Family-friendly holiday rentals in Whitestown

5 out of 5 average rating, 371 reviews

A spacious common room features a leather sofa and a vintage faux fur chair, with a large wooden dining table that accommodates six. Creative lighting hangs from a driftwood chandelier. Large windows frame serene views of the outdoors, enhancing the inviting atmosphere.

Home in Broad Ripple

Broad Ripple Treetop Lodge on the Park

1 of only 10 elite Airbnb PLUSs in Indy, chosen for unique design & decor, outstanding service & amenities. Treetop Lodge is a beautiful, restful 2nd floor lodge retreat, a creative space with charm & tasteful, whimsical touches. Features a large common room, 2 bdrms w/ quality queen beds, bright FULL kitchen, private front door entrance, large balcony deck, all white linens & free laundry service! We're directly ON 62-acre Broad Ripple Park & just a short walk to iconic Broad Ripple Village!

The kitchen features white cabinetry and a spacious island with a light-colored countertop. Modern stainless steel appliances are present, along with a sink positioned below a window. Three pendant lights hang from the ceiling, illuminating the area with a soft glow.

4.99 out of 5 average rating, 114 reviews

Absolute GEM! 5 Mins Grand Park, Spacious Backyard

Westfield gem! Just 7 quick minutes to Grand Park! Close to Downtown Indianapolis (32 mins), Ruoff Music Venue (27 mins) and all that the Indianapolis & surrounding areas have to offer. Spacious 4-bed, 2.5-bath home sleeps 11 guests comfortably. Includes beautiful fully stocked kitchen, 2-car garage, TVs, Movie Theatre, games, fenced backyard, and patio for your enjoyment! Stroll on the Monon Trail. Enjoy family-friendly parks. So many restaurants to choose from, too! Your seamless stay awaits!

4.96 out of 5 average rating, 420 reviews

A cozy living area is presented, featuring a comfortable gray sofa and an armchair with a patterned fabric. A wooden coffee table stands at center, while a light fixture and an artwork are included on the walls. Natural light filters through the white blinds of the window.

Cottage in Indianapolis

Hidden Orchard Guest Cottage

Enjoy your stay at our comfortable cottage, tucked away in a quiet neighborhood off the White River (10 min. from downtown & Broadripple; less than 5 min. drive from Newfields, 100 Acre Woods, and Butler University; AND walking distance to the Fitness Farm). Feel at home in this fully furnished cottage, with its up-to-date kitchen, cozy bedroom and tech-friendly living room, equipped with hi-speed Wi-Fi, Netflix and YouTube TV. There’s also a private patio with a fire pit for you to enjoy!

4.99 out of 5 average rating, 146 reviews

A vibrant living room features a deep blue sofa adorned with colorful pillows and a plush throw. A gallery wall of framed art creates a lively backdrop. A light pink area rug anchors the space, complemented by a decorative coffee table and a stylish lamp. Natural elements are included with a potted plant.

Home in Windsor Park

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.

A modern kitchen is featured with dark cabinetry and a spacious island. Stainless steel appliances are positioned for convenience. Natural light fills the area, highlighting the marble countertops. A cozy seating area can be seen in the background, creating a welcoming space for family gatherings.

4.98 out of 5 average rating, 107 reviews

Rolling Hill Retreat @ GrandPark

Relax with the entire family at this completely renovated, peaceful retreat in Westfield. This 3 bedroom/2 bath ranch is conveniently located 8 minutes from Grand Park. The home accommodates up to 10 people comfortably. The fully stocked kitchen is the heart of the home with new appliances and breakfast bar seating. Both baths have double sinks to make getting ready a breeze. Enjoy the private backyard space with a tranquil creek or walk to the nearby Monon Trail with over 25 miles of trails.

4.97 out of 5 average rating, 202 reviews

A charming cottage exterior is framed by a blossoming tree in the foreground. The wooden deck features a railing and is accessible through a glass-paneled door. Nearby, lush green grass extends toward an open field in the background, suggesting a serene rural setting.

