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Holiday rentals in Monroe County

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Top-rated holiday rentals in Monroe County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A sprawling green field stretches towards the horizon, filled with soft clover and dotted with trees. In the foreground, a planter holds bright flowers, adding colorful contrast to the natural landscape. The sky is lightly clouded, enhancing the serene atmosphere.
Guest suite in Bloomington
4.99 out of 5 average rating, 146 reviews

Peaceful apartment space in beautiful farm house

Our lovely farmhouse is minutes from Lake Lemon, Griffey Lake, Indiana University & many spots in Bloomington. Conveniently not far from I-69, we're 20 minutes away from Nashville. This is a basement apartment with private bedroom, private bathroom, large living/dining area, & kitchenette. Shared front door & ~10 steps inside main floor. The ranch is 50+ acres with 8+ acres of woods for hiking, pastures with cattle, a heated pool & patio area, & a beautiful front porch looking over the ranch.

Top guest favourite
The entrance to the cabin features a covered porch with rustic wooden supports and decorative string lights. A welcoming outdoor seating area is visible in the background, surrounded by lush greenery and shaded by nearby trees. The path is lined with stones and small plants.
Cabin in Unionville
5 out of 5 average rating, 483 reviews

Cozy Cabin Close to University 1

The Red Rabbit Inn is located just 15 mins from the Indiana University campus and just 20 mins from Nashville, IN , this architecturally designed cabin features the works of local artisans. Beautifully landscaped on a secluded, wooded pond, this cabin includes a loft bedroom with KING bed, bath, full kitchen, gas fireplace, satellite TV & Wifi, with your own private deck, outdoor hot tub, fire pit area & gas grill. Cabin sleeps 2 guests. Located near Lake Lemon, in a beautiful serene setting.

Top guest favourite
A spacious living area is presented with hardwood floors, natural light filtering through new windows. A black sofa is centered around an orange coffee table. Two woven armchairs and a decorative area rug complete the inviting space, along with wall art and a small writing desk.
Home in Bloomington
4.97 out of 5 average rating, 177 reviews

Pumpkin House. Chic downtown spotless fenced yard

Over 60 restaurants, bars, coffee shops, theater, comedy club, shops, health food grocery all in a very short walking distance. This is the perfect place for an active guest to experience boho Bloomington or attend IU events. Quality linens, SPOTLESS, uncluttered, new everything including beds,kitchenware etc. Designated parking for 2 and free street.Fast fiber 500Mbps speed internet and new Roku smart TV's. Third party booking allowed with approval from host and contact information of guests.

Top guest favourite
An exterior view of a modern studio is presented, showcasing a dark exterior surrounded by lush greenery. Two bright red chairs are positioned at the entrance beside twin planters, and a statue is seen on the ground. Trash bins are discreetly placed to the side.
Cottage in Bloomington
4.97 out of 5 average rating, 271 reviews

Relaxing Retreat in the Woods

Relaxing retreat on 16 acres of woods , minutes from shopping, restaurants, Lake Monroe and the I.U. stadium--a 13 minute drive for basketball and football fans. Fire pit, grill, hammock, board games, kitchenette, CD, record player. No cable /television. Cell phone service and internet available if sometimes a bit spotty. The studio is in the woods so you may see or encounter wildlife including deer, opossums, raccoons, snakes, bobcats, coyotes and birds. Owner lives on property.

Guest favourite
A bright guest room features large windows allowing natural light to illuminate the space. A spacious bed sits next to a woven storage trunk, while a cozy armchair is positioned nearby. Area rugs add texture to the hardwood floor, creating a comfortable atmosphere.
Guest house in Bloomington
4.94 out of 5 average rating, 109 reviews

Private Cottage House One Mile from Downtown!

This guest suite is *one mile* from campus and downtown and located in a safe, quiet residential neighborhood! Here you will be walking distance to Kirkwood and steps away from a local coffee shop, restaurant, and 2 parks! The space is complete with ample natural lighting (+ custom blinds for privacy), premium features like heated floors, and privacy for guests to enjoy a quiet, relaxing stay steps away from Btown's best nestled into a quiet backyard (often with deer!). No idiots.

