Holiday houses in Indianapolis

Alumni owned Bungalow 1 block from Butler

Feel at home in this charming 2 bed/1 bath bungalow in a quiet, historic neighborhood! The property features refinished hardwood floors, comfortable furnishings, thoughtful decor and updated fixtures in the bathroom. A modern kitchen offers new appliances, the essentials for cooking, a charging station, and a coffee bar with snacks. Retreat to the spacious fenced in yard and lounge on the patio. History is important to us so we updated the space while staying true the original character & feel.

#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.

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.

Downtown Indy Circle City Suites

Access to-free coffee, tea, 24/7 gym/cycling. Relax in courtyard w/gas fire pits, outdoor big TVs, outdoor sitting, 2 hammocks, 2 grills. Walking distance-Circle, shopping, Mass Ave, Sporting events-PACERS, FEVER, Concerts, & the COLTS. Canal, ZOO, butterfly pavilion, Uber to the Indy 500 track, children's museum. Enjoy local wineries, breweries, nightlife, & live music. Grocery store, pharmacy close by. Or, keep it simple. Stay and Relax, watch TV, cook in the fully equipped kitchen.

The Homestead

Located in the chic, cosmopolitan suburb of Meridian Kessler buzzing with galleries, cafés, restaurants, studios, one-off retailers, and the weekend markets and neighborhood festivals. Just minutes from Broadripple & 15-18 min. from downtown Indianapolis, Keystone, and Carmel. It's the perfect base to enjoy local events, or visit students attending local universities. The Penn House is an exclusive-use four-bedroom, home-from-home for up to eight guests. The space: 2 king, 2 queen

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.

Style and Comfort in this adorable bungalow!

Cozy & upscale bungalow located in the heart of Speedway, Indiana. Enjoy a small, but polished bungalow built in the 1930s. 2 bedroom, fully stocked kitchen, fenced private yard, and great location to all things racing and Indy! 5 Short miles to downtown & a 15 minute drive to the convention center. 1 dog is welcome! (More with written permission) Please share a bit of the nature of your trip, your hometown, & breed of your dog. No Cats or other type animals.

Downtown Private Suite Convention Center Access

The Gallery is a 2 bedroom 1.5 bathroom suite with amazing city views. Located on Illinois and Market Street, you will have a birds eye view of Monument Circle and The Arts Garden. Enjoy a clean, spacious, and private stay while being close to all Indianapolis has to offer. Lucas Oil, the Indianapolis Convention Center, Gainbridge Fieldhouse, and popular restaurants are all in walking distance All art work on display are sourced from local artists.

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.

Downtown~King Bed~Parking~Balcony~Restaurants~Bars

• Children's Museum 5 minutes away • Lucas Oil Stadium, Pacers Center, and Convention Center 15 mins away • Restaurants, bars and grocery store within 5 min walk • MLK Park is a 5 min walk • Indiana State Fairgrounds 10 mins away • 30 mins to Grand Park • Fully equipped kitchen • Monon Trail access 3 blocks away • Netflix included • Washer/dryer included free • Variety of churches nearby • No parties • Send us a message!