Family-friendly vacation rentals in Prospect

4.86 out of 5 average rating, 313 reviews

A bright living room is furnished with a gray sofa and two blue armchairs. A glass coffee table is centered on a colorful area rug. A flat-screen TV sits on a wooden console, and a bookshelf is visible, filled with various books. Natural light enters through multiple windows.

Cottage in Germantown

Tyler Park Cottage in the Highlands

Adorable, light-filled cottage in the beloved Highlands neighborhood. An easy ten minute walk in one direction will put you on Bardstown Road, full of dining and bars, while a 15 minute walk in the other will land you in the hip Germantown-Schnitzelburg neighborhood. A short (6 minute) drive to downtown, 11 minutes to Churchill Downs. You'll find wireless internet, clean towels and sheets, basic kitchen and bathroom amenities, coffee maker, a flat screen TV with Apple TV, and keyless entry.

A charming exterior of a renovated shotgun-style home is showcased, featuring a light-colored façade and decorative blue shutters. A small front porch invites visitors, with a neatly maintained garden bed displaying colorful flowers and a fenced yard providing privacy.

4.95 out of 5 average rating, 244 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!

4.79 out of 5 average rating, 154 reviews

A living area is presented with a stone fireplace as a focal point, topped by a flat-screen television. Natural light filters through two windows, complemented by a leafy indoor plant. Cozy seating includes a bright yellow armchair and a textured green throw pillow.

Home in Crescent Hill

The Hillcrest- Great Crescent Hill Location!

Great space in Crescent Hill part of Louisville. Easy access to downtown, Expressway University of Louisville & Waterfront Park areas. Walking distance to Bars & Restaurants on Frankfort with shopping in the area. The space is furnished clean and minimalistic, vintage themed. Great for families or friends all getting together. Three nice sized bedrooms. One full bathroom upstairs and a half bathroom downstairs in basement. Main floor has a dining room seating 8, kitchen & living room.

A cozy living room features two black leather armchairs adorned with blue accent pillows. A round coffee table with a glass top sits on a colorful patterned rug. A modern television is mounted above a black fireplace, flanked by built-in shelves filled with books.

4.92 out of 5 average rating, 123 reviews

5 bedroom/4 bath Walk to All, Historic Highlands

4 traditional bedrooms (5th convertible den/bedroom), 4 bath with great deck, porch and patio. 2 king bedrooms, 2 queen bedrooms, 1 queen sleeper and den double sleeper. Fabulous 3rd floor primary suite, updated baths, stylish mod kitchen. Beautifully remodeled 2500 sq. ft. house in Cherokee Triangle, walk to everything- restaurants, parks, cafes, shops! Just 1/2 block off Bardstown Road and 1 block from Cherokee Park. Walk to dozens of restaurants, shops, café, theatres and two great parks.

Home in Central Business District

A charming red brick building exhibits a vibrant yellow entrance, flanked by manicured greenery and trees. Large windows invite natural light, while a wrought-iron fence surrounds the inviting front yard, completing the home’s welcoming exterior.

4.83 out of 5 average rating, 211 reviews

615 E Washington, Nulu Bourbon Trail

RECENTLY MADE AVAILABLE FOR DERBY 2025 - Ask about Specials NULU/Downtown Urban & eclectic downtown home 1/2 BLOCK to ANGELS ENVY BOURBON DISTILLERY & SLUGGER FIELD!! 3,000 square feet of living space 1,500 sq ft patio -High-end kitchen with chef-ready appliances -Dining room and wet bar room for congregating with friends -2.25 bathrooms rival high end hotels -Bedrooms with plush memory foam mattresses and linens. -Experience is completed w SONOS to enjoy whole home sounds.

4.99 out of 5 average rating, 135 reviews

A spacious living area features a gray sectional sofa positioned near a cozy area rug. Natural light filters through multi-pane windows, illuminating the warm wood ceiling and the contrasting light yellow walls. A wooden entertainment unit, complete with a mounted television, adds functionality to the space.

Farm stay in Pendleton

Fossil Creek Woodlands...Rustic, Private, Retreat

Fossil Creek provides a rustic relaxing environment for family and friends to escape the hustle and bustle of every day life and enjoy beautiful Kentucky woodlands. Our home is situated at the base of 65 wooded acres in Oldham County Kentucky. Its name comes from the plethora of fossils that can be seen in the creek that runs along the front of the property. Our place is great for couples, families, reunions, retreats and church groups.

4.86 out of 5 average rating, 165 reviews

A cozy living area features a brown sectional sofa and a wooden coffee table on a striped rug. A tall lamp provides soft lighting, while built-in shelves display decorative items. Light enters through shuttered windows, enhancing the room's inviting ambiance.

