Holiday rentals with a pool in Brown County

5 out of 5 average rating, 18 reviews

Treetop Hideaway

Treetop Hideaway is located on Eagle Pointe Golf Resort which offers Sahm’s restaurant bar & grill, seasonal weekend live bands, pool, tennis/pickleball courts. We are minutes away from Fairfax State Park, Lake Monroe beach and marina and Fairfax Bar & Grill. Approximately 25 minutes from Indiana University. Treetop Hideaway features a one bedroom (Queen bed), the loft has a Queen bed along with a futon that opens up to a full size bed. One bathroom, washer/dryer, private deck and free WiFi.

4.97 out of 5 average rating, 36 reviews

Flat in Bloomington

Lakeview Retreat

Relax at this lake front calm, stylish condo with breathtaking views and nature at Lake Monroe at Eagle Pointe Golf Resort. The resort includes a wonderful restaurant, poolside bar with TVs, live music, driving range, golf course, and 2 pools. Just a 10 minute easy drive away is the beach and marina where you can rent boats, jet skis and kayaks. The condo is only 20 min from IU and the deck offers a full amazing view of the lake. The condo features a full kitchen, free wifi, and washer/dryer.

5 out of 5 average rating, 58 reviews

The Retreat - At Lake Monroe

Come relax in our calm and stylish space! Perfect for your romantic getaway, a game at IU, or a relaxing weekend of peace and quiet. Our condo offers a fully appointed kitchen, comfortable memory foam mattress, a 70' Smart TV, and a beautiful back deck for soaking up the sun or enjoying the fall colors! Outside enjoy our community pool, golf course, and on site restaurant! A short drive from IU, local wineries, state parks and more! Welcome to Vacation! Welcome to The Retreat - At Lake Monroe

5 out of 5 average rating, 10 reviews

Forest Getaway & Golf; Lake Monroe; IU

Escape to a serene condo, where you’ll enjoy complete privacy on a screened-in porch nestled in the woods. Steps from The Golf Club at Eagle Pointe, you’ll have access to a range of amenities, including a restaurant, pool (End of May-Sept) with bar, 6 pickleball courts, cornhole, bocce ball, and fitness classes. A short drive to Bloomington, the condo is the ideal for visiting IU while enjoying a relaxing weekend. FREE State Park pass, pickleball paddles/balls provided (must reserve a court).

5 out of 5 average rating, 21 reviews

"Indiana Beach Home" Resort Living For 10 + Pool

2025 Special: stay 4 nights get a 5th night FREE, contact for details. Fabulous Family Estate @ 5,300 Sq. Ft. of Luxury Living Custom Builder's Personal Home Yours to Enjoy ! 5-10 mi to Indiana University & Lake Monroe, Golf Courses, 3 State Parks & French Lick Casino. 4 Bdrms w/ private Baths, 3 Kings, Queen/Twin Bunk Beds, Two Pull-out Couches: Double & Twin. Multi-TV Areas, Gourmet Kitchen, Private Pool. Weddings & Bachelorette Weekends ! Cleaning Fee: $149 per stay, Dogs: $25 per stay

5 out of 5 average rating, 26 reviews

Pointe Retreat at Lake Monroe Enjoy resort life!

Welcome to Pointe Retreat! located just 20 minutes from downtown Bloomington & minutes from Fairfax Beach and Marina! You can relax and recharge in our 2B/2B condo nestled within the Eagle Pointe Golf Club Resort, just steps to the clubhouse! Play a round @ the golf course, try pickleball and relax in the pool or at the cabana bar! Indulge at Sahms restaurant, which boasts an outdoor dining venue including live music F/S. Message that you have read and agree to house rules for approval!