Farm stay in Thorntown

Heavenly Acres Farm and Learning Center

Experience a relaxing stay, spending time watching chickens happily foraging or barn animals as they graze in the pasture. Take a walk by the creek, taking in the country sunset.Enhance your experience by interacting with the animals during a farm tour or helping with daily chores. We also offer a variety of learning opportunities as we share how we process fiber, health care for animals or maybe a simple hay ride. Here at Heavenly Acres we want to provide you with a unique farm experience.

4.94 out of 5 average rating, 186 reviews

The exterior of the bungalow showcases a charming design with white brick and dark trim. Lush greenery surrounds the home, including a neatly landscaped area and a stone pathway leading to the entrance. The well-maintained yard features grass and a spacious patio area.

Home in Broad Ripple

The Broad Ripple Bulldog Bungalow

The Bulldog Bungalow in Broad Ripple- pet friendly, renovated bungalow home in the HEART of Broad Ripple Village in Indianapolis. Our beautiful home is just 3 blocks to Broad Ripple Avenue, so you can walk to everything the area has to offer such as restaurants, shopping, pubs, parks, and more. Take a stroll, ride a bike, or jog on the Monon Trail 1 block away. Enjoy a meal in the updated kitchen or relax in the fenced backyard with fire pit and hot tub (seasonal tub- closed May-September).

4.95 out of 5 average rating, 128 reviews

The living area features exposed wooden beams and a large stone fireplace as the focal point. A leather sofa is positioned across from a wooden coffee table. A patterned rug adds color to the rustic space, complemented by a decorative armchair and soft lighting from nearby lamps.

Cabin in Greenbriar

Kit’s Cabin - Log Cabin Retreat in Indianapolis

Welcome to our 150-year-old log cabin, nestled in the heart of Indianapolis! This cozy retreat offers a tranquil getaway while being just minutes away from all modern conveniences and only 20 minutes from downtown. Step inside and be greeted by the rich history of exposed wooden beams and a large stone fireplace. Our authentic rustic decor and cozy cabin amenities will transport you to a simpler time. Come experience the magic of Kit’s Cabin, where historic charm meets modern comfort.

4.98 out of 5 average rating, 47 reviews

The modern living area features a vibrant blue sofa paired with two yellow chairs, set against a light wood coffee table. A large TV is mounted on the wall, and a desk is positioned nearby. Natural light enters through the patio doors, complemented by dark blue curtains.

Flat in Whitestown

20 mins DT | Sleeps 9 | Sunrise Glow Spacious Gym

Welcome to Whitestown, IN — proudly hosted by TIBO Ventures. Standout Features: • Modern *2-BR, 2-BA* with stylish decor • Fully equipped kitchen w/ new appliances & quartz countertops • Both bedrooms king-size beds and walk-in closets for max comfort • Private balcony for relaxing Amenities:* ✔ 24-Hour Gym ✔ Pickleball Courts & Pool ✔ Built-in Desk for remote work ✔ Pet-Friendly community with Dog Park ✔ High-Speed Fiber Internet ✔ Close to dining and shopping ✔ Free On-site Parking

4.94 out of 5 average rating, 108 reviews

A charming one-room cabin features a wooden exterior with a green metal roof. Two blue chairs are placed on the small porch beside a door, which invites guests to enjoy the surrounding greenery in a tranquil setting.

Cabin in Bainbridge

Covered Bridge Cabin (on Big Walnut Creek)

Retreat and renew in this charming one-room cabin right by Big Walnut Creek and Baker's Camp Covered Bridge. Fish, kayak, or swim; hike or birdwatch in a nearby preserve; read, write, find inspiration. With sweet-smelling poplar walls, the cabin offers a full bed by a picture window, small TV, writer's desk/library, AC, fans, baseboard heat, kitchenette, toilet, sink, outdoor shower (before first frost), small porch, grill, and a fire pit. (No wifi in cabin!) Simple and beautiful.

Guest house in Brownsburg

The exterior of a two-story guest house is surrounded by autumn foliage, showcasing wooden decking with a railing. The entrance features large windows, allowing natural light to brighten the space. A pathway leads from the front, bordered by seasonal plants.

