Holiday rentals with outdoor seating in Bloomington

Chic Retreat Small Town Charm, City Sophistication

The ultimate escape, at Wells on Main Guesthouse & Gatherings where small-town charm meets big-city sophistication. Whether it’s a romantic getaway, girls’ weekend, or just time to recharge, our elegant retreat has you covered. Couples can cozy up in dreamy spaces and create lasting memories. Gather your best friends for laughter, wine, and chic relaxation in a stylish setting. With local charm and upscale comfort, every moment feels magical. Book now and discover your home away from home! ❤️

House of Games - Play, Relax, Unwind

Ready to get your kicks on Route 66? Your group of up to 11 will have a blast playing more games than you’ve ever seen in a vacation home. House of Games lives up to its name with skee ball, ping pong, air hockey, pop-a-shot, foosball, classic game-console room – and more. Guests praise the variety and fun of 10 arcade games. Kiddos love it here, and families cherish spending time playing games together. Relax in the backyard with firepit, grill, hammock. All this – plus free soda + ice cream.

Linden Street Bungalow

Centrally located, safe and family friendly Backs up the the Constitution Trail Very short walk to Keg Grove Brewery Minutes to both ISU and IWU Campuses Adorable Living/Dining Room Bedroom with a full bed and half bath. Upstairs Bedroom with queen size bed 2nd floor loft area has a twin size daybed that can be turned into a king size bed Full bathroom upstairs. Finished basement with an additional living area and a 3/4 bath (bath and sink, but no toilet) Great front porch and back porch.

Remarkable Mid-century Modern Time Capsule.

Our wonderful home is very unique in many ways. The original home was built in 1870 and is situated on Pine Hill Homestead, one of the original homesteads of Bloomington. From the 1960s it was renovated by then owner and architect, C.Eugene Asbury. Since the renovation, our home has remained his vision and allows you to take a step back in time for what life was like in the 50s and 60s with furniture and lighting from that timeless era. We are happy to host short and long term visitors.

Piper’s Porch AirBnB

Hello friends! My name is Heather. I have a golden doodle , Piper, hence the name of this abode here:). It’s been a dream of mine for years as I love people & love to pamper them. (Piper loves people just as much as myself..☺️) My 2-story home is built right around 1900 . They will have the entire upstairs. The bedroom consists of 1 queen bed, full bathroom, walk in closet. There is a sitting room with a futon, and coffee bar which is equipped with a fridge, microwave, & kuerig.

White Oak Oasis

White Oak Oasis is the perfect escape for weary travelers, busy families, working professionals, and couple's getaways alike! Come rest mind and body in a quiet, cozy townhome situated just off Bloomington's White Oak Lake. Guests can expect family-friendly amenities and a clean, comfortable environment. The location is walkable or just a short drive to all Blo-No has to offer. Book a stay at White Oak Oasis and make us your "home away from home" no matter the reason for your visit!

The Schoolhouse Cabin - Hot Tub & Game Room!

A charming getaway near the lake and woods of Lake Bloomington in Central, IL. Originally built as a schoolhouse one hundred years ago, this cabin has character and unique features for days! The comfortable and eye catching furnishings and decor, along with great amenities, big and small, you’ll find the Schoolhouse cabin to be just what you need for a relaxing getaway. Enjoy the hot tub, heated game room outdoor bed or the multiple reading nooks. Oh, and never a cleaning fee!

2 king beds! Large luxury home with pool table

Charming home in a family-friendly neighborhood in north Normal. Five minutes to ISU, 11 minutes to Rivian. Newly remodeled and fresh. Adorable front porch with rocking chairs. Basketball court in the back yard! Back patio with pergola. This super spacious home features three large bedrooms and three full bathrooms, plus two sofabeds. Includes two king beds! Perfect for a family or a traveling executive who is in search of a luxury home. Lots of amenities are included!

Cozy Home with LOTS of space -1 mile to ISU & IWU

Cozy home that "feels just like home!" Plenty of space in this bungalow for a relaxing getaway, business trip or family & friend events! Updated with modern decor, plush linens and bedding, fenced in yard, 1/2 mile from uptown; great for walks to dine and shop. Everything in the home was chosen with 'comfort' in mind. Location, atmosphere of the house, comfort and space for hosting friends & family are guest favorites!