Family-friendly holiday 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

Guest favourite
Guest suite in Oldham County
4.79 out of 5 average rating, 78 reviews

WATERFALL WALKOUT HILLTOP SLEEPS 10+, 4 BR 2BA

JamieRating, 5 stars2 months ago
This is a perfect hideaway and wonderful place to stay (especially if you are a Christian). I miss it already! So peaceful.
Superhost
Home in Brandenburg
4.94 out of 5 average rating, 271 reviews

Luxury lakehouse retreat with picturesque views

JenniferRating, 5 stars4 weeks ago
This was my second stay here and never disappoints! The place is always clean, with wonderful amenities and the host goes above and beyond to make you feel at home. I Would definitely continue coming.
Home in Fern Creek
4.67 out of 5 average rating, 51 reviews

All You Need and More!

BradRating, 5 stars2 months ago
This house is in a very nice neighborhood with plenty of restaurants and shopping nearby. There's plenty of room for a big family/group. I had another Airbnb host cancel my reservation only 2hr before check in. I was already on the highway with my family and Barksdale management moved this property up on their cleaning list as it had just been vacated around noon in order to accommodate us. I can't say enough for how much we appreciated that. Thank you so much for saving our weekend!!!
Guest favourite
Home in Louisville
4.93 out of 5 average rating, 160 reviews

Southern Comfort-Hottub wlk 2 Resturant Row & Shop

HaydenRating, 5 stars1 month ago
Within walking distance of several restaurants and a quick drive to a lot of greats bars and other things to do.
Home in Bloomfield
4.81 out of 5 average rating, 97 reviews

Derby Special Lodge With Churchill Downs Parking

JackRating, 5 stars1 month ago
The home is down several dirt roads .. very excluded. The views make it worth the Trip. Plenty of areas to cook with multiple living spaces.
Superhost
Home in Louisville
4.97 out of 5 average rating, 29 reviews

2.0 Southern Comfort Highlands-Cherokee Triangle

RyaneRating, 5 stars8 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.

Family- and pet-friendly home rentals

Top guest favourite
Cottage in Prospect
4.86 out of 5 average rating, 170 reviews

Cottage in Louisville,KY on Scenic River Rd

LauraRating, 5 stars3 weeks ago
Very comfortable home close to everything. Would definitely stay here again.
Guest favourite
Home in Central Business District
4.83 out of 5 average rating, 217 reviews

NULU - Walkable, Spacious & loads of personality!

DavidRating, 5 stars1 week ago
Great location. Lots of room for families or couples. Peaceful back patio, etc
Top guest favourite
Home in Elizabeth
4.98 out of 5 average rating, 133 reviews

Cabin on Lake Close to Louisville Ky

AshleyRating, 5 stars4 weeks ago
This home was very relaxing and comfortable.
Guest favourite
Home in New Albany
4.95 out of 5 average rating, 197 reviews

Spacious Historic Home, Louisville Adjacent

KellyRating, 5 stars4 weeks ago
My family and I came down to New Albany for my daughter's wedding. Without knowing the area we were very pleased with this home. This house is amazing! It felt like it went on forever and everytime you turned a corner there was an other room. Thank you for making our stay memorable.
Top guest favourite
Townhouse in Louisville
4.98 out of 5 average rating, 180 reviews

Charming 2 BR home by Emerson Park & Gardens - UL,

KristenRating, 5 stars2 weeks ago
Loved this place and would 100% stay there again! Such a great neighborhood too!
Guest favourite
Apartment in Original Highlands
4.93 out of 5 average rating, 199 reviews

Large Townhouse, Walk to All! King beds, 2.5 baths

MichaelRating, 5 stars2 weeks ago
Nice safe place for the value. Wasn’t a fan of the parking with a large SUV and current remodeling but it was safe and clean. The living area was spacious and comfortable. Rooms were clean.
Guest favourite
Home in Louisville
4.96 out of 5 average rating, 269 reviews

