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! ❤️

Riding Heights

Welcome to @RidingHeights – our cute mid-century modern/bohemian style bungalow home. The décor is colorful, unique and functional. It is 900 square feet featuring an open concept, large kitchen and large bedroom with a king sized bed! The house is located a half block away from the Rock Island Trail, it is the longest trail in the area. The Heights Strip is only minutes away! Two street bikes are provided by us for your convenience. Message us about bringing a pet and we will consider them.

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.

5 Acres | Peace & Privacy | 5 minutes to Blm

Enjoy the perfect blend of privacy, convenience and tranquility at this stylish and comfortable studio, your gateway to everything Bloomington/Normal has to offer. Just 8 min. from downtown Bloomington and 15 min. from ISU/Uptown Normal. Unwind and get cozy, play a game of pickleball or take a walk around the quiet neighborhood. Comfortable furnishings, well-equipped kitchenette, complimentary coffee, and grill for your convenience. We thought of everything, so you don't have to!

Day Tripper...In the Heights

This charming bungalow just a two block walk to Heights restaurants and shops has been redesigned with custom woodwork throughout. Custom woodwork with gold accents throughout. We have been designing and selling upscale affordable housing for the past 20 years and decided to expand into the short term rental market with this dedicated AirBnB space as well as our “Imagine...In the Heights” and "Blackbird...On the Drive" locations. Relax and enjoy your stay!

Full studio apartment by the best Springfield park

Historic home attic converted to a private 3rd floor apartment, featuring private kitchen and bathroom. Located just two blocks from what many would agree is the best park in Springfield, with a pond, a botanical garden, tennis courts, a playground, and nice roads to run, walk, bike, or skate on. We are also very close to downtown as well as other commercial areas. This space is on the 3rd floor with private access from outdoor stairs and keypad entry.

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!