Vacation rentals with a pool in Monroe County

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.

Location · Value · Biking

Cottagecore Retreat • Pool • 2 Queen En-suites

This townhouse offers the amenities guests love most, including a seasonal pool, nearby walking trails, and walkable spots for coffee and dining. A quiet and comfortable 2-story retreat in one of Bloomington’s most sought-after areas. Why Guests Love it ⬇️ ⭐️ Sleeps 6 ⭐ 2 private en-suite bedrooms ⭐ Pet-Friendly ⭐ Self-Check in ⭐ 12 minutes to Indiana University ⭐ 14 minutes to Lake Monroe ⭐ Walk to restaurants & coffee shops ⭐ Seasonal community pool access Family-owned and locally hosted

Location · Cleanliness · Comfort

3 Bedroom Condo close to IU campus & Lake Monroe

Relax with your whole family or maybe a small group. The 3 bedrooms and 2.5 bathrooms, can accommodate multiple people. We also have a full couch in the living room to fit at least 2 people and a blow-up mattress, if needed. Private patio with fire pit, grill, seating area on the 18th hole. A private pool for the residents of Eastbay, 18 hole golf course, clubhouse with a pool, bar and Sahm's restaurant. 15-20 minutes to IU's campus and minutes from Lake Monroe beach, hiking trails & marina.

Value · Location · Bathroom

Authentic Peace Villa•Indoor Pool•IU•20+ Guests

Welcome to Authentic Peace Villa located in the heart of Bloomington and minutes from Indiana University. Relax at our oasis while easily accessing Downtown, College Mall, and IU football and basketball games. This spacious home features a luxurious indoor swimming pool, 3 outdoor patios, a large chef’s kitchen with two ovens and two dishwashers, two living areas, a fenced in yard, and a basketball hoop. Babies and young kids welcome! Books and games included. Play pen available upon request.

Location · Family · Walkability

Treetop Hideaway (Condo)

Treetop Hideaway is a condo located on Eagle Pointe Golf Resort offering a 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.

Location · Family · Quiet

Lakeview Retreat

Relax at this lake front stylish condo with breathtaking views and nature at Lake Monroe at Eagle Pointe Golf Resort. The resort includes a restaurant, at times weekend live music, driving range, and golf course The condo has a pool in the summer. 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.

Value · Family · Hospitality

Beautifully Remodeled Lake Condo near Bloomington

Escape to this freshly remodeled upper-unit condo (August 2025) with all-new furniture and décor—your serene getaway on Lake Monroe. Wake up to deer grazing in the wooded ravine below and sip coffee from your private balcony surrounded by nature’s quiet. Inside, you’ll find a bright, modern space designed for both comfort and productivity. A dedicated workspace makes remote work effortless, while the cozy living area invites you to unwind after a day of golf, pickle ball, pool or lake time.

Location · Value · Breakfast

Fantasy Island - Eagle Pointe on Lake Monroe

Welcome to “Fantasy Island”. Whether you’ve visited the islands or not, you will feel the aloha here in this stylish, peaceful condo in the trees. Offering 2 bedrooms and two bathrooms, screened in lanai and comfy oversized couch to snuggle in. The condo is located at Eagle Pointe gated community on Lake Monroe. Amenities include, golf course, clubhouse, pool, cabana bar, fully remodeled restaurant and so much more. Perfect for couple’s getaway, friends trips, golf trips & summer vacation.

Location · Family · Grill

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).

Value · Location · Hospitality

The Retreat - At Lake Monroe

Come relax in our calm and stylish space! Perfect for a romantic getaway, game at IU, or a weekend of peace and quiet! Unleash your inner chef in the well appointed kitchen, binge your favorite shows on the 70' Smart TV, or unwind on the beautiful back deck while enjoying the fall colors! Outside, enjoy our community pool, golf course, and on site restaurant. Or, take a short drive to explore IU, local wineries, and state parks! Welcome to Vacation! Welcome to The Retreat - At Lake Monroe

Value · Location · Decor

Rural Escape

Only a 10 to 15 minute drive from IU campus or IU Stadium, our place is a recently remodeled 2 bedroom, 1 bathroom, half of a duplex (right side). Located in a country neighborhood setting, this home is minutes away from westside stores, restaurants, and downtown. It is also close to Lake Monroe, Griffy Lake, McCormick Creek and Brown County for those nature lovers. Come stay for work, an outdoor adventure, an IU game or to visit IU. We allow up to two pets per stay, ask for details!

Location · Family · Cleanliness

The Eagle's Nest & Bird Watching; Lake Monroe; IU

Escape to a serene condo, where you’ll enjoy bird-watching on a corner porch nestled in the woods. Steps from The Golf Club at Eagle Pointe, you’ll find a restaurant, pool (End of May-Sept) with bar, pickleball courts, cornhole, and bocce ball. Bird-watching books and binoculars provided to spot eagles! 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).

Location · Family · Outdoor spaces