Holiday rentals with a pool in Bloomington

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.

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

Relaxing Family Cabin with Hot Tub in Nashville

Relax with the whole family at this peaceful cabin with built in entertainment! Pool, hot tub, game room, and more! At Almost Heaven, you will have found what you were looking for. Accommodating up to 5, this cozy 3 BR, 2 bath cabin will make your Brown County stay quite special. Refresh and relax with a swim any time of the day or night without having to share it with anyone! It's Almost Heaven! Decks in the front & back, games in the basement, fire pit, peacefulness, it’s all here! Crib avail.

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.

Lake Monroe 2/2 IU Bloomington

Nestled by Lake Monroe, Eagle Pointe in Bloomington, IN, is a sought-after residential and recreational community. Its championship golf course is a highlight, set amidst natural beauty. The marina, lakeside dining, and outdoor activities add to its charm. Escape to Eagle Pointe for a tranquil retreat in southern Indiana's scenic landscape. Whether you crave relaxation, adventure, or a tranquil getaway, we invite you to unwind and appreciate the natural beauty of southern Indiana's landscape.

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.

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.

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).

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

Rural Estate

Located near the Monroe County fairgrounds & airport; this ranch-style estate is a fun getaway for the whole family. While at the estate, enjoy family time around the dining table or bar, or hang out in the great room with 10-in-1 game table and 65" TV, or relax on the wrap-around back deck. The garage is included in the rental. Shopping & Restaurants are a 10 minute drive; guests can get to IU campus, Memorial Stadium or the IU Health Hospital in 20 minutes, or Lake Monroe in 30 minutes!

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).

Hot Tub | Game Room | Theater | Fire Pit | Pool

🌲 Secluded Retreat on 3 acres | Pool, Game Room & Theater Experience 🌲 ✨ Highlights: 🏊 Pool & Hot Tub: Relax poolside or unwind in the hot tub after a day on the lake 🔥 Fire Pit Oasis: Secluded fire pit surrounded by Adirondack chairs for the perfect evening vibe 🎬 Movie Theater: 75” screen + sectional for cozy movie nights 🎯 Massive Game Room: Pool table, poker table, putting green, skee ball, darts & more 🌅 Expansive Deck: Wraparound deck with outdoor dining for 8