Holiday rentals in Bloomington

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

Cozy home with Plenty of Space for a relaxing getaway, business trip or family & friend events! Fenced in yard, 1/2 mile from uptown for shopping and dining, 1/2 mile from the Constitution Trail. Location, comfort & space are guest favorites 😊 Host birthdays, graduations, wedding showers, or holiday gatherings in comfort and privacy. If more space is needed for larger groups, the home immediately next door to this one also sleeps 10 and may be available, message me on this if needed!

East St home close to Dtown and Universities

Welcome to your home away from home! This freshly remodeled 2 bedroom 1 bath retreat blends stylish comfort with functionality. Step into an open concept living space featuring a fully equipped kitchen, in unit washer/dryer and all the modern touches you need for a seamless stay. Relax indoors or step outside to enjoy in the private backyard, complete with new patio, and spacious front deck. Whether you are here for work or play this peaceful escape has everything you need to feel at home.

VibingVictorian Walk DT, The Castle& Local Dining

Welcome to our music themed private unit just blocks from Bloomington's Castle Theatre and several wonderful dining establishments. Our accommodations provide dining room for 6, ONE BEDROOM w/queen, a living room w/ Queen sofa bed + closing french doors to provide privacy. Full kitchen, bath&HEATED floors! Custom artwork created by host; We can't wait to welcome you to this fun space and hear your feedback. Also see our other listings “Campus Cottage”, “Black Beauty” and “Spotlight Studio”.

Cozy Loft Apartment with Projector Setup

Cozy loft apartment just minutes from downtown Bloomington. Enjoy an open living area with a comfy sofa, rustic coffee table, and a wall projector for streaming movies or shows. The loft features a very comfortable full bed overlooking the space, giving it an airy feel. A compact kitchenette with fridge and microwave makes quick meals easy. Perfect for travelers seeking a simple, affordable stay near downtown shops, dining, and the university. *No smoking! *Active camera outside the unit!

Private Wooded Escape | Hot Tub | Fire Pit | Games

Welcome to Hidden Grove, a "Beyond the Path" vacation retreat where your experience comes first. This serene, luxury escape sits on 2 private wooded acres just 10 minutes south of Bloomington, IL—soak in the hot tub under the stars, sway in the hammock with a good book, toast s’mores by the fire, then head out for nearby hiking, outdoor adventures, and charming local restaurants and entertainment for a truly rejuvenating getaway. If you are looking to reset, this is the place!

The Courthouse Loft-History, hot tub, and coffee!

The Courthouse Loft resides in the historic courthouse used in the mid 1900s on the second floor of The City House. The original railing and gate of courtroom divides the 825 soft studio style layout. Loft has a separated bath and laundry and a patio with hot tub! Mid century and historic style will wrap you in comfort and luxury during your stay. We are above a coffee shop, so pop downstairs for breakfast and your morning brew! Oh, and never a cleaning fee!

Vintage Loft @ Front St. Social

Step through the gold door and experience the charm of downtown El Paso in this fully remodeled 1-bedroom, 1-bath studio loft apartment. Located above Front St Social in a historic storefront built in 1894, the apartment combines vintage character with modern amenities. Updated in 2024, it features a kitchenette, new bathroom, and eclectic furnishings. Perfect for short-term stays, this cozy space offers convenience and comfort in the heart of our hometown.

Bed & Bath, 4K 55” TV, Kitchenette Apt (2F)

Enjoy an entire apartment just for you, perfectly designed for work or relaxation. This spacious retreat features a queen bed, a dedicated desk, and a 55-inch 4K TV. Your private space includes a bathroom with toiletries and a full kitchenette equipped with all-new appliances, including a fridge, coffee maker, microwave, and free snacks. Washer, dryer, and streaming services (Netflix, Disney, and Hulu) are available upon request.

The MidCity Loft | Downtown Bloomington

Walk to Grossinger Motors arena, Castle Theatre & Bloomington Center for Performing Arts! Cozy, modern loft in the heart of downtown Bloomington, steps from restaurants, coffee shops, bars, and events. Park once and walk everywhere. Located in a quiet, secure building, it offers a calm retreat after games, concerts, or work. Ideal for weekend getaways or business trips, this space blends downtown convenience with comfort.

Bloomington Loft steps from Downtown

The Loft is nestled in a historic building renovated by renowned Bloomington artist Harold Gregor. Located in vibrant Downtown Bloomington, this open, airy space boasts vaulted ceilings and a skylight for natural light. Enjoy a fully equipped kitchen, 1 Gig Xfinity Wi-Fi, HBO Max, and 125+ cable channels. Sleep soundly on a luxurious double-padded 20” queen mattress—comfort and style combined for your perfect stay.

Retro Retreat | Hot Tub, Arcade & Tiki Backyard

Experience uniqueness and fun vibes from your childhood featuring 90’s, 80’s, 70’s, and 60’s themed rooms! Whether you remember Pac-Man, Friends, Queen, Scrabble, the Beatles, Rubik’s cubes, or phone lines, there’s something here to relinquish those memories. Guests rave about the entertainment, outdoor setting, uniqueness, inviting floor plan, and the central location, which is near shopping, dining, and more!

Jefferson Gem

The Jefferson Gem is a cozy and chic mood all its own. She was carefully crafted to deliver on comfort and function, while guests experience something new in this home away from home. The 2 BR, 1 BA first floor unit (house is a duplex) has plenty of space for your party of 4, with a deck, a closed in porch, and cozy back yard acting as extensions of your living space. Baby gear available - just let me know!