Home near the Highways

SamRating, 5 stars1 week ago
This place IS the Air BnB that you always hope for! It meets expectations I didn’t even know I had….. highly, highly recommended!
Guest favourite
Guest house in Crescent Hill
4.9 out of 5 average rating, 135 reviews

Cottage Park Carriage House. Rest w/Hollyhock

William LoriRating, 5 stars3 weeks ago
Wonderful accommodations with many generous amenities, including a little coffee bar with lots of coffees, many spices for cooking, and everything you need in the bathroom, including body wash, shampoo, conditioner, and hairdryer. A perfect accommodation for those who love to travel light. The apartment is in a lovely neighborhood and has its own private entrance, up some outside stairs. It was clean and spacious. Thanks for a wonderful stay. We can’t wait to return.

Family-friendly home rentals with a pool

Guest favourite
Guest suite in Louisville
4.96 out of 5 average rating, 373 reviews

Cherokee Park Oasis with Private Entrance

JasonRating, 5 stars1 week ago
Nice peaceful place to spend the night. Everything was great, but the pool was the best part of it.
Guest favourite
Cottage in Taylorsville
4.79 out of 5 average rating, 133 reviews

Anchor Rental

AlexRating, 5 stars1 month ago
Went to the Kentucky Derby with a group of friends. He graciously left us a derby care package at check-in. This place was perfect for 8 guys who just were looking for a place to sleep and have a BBQ in the driveway. Pillows could use an upgrade, and the closet in the bunk bed room had games and toys thrown about, but overall a good place to stay and worth the money of the rental.
Superhost
Guest house in Pendleton
4.87 out of 5 average rating, 68 reviews

The Waterfall Place, Suite and Walkout!

KatRating, 5 stars2 weeks ago
We had a great stay! We were there for a bachelorette trip and it was the perfect spot. It was secluded in this beautiful spot in the woods, the rooms were big and spacious. The waterfall was an amazing touch and the brides only request was a pool and hot tub; and Alicia had both! Very much recommend this place for a getaway with your friends.
Guest favourite
Guest house in Shepherdsville
4.94 out of 5 average rating, 54 reviews

Bourbon Country/ Derby Guest House

KaseyRating, 5 stars8 months ago
RaMona and Steve were extremely friendly and even reached out to us before we got there about what the weather was going to be like. For my first time using Airbnb, I could not have picked a better location and hosts.
Guest favourite
Cottage in Taylorsville
4.9 out of 5 average rating, 125 reviews

Best view of the lake two bed two bath cottage #4

LillyRating, 5 stars2 weeks ago
Had a very nice time here, enjoyed the hot tub and watching T.V.
Top guest favourite
Home in Louisville
4.97 out of 5 average rating, 248 reviews

NEW Hot Tub, Expo, King Beds, Downtown, Churchill

BrianRating, 5 stars1 month ago
This house is absolutely fantastic. Super clean, super comfortable. The beds and pillows are amazing. I would highly recommend this house for any gathering. We were a group of four men doing bourbon trail related things, and relaxing at night next to the fire pit and in the hot tub.
Top guest favourite
Home in Louisville
4.97 out of 5 average rating, 34 reviews

Highlands Oasis- Summer and Winter Retreat

JacksonRating, 5 stars2 months 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
4.69 out of 5 average rating, 74 reviews

"On the Rocks" Bourbon Trail Getaway

DavidRating, 5 stars1 month ago
We loved our stay here and Cliff was wonderful. We were three couples and there was plenty of room. This house is larger than it appears from the pictures. We had an issue with the gate code being different than what we were given but Cliff was instantly available, very nice, and got us in. It's a beautiful home and we'd stay there again. Very quiet, places to walk, and clean. I think if you switched the bunk beds with a Queen sized bed from downstairs it would be set up better for Adult couples. Thanks so much for our stay and we loved our Kentucky trip!

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