Family-friendly holiday rentals in Indianapolis

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.

Eco-Friendly Downtown Indy Carriage House

Our carriage house (built 2019) sits behind our historic home on the near eastside of Indianapolis. We curated the space with the modern traveler in mind- from the design to the local coffee and art. We want your stay to give you the comforts of home while inspiring you by the city we love! A bright and modern space in a downtown neighborhood close to everything Indy has to offer! Close to Bottleworks, Mass Ave, and most downtown locations. Non-toxic supplies cleaning methods. Kids welcome!

Skyline View Condo, Best downtown spot, Park FREE!

There’s no better place to explore downtown Indy than our stylish condo in the heart of it all. We have free parking on site, but you won’t need your car! Step outside the front door and make your way to the vibrant entertaining and dining options of Mass Ave and The Bottleworks District, or stroll the historic cobblestone streets of Lockerbie. Wineries, breweries, coffee shops, antique dealers and entertainment venues are all minutes away. At night, you’ll enjoy the sparkling skyline view.

Monument Circle 1BR · Skywalk · Free Parking

🏛️ The Circle Suite The ONLY downtown apartment building with Skywalk access — walk indoors to the Convention Center, restaurants & Lucas Oil without stepping outside. Save $44/day with FREE garage parking. ⭐ "Amazing host, extremely responsive and helpful. The place is right in the center of the city. Could not have asked for a better accommodation." —Philip Modern 6th-floor 1BR · queen + sofa bed (sleeps 4). Fast WiFi, workspace, full kitchen, laundry. Superhost · Guest Favorite.

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.

Carriage house Ft. Square/close to downtown

Enjoy a private studio that is located in the Historic Fountain Square neighborhood. It is close to a variety of great restaurants and dining, art and culture, the city center. Within a 15 minute walk, you can be at the heart of all of the action of the conventions and activities that Indianapolis has to offer to the metropolitan region. It is within walking distance to the Cultural Trail, which leads through downtown and allows for walks or bike rides along the canal.

#IndyModPod Guest Suite Only! | No Cleaning Fees!

Hello, Fellow Traveler! Small, but mighty! This unique guest suite, located on the first floor of a modern three-story home, is perfect for short or extended stays. Enjoy all the essentials in a cozy space just steps away from some of Indy’s best neighborhood spots—restaurants, coffee shops, distilleries, and breweries! Plus, a quick stroll or bike ride down the iconic Monon Trail will take you to the vibrant Mass Ave dining and entertainment district!

The Juke: Spacious Downtown Condo on Mass Ave!

Beautiful immaculately furnished and equipped condo located in the heart of Indianapolis’s famous Mass Ave and conveniently across the street from the Old National Centre. Whether you’re staying for business or for pleasure, it has all aspects covered. Take a 5 minute electric scooter ride to the Convention Center and all major venues or walk out the front door to be immediately be surrounded by shopping, great food, fun and excitement.

Private, one car garage, hot coffee

Welcome to Robin's Nest, my cozy, modern, open-concept home in Indy! This inviting space includes 2 bedrooms, 1 bathroom, and 2 queen beds. Enjoy amenities such as a coffee bar, fire pit, and workstation. Let your fur babies run free in my fully fenced-in yard. You’re in close proximity to Lucas Oil, the Convention Center, and Gainbridge Fieldhouse, Murat, and many major hospitals are in a 10 mile radius.

The Indy Cottage - NEAR MASS AVE DISTRICT 🌿🌻

ALL ARE WELCOME HERE! The Indy Cottage is a newly renovated home built in 1912! This gorgeous 2 bedroom bungalow is located less than 5 minutes away from the popular Mass Ave area downtown Indianapolis. This home is in a very up and coming neighborhood. Mass Ave is full of restaurants, bars, shops, and the newly renovated Bottleworks District! This home has been completely renovated for that luxury feel.

White River Retreat

Escape to a private retreat on the White River in Indianapolis! This custom-built home offers a peaceful, open-concept space with a stone fireplace, pool table, and jetted tub. Enjoy 12 acres of shared grounds with river access, kayaks, and fire pits. Perfect for a unique getaway, feeling worlds away yet close to everything. Ideal for couples or small groups seeking tranquility and adventure.

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.