4.95 out of 5 average rating, 43 reviews

Home in Columbus

Pool House on National Rd

Welcome to "The Pool House on National Rd" this unique updated home has 3 bedrooms, 3 full bathrooms and sits on a large lot in a super convenient location. You are less than 5 minutes driving time from Nexus Park, Hospital, Shopping & restaurants. There are sidewalks if you choose to walk also. Enjoy the gourmet kitchen w/a large island and new SS appliances. The backyard oasis is the perfect entertainment spot with a large in ground lap pool, privacy fenced yard & an enclosed back porch.

4.92 out of 5 average rating, 377 reviews

YOUnique 3+ bedroom, spa/hot tub, huge deck

Our place is close to Indiana University, IU athletics, I-69/37 to Indianapolis, great views, family-friendly activities, nightlife, restaurants and dining. You’ll love our place because of the privacy - and the friendly neighbors (us), the beautiful outdoor space, the kitchen/great room, the hardwood floors, and the volleyball court and large yard. Our place is good for couples, solo adventurers, business travelers, families (with kids), big groups, and furry friends (pets - but no cats).

5 out of 5 average rating, 25 reviews

Cabin in Freetown

NEW! Pool+16 secluded acres! Hot tub+arcade+pond!

Come enjoy our 16 ac of private paradise in Brown County, surrounded by Hoosier National Forest! Relax in the heated pool or hot tub, grill on the patio or cook in the chef's kitchen, and enjoy fun in the game room playing pool or classic arcade games. Outdoors, explore the woods while hiking, paddle on the pond, or bring your poles for catch-and-release fishing! Book now for July 8-10, August weeknights, and Labor Day weekend (Sunday-Tuesday). Seasonally decorated from Nov-Jan

5 out of 5 average rating, 7 reviews

Cabin in Nashville

Lookout Views, Swim Spa, 5 Acres

Welcome to Helmsburg Homestead, a historic 1800s log cabin in Nashville, Indiana! Relocated from Brown County State Park, it features hand-hewn poplar logs, a chiseled stone fireplace, and a perfect blend of rustic charm and boho-chic interiors. Enjoy a large great room, spacious kitchen, four-season room for games or TV, cozy reading room with scenic views, and a swim spa. Set on 5 picturesque acres with lookout views, it’s just minutes—not miles—from the charming village of Nashville!

5 out of 5 average rating, 11 reviews

Flat in Bloomington

Treetop Retreat

Take it easy at this unique and tranquil getaway in Eagle Pointe on Lake Monroe. This chic condo is ready for you to relax and unwind. Enjoy coffee and wildlife on the deck, or have your meals at Sahm's in the clubhouse, .1 miles away! This condo gives you access to two swimming pools, golf, pickle ball courts, tennis courts and basketball courts, with reservations made at the club house. The clubhouse has a gym and saunas. While you are there, make reservations for a tee time!

4.94 out of 5 average rating, 16 reviews

Flat in Bloomington

Resort & Lake Living Close to IU

Indulge in a serene getaway at our stunning Lake-themed condo on Lake Monroe at Eagle Pointe Golf Resort. Enjoy the Resorts restaurant, poolside bar, Live music, 2 pools, Pickleball/Tennis/Basketball courts, weight room, sauna, driving range and golf course! Just around the corner is the beach and marina and only 20 minutes to IU stadiums! Unwind on the deck with a “Winter water view” of the lake. Our home features a full kitchen, washer/dryer, Free WiFi and more.

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Popular amenities for Brown County rentals with a pool

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Wifi

Pool

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Air conditioning

House rentals with a pool

5 out of 5 average rating, 10 reviews

Immaculate Lakeside: Golf, Pool, Tennis, PB Courts

ChristopherRating, 5 stars4 weeks ago

The host is an artist so the place is eclectically decorated. We had fun playing pickleball on the nearby court which was also set up for tennis and basketball

4.78 out of 5 average rating, 88 reviews

Private Retreat w/ Pool, Hot Tub and Dining Hall

JessRating, 5 stars1 month ago

Great stay overall! We had 16-18 people and the property slept us all comfortably with plenty of space to eat and relax. Much cleaner than other places we have stayed as a group. Quiet neighborhood and great hot tub! We would love to come back.

