, 22 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

4.79 out of 5 average rating, 70 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

4.83 out of 5 average rating, 6 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.

Top guest favourite

Home in Palmyra

5 out of 5 average rating, 24 reviews

Hummingbird Vine w/ Hot Tub

Minutes away from so many other cities, and so many cool things to do and see; Yet, you are far enough away to enjoy a bit of country style. Make sure to research the surrounding area if you like to partake in hiking, mountain biking, fishing, gaming, horse betting, shopping, wine tasting, caving, canoeing etc. There are many museums & numerous historical sites. Sit back and enjoy a bit of seclusion while watching the beautiful sunrises and sunsets in the relaxing hot tub that awaits.

Cabin in Paoli

5 out of 5 average rating, 3 reviews

The Outpost Cabin at Wilstem

Wake up to breathtaking safari views and enjoy an exclusive, once-in-a-lifetime experience—an optional private visit from one of our resident ELEPHANTS, available only at The Outpost Cabin requested after booking. Outpost Cabin is our newest retreat at our animal park, offering 2 cozy bedrooms with queen beds and a sleeper sofa, comfortably hosting up to 6 guests. Enjoy a fully equipped kitchen, 2.5 baths, an electric fireplace, outdoor fire pit, and two TVs for ultimate relaxation.

Cabin in Paoli

4.6 out of 5 average rating, 42 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

Top guest favourite

Home in Ferdinand

5 out of 5 average rating, 23 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 (Eagle Pines Cabin, sleeps 4). 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.

Top guest favourite

Home in Ferdinand

5 out of 5 average rating, 20 reviews

Eagles Nest Plus/Eagle Adventures LLC

Eagles Nest Plus is our Eagles Nest rental PLUS the master BR & bath. It 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, Eagle Pines Cabin. In 2025, the pool & hot tub are no longer shared spaces. This rental has exclusive use of pool and hot tub. For more info check out our website visiteagleadventures. We provide e'thing you'll need for a great vacation.

Cabin in Eckerty

4.88 out of 5 average rating, 8 reviews

A-Frame #4 on Patoka Lake

This A-Frame sleeps 4 people. Upstairs in the open loft is a King size bed with TV and Satellite. The kitchen has a stove top and mini fridge and is supplied with basic cooking utensils. The living area has two twin beds, TV with Satellite and DVD player and a couch. The bathroom has a stand up shower and is supplied with towels and basic toiletries. Not pet friendly. We do not allow visitors, everyone on the property must be a registered guest.

Guest favourite

Home in Huntingburg

4.94 out of 5 average rating, 17 reviews

The Castle

Bring the whole family to this great place with lots of room for fun! Located 15 miles from Holiday World & Splashin’ Safari. Five minute walk to the city pool, and League Stadium, where the movie “League Of Their Own” was filmed. Also home of the Dubois County Bombers. 4 bedrooms, 3.5 baths. 4000 square feet. Above ground pool, Hot Tub, 4 Sun loungers, outdoor furniture & enclosed outdoor dining area. Spacious kitchen, Movie room & more!

Flat in French Lick

French Lick Villas Hideaway

The French Lick Resort Nestled among the hills of the Hoosier National Forest resides a classic American destination: including three golf courses, two rejuvenating spas, and a spacious, single-level casino. This unit is a beautiful and Spacious 2 bedroom 2 bathroom unit that sleeps 8 over the July 4th holiday. The French Lick resort offers several pools and hot tubs and outdoor activities such as hiking, antique shops and exploring, golfing.

Top guest favourite

Home in Paoli

4.98 out of 5 average rating, 48 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)