Family-friendly holiday rentals in Indianapolis

#IndyCozyCottage | Historic Cottage Near Downtown

Hello, Fellow Traveler! Welcome to our cozy historic Indy cottage in a quiet neighborhood retreat just minutes from downtown. Enjoy coffee on the porch, a fenced yard for pets, and easy access to Mass Ave, Bottleworks, and Lucas Oil Stadium. Thoughtfully updated for comfort and style while keeping its original charm! This quaint home features a king bedroom with walk-in closet, updated and stocked kitchen, secondary flex bedroom/office, and two-car garage. Perfect for your next Indy adventure!

The Jewel Box—Historic Tiny Home—Walk Downtown

Experience the charm of The Jewel Box, a beautifully renovated 1924 tiny home in the historic Indianapolis neighborhood of Windsor Park. Just steps from the Monon Trail, lush 31-acre Spades Park, & minutes from the trendy and upscale hub of the city: Mass Ave & the Bottleworks area. Enjoy boutique shops, lively bars, entertainment, & fine dining all within walking distance. With rich jewel tones, layered textures, & colorful artwork, the space offers playful luxury in a cozy, artistic retreat.

Kit’s Cabin - Log Cabin Retreat in Indianapolis

Welcome to our 150-year-old log cabin, nestled in the heart of Indianapolis! This cozy retreat offers a tranquil getaway while being just minutes away from all modern conveniences and only 20 minutes from downtown. Step inside and be greeted by the rich history of exposed wooden beams and a large stone fireplace. Our authentic rustic decor and cozy cabin amenities will transport you to a simpler time. Come experience the magic of Kit’s Cabin, where historic charm meets modern comfort.

The Fountain Square Flat - *No Cleaning Fee*

Step into your private guesthouse retreat in the heart of Fountain Square. This newly built, mid-century modern carriage house offers comfort, style, and total privacy. Enjoy fast Wi-Fi, self check-in, and free private parking— just over 1 mile from Lucas Oil Stadium and Gainbridge Fieldhouse and a short walk to restaurants, bars, and live music. Perfect for couples, solo travelers, or remote workers looking for a sleek, walkable stay in one of Indy’s most vibrant neighborhoods.

Pop Culture Container Home - rooftop & greenhouse

“The Shadowbox" pop culture container home in downtown Indianapolis is one of three container homes located on the lot. The home is comprised of 7 shipping containers with an added greenhouse & rooftop deck overlooking the city skyline. The floor to ceiling windows on the first & second floor both face & provide a unique perspective of Fall Creek River. The home has a large back yard. Plenty of comics, action figures & games to keep you entertained throughout your stay.

Charming Meridian Kessler Carriage House

Built over a century ago and lovingly updated, this second-floor retreat sits in the heart of Meridian Kessler — one of Indy's most beloved midtown neighborhoods, walkable and tree-lined. Thoughtful touches throughout: curated furnishings, fiber WiFi, and a coffee setup worthy of a slow morning. Just right for one or two. Close to great food. Feels like home. Falling for Meridian Kessler? We're happy to share our favorite spots — and we know great realtors too.

The Prescott- Historic Glamour. Bold Luxury

Welcome to the Prescott. A bold, exciting & fierce luxury rental in the center of beautiful historic & walkable downtown Irvington. 5 miles from downtown Indianapolis. Enjoy this historic home built in 1908; reimagined & curated in 2024. Experience an upscale stay with modern comfort & historic elements where BOLD is always at the forefront. Just steps from your front porch, you will find Snug, a cocktail and whiskey pub with light bites.

Modern duplex in charming downtown neighborhood

This reimagined century-old property features a gas fireplace with wood-panel surround, home office workspace, tiled bathrooms, hardwood flooring, and plenty of space to relax. Cook in a refurbished kitchen of quartz countertops and stainless-steel appliances, and truly find yourself at home away from home. This property includes 2 bedrooms: 1 king, 1 queen. Parking is available on the street, with no extra cost or pass required.

Unique A-Frame Retreat•Prime Location•Custom Bath

Perfect for families, friends, or weekend getaways — this unique A-Frame cabin offers peaceful privacy, a fire pit + patio, screened porches, and easy access to downtown Indy and Broad Ripple! Unique architecture and comforting features makes this home one you won't want to leave. Great for a romantic weekend getaway, a family trip with plenty of space for all, or a gathering of friends.

Cottage w/ ~Solarium~ in heart of Broad Ripple!

Nestled in historic Broad Ripple, indulge in the charming ~Solarium~ Cottage in an unbeatable location. Walking distance to Broad Ripple Village, Broad Ripple Park, the Monon Trail, and the White River and central to everything in Indy. It’s the perfect blend of character and convenience year-round with the added extra of a solarium. Enjoy the best of Indy any time of year!

Perfect Downtown Carriage House - Walkable!

New construction, surrounded by history, in the middle of it all. Steps from Mass Ave and Bottleworks, feel at home in the king-sized Sleep Number bed, luxurious shower, and full kitchen, brand new appliances, including laundry. YouTube TV, Netflix, Prime, Disney+, MLBTV, and more all available on the TV! Great for a weekend getaway, even better for an extended stay.

Private and Charming Carriage House Downtown Indy

Fully modern and new private space in my charming carriage house. It has all the amenities you would need to enjoy and explore the beautiful city of Indianapolis. If you are here for work or pleasure, it is perfectly located and easy access to all Indy has to offer so come and explore Indianapolis and all it has to offer.