4.86 out of 5 average rating, 606 reviews

Cozy Guest House in the Big Woods

Guest house located in the rear grounds of main home. Sidewalk access. 20 minute drive to downtown Indy.Full kitchen & 3/4 bath. This means toilet, sink & 42" shower (no tub).Entire house can sleep 1-3. Price is for 2 guests. Add’l fees for add’l guests & pets (no pit bulls) The upstairs has a king bed & down stairs a twin futon. This area is heavily wooded so the occasional critter can be seen & there will be spiders from time to time (part of wooded living).

5 out of 5 average rating, 16 reviews

Flat in Whitestown

IRIE Living-Retreat Kg 2Bd+Gym+Pool!

IRIE Living-Retreat Kg 2Bd+Gym+Pool! Discover your perfect home base in Whitestown, IN! This is modern 2-bedroom apartment is ideal for families, friends, or teams visiting Farmers Bank Fieldhouse, nearby shopping spots, or downtown Indianapolis, just a short drive away. Whether you're here for a tournament, a weekend getaway, or a business trip, you'll enjoy all the amenities you need for a comfortable, stress-free stay.

Popular amenities for Whitestown family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 192 reviews

A charming entrance is showcased, featuring double yellow doors framed by stone walls and wooden beams. A wooden swing with decorative elements rests on the porch, surrounded by carefully arranged landscaping and a welcome mat positioned at the entrance.

Barn in Indianapolis

Black Barn Indy-Secluded Suburban Retreat!

4.89 out of 5 average rating, 132 reviews

An outdoor area features a spacious patio with a hot tub and lounge seating beneath a covered gazebo. Bistro lights create a warm ambiance, while a fire pit is placed in the center, surrounded by cozy seating options. A wooden privacy fence encloses the space.

Home in Indianapolis

Hot Tub, fully fenced, and dog friendly!

A hot tub is situated on a wooden deck, surrounded by trees that provide a sense of privacy. The tub is covered with a green lid, and a textured mat lies in front of it on the deck. Natural light filters through the branches.

4.91 out of 5 average rating, 104 reviews

Woodsy Retreat with Hot Tub close to Grand Park

4.9 out of 5 average rating, 102 reviews

A modern living area features a gray sectional sofa with decorative blue pillows, positioned against a patterned dark wall. A dark wood coffee table sits in front, complemented by a colorful area rug. Empty picture frames adorn the wall, enhancing the room's aesthetic.

Flat in Fishers

Unique Vintage - 2bed/2Bth - 2 King Beds

4.96 out of 5 average rating, 187 reviews

A modern living area features a light-colored sofa adorned with a decorative throw and pillow. A geometric accent wall serves as a backdrop, while a wooden coffee table with decorative items is positioned in front. A lamp and a small dining area with a chair are visible.

Flat in Fishers

King Bed - 1B/1BTH - POOL

Home in Bates - Hendricks

A hot tub is situated on the roof deck, featuring flowing water and seating nearby. The backdrop includes a view of rooftops and trees, with soft hints of a sunset sky visible in the distance.

4.98 out of 5 average rating, 278 reviews

Bates Hendricks Luxe with Roof Deck

4.89 out of 5 average rating, 124 reviews

A two-story home is shown with a combined brick and yellow exterior. Tall trees provide shade in the front yard, which features well-maintained grass and landscaped bushes. A bright sun decoration is mounted on the front of the house.

Home in Indianapolis

Quiet 4 bedroom spacious home near Broad Ripple

Guest suite in Greenfield

4.95 out of 5 average rating, 641 reviews

25 Min. to Anywhere in Indy! No cleaning Fee!

Family- and pet-friendly home rentals

4.9 out of 5 average rating, 154 reviews

A two-story house with a stone chimney is surrounded by trees and a spacious lawn. A wooden deck extends from the upper floor, offering outdoor seating. The gravel driveway leads to the entry, providing access below to garage spaces. The clear blue sky complements the serene atmosphere.

