Family-friendly holiday rentals in Bloomington

Stunning | 3128 Sqft | Screened Porch | 5 miles>IU

Welcome to Grosvenor’s Place! A spacious 5BR family-run Airbnb tucked away on a quiet cul-de-sac surrounded by woods, yet just 5 miles from IU, shopping & restaurants. Perfect for IU weekends, graduations, reunions & family getaways! Why Guests Love It ⬇️ ⭐ Sleeps 16 ⭐ 5 Bedrooms • 9 Beds ⭐ 2 Air Mattresses + Full-Size Crib ⭐ Wooded Setting ⭐ Pet Friendly — $400 Fee ⭐ Fenced Side Yard ⭐ Self Check-In ⭐ 2 Living Areas ⭐ Den with Bar ⭐ 3 TVs ⭐ Foosball & Games ⭐ Screened Porch ⭐ Fire Pit & Grill

Blue Lemon Bungalow - Quiet Getaway in Town!

Blue Lemon Bungalow is an adorable, newly renovated two bedroom in Bloomington with full living, dining, kitchen, and washer/dryer. In town with a country vibe. It has a huge yard with old growth trees, yet it is only a 5 minute ride to Downtown Court House Square or Indiana University Memorial Stadium. A large front porch with festive lighting gives you a place to enjoy the view. We have taken special care to make Blue Lemon Bungalow extra comfortable and stylish. Well behaved pets considered.

The Loft House - 3 Bedrooms - IU Bloomington

Located near Indiana University in Bloomington, Indiana, our house is a clean, 3 bedroom house with vaulted ceilings, sleeping loft and open living area. This is not a big house, but our house will comfortably sleep six and can accommodate up to nine individuals. The house is located minutes away from IU, the mall, and downtown. Bryan Park is only two and a half blocks away. Walk to shops and Soma Coffee House & Juice Bar. Come stay for work, an IU game or a visit with your IU student.

5 Min IU, Bright Sunroom, Giant Sectional, Parking

A spotless, thoughtfully curated home designed to feel comfortable, calm, and genuinely livable — not a bare rental. Guests consistently mention the immaculate cleanliness, comfortable beds, oversized sectional, and thoughtful extras that make settling in easy. Located in a residential neighborhood, under 10 mins to IU, downtown, stadiums, dining, parks, and Kroger. This home is ideal for campus visits, couples, small groups, and professionals who value comfort, cleanliness, and a calm place.

Cozy Cottage : easy + peaceful w/ private backyard

This 2 Bdr / 1 Ba cottage is a sweet mix of peace and quiet + easy access to the best of Bloomington. Cozy updated interior + lovely screened in back porch facing a fully fenced in backyard - your own space to breathe deeply. Lovely neighborhood walkable to coffee + lunch, steps to amazing Bryan Park, under a mile to Sample Gates & downtown, easy drive to stadium, etc. Baby and kid essentials provided, fully equipped kitchen, fire pit, grill, bicycles... we so look forward to hosting you!

Elevated Wilderness | Mindful Retreat | 2 Kings

Executive Forest Sanctuary/2 King Beds, Hot Tub & Trails Escape to an architectural masterpiece set on 40 wooded acres. Designed for professionals, couples, and active adults seeking a high-end nature reset, Cabin Porch Paradise balances seclusion with proximity to Southern Indiana’s best destinations. Whether you are unwinding in the spa amenities, working remotely via high-speed fiber, or exploring the surrounding lakes and state parks, this is your ultimate ridge top retreat.

The Clover House Near IU/Stadium

Kick back and relax in this calm, stylish space. 4 bedroom, 2 bath, 2100sqft. 5 TVs throughout the house. Located in the best location of Bloomington! 3 Queen beds, one twin, and one twin trundle with a twin pull out. Dog friendly (NO CATS). Close to IU, Stadium, Cascades Park/Golf Course, Liwer Cascades walking trail head, dining, and shopping. Early/late check in/out offered for $20. Add my listings to your wishlist by clicking the ❤️ in the upper right corner!

Cheerful & Cozy In-Town Cabin, Upper Unit

Relax and getaway in our safe, centrally located, co-housing community. Next to the local YMCA and local walking paths. This authentic log cabin has been completely renovated with a studio-style open bedroom, kitchenette, living room, porch, and bathroom. There is no TV, but there is Wi-fi. You'll be staying in the upper level of the cabin. The upper level is a separate unit, also on Airbnb. The units share no interior access and are completely separate units.

Modern Nashville Home in the Woods

Welcome to Plāhaus — a modern retreat tucked into the woods of Brown County. #1 Most-wishlisted Airbnb in Indiana per Airbnb Designed for solitude, relaxation, and connection with nature, Plāhaus blends modern architecture with peaceful surroundings. Take in the views from the balcony, gather around the firepit, or explore nearby Nashville’s shops and restaurants. Perfect for romantic getaways, family escapes, or simply recharging from everyday life.

Strawbale Bungalow. Bloomington, Indiana, USA.

Art and book filled. Located in Bloomington Indiana. My 1920s bungalow includes two guest bedrooms with queen sized beds, down comforters, feather/down pillows, line curtains and private bathroom. The guest area also includes a garden porch, private entrance, living room and, dining area with microwave, small refrigerator and handmade maple table. NO KITCHEN. The bathroom is between the bedrooms and includes a Toto washlet bidet and EO toiletries.

Bungalow on Washington

This 3 BR 1.5 BA is a clean, green, efficient bungalow located within walking distance to downtown, Bryan Park, Switchyard Park, and the B-Line trail. You can skip, hop, jump or even ride a bike to Bryan Park, B-line trail, Hopscotch Coffee, or Indiana University (1 mile away). The house is welcoming to adults and children alike, with warming characteristics for zen and play. This home is warming location for friends and family traveling together.

Bloomington Lake-View home on 40 secluded acres

New Lake home that sits on 40 acres of woods with gorgeous views. Large wrap around porch with outdoor seating and chill space. Fall, winter and spring provide amazing views of Lake Monroe. While summer allows for easy access to Lake Monroe. Plenty of room to park a boat or have multiple cars. The home has modern decor with wood stove, new appliances, surround sound and all of the amenities you need for your stay. Just 20 minutes from IU.