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.

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.

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!

Uptown Suite Modern Studio Downtown on the Square

Discover Uptown Bloomington, a chic studio located on Bloomington’s Square directly above the #1 TripAdvisor-rated Samira Restaurant. Immerse in modern art and vibrant colors, unwind in comfort, and relish in a delicious meal at Samira Restaurant. Explore campus, downtown, and nearby hotspots, or relax with a 55-inch Smart TV. Hosted by Samira & Tareq, every corner holds special details for a memorable stay. Indulge in luxury, convenience, and personalized hospitality in Bloomington's heart.

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!

Lil BUB's Really Nice Apartment - EAST

We are conveniently located within walking distance of Downtown, Bryan Park, and The B-Line Trail, 1 mile to IU Campus, 1.8 miles to Assembly Hall, and 3.5 miles to IU Hospital. Our beloved luxury apartment is one of the nicest places to stay in town. It underwent a ground-up bespoke renovation with white oak hardwood floors, quartz countertops and premium appliances, rivaling a premium suite at a boutique hotel with the added privacy, charm, and amenities of a home for a great price.

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!

Downtown Bungalow - Walk to IU

Charming Prospect Hill Retreat Nestled right next to Downtown in the heart of Bloomington’s beloved Prospect Hill neighborhood, this beautifully maintained 2-bedroom, 1-bath home offers comfort, character, and convenience in equal measure. Located just a short stroll from the IU campus, locally-owned coffee shops and restaurants, grocery stores, B-Line Trail, and FAR Art Gallery, you’ll love how easily and comfortably you can visit, live, work, and unwind here.

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.