Family-friendly vacation rentals in Crestwood

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Top-rated family-friendly rentals in Crestwood

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A cozy front porch features woven chairs arranged around a small table, inviting relaxation. Lush green ferns are placed in terracotta pots, complementing the rustic wooden beams and the log cabin's natural surroundings.

Cabin in La Grange

The Log Cabin at StoneLedge

Please note the Log Cabin is a private home BUT the entire cabin is not avaliable for use when booking 4 guest or less. Nestled on an expansive 80 acre horse farm the log cabin is the perfect escape. Hike the 30+ acres of woods that boast a creek and waterfall. Relax on the cozy front porch while enjoying the sounds of nature. The Log Cabin is 10 minutes off of I71 exit 22. Less than 3 minutes to Ashbourne Farm & approximately 10 minutes to Hermitage Farm. ***PLEASE READ THE ENTIRE LISTING

FamilyKitchenAccuracy

4.97 out of 5 average rating, 143 reviews

Top guest favorite

A spacious living area features large windows allowing natural light to fill the room. A comfortable couch and a reclined chair offer seating, with a coffee table in front. A fireplace serves as a focal point, framed by decorative elements and bookshelves.

Home in Louisville

Home near the Highways

Comfortable, clean home in a quiet neighborhood Garage and driveway parking 3 Kings, 2 Queens, 2 Full beds, 2 Futons, 1 Loveseat Sleeper Sofa, 1 Couch Individual coffee makers in rooms with complementary coffee Peaceful front porch. Back and patio with gas & charcoal grills and green view Pet Friendly. Scroll down to "Other Things to Note" for more info. 2.5 miles to I-265. 3 miles to I-64. 20-30 minutes to most places in Louisville. 1 mi to a fuel, groceries, restaurants & banking

FamilyIndoor spacesDecor

4.96 out of 5 average rating, 322 reviews

Top guest favorite

A charming two-story brick guest house is set against a lush green lawn. The exterior features large windows and a welcoming front porch with two white chairs. A gently curving driveway leads to the entrance, framed by manicured shrubs and a nearby tree.

Guesthouse in Prospect

Prospect Guest House

Take it easy at this unique and tranquil getaway. Newly remodeled, new bathroom and kitchenette. We live in the house next door, but guest house is private and very quiet. Nestled in horse country-neighboring horses graze in adjacent fields. Queen bed upstairs, converted sofa queen in loft. Air bed also available. Lots of closet space, extra large bathtub, internet and streaming TV. Great location whether you are touring the Bourbon Trail or attending any of the The Kentucky Derby events!

FamilyKitchenGetting around

5.0 out of 5 average rating, 137 reviews

Top guest favorite

The living room features a classic design with rich green walls and a mix of hardwood and patterned flooring. Two ornate armchairs are positioned opposite a dark wood coffee table, with a leather sofa off to the side. Large windows allow natural light to fill the space.

Home in La Grange

The Lady Jinx Home - 3 BR/2.5 Bath - Entire Home

“The Lady Jinx” is a renovated 3 BR/2.5 Bath, Princess Anne-style Home built in 1895. This 2-story has tons of character from the detailed wood trim to the stain glass windows to the original interior doors to the gorgeous wood floors. The home is located in downtown La Grange, the only town in America that has an active train running along it’s Main Street, & is within walking distance to restaurants, shopping boutiques, museums, parks and entertainment with being only one block away!

FamilyKitchenAmenities

4.96 out of 5 average rating, 104 reviews

Guest favorite

The interior space of the Airstream showcases a modern design with reclaimed wood floors and white walls. A spacious kitchen features concrete countertops and various appliances. A cozy seating area includes a daybed, while the rear sleeping area is softly illuminated, creating a comfortable atmosphere.

Camper/RV in Louisville

The Grace Airstream at Progress Park in Derby City

Skip the packing & extra costs - everything you need is already here. Perfect for groups, families, or midweek getaways. The Grace combines comfort, convenience, & a one of a kind outdoor experience. Enjoy your own private space PLUS access to boating, games, & more. All included with your stay. Show up, settle in, and start relaxing. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunk house. *KY DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

Indoor spacesFamilyLong stay

4.97 out of 5 average rating, 344 reviews

Top guest favorite

A spacious studio-style room features a four-poster bed with white bedding. A comfortable armchair sits nearby, and a flat-screen TV is positioned on a wooden entertainment unit. Natural light enters through patterned curtains, illuminating the warm wood flooring.