Home in Indianapolis

White River Retreat

4.97 out of 5 average rating, 115 reviews

Home in Meridian Kessler

Surf House | Stylish Indy Charmer | Walkable

Superhost

The front view of the house showcases a classic white exterior with a welcoming entrance. Lush green shrubs frame the entrance, and a driveway leads to a detached garage seen in the distance. A clear blue sky complements the home's inviting appearance.

Home in Brownsburg

4.84 out of 5 average rating, 124 reviews

Cozy and Comfortable, great Fall destination!

4.92 out of 5 average rating, 555 reviews

The kitchen features dark wood cabinetry and stainless steel appliances, including a microwave and oven. A circular dining table with colorful dishware is visible. Light enters through the window, illuminating the hexagonal tile flooring, enhancing the functional layout.

Home in Speedway

Adorable Bungalow 3 blocks from the 1st TURN

Superhost

A bright living area features a comfortable brown leather sofa paired with two armchairs, accented with yellow cushions. A wooden coffee table sits at the center, and a wall-mounted map adds visual interest. Light fixtures provide illumination, highlighting the soft blue wall color.

4.89 out of 5 average rating, 144 reviews

Ranch at Carmel City Center

An open living space features a cozy seating area with a gray sofa and armchair, alongside a wooden dining table with chairs. Natural light fills the room through large windows, highlighting the modern decor, including a flat-screen TV mounted above a fireplace.

4.96 out of 5 average rating, 102 reviews

Lego Ranch at GrandPark 3BR 2B pets wlcme

4.93 out of 5 average rating, 138 reviews

A modern living area showcases a comfortable sofa, paired with a textured rug. A flat-screen television sits on a wooden stand. The open kitchen features a large island with seating for four and sleek appliances, enhancing the inviting atmosphere of the space.

Home in Greenfield

The Rosie Roots - Cozy House & Pet Friendly

A game room is featured, showcasing a pool table with a green felt surface, surrounded by wooden seating. The room is illuminated by overhead lights, creating a bright atmosphere. A foosball table is visible in the background, with a soft couch positioned against the wall.

4.86 out of 5 average rating, 118 reviews

Spacious 4BR + Game Room | Sleeps 17 | Grand Park

Family-friendly home rentals with a pool

Guest house in Noblesville

A clear blue swimming pool is set against a backdrop of lush green trees and a bright sky with scattered clouds. The pool area is surrounded by a spacious concrete deck, providing an open and inviting space for relaxation and leisure.

4.94 out of 5 average rating, 17 reviews

Grand Park Nest close to Westfield & Carmel Center

4.94 out of 5 average rating, 125 reviews

Cabin in Poland

Captain Bill’s Lake House with Heated Pool

5 out of 5 average rating, 131 reviews

Home in Pendleton

Sunset Oasis | Water Views + Fenced Yard

Superhost

The in-ground pool is illuminated in a vibrant blue hue, surrounded by a well-maintained patio. Soft lighting along the edges creates a serene atmosphere, complemented by two lounge chairs positioned nearby. The area offers a tranquil setting for evening relaxation.

4.66 out of 5 average rating, 32 reviews

Grand Park Retreat with Private Pool

Guest suite in Greenfield

A spacious guest suite is illuminated by natural light from large windows. A cozy seating area is visible beside a desk and a wall-mounted television. Attractive bedding with striped patterns adorns a sizable bed, complemented by a plush carpet and tasteful decor.

4.92 out of 5 average rating, 109 reviews

Peaceful & Luxurious Suite

4.99 out of 5 average rating, 100 reviews

Home in Greenwood

Entertainer's Dream w/ Pool and Games

Guest suite in Indianapolis

A dedicated entertainment area features several plush reclining chairs arranged for comfortable viewing. A projector screen is positioned for movie nights, while a pool table adds a recreational option. Art pieces decorate the walls, and soft lighting creates an inviting ambiance.

4.99 out of 5 average rating, 74 reviews

Stylish Basement wAmenities/ Lounge; Close to DT

A newly renovated pool is surrounded by a spacious patio, featuring lounge chairs for relaxation. Lush greenery and tall shrubbery provide privacy, while the clear blue water reflects the overcast sky. A fenced yard offers safety and openness for outdoor activities.