Family-friendly vacation rentals in Crestwood

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Crestwood family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Home in Brandenburg
4.94 out of 5 average rating, 267 reviews

Luxury lakehouse retreat with picturesque views

RobertRating, 5 stars4 days ago
My family and I had a wonderful time. The house was clean, well-cared for, and very spacious for the 7 of us. The kitchen was stocked with everything we needed to cook our meals. We made use of the kayaks, raft, and paddle board that were available. The owner was very responsive and easy to get in touch with.
Home in Louisville
4.72 out of 5 average rating, 112 reviews

Hot tub-Expo/Convention Center*Downtown*Zoo*Derby

EmilyRating, 5 stars11 months ago
We enjoyed our stay close to Churchill Downs for Derby Week activities.
Top guest favorite
Cabin in La Grange
4.98 out of 5 average rating, 170 reviews

Running Creek Log Cabin

JessicaRating, 5 stars1 week ago
We loved staying here and it was the perfect location for our family Easter! I truly can’t say enough great things about this cabin and the owners! It was very clean and well appointed with anything you need and the owners were very accommodating and kind! They helped with a couple requests, including a pack and play and high chair. We were able to cook a large Easter dinner with the stocked kitchen appliances and cookware. The property is very serene with plenty of privacy and great options for hiking around. The location is also not too far to get to the grocery store and restaurants. Lastly, the pool table and hot tub were a hit! We highly recommend to stay here and know we will definitely be back for another stay!
Home in Louisville
5 out of 5 average rating, 13 reviews

Great patio - Northeast Louisville

MaureenRating, 5 stars11 months ago
This house was perfect for our family (8 adults). Julie was very responsive, even when we locked ourselves out of the house late on night. Nice neighborhood too!
Top guest favorite
Home in Louisville
4.97 out of 5 average rating, 245 reviews

Bourbon Trail Hot Tub Retreat King Beds, Spacious

ChrisRating, 5 stars3 weeks ago
This house we great for large groups. We originally had 11 people coming but ended up with only 8. The house was older with a ton of character. It looks like it is a very up and coming neighborhood that has had a lot of work done to it. We came in for a work trip at the expo center and this house was only a 5 minute drive to it each day. Hot tub was awesome and back yard was nice. Will look at renting this house again for next years convention.
Cottage in Taylorsville
4.69 out of 5 average rating, 71 reviews

"On the Rocks" Bourbon Trail Getaway

HopeRating, 5 stars3 months ago
Cliff was very helpful and responsive, we were in town on a job so there was plenty of space for people who don’t normally travel together. It was a very cold week so the hot tub was just what we needed! Would absolutely recommend.
Superhost
Home in Louisville
4.97 out of 5 average rating, 29 reviews

2.0 Southern Comfort Highlands-Cherokee Triangle

RyaneRating, 5 stars6 months ago
One of the best Airbnb’s I’ve stayed in! Lots of extra little amenities, the decor was unique and well thought out, and the location was perfect. We travel to the area often and would definitely book again.
Top guest favorite
Home in Louisville
4.99 out of 5 average rating, 242 reviews

NEW Hot Tub, Walk 2 Park, Whole Foods, Movies Mall

BethRating, 5 stars3 weeks ago
Great Airbnb in a cute, quiet neighborhood. The house was spotless! The bedrooms were a nice size with plenty of room. We enjoyed the two living spaces and the large dining room table. We would definitely book again if ever in the Louisville area! Thank you for an enjoyable stay!

Family- and pet-friendly home rentals

Top guest favorite
Cottage in Prospect
4.86 out of 5 average rating, 165 reviews

Cottage in Louisville,KY on Scenic River Rd

JaimeRating, 5 stars4 weeks ago
I had a fantastic stay at this Airbnb! The place was clean, comfortable, and exactly as described. The host was friendly, responsive, and made check-in a breeze. The location was perfect—close to everything but still quiet and peaceful at night. I especially appreciated the little touches and clear instructions. Highly recommend and would definitely stay here again!
Superhost
Home in Butchertown
4.93 out of 5 average rating, 296 reviews

Guesthouse on Story- Bourbon Trail

CarolynRating, 5 stars1 month ago
This was our second stay at Guest House on Story, and was definitely as good, if not better than the first. Kim is an excellent and responsive host who strives to make sure your stay is exactly what you need. We had a large group of adults visiting Louisville to celebrate a birthday weekend, and we had plenty of space to spread out and relax. The area has fun walkable bars, breweries, and cocktail lounges, along with restaurants! Highly recommend Tartan House and Biscuit Belly. Guests should be aware as others have mentioned that given the location in Butchertown, there is occasionally a notable smell outside. It very much depends on the direction of the wind and day/time of the week. Do know though that you cannot smell this inside the house! We caught a whiff outside here and there, but definitely not the entire time. Highly recommend Guest House on Story, and I'm sure we will stay again when in Louisville with a large group.
Superhost
Home in New Albany
4.95 out of 5 average rating, 194 reviews

Spacious Historic Home, Louisville Adjacent

JavenRating, 5 stars1 week ago
This was my first time visiting Kentucky and this Airbnb was amazing. Chose to the city but far enough for orange and quiet.
Superhost
Apartment in Central Business District
4.76 out of 5 average rating, 123 reviews

Downtown Convenience with Privacy!!

