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.

Broad Ripple Treetop Lodge on the Park

1 of only 10 elite Airbnb PLUSs in Indy, chosen for unique design & decor, outstanding service & amenities. Treetop Lodge is a beautiful, restful 2nd floor lodge retreat, a creative space with charm & tasteful, whimsical touches. Features a large common room, 2 bdrms 1 King bed, 1 queen, bright FULL kitchen, private front door entrance, large balcony deck, all white linens & FREE LAUNDRY SERVICE! We're directly ON 62-acre Broad Ripple Park & just a short walk to iconic Broad Ripple Village!

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.

Free Parking · Skywalk · Walkable Downtown 1BR

🏙️ The Loft Suite The ONLY downtown apartment building with Skywalk access — walk indoors to the Convention Center, Lucas Oil & restaurants without stepping outside. Save $44/day with FREE garage parking. ⭐ "Beautiful apartment — even more beautiful than the pictures! Perfect location for taking the Skywalk to the convention center or Lucas Oil!" —Brittany Modern 1BR with city views · queen + sofa bed (sleeps 4). Fully stocked, fast WiFi, in-unit 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.

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.

#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!

Cozy Tiny House Nestled in the Trees

Take it easy at this unique and tranquil getaway. In a charming tiny house surrounded by trees and birdsong, you can unplug and relax without going too far off the beaten path. Only a 15 minute drive from downtown, we’re conveniently located between Fountain Square, Irvington, Beech Grove, and Wanamaker. Curl up with a cup of tea and a good book, sit on the patio and watch for deer, or take a walk around our fledgling 9-acre permaculture farm.

Bright Downtown Indy Studio Near Mass Ave Walkable

Cozy, 1BR studio in Cottage Home neighborhood, just east of downtown Indianapolis. Perfect for work trips, or a quiet weekend getaway. Walk to Mass Ave, Bottleworks, the Factory Arts District, top restaurants, shops, breweries. Minutes from Gainbridge Fieldhouse, Lucas Oil Stadium, and Monument Circle. Ideal for concerts, sports, and downtown events. Fully furnished with full-sized appliances and fast Wi-Fi. Warm, cozy, winter retreat!

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.

Carriage Home with early check in

Discover the perfect blend of historical charm and modern convenience in our cozy home, located in the heart of Indianapolis' Old North Side. Offering early check-in, you can kick-start your exploration of the city without a moment's delay. Our prime location ensures you're just moments away from downtown's bustling scene, the Indiana Convention Center, Gainbridge Fieldhouse, and Lucas Oil Stadium. Free Parking Free Coffee

Loft Apartment: Beautiful Farm and Country Views

This beautiful, over the garage private apartment is located in a wooded area across from our 94 acre farm. A very peaceful setting to wind down and enjoy the nature around you. Conveniently located 15 minutes from the airport and 30 minutes from downtown Indianapolis. A work space is also available that overlooks this beautiful farm!! Also perfect for couples or small families to enjoy some time in the country!