Home in Morgantown

4.67 out of 5 average rating, 9 reviews

Country Resort Vacation Cabin

CamilleRating, 5 stars4 weeks ago

This airbnb was true to the pictures posted on the web. It was clean, and in a very quiet location, wish we could have taken advantage of the pool, but we knew the pool would be closed. The home had everything we needed and would stay there again.

Home in Springville

5 out of 5 average rating, 4 reviews

Hoosier Hangout: seasonal pool, game room, theater

BerniceRating, 5 stars3 days ago

Family of 5 and plenty of room/beds/space for everyone. All our needs were met. It really was a “just bring your clothes/personal items only as that’s all you’ll need” situation. A great place for kids as well since there was a pool, pool room, theater room, recreation room, etc. there was even an office area with a desk which helped tremendously as I typically work from home. Tons of parking space also. Angelique was responsive and helpful with any questions. She even went above and beyond to work with us to help extend our stay at the last minute due to our home reconstruction took longer than expected.

Home in Seymour

Pink Castle with YEAR ROUND heated spa pool

LawrenceRating, 5 stars1 week ago

Great, thank you look forward to coming back next year

4.78 out of 5 average rating, 82 reviews

Walk to IU• Private Deck• Playground• Outdoor Pool

AbbieRating, 5 stars1 week ago

This house had literally everything we needed to have a comfortable stay. We felt like it was a very safe neighborhood we didn’t have any problems. It’s so close to many fun things we enjoyed!

4.62 out of 5 average rating, 47 reviews

The Authentic Peace Villa 3BR 8 Beds & Indoor Pool

EmmaRating, 5 stars3 months ago

Our group loved our stay and the pool! Plenty of room for all of us- lots of beds/sleeping space, plenty of seating options in the living areas, enough room for us to all eat together. We definitely enjoyed our stay!

4.67 out of 5 average rating, 3 reviews

Magnificent 4BR House in Bloomington with Hot Tub

BRADRating, 5 stars13 months ago

Property was accurate to description and photos online. Couch should not be considered as sleeping option for adults.

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Apartment rentals with a pool

5 out of 5 average rating, 12 reviews

Cozy Retreat : Golf, Lake & Nature at Lake Monroe

AmyRating, 5 stars8 months ago

Outstanding place to stay, super clean, new and well appointed. Excellent host, very responsive. The setting is beautiful too.

5 out of 5 average rating, 5 reviews

Cozy 1BR Condo @ Eagle Pointe-Close to IU

ThawnglianRating, 5 stars6 months ago

This place was nice and super clean. It felt like a home .I recently had the pleasure of staying and I am thoroughly impressed. The property is well-maintained, offering modern amenities, a clean and comfortable living space, and excellent security measures. I would highly recommend this condo to anyone seeking a quality .

5 out of 5 average rating, 8 reviews

Bloomington Condo at Lake Monroe

JenniferRating, 5 stars9 months ago

We thoroughly enjoyed our time at the Hudson Hideaway. Views were amazing and neighborhood was quiet and serene. Shirley was super responsive and helpful and her home was spotless. She really made us feel welcome and even left us a snack basket and several beverages which was a very welcome gift after our long drive. She certainly knows how to make a house a home. We look forward to returning to this community in the future.

4.7 out of 5 average rating, 20 reviews

Woodland Escape Condo

PatriciaRating, 5 stars7 months ago

We loved the setting in front of woods, having a great restaurant in walking distance, the screened porch, and the price was great!

4.9 out of 5 average rating, 58 reviews

3 Bedroom Condo close to IU campus & Lake Monroe

TristanRating, 5 stars1 week ago

Great place to stay if you’re enjoying lake Monroe, visiting Bloomington, or going to campus. Quiet and right off the golf course. Will not hesitate to stay again if I’m back in the area!