Tiny home in La Grange

Brakeman's Cottage

"All Aboard the Brakeman's Cottage! Experience the charm of this tiny house listed on the National Register of Historic Buildings in LaGrange, Kentucky. Nestled just feet from the train tracks in the heart of downtown, it offers a unique experience. Situated across from the train observation tower and within walking distance of the best restaurants and quaint shops, our newly remodeled property features private off-street parking. Step into history with modern comforts at Brakeman's

Indoor spacesKitchenWalkability

4.98 out of 5 average rating, 276 reviews

Superhost

Home in La Grange

Hot Tub-King Bed-Coffee Bar-Arcade-Fire Pit!

Centrally located in La Grange, the Kindness Capital of Kentucky. Welcome to the hallmark of small towns where the train rolls down Main Street over 30 times each day. Walk to locally owned donut and coffee shops, Farmer’s market, playground with splash pad, and restaurants. Spend your day on the Bourbon Trail or Churchill Downs before relaxing in the Hot Tub. Driving distance to the Creation Museum and Ark Encounter, The Slugger Museum, Falls of the Ohio, and Mega Caverns.

Indoor spacesFamilyTV

4.91 out of 5 average rating, 142 reviews

Top guest favorite

A patio area features several blue chairs positioned on a textured surface, with a stone bench visible nearby. Lush green trees surround the space, providing a natural backdrop. In the distance, a red structure can be seen, framed by the greenery.

Guest suite in Prospect

Private Prospect Flat

Two bedroom apartment located on picturesque Covered Bridge Road in Prospect, KY. There is a separate entrance with plenty of parking. Beautiful views of Kentucky landscape from every window. Our property is four acres with a meandering stream, forest, and fields. There is a fully stocked kitchen including a dishwasher. The main bedroom includes a work space area and two closets. Feel free to grab a few eggs for breakfast if there are eggs in the nesting boxes.

FamilyKitchenOutdoor spaces

4.97 out of 5 average rating, 272 reviews

Top guest favorite

A stylish living area features a modern gray sofa accompanied by two blue accent chairs. A large flat-screen TV is mounted above a black fireplace. Natural light enters through multiple windows, which frame views of the surrounding greenery, enhancing the room's serene ambiance.

Home in Louisville

Charming Bungalow on 1.5 Acres in Amazing Location

Peaceful. Private. Clean. Comfortable. Convenient. Hummingbird is a charming updated bungalow in one of Louisville's most coveted neighborhoods. Nestled on 1.5 acres of a historic street, you'll enjoy a park-like setting teeming with wildlife. Private, yet offering easy access to shopping, dining, entertainment, and major highways, this hidden gem is sure to please. Whether here work, fun, or both, you’ll love your time at Hummingbird.

KitchenFamilyCondition

4.98 out of 5 average rating, 138 reviews

Top guest favorite

Cottage in Prospect

Cozy Cottage on Famous Kentucky Farm

Curl up by a wood-burning fireplace in a charming 2-bedroom cottage on Foxhollow Farm - Kentucky's most beloved farm stay, featured on Bravo's Top Chef. Perfect holiday escape: 1,300 rolling acres, horse views from the porch, private nature trail, and Thanksgiving/Christmas/New Year's availability. Just 20 min from Louisville's holiday events, bourbon trail, and Churchill Downs. Book your winter retreat now, holiday weekends fill fast!

FamilyKitchenHospitality

4.99 out of 5 average rating, 137 reviews

Top guest favorite

A cozy living area features a large sectional sofa and a colorful area rug. Natural light enters through two windows, illuminating the room. A ceiling fan enhances airflow, and decorative elements include a shelf with framed artwork.

Home in La Grange

Little Blue Cottage on Main Street, La Grange KY

Our quaint blue cottage right on Main Street gives you a front row view to one of the last main rail lines through a downtown area in America! -Walking distance to multiple restaurants, coffee shops, and antique stores -10 minutes from Jefferson's Reserve Distillery -25 minutes from downtown Louisville - Central to the bourbon trail with over 20 distilleries less than an hour away - On the Alley Loop as showcased on HGTV

FamilyIndoor spacesView

4.96 out of 5 average rating, 240 reviews

Top guest favorite

The exterior of a renovated farmhouse is surrounded by lush greenery. A spacious porch with seating is visible at the front, while a gravel path leads to the inviting entrance. The structure features a metal roof and warm-colored trim that complements the natural setting.

Farm stay in Goshen

The Coop

This 2 bedroom house is a renovated old farmhouse located on the site of a small vegetable farm and native plant nursery. The back deck overlooks the woods, where you can watch the wild birds and keep an eye on the free range chickens. This is a quiet spot for a retreat, but also 25 minutes from downtown Louisville. The Coop has a fully stocked kitchen and comes with eggs right from our flock....

KitchenIndoor spacesBackyard

4.97 out of 5 average rating, 383 reviews