Vacation 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).

Tiny Home, Big Charm! | Hot Tub, Blackstone Grill!

The Sunny Door Cottage | Tiny Home, Big Charm Step through the cheerful yellow front door and into a space of relaxation and simple luxury. Originally built in 1886, this freshly renovated 700 sq ft tiny home blends modern updates with timeless charm. Inside, you’ll find touches of the past like an exposed brick chimney stack paired with updated appliances and a cozy sliding barn door to the bedroom. The Sunny Door Cottage invites you to slow down, snuggle up, and fall in love with Franklin.

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.

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 Downtown Retreat - Walkable to Everything

A cozy, updated craftsman home in the heart of downtown Greenwood that we affectionately call "The Pearl". Walkable to restaurants, shops, parks, and a convenience store. Only a 20-min drive to downtown Indy, Lucas Oil Stadium, Indianapolis Zoo, Fountain Square, and the convention center. It's a great hub for your greater Indianapolis adventure! It's a great space for families, small groups, and co-workers with an open layout that allows everyone to gather together or spread out.

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

Spacious home 20 min from downtown.

This updated, spacious home is near a walk/run/bike trail and has been furnished to meet your needs while in Indy. Upstairs are 3 bedrooms and a loft as a 4th bedroom. It has a semi-private backyard patio w/fire pit and seating for 6. This 2-story home is in a quiet neighborhood just minutes from concerts, sporting events, restaurants, the zoo, Indianapolis Children's Museum, the Canal, and much more! Also, we're just a 20-minute drive from the airport. No pets please.

Pool Pad | 7 Min DWTN/Gainbridge | 15 Min Airport

Work & relax in this calm & stylish space. A cozy home with spacious main bath with tub & skylights, plush king bed in main bedroom, full kitchen, games: Jenga, bucket pong, outdoor fire pit, charcoal grill, a private pool surrounded by a deck for tanning, lounging, & eating. A desk for working, 1 car garage + 1 driveway parking makes this home ideal. Located in a very quiet and calm neighborhood just 7 mins from everything downtown. (Pool OPEN mid April-September)

*Home away from home, 15 min. to Indy downtown

Enjoy your home away from home in a quiet neighborhood just minutes from all the attractions of downtown Indy. 5 minutes from the highway with lots of restaurants and stores nearby. 15 minutes to the Lucas Oil Stadium, 20 minutes to the Convention Center, Indianapolis Zoo, and White River State Park. 25 minutes to the Motor Speedway. Home is fresh, comfortable, and stylish. Stocked kitchen, fully fenced backyard with a fire pit and a picnic table.

The Country Gathering - Sleeps 4 - Greenwood/Indy

5 YEARS AS SUPER HOST!!! The Country Gathering is in the upstairs of a Carriage House that was built on the property of a large home, located on the border of Greenwood/Bargersville in Johnson County, Indiana. The Carriage House has charm and character with a wooded backyard sitting on 4 acres. Sit or swing on the beautiful covered porch while you enjoy the view of the lake and fountain or feel free to walk around and enjoy the park-like setting.

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.

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.