Pet-friendly 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).

#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.

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.

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.

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.

The Onyx Cottage - Very Cozy and Private

Welcome to your own private cottage. A completely furnished space with all the amenities you can expect in a big house. Home is fully air conditioned and heated. The bedroom does not have a door on purpose due to the design of the small space. You are welcome to bring your furry family (pets) along. You're a mere 5 minutes from the Fountain Square cultural district, with its independent eateries, 12mins from downtown, 18mins from airport & right on the interstates for fast travel.

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.

*Home away from home, 20 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.

Stately 3BR townhouse in historic Irvington

Nestled in the heart of Irvington’s historic district, the Parker Lane is a tastefully furnished home with a nod to mid-century modern design - a spacious duplex with three bedrooms and two bathrooms, and outfitted with a generously stocked kitchen, so you have the option to cook meals and brew up fresh coffee during your stay. Stroll the brick lined streets of Irvington and discover the local shops, restaurants, and coffee houses.

La Cochera Indy East - No Cleaning Fee!

Contemporary, clean carriage house on a large East Indianapolis property. Private keypad entrance with easy self check-in and on-site parking for up to two cars. Comfortably sleeps the whole family with a king bed and a stylish queen-size sofa bed. Important details: • No parties or events • Local guests require prior approval • Early check-in available for $35 (when possible) • $20–$40 linen fee for use of sofa bed

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.