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.

Pumpkin House. Chic downtown spotless fenced yard

Over 60 restaurants, bars, coffee shops, theater, comedy club, shops, health food grocery all in a very short walking distance. This is the perfect place for an active guest to experience boho Bloomington or attend IU events. Quality linens, SPOTLESS, uncluttered, new everything including beds,kitchenware etc. Designated parking for 2 and free street.Fast fiber 500Mbps speed internet and new Roku smart TV's. Third party booking allowed with approval from host and contact information of guests.

The Sanders Store

The Sanders Store, formerly known to Bloomington natives as Hays Grocery, is a landmark on Fairfax Road. Originally erected in 1913, the Sanders Store operated as a grocery for the Sanders community until 1967. The space was vacant and largely used for storage until 2019 when it was obtained, historically designated, fortified and reimagined into a deluxe vacation rental that sleeps 7! Six miles from downtown Bloomington and the Fairfax Marina at Lake Monroe. Great for IU events or boating!

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.

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.

Great offer! Private entrance, Spacious, King-IU

Seasoned and experienced superhosts host this charming private suite with a private entrance. It has one bedroom with a king size bed. The house is on a very quiet street. You may not even know you're in the middle of town. You may see deer and other animals roaming around the neighborhood. The space includes private bathroom, kitchenette, and a sitting area with a loveseat and a small dining area.