Vacation rentals with breakfast in Jefferson County

Guest suite in Louisville

A modern entrance is showcased with a sleek black door featuring decorative panels. Lush greenery and blooming hydrangeas frame the stone pathway, which leads towards the door. Subtle outdoor lighting enhances the welcoming atmosphere as the pathway is bordered by neatly arranged stones.

4.97 out of 5 average rating, 137 reviews

Action City! Extravaganza at Bardstown Rd!

In the HEART of the Highlands, this spot sits near the corner of the main strip- just steps to Bardstown Rd. A few minutes drive to anywhere in city limits! And exactly where YOU want to be! Action Packed: Restaurants, Shopping, Bars, Parks, and Church- all walkable. A surprise local GIFT CARD given with each stay! This place is stylish, chic, cozy, and extremely quiet, as double pane windows have been installed. Recently renovated, it houses all the essentials for a weekend or week long stay.

4.83 out of 5 average rating, 109 reviews

A wooden deck is visible through multiple window panes, featuring several lounge chairs arranged for relaxation. Surrounding greenery offers a serene backdrop, and a glimpse of a nearby structure can be seen beyond the deck.

Bungalow in Louisville

Sweet Highlands Victorian 2Blocks off Bardstown Rd

My place is close to nightlife, public transport, parks, and the city center. You’ll love my place because of the high ceilings, the coziness, the comfy bed, the light, and the kitchen. My place is good for couples, solo adventurers, business travelers, families (with kids), and big groups. Nulu and downtown are minutes away. You can stroll down our lovely sidewalks and look at the beautiful Victorian houses and trees, enjoy some great food, with lots of quirky shops just footsteps away. Enjoy!

4.88 out of 5 average rating, 128 reviews

An outdoor deck features cozy seating arranged around a fire pit, with soft lighting from overhead string lights. A jacuzzi tub is positioned nearby, and a grill is available for outdoor cooking. Surrounding greenery provides a sense of privacy.

Home in Louisville

Parkside Retreat

Situated off of a parkway with mature trees lining the street, this parkside retreat is close to most everything. We are a short drive to Churchill Downs, Downtown, the Airport. Our home sits on one of the most beautiful streets in the entire neighborhood. We are 7 houses from Iroquois Park. It is terrific for walking, hiking, or just having a picnic. We have a privacy fence with a jacuzi tub on the deck. Many updates make this home the perfect choice to relax after a day of fun activities

4.95 out of 5 average rating, 339 reviews

Cabin in Louisville

Captain's Cabin: Bourbon Trail, History & Romance

Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 4 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

4.97 out of 5 average rating, 340 reviews

A wooden sliding door leads to a cozy bedroom with a patterned bedspread atop a low bed frame. Glazed double doors reveal light streaming into the room, while warm wood flooring continues into the hallway, enhancing the inviting ambiance.

Home in New Albany

Charming shotgun nestled in historic mansion row.

New Albany is returning to its former glory. Once ranked highly for Ohio river personal & business adventures. Revisit history. Stroll down Main Street, one block over, and sense and experience the grandeur of 1900’s mansions. Imagine the pride of William Culbertson seeing his 1867 showcase home been built. 1010 Market is hardly a shadow of that splendor yet it greets you with tremendous loving charm. This pocketbook sized “ mansion” offers you a quiet, comfortable retreat.

A wooden deck featuring a clean railing surrounds a doorway, with two tall windows flanking it. Potted plants are placed on the ledge beneath the windows. Sunlight filters through the leaves of a nearby tree, creating a fresh and inviting appearance.

4.89 out of 5 average rating, 132 reviews

Cottage Park Carriage House. Rest w/Hollyhock

The Carriage house is located behind a historic mansion in beautiful Crescent Hill. Situated next to a park, this ideal location is still one block away from Frankfort Ave. shopping & dining, conveniently located near downtown, Churchill Downs, & four blocks from the Largest park in downtown Louisville. Newly designed and renovated-includes two separate bedrooms, office area, full kitchen, bathroom, & laundry. Free wifi, & parking. Refresh and relax in this satisfying getaway!

4.99 out of 5 average rating, 154 reviews

The exterior of a charming two-story brick home is showcased, featuring a gabled roof and multiple front-facing windows. A well-maintained lawn surrounds a stone walkway leading to the entrance. Flower beds with vibrant blooms enhance the welcoming appearance of the home.

Home in Louisville

Two Bedrooms walking to Expo Center & KY Kingdom!

Spacious private two bedroom in charming Louisville neighborhood. Perfect location is close to everything! Bus Stop and Multiple Restaurants (short walk) Interstate 264 (1 mile) KY Expo Center (1.1) Norton Hospital (1.2) Interstate 65 (1.4) UofL (1.5) Kentucky Kingdom (1.5) Louisville Zoo (2.1) Airport (2.3) Mega Cavern (2.6) Churchhill Downs (2.8) Bardstown Road (3.0) Derby City Gaming (3.4) 4th Street Live (4.3) Waterfront Park (4.5) Yum! Center (4.6) Slugger Museum (5.0)

A charming balcony features a wooden table surrounded by four slatted chairs. A potted fern hangs gracefully from the angled ceiling, with views of lush greenery visible beyond the railing, creating a serene outdoor space.

4.98 out of 5 average rating, 285 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.

A charming entrance is framed by neatly trimmed hedges and flower decorations. The door, painted in a warm coral hue, features two inviting windows with curtains. Lanterns are mounted beside the door, warmly illuminating the pathway of stone tiles leading to the entrance.

4.91 out of 5 average rating, 539 reviews

Cute Carriage House off Frankfort Avenue

Welcome to "The Cute Carriage House at Frankfort Avenue". Experience serenity in a genuine "tiny house” that comfortably accommodates two people. There are several sleeping options that I will mention below. We are located a short block from premier restaurants and shops on Frankfort Avenue in the classy Clifton Neighborhood...and close to Cherokee Park and the cool Bardstown Road. FYI https://www.leoweekly.com/2020/10/the-winners-of-the-2020-readers-choice-awards/

4.95 out of 5 average rating, 395 reviews

A wooden shelf displays a collection of dark tableware, including stacked bowls and several glasses. The arrangement highlights a modern aesthetic, complemented by artworks in the background.

Apartment in Louisville

Sunny Clifton Loft

Recently renovated studio apartment with loads of natural light, steps from award-winning local restaurants, bakeries, bars, and housed above our independent record store. We do our best to AirBnB ethically & responsibly.. Revenue from this unit helps to 1) keep on-site residential rents affordable & increase-free 2) maintain the historic building & protect it from outside development while 3) help us steer our future as a brick and mortar independent business.

A charming bathroom features exposed brick walls and a vintage appeal. A white vanity with a sink is complemented by a wall mirror. Shelving holds neatly folded towels, while natural light enters through wooden shutters. A decorative tile floor adds character to the space.

4.99 out of 5 average rating, 135 reviews

Charming Carriage House in Old Louisville

Charming carriage house in historic Old Louisville neighborhood near Churchill Downs, convention center and downtown attractions. Unique, newly renovated space with 3 bedrooms, 3 queen beds/1 twin bed, 2 full baths each with shower, kitchen, patio/deck and 5G high speed internet. Also 2 Roku TVs with popular streaming channels like Fubo, Prime, Apple TV and Netflix, washer/dryer, parking spots at back of house plus on street parking in front of Carriage house.