Cottage in Prospect

Cottage in Louisville,KY on Scenic River Rd

My place is close to Downtown Louisville (7 miles along scenic River Road), restaurants (Captain's Quarters Riverside Grille, Pine Room, Blackstone Grill, Gustavo’s, Prospect Village Shopping Center 1 mile (grocery, pharmacy, Starbucks, fast food, dry cleaning), Farmer's Market, marina, liquor store, expressways (20 minutes to airport). You’ll love my place because of the views & location.

4.96 out of 5 average rating, 309 reviews

A spacious kitchen area features wooden cabinetry and modern appliances, including a stove and microwave. A brick column adds a rustic charm to the room. A round table with four barrel-style chairs is positioned underneath a wall clock, enhancing the inviting atmosphere. Artwork of a horse is displayed above a counter.

Bungalow in Germantown

Charming Bourbon Bungalow - 1 Mile from Downtown!

You will love this quaint Germantown house located 2 miles from almost anywhere you would want to be in the city! Two bedrooms and one bath await you, along with a full kitchen, large living space, and spacious back yard. Close to many great restaurants, downtown attractions, the Highlands, Churchill Downs, the riverfront, and many great parks. Don't wait--book now!

4.95 out of 5 average rating, 699 reviews

A large black barn sits prominently in the image, complemented by lush green trees and shrubs. A gravel path leads towards the entrance, which is framed by manicured grass. The expansive farmland stretches into the background, under a clear blue sky.

Farm stay in La Grange

The Cottage at StoneLedge 2 bedroom/1bath

Nestled on an expansive 80 acre horse farm, the cottage 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. If traveling with pets please note prior approval is required and be sure to read the pet policy in 'other things to note'. Thank you for your consideration.

4.93 out of 5 average rating, 260 reviews

An open living area features a gray sofa and two armchairs surrounding a coffee table set on a decorative rug. Light streams through the three windows, illuminating the wood flooring. A dining table is set to the side, and kitchen appliances are visible in the background.

Apartment in Louisville

The Highlands Original Condo

Our brand new renovated 1BR condo is located in a famous Highlands' neighborhood. Conveniently located about 5-8 minutes from Churchill Downs, KFC Yum Center, Cardinal Stadium, Convention Center, Center for the Arts, Downtown Distilleries, NuLu&Germantown areas, 12 minus from the airport. Walking distance to many great restaurants, bars, shops, and parks.

A welcoming living area is highlighted by soft green walls and hardwood floors. A round table with a flower arrangement sits at the center, surrounded by a cozy sofa and a lounge chair. A television is positioned on a shelf, with doorways leading to other rooms.

4.96 out of 5 average rating, 222 reviews

Charming Shotgun Style Home, Great Location

This updated shotgun house is thoughtfully decorated with hints of handcrafted detail. Outdoor spaces include a front porch and a private patio. Cozy with a modern vibe. It can sleep up to 6. An ideal choice for couples, families, or a getaway with friends. Perfect for The Kentucky Derby and all Louisville has to offer.

4.94 out of 5 average rating, 125 reviews

A spacious bathroom is depicted, featuring a modern vanity with a mirror above. A stacked washer and dryer are seen in the corner, with a doorway leading to a room adorned with exposed brick in the background. Natural light brightens the area, enhancing the clean design.

Home in Highlands

Barret House, Modern living in the Highlands!!

Fully furnished luxury duplex, 3 bedrooms (recently added king, and also two queen beds) and 2 full baths, 2 chefs kitchens, with hide-a-bed and futon in second floor common area; This rehab has been designer decorated with a huge living area, it close to some of the finest restaurants in town. *No locals, please*

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Family-friendly home rentals with a hot tub

4.72 out of 5 average rating, 112 reviews

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

4.98 out of 5 average rating, 170 reviews

The cabin features a rustic exterior with a warm wooden facade and a distinct red metal roof. A wide porch wraps around the front, complemented by natural wooden railings. Large windows provide ample light, and the surrounding greenery adds to the serene atmosphere.

Cabin in La Grange

Running Creek Log Cabin

A spacious yard is highlighted by a large tree providing shade. A playset with yellow and green slides is visible alongside a well-maintained lawn. Flowerbeds enhance the landscape near a patio area, contributing to the family-friendly outdoor space.

5 out of 5 average rating, 13 reviews

Great patio - Northeast Louisville

A grand two-story brick home is showcased, featuring multiple peaked roofs and expansive windows. Symmetrical landscaping adds to the curb appeal, with neatly trimmed shrubs and a manicured lawn. A wide pathway leads to the front door, framed by steps and elegant railings.

Home in Fern Creek

4.67 out of 5 average rating, 51 reviews

All You Need and More!

A cozy living area is furnished with a navy blue sectional sofa and two red chairs. Natural light enters through large windows adorned with teal curtains. A round wicker coffee table sits at the center, accompanied by a potted plant, while art is displayed on the walls.

