Holiday rentals in Greenwood

Cheerful & cozy farmhouse 2 bedroom home

Kick back and relax in this stylish space that is right down the street from Old Greenwood & less than 20 mins to Downtown Indianapolis. This tastefully updated home exudes "peaceful and cozy" w/ 2 bedrooms w/ brand new luxury king sized mattresses, 1.5 baths w/ walk-in tile shower, charming living room w/55" TV, Fiber internet, front load washer and dryer, dining table for 4+ bar seating, and a tranquil backyard space that is fully fenced, (dog friendly for an extra $75 cleaning fee, NO CATS).

The Loft at East Main

Be our guest at this brand-new upstairs urban apartment with small-town vibe. Located 4 minutes from I65, giving you easy access to Indy Motor Speedway, Lucas Oil Stadium and various downtown concerts and events. 15 minute drive south takes you downtown Franklin, featuring charming shops and trendy dining. The apartment boasts a full open-concept kitchen and living room, cozy separate bedroom, ensuite bathroom and on-site laundry facilities. Book your stay now to be one of our first guests!

Charming 2-bedroom home on Greenwood bike trail

Cozy up with the whole family in this lovely two-bedroom, one-bathroom home. This stay includes a king and queen bed, with a TV in each bedroom. Grab a bite to eat at one of the many local restaurants or whip up your own meal in the fully-stocked kitchen. A dishwasher, microwave, air fryer, Keurig, pet bowls, and toddler dishes/utensils are included. Be sure to take advantage of the fenced-in backyard, fire pit, and gas grill. You will find a treadmill, elliptical, and weights in the garage.

Convenient 2 bedroom*King Bed*

Your family will be close to everything when you stay at this centrally-located home. The unit is part of a duplex, featuring a driveway for off street parking. The 2 bedrooms are equipped with a king bed in one and an oversized daybed in the other. The living room has not only a 55" smart TV, but also a dedicated work space. The fully stocked kitchen and outdoor grill will make meal times a breeze. Looking for something to do? Enjoy the collection of games provided for your enjoyment.

Entire home in Greenwood near shopping. +Pets

Modern home with room for the whole family. Less than 5 min from food, shopping. 26 min to downtown & airport. Full of personality w new appliances, furnishings, flooring, art, games/activities. 2 queen bedrooms, full bath, queen sleeper sofa & queen air mattress. Kitchen, living room, wash/dry, Wi-Fi/smart TV. Books, games/activities. Pet-friendly fenced yard on pond—cozy, private & relaxing. I have rental cars at Greenwood & Indianapolis Airport throughTuro - please inquire for the link.

Cozy Cottage 14 mi. S of Indy In Bargersville, IN

Relax and unwind in this spacious three bedroom, one bath ranch home situated on one acre. The house is on about 1/2 the acre. The house is situated in Bargersville, Indiana in Johnson County, IN on the southern edge of Greenwood located in Center Grove Area. The garage area is not accessible. Vivint Home Security system with doorbell camera. I will email your unique code once you complete reservation. Central a/c & heat. Bedroom off kitchen has window a/c. We live about 1/4 mile away.

Convenient Comfort in the Heart of Indy

The whole group will enjoy easy access to everything from this completely renovated, centrally located 3 bedroom home. Located just one block from the University of Indianapolis campus as well as these other popular Indy destinations: Lucas Oil Stadium-10 minutes Indianapolis Motor Speedway-20 minutes Gainbridge Fieldhouse-10 minutes Indiana Convention Center-10 minutes Indianapolis Zoo- 15 minutes Indianapolis International Airport-20 Public Pickleball courts are a 5 min walk.

Private Movie Theater Game Room Sleeps 8 Indy

Movie Theater Home • 3BR • Sleeps 8 • Near Indy Relax in this peaceful 3-bedroom entertainment home with a private movie theater, pool table, and game room. The home features two bedrooms with twin beds and a large master bedroom with king bed and private bath. Enjoy a 55” Smart TV, fully equipped kitchen, and dining space. Downstairs offers surround sound theater seating and games. Step outside to a private patio with seating and grill. Located 15–20 min from Downtown Indianapolis.

Farmhouse Style Home with Spa-Firepit-GameRoom

Welcome to OliveBranch—a modern farmhouse style retreat with resort-style comfort. Perfect for a family getaway, a weekend with friends, a quiet retreat, or work. ✔ Family-friendly neighborhood ✔ 20 min to Downtown Indy, 10 min to Greenwood Mall ✔ 30 min to IND Airport, 45 min to Brown County State Park ✔ Private spa, firepit, grill, and game/media room ✔ 5 Smart TVs ✔ Ultra-fast WiFi ✔ Fully stocked kitchen and bathrooms ✔ Highchair, stroller, and Pack 'n Play for little ones

New 2B/1B house - sleeps 5!

Stay just minutes from downtown Franklin in this cozy 2-bedroom home. It's perfect for traveling professionals, small families, or weekend getaways. Enjoy a fully equipped kitchen, fast WiFi, and a dedicated workspace—ideal for remote work or longer stays. Relax in the comfortable living room with streaming TV, or unwind outside on the large deck with a fenced yard. • 10 minutes to Johnson Memorial Hospital • 30 minutes to Indianapolis • Close to local shops, dining, and events

Entertainer's Dream w/ Pool and Games

You won't find a more well equipped home in the area than you will at Hometown Hideaway. Hometown Hideaway is luxury at its finest with 4 bedrooms, 2.5 baths, 2 separate living spaces, plus an amazing game room with pool table, 65" Smart TV, shuffleboard, and plenty of seating. Don't forget the fenced backyard with private heated pool and seating galore for you and all of your guests. Plenty of room for rest and relaxation indoors and out.

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!