Family-friendly vacation rentals in Crestwood

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Crestwood

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Guest favorite

Apartment in Louisville

4.94 out of 5 average rating, 232 reviews

Chic, Luxurious Carriage House in Ideal Location

Selected by Architectural Digest as best Airbnb in Kentucky. Sink into the rounded, studded armchair under exposed wooden beams at a characterful retreat with minimal, modern style. This historic space contrasts deluxe touches including the 6-foot soaking tub with sash windows and a sliding barn door. This fully furnished apartment is perfect for a getaway weekend or for short to medium rental as an executive apartment. The historic property has been lovingly renovated as a luxurious apartment with high-end finishes while maintaining the historic character of its past as a carriage house. You enter the apartment through a hallway that houses a dedicated washer and dryer. Upstairs features a large living/working space, a beautiful kitchen with brand new-high end appliances, and a 50" 4K smart TV. The sliding barn door separates the bedroom, where you will also find a large walk-in closet, a marble bathroom with a 6 foot soaking tub, and a brand new queen sized Tuft and Needle mattress. We will meet our guests and orient them to the house and neighborhood, or provide self check-in depending on preference. For the remainder of your stay, we will be close by for any additional needs. Cherokee Triangle is one of the most historic neighborhoods in Louisville, built in the late 19th century and part of the larger Highlands area. The tree-lined streets are a short walk from the restaurants, bars, and boutiques on Bardstown Road. You do not need a car around here - everything is a short walk away. Parks, restaurants, shops, grocery stores are all within 5 minutes on foot. Downtown or Churchill Downs are is a 5-10 minute drive away. Street parking is available.

Aug 13 – 20

ﺩ.ﺇ550 per night

Guest favorite

Home in Louisville

4.95 out of 5 average rating, 228 reviews

Highlands Haven Cottage

This luxurious and charming 1 bedroom home in the prime area of Louisville and The Highlands, is walking distance to the Douglass Loop area of shops and dinning, the Bardstown Rd corridor of shops and dinning and more starts at The Loop, as well as the locally famous Farmers Market on Saturday mornings! This 800 sf fully furnished home features 1 bedroom, 1 bath, a large & bright family room, and a fully outfitted kitchen, is literally minutes to lots of local amenities, dining, shopping, etc!

Jan 18 – 25

ﺩ.ﺇ484 per night

Guest favorite

Home in Louisville

4.96 out of 5 average rating, 227 reviews

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

Nov 27 – Dec 4

ﺩ.ﺇ1,249 per night

Guest favorite

Apartment in Louisville

4.98 out of 5 average rating, 250 reviews

Spacious & Artsy Highlands 3 Bedroom for Up to 6

There is more room than meets the eye in this surprisingly spacious and uniquely designed space! The lower level of our house (technically the basement) is designed to be an apartment, offering 1400 sq. ft. of relaxing and spacious fun. This is a great space and value for up to six people. The space is closed off from the rest of the house with total privacy. We’re located in a quiet neighborhood in the Highlands and conveniently located to a diverse set of restaurants, highways and grocery.

Nov 14 – 21

ﺩ.ﺇ400 per night

Guest favorite

Guesthouse in Louisville

4.93 out of 5 average rating, 284 reviews

Charming Carriage House with 2 private baths.

Our home and Carriage House in is an extremely nice, safe beautiful neighborhood. I know many guests including myself are even more concerned with cleanliness. Rob and I have always taken extreme pride in assuring our guest house is spotless. However, we have taken it up another notch. We have purchased a Utilizer that sanitizes areas with it's ultraviolet light. We use this machine after each guest to ensure the air and every surface is sanitized. It is truly home away from home!!!

Aug 25 – Sep 1

ﺩ.ﺇ358 per night

Guest favorite

Guest suite in Louisville

4.98 out of 5 average rating, 180 reviews

Spacious Lower-Level in Quiet Neighborhood

This is a spacious, walk-out lower level with a private entrance. Our quiet neighborhood is 1 1/2 miles from I-265, which means easy access to Louisville or beyond the city to bourbon country. It has a large living area and a fully equipped kitchen. Adventure lovers will like being 5 miles from The Parklands. Downtown Louisville is 20 minutes away. The space has 1 queen bed, 1 double bed, and twin bunk beds. It sleeps 5-6 comfortably. We live upstairs so we are available if needed.

Aug 22 – 29

ﺩ.ﺇ509 per night

Guest favorite

Home in Louisville

4.95 out of 5 average rating, 147 reviews

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

May 21 – 28

ﺩ.ﺇ1,014 per night

Guest favorite

Guesthouse in Louisville

4.98 out of 5 average rating, 245 reviews

Highlands Carriage House

Secluded Retreat in the Heart of the Highlands! Perfect for DERBY! Our carriage house is perfectly located in the heart of all Louisville has to offer. We are only steps from the finest dining, entertainment, pubs, shopping, parks, and coffee in Louisville. Bustling and eccentric Bardstown Road is only half a block away, yet the Carriage House feels secluded and very private. It is located 5 miles from Churchill Downs, 7 miles from the airport, and 2 miles from downtown.

Aug 28 – Sep 4

ﺩ.ﺇ393 per night

Guest favorite

Cabin in La Grange

4.98 out of 5 average rating, 157 reviews

Running Creek Log Cabin

Our cabin is about 6 miles to dock your boat onto the Ohio River. A 15 minute drive into downtown Lagrange for more shopping including food and boutiques. We are 30 drive into Louisville and 1 hour 15 min. drive to Cincinnati Ohio. It is on a 5 acre property and attached by a driveway to a home that we call Southwest Retreat that is on airbnb and 5 acres. We have a security camera on the outside of the house on the front porch facing the driveway.

May 28 – Jun 4

ﺩ.ﺇ1,253 per night

Guest favorite

Guesthouse in Louisville

4.96 out of 5 average rating, 664 reviews

Germantown Carriage House w/garage

Germantown is a quaint neighborhood revitalized with restaurants, coffee shops and pubs. This newly constructed carriage house has all the amenities for any length of stay, including garage parking with room for bikes or kayaks. Only 2 miles from downtown Louisville, Germantown is nestled between the energetic and historic Highlands neighborhood, beautiful historic Old Louisville, and hipster NULU. Keyless entry makes for seamless check in and out.

Aug 22 – 29

ﺩ.ﺇ318 per night

Guest favorite

Home in Louisville

4.95 out of 5 average rating, 113 reviews

HOUSE ON HERRICK

Fully renovated home in the heart of Historic Middletown. Hardwood and tile floors throughout. Queen size memory foam mattresses in both bedrooms and a full-size blowup mattress can be used in the living room if needed. 3 blocks from Main Street where you will find restaurants, shopping, and antiques! 15 minutes from Churchill Downs! Less than 1 mile to Interstate 64 with a quick Uber ride to downtown, Crescent Hill, and the Highlands.

Oct 20 – 27

ﺩ.ﺇ447 per night

Guest favorite

Apartment in Mount Washington

4.94 out of 5 average rating, 173 reviews

“Crossroads” connecting Louisville and Bardstown

This apartment is good for couples, solo adventurer and business travelers. It is 10 miles south of Louisville, 18 miles north of Bardstown, 18 miles west of Taylorsville Lake and 1 hr away from Lexington. It is close to a very cool park, The Parklands, where you can hike, bike and kayak. The apartment is centrally located in the “crossroads” of several really cool communities in horse country, Kentucky.

Apr 6 – 13

ﺩ.ﺇ358 per night