4.97 out of 5 average rating, 245 reviews

Bourbon Trail Hot Tub Retreat King Beds, Spacious

A comfortable living area features a sectional sofa adorned with colorful pillows, complemented by a stylish armchair and an accent chair. Decorative art pieces are displayed on the walls, and natural light filters through the window, highlighting a patterned area rug beneath a coffee table.

4.97 out of 5 average rating, 29 reviews

2.0 Southern Comfort Highlands-Cherokee Triangle

A private hot tub is situated on a paved area, surrounded by a wooden fence for added privacy. Colorful flower pots with blooming flowers are positioned nearby, complementing the fresh green grass. Two red chairs sit in the backyard, inviting relaxation.

4.99 out of 5 average rating, 242 reviews

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

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Family- and pet-friendly home rentals

4.93 out of 5 average rating, 296 reviews

Home in Butchertown

Guesthouse on Story- Bourbon Trail

4.95 out of 5 average rating, 194 reviews

A cozy library area features two plush armchairs facing a dark wood bookshelf filled with books. Artwork adorns the walls, and natural light filters in through the two windows, creating a warm and inviting reading space.

Home in New Albany

Spacious Historic Home, Louisville Adjacent

Apartment in Central Business District

The bathroom features a modern design with a shower area, showcased by a colorful shower curtain. A large round mirror enhances the space above a sleek vanity. A combination of neutral tones and natural light completes the tranquil atmosphere.

4.76 out of 5 average rating, 123 reviews

Downtown Convenience with Privacy!!

4.88 out of 5 average rating, 185 reviews

A wooden sign is displayed on a wall, featuring the text 'Welcome to Our Nest' in an elegant cursive font. The sign has a rustic design with a whitewashed finish, and a pink ribbon is tied at the top for hanging.

Loft in Crestwood

Welcome to the Nest!

A vibrant game room features a foosball table at its center, surrounded by warm red walls adorned with framed photographs. An acoustic guitar leans against a cabinet, while a cozy chair complements a desk area. The kitchen is visible through an open doorway in the background.

4.96 out of 5 average rating, 262 reviews

Home near the Highways

4.84 out of 5 average rating, 108 reviews

An antique wooden dresser is positioned against a patterned wall, featuring a large central mirror flanked by two vintage glass lamps. A decorative basin is placed in the center, with intricate details on the dresser's front and wooden floorboards visible below.

Bungalow in Louisville

Sweet Highlands Victorian 2Blocks off Bardstown Rd

4.89 out of 5 average rating, 523 reviews

A spacious bedroom features a king-sized Sleep Number bed with neutral bedding and decorative pillows. Soft light is provided by bedside lamps, illuminating the artwork above the bed. Natural light enters through a window, and a door leads to the adjoining area.

Home in Highlands

Charming home in the Highlands

4.98 out of 5 average rating, 167 reviews

Home in New Albany

Family-friendly! Walkable to downtown shops!

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Family-friendly home rentals with a pool

Guest suite in Louisville

A heated saltwater swimming pool is surrounded by a concrete patio and lush greenery. The area features a spacious cabana with seating, a chaise lounge, and colorful pool floats. Nearby, a small garden and manicured lawn enhance the outdoor setting.

4.96 out of 5 average rating, 369 reviews

Cherokee Park Oasis with Private Entrance

Guest suite in Oldham County

4.79 out of 5 average rating, 77 reviews

WATERFALL WALKOUT HILLTOP SLEEPS 10+, 4 BR 2BA

4.89 out of 5 average rating, 65 reviews

Guesthouse in Pendleton

The Waterfall Place, Suite and Walkout!

Guest suite in Jeffersonville

4.93 out of 5 average rating, 182 reviews

Come Explore Jeffersonville & Louisville

A serene backyard is highlighted by a rectangular swimming pool surrounded by a tiled patio. Lounge chairs are positioned beside the pool, and structured seating areas with metal chairs provide space for relaxation. The area is adorned with greenery and a small shed is visible in the background.

4.97 out of 5 average rating, 34 reviews

Highlands Oasis- Summer and Winter Retreat

A spacious living area features a comfortable sofa and armchair arranged around a coffee table, with a grand piano visible in the background. Natural light fills the space, highlighting decorative artwork and a handmade rug underfoot, complemented by elegant light fixtures and architectural arches.

4.91 out of 5 average rating, 149 reviews

Sleeps 16, Highlands Area, Heated Pool, Hot tub

A cozy playroom features a large sectional sofa with decorative cushions. Two small armchairs in soft colors provide seating, while a television is mounted on the wall. Various toys and colorful storage bins are visible, enhancing a family-friendly environment.

5 out of 5 average rating, 3 reviews

Derby Week in the Heart of the Bluegrass