TerrenceRating, 5 stars3 weeks ago
Had a very good stay, conveniently located to get around and visit .
Superhost
Loft in Crestwood
4.88 out of 5 average rating, 185 reviews

Welcome to the Nest!

Ashley Rating, 5 stars5 days ago
The Nest was perfect for our family of five’s weekend getaway. We love the area and felt safe and comfortable in the neighborhood. Scott was a great host and very responsive to our questions. We will definitely stay here again.
Guest favorite
Home in Louisville
4.96 out of 5 average rating, 262 reviews

Home near the Highways

TiffanyRating, 5 stars2 months ago
My family and I loved Ross place!!! His communication was quick and left very clear instructions. Upon arrival, he even left music on to welcome us. The home was exactly as pictured and was very peaceful. It accommodated our needs and highly recommend 👌.
Guest favorite
Home in Highlands
4.89 out of 5 average rating, 523 reviews

Charming home in the Highlands

ShawnaRating, 5 stars3 weeks ago
Great place, love the outdoor sitting and easy parking. Great communication, Easy entry , close to YUM CENTER
Top guest favorite
Home in New Albany
4.98 out of 5 average rating, 167 reviews

Family-friendly! Walkable to downtown shops!

JennaRating, 5 stars1 day ago
What a beautiful home!! We stayed here to break up a drive home from Florida and we all loved it. We had everything we needed, the house was clean, and the beds were comfy. The kids loved playing in the “treehouse”. Brad was kind and communicative. We would love to stay here again!

Family-friendly home rentals with a pool

Top guest favorite
Guest suite in Louisville
4.96 out of 5 average rating, 369 reviews

Cherokee Park Oasis with Private Entrance

AmyRating, 5 stars9 months ago
Beautiful neighborhood and wonderful pool area! The place was exactly as described and the host provided clear, easy to follow instructions to get in. My kids loved the pool especially! We’d definitely stay again if in Louisville!!
Guest favorite
Cottage in Taylorsville
4.79 out of 5 average rating, 131 reviews

Anchor Rental

BethRating, 5 stars2 months ago
It was perfect for our family and was close to the family that we travelled to visit!
Superhost
Guest suite in Oldham County
4.79 out of 5 average rating, 77 reviews

WATERFALL WALKOUT HILLTOP SLEEPS 10+, 4 BR 2BA

DavidRating, 5 stars3 months ago
Our family of 6 stayed between Christmas and New Years. Like Alicia and Glenn, we also homeschool our four kids (ages 12-6). We were worn down from the holidays and daily life, so were looking for a refreshing time away from home. Our stay was exactly that. The home and property were extremely peaceful being out in the woods. We did several trail walks and explored the creeks around the property. The kids thought the circular nature of the home, and hot tub were fun too. I appreciated the various Christian decor in the home, it gave me some things to think about as we hung out. But even more than all of that, we had a wonderful chat with Alicia and Glenn that was very refreshing to our spirits. If you are looking for a peaceful, quiet getaway that is focused on Jesus and the holy spirt this is the place for you. Make sure you read all the description in the listing so you know what you are renting. If you do that, you'll be very pleased :) In Christ, Dave & Maura
Guest favorite
Guesthouse in Pendleton
4.89 out of 5 average rating, 65 reviews

The Waterfall Place, Suite and Walkout!

BrianaRating, 5 stars1 month ago
This place is a slice of heaven. It’s quiet and perfect for a group of family / family friends / and for myself a bachelorette group. We enjoyed the tranquility and the feeling of right at home! The house was cute and clean. You get your bang for your buck here. My only advice would be if you book, bring a car that can climb a hill, as the home is on top of (what feels like) mountain! But makes for gorgeous views.
Top guest favorite
Guesthouse in Shepherdsville
4.96 out of 5 average rating, 52 reviews

Bourbon Country/ Derby Guest House

MelanieRating, 5 stars9 months ago
Ramona and Steve were fantastic hosts. They made us feel right at home. Their location is beautiful and peaceful and just good for the soul! If my family and I are ever in the area again we will definitely love to visit again!
Top guest favorite
Home in Louisville
4.97 out of 5 average rating, 34 reviews

Highlands Oasis- Summer and Winter Retreat

JacksonRating, 5 stars1 week ago
A wonderful home hosted by wonderful people. I can’t thank Amy and Carol enough for being incredible hosts and opening their home to us. Would certainly recommend this to anyone considering staying in the area!
Cottage in Taylorsville
4.84 out of 5 average rating, 111 reviews

Shore Thing #20

JakeRating, 5 stars2 months ago
We’ve stayed here several times over the last few years and we plan on continuing to do so on our annual Kentucky trip.
Home in Spencer County
4.55 out of 5 average rating, 47 reviews

ShoreThing #21

LanaRating, 5 stars2 months ago
Great place

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