Family-friendly 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!

Indoor spaces · Kitchen · Accuracy

Special - 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.

Family · Indoor spaces · Backyard

Timber Time in Hudson Hideaway

Looking for a break from the busyness of life, to relax and enjoy nature? Step back in time in this tranquil and rustic home. In a remote location and surrounded by timber, this property is perfect to unwind, enjoy a sunset, and view the stars in a wide-open sky. The large yard allows for all kinds of activities and the circle drive provides easy RV, trailer, and boat access. Located next to Evergreen Lake/Comlara Park, the hiking and biking trails, boat ramp, and beach are just minutes away.

Indoor spaces · Kitchen · Location

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 a week long stay and receive 40% off ❤️

Family · Kitchen · Solo travel

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.

Family · Kitchen · Amenities

Modern Ranch Home, Quiet Neighborhood - EV Charger

Light filled and snuggled in the mature trees of Maplewood neighborhood. This single story brick home is centrally located; close to Uptown and Downtown, the campuses of ISU and IWU and less than 10 minutes from Rivian and State Farm. Newly renovated and designed with a modern aesthetic, our guests come to explore Bloomington/Normal but tell us they are just as happy spending time and relaxing at our Modern Ranch. Newly installed electric vehicle charger is available during your stay!

Family · Indoor spaces · Cleanliness

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!

Indoor spaces · Family · Location

Peaceful Wooded Cabin, 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!

Kitchen · Indoor spaces · Hot tub

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!

Kitchen · Indoor spaces · Beach

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.

Family · Kitchen · Location

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.

Indoor spaces · Family · Accuracy

Arcade House - Hot tub, XL game room, fire pit

Voted a Top Place to Visit in Illinois, this private retro playground is where arcade lights glow and movie nights come alive. Play games, soak in the bubbling hot tub, and wind down around the firepit under string lights. Perfect for families, friend groups, birthdays, bachelorette/bachelor gatherings, and celebrations, this one-of-a-kind Bloomington getaway is 3-minutes from downtown!

Family · Indoor spaces · Getting around