Top guest favourite
A modern kitchen is featured with dark cabinetry and open shelving displaying dishes. A patterned backsplash adds visual interest, while stainless steel appliances, including a refrigerator, microwave, and dishwasher, provide functional amenities. A vase of flowers brings a touch of color to the countertop.
Guest suite in Bloomington
4.99 out of 5 average rating, 139 reviews

Campus-Side Retreat in the Woods

Across the street and walking distance to IU's sports facilities, this chic and modern wooded retreat is a short drive or bike to downtown Bloomington's vibrant nightlife and community activities. The studio apartment boasts a skylit bathroom, a full kitchen with custom-made cabinets, washer/dryer on site, and professional decorating. It’s only a short drive, or slightly longer hike to Griffy Lake, only one mile to IU Health Bloomington hospital, and minutes to I69.

Top guest favourite
Cabin in Unionville
4.99 out of 5 average rating, 189 reviews

Unwind in Timeless Elegance: Sanctuary with a View

Embrace a Serene Winter Sanctuary ​Experience the magic of a true winter escape at Cabin Porch Paradise. Now that the fresh powder has settled, the cabin has transformed into a quiet, white-capped sanctuary perfect for those seeking peace and natural beauty. 4-WD or All-WD recommended. ​Whether you are watching the snow glisten from our expansive porch or curling up by the fire, it is the ultimate setting to witness the power and stillness of nature.

Top guest favourite
The entrance features a cozy porch with a small table and chairs surrounded by greenery. A decorative broom is suspended from the porch’s overhang, and a stone pathway leads to the front door, accented by the house number displayed on a stone pillar.
Guest suite in Bloomington
4.95 out of 5 average rating, 1,349 reviews

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.

Top guest favourite
A cozy living area is furnished with a dark sofa and a wooden coffee table adorned with a green runner. A bookshelf filled with books and decorative items is placed against the wall, along with a coat rack. Soft lighting accents the space, creating a welcoming ambiance.
Guest suite in Bloomington
4.93 out of 5 average rating, 150 reviews

Private entrance, cozy lower level pad

Private entrance to a lower level living area, queen size bed and bathroom. Living Area includes a breakfast table, refrigerator, microwave, Keurig coffee maker, coffee, electric tea kettle, tea, sweetener and creamer. Bedroom includes a closet and chest of drawers. Enjoy free wi-fi and a space completely to yourself. Come and go as you please! We are 2 miles from IU campus, downtown, shopping, and entertainment. We welcome everyone!

Top guest favourite
Guest house in Bloomington
4.96 out of 5 average rating, 403 reviews

Private Studio, 5 Min IU, Kitchen, Private Parking

Intentionally designed to feel comfortable, calm, and easy to settle in. At ~400 sq ft with a slanted ceiling, it's ideal for solo travelers or couples. Guests describe the studio as cozy, spotless, and surprisingly well-equipped — with everything needed for a comfortable stay. Minutes from IU, downtown, dining, parks, and Kroger, you’re close to everything without the hassle. Please inquire about discounted rates for extended bookings.

Guest favourite
A spacious bedroom features a king-size bed with light blue striped bedding and two bedside lamps. A wooden dresser and a small desk are visible. A light rug covers the hardwood floor, and artwork adorns the walls, enhancing the cozy ambiance.
Home in Bloomington
4.87 out of 5 average rating, 182 reviews

Great offer! Private entrance, Spacious, King-IU

Seasoned and experienced superhosts host this charming private suite with a private entrance. It has one bedroom with a king size bed. The house is on a very quiet street. You may not even know you're in the middle of town. You may see deer and other animals roaming around the neighborhood. The space includes private bathroom, kitchenette, and a sitting area with a loveseat and a small dining area.

Top guest favourite
A cozy bedroom features a queen bed with a textured gray coverlet and matching pillows. A simple nightstand is positioned beside the bed. Natural light enters through a nearby hopper window, illuminating the wood floor and softening the neutral wall tones.
Guest suite in Bloomington
4.96 out of 5 average rating, 112 reviews

Cozy Little Suite

This guest suite with private entrance is in a quiet, older neighborhood near the IU campus. The booking includes a recently remodeled basement bedroom with en suite bathroom. It's locked off from the rest of the home in which the host family lives. The bedroom includes a queen bed, mini-fridge, microwave, and Keurig. The bathroom has a glass-enclosed shower.

Popular amenities for Monroe County holiday rentals

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  2. United States
  3. Indiana
  4. Monroe County