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.

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.

Your Comfy Indy Suite

Safe, peaceful suburban neighborhood. Only 15 minutes from downtown Indy. Easy drive to IUPUI, Convention Center, Lucas Oil Stadium. Free parking at your door. Great for long term stays. Fully stocked kitchen. Free laundry facilities. Padded office chair and fast Wi-fi at your laptop workstation. 55" Vizio 4K HDR Smart TV. Moon Pod Zero Gravity Chair for therapeutic relaxation. Queen-size Sealy Plush Pillowtop hybrid mattress, with 2 standard foam pillows and 2 MyPillows.

Lovely home in quiet and friendly neighborhood!

This charming 3 bedroom 2 full bathroom home is ready to make you feel right at home! Located just 2 minutes from St Francis Hospital, 10 minutes to downtown Greenwood, 19 minutes to downtown Indy, the home is just minutes from all kinds of restaurants, shopping, and entertainment, yet provides a tranquil retreat in a quiet, friendly neighborhood. Travel nurse? Loved one in the hospital and you want to be near? Work or internship? Just need a vacation? This is the place for you!

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

Charming updated family home with Treehouse deck

Enjoy the newly renovated open-concept kitchen and family room! Outside, you can enjoy the large fully fenced in yard on the oversized deck which has an additional treehouse upper deck. This home is great for small gatherings but also for a quiet, peaceful, clean and safe spot to rest and relax. You can get to downtown Indianapolis in 15-20 minutes if you are in town for a conference or convention. Pets are welcome! Please make sure to add pets to your reservation.

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.

The Howdy Inn – Rustic Charm & Modern Comfort

Welcome to The Howdy Inn! Just steps from downtown Franklin, this cozy and centrally located retreat puts you right where you want to be. Stroll to charming shops, local eats, and small-town favorites, then come back to relax in comfort. Whether you're sipping coffee in the morning or unwinding after a day out, The Howdy Inn is your warm, welcoming home base, full of charm, convenience, and a little extra hospitality.

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.