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.

Cozy Midtown Retreat

I like to brag that this is the cutest studio apartment in the city. It's in a brick Arts & Crafts apartment building built in 1915 and retains a lot of its original architectural features. It's furnished with an eclectic mix of antiques & modern pieces, decorated with original & vintage artwork, & stocked with vintage dishes and silverware. If you like drinking from a Ball jar, this is the place for you! It's furnished for comfort and privacy. It's high ceiling and windows give it character.

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.

Fletcher Place Bungalow-Best Downtown Location!

This adorable aqua bungalow is located in the Fletcher Place Neighborhood just steps from some of the best restaurants, sporting events & concert venues in Indianapolis. This home has a lot of modern touches! Attention to detail has been given to ensure a comfortable & enjoyable stay. We want it to be your "home away from home" while you're in Indy! There's so much to do within walking distance. We allow 1 smaller sized dog for a fee. Need anything? Just ask! We're right next door.

Urban Jungle on Massachusetts Avenue - Downtown 🌱

Located in the heart & soul of downtown Indianapolis on Massachusetts Avenue. This 2 bedroom, 1 bathroom condo is a few steps away from the best retail & dining that Indy has to offer. You are right above a cupcake shop which is never a bad thing. 🙂 Very close proximity to: -convention center (1.1 miles) -bottleworks district (.4 miles) -sporting events (1.5 miles) -concerts (100 steps away from Old National Centre & the Egyptian room) -fine dining (Walkable) -retail shops (Walkable)

Historic Charmer

My home is a very quaint, clean, and private space in a very walkable and welcoming community. Historic Irvington is full of several eateries, coffee shops and a brewery within steps. Just follow the Pensey Trail south a block to explore this exciting community. Or, take the trail for a light run or bike ride! Minutes from downtown my space is perfect for a weekend away, a cozy bed while out traveling, or an easy effortless way to travel for work or one of Indy’s many great conventions.

Lux House Furnished for Comfort

Welcome to our charming house in the heart of Indianapolis! Just minutes from the Convention Center, Lucas Oil Stadium, Gainbridge Fieldhouse, Bottleworks District, and Mass Ave, our location is perfect for exploring. Enjoy modern comforts in a historic setting with a cozy living area, a fully equipped kitchen, comfortable bedrooms, a modern bathroom, one garage space, free coffee, fast wifi, and high-quality furniture for a comfortable stay. Book now for an unforgettable experience

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.

#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 Rabbit Hole Retreat: A+ walkability eclectic

Stay at The Rabbit Hole Retreat, a whimsical Wonderland-themed retreat in historic Fletcher Place~one of Indianapolis’ most walkable neighborhoods. Steps from Amberson Coffee, Milktooth, restaurants, breweries, and Fountain Square nightlife. Minutes to Lucas Oil Stadium, the Convention Center, and downtown. Sleeps 4 with king bed, sofa bed, fast WiFi, full kitchen, reserved parking, and backyard with fire pit, grill, and mini putt-putt.

Cute Little Downtown Home

You and your family or friends will be close to everything when you stay at this centrally-located place. Conveniently located in Fountain Square, this shotgun style home is located within easy walking distance to everything Fountain Square and Fletcher Place have to offer. A 6 minute .2 mile walk to the HiFi and Annex concert venues. Just a short Uber or scooter ride to Mass Ave., Lucas Oil Stadium, or the Convention Center.

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.