Vacation rentals with outdoor seating in Highlands

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Top-rated outdoor seating rentals in Highlands

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Top guest favorite

A welcoming living area features rich wood accents and natural decor, complemented by a vibrant area rug and various framed artworks on the walls. A spacious leather sofa is positioned next to a low coffee table, while a bar with seating is visible in the background.

Apartment in Tyler Park

4.98 out of 5 average rating, 101 reviews

The DerbyBirdie - The Highlands (by Tyler Park)

The DerbyBirdie would love to welcome you on your next trip to Louisville! This well-appointed second floor private apartment has all the comforts of home. Charmingly situated in the verdant Tyler Park neighborhood, AND within safe walking distance to Bardstown Rd, Germantown, & Old Forrester’s Paristown Hall. Also less than 4 miles from Churchill Downs, University of Louisville, The KY Expo / International Convention Center & Downtown. Perfect for couples or more private Individuals. Come Stay!

Top guest favorite

Home in Cherokee Triangle

4.94 out of 5 average rating, 174 reviews

2 br home, walking distance to much entertainment

Home located in the historic Irish Hill neighborhood, just a short walk to popular Baxter Ave and Bardstown Rd, famous for its restaurants, coffee shops and nightlife. Downtown and Nulu are a very short drive away, many great bars and distilleries are walking distance. Home built in 1879, entirely renovated with a modern kitchen, fully fenced backyard, private parking and fire pit.Master bedroom has a king size bed and it’s own bathroom with jetted tub. We look forward to your visit, thank you!

Top guest favorite

A spacious interior showcases a multi-level layout with open sight lines. The upper area features a sleek railing and views of the large living space below, which includes modern furnishings and a dining area. Natural light floods through several windows, enhancing the airy atmosphere.

Home in Highlands

4.98 out of 5 average rating, 107 reviews

Highlands Lookout-3BR 3.5BA-Walk to Tons +Parking

Welcome to Highlands Lookout, your ultimate spot for a good time on Bardstown Road in the lively Highlands of Louisville! 3 Huge bedrooms plus 3.5 Baths. Perfect for guys' or girls' weekends, concerts, and conventions. Immerse yourself in the vibrant atmosphere of "Keeping It Weird." Unwind on our balcony or mix up a cocktail at our wet bar. Close to distilleries, bars with rare bourbons, downtown, racetrack, and the airport. Your gateway to a thrilling Louisville adventure! Off street Parking!

Guest favorite

A modern living area is depicted, featuring a white built-in shelf surrounding a gas fireplace. Above the fireplace, a flat-screen television displays various streaming options. The shelves are adorned with decorative items and storage baskets, adding organization to the space.

Condo in Highlands

4.93 out of 5 average rating, 212 reviews

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

Large, 3 story townhouse sleeps 6 in 1600 sq. ft. Step out the door to best walking neighborhood in Louisville. Great coffee shop 150 ft. away, with a dozen places to eat, from fancy to casual, within the block. Parks, movies, live music are 10 minute walk or less away. 2 King bedrooms, each with full bath, 1 queen and 1 twin daybed w/ trundle. Fully equipped kitchen, 3 large smart tvs, wifi and cable! Kitchen fully equipped, from quality appliances to pots/pans/plates/cutlery/glasses/etc.

Guest favorite

A modern kitchen is showcased, featuring sleek cabinetry and an island with seating for four. Three pendant lights hang above, providing warm illumination. The stainless steel appliances include a refrigerator and a microwave. Natural light enters through large windows, adding brightness to the space.

Home in Germantown

4.93 out of 5 average rating, 189 reviews

Private Parking in GTownWalk to Coffee,Shops,Bars!

Shotgun Rye is ready to host your stay in Louisville! Located close to everything cool in Germantown and Highlands area! People visit for Bourbon Tours, Ky Derby, Conventions, Expo Ctr, UL graduations and sporting events, live music and so much more! Completely remodeled with all the modern conveniences & a comfortable, casual touch. But with so much to see and do in Louisville you’ll load up your itinerary with unforgettable experiences. Great location walk to bars, restaurants and shopping!

Top guest favorite

The exterior of the stone cabin is framed by lush greenery and flowering plants. Sunlight casts soft shadows across the textured stone walls. A decorative statue stands on a pedestal near the entrance, complementing the natural surroundings.

Cabin in Louisville

4.99 out of 5 average rating, 242 reviews

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Top guest favorite

The home's inviting facade features white clapboard siding and large front windows adorned with classic trim. A welcoming entrance is highlighted by a beautiful door, surrounded by potted flowers and greenery. The well-maintained yard includes a small walkway that leads to the entrance.

Home in Highlands

4.91 out of 5 average rating, 202 reviews

Cheerful, centrally located 2 bedroom shotgun home

This welcoming home is central to Louisville's most popular and lively neighborhoods, walking distance to many favorite spots. Natural light and unique art fill the home. There is a large deck that overlooks a beautiful cemetery behind the home, and is a perfect place enjoy morning coffee or sunset dinner. A coffee/tea bar is located in the fully equipped kitchen. Charging stations and white noise machines are found in both bedrooms. 2 workstations and a smart TV are also available.

Guest favorite

A resort-style pool area is surrounded by lounge chairs, featuring a separate hot tub nearby. The pool is framed by landscaped greenery and a contemporary building exterior, with multiple balconies visible in the background.

Apartment in Central Business District

4.88 out of 5 average rating, 245 reviews

4th Street Suites - Luxury King Bed Suite

Wake up to the best of Louisville! Imagine starting your morning in a cozy king bed, strolling to 4th Street Live for brunch, and exploring nearby restaurants, bars, and theatres. Spend the afternoon lounging by the pool or soaking in the hot tub, then watch the city lights twinkle from the 7th‑floor terrace. This stylish suite is your launchpad for urban adventure—and a quiet, relaxing escape when it’s time to rest. Come make it yours and experience the heart of the city!

Top guest favorite

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.

Guesthouse in Tyler Park

4.98 out of 5 average rating, 306 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.

Guest favorite

A spacious bedroom features a large bed with dark bedding centered on wooden floors. Two cozy armchairs are positioned nearby, complemented by a vibrant area rug. A decorative mirror and framed artworks adorn the walls, while a bookshelf holds an array of books, adding character to the space.

Guesthouse in Schnitzelburg

4.96 out of 5 average rating, 238 reviews

Comfortable-relaxed space to find your inspiration

Located in the Germantown neighborhood of Louisville, this peaceful efficiency apartment in a traditional "shotgun" home, built in the 1890s, is within 10 minutes of nearly all of Louisville’s airport traveler’s attractions. Guests enjoy great sleep on top bedding and attention to detail. Sit on the front porch and let time slip by or spend the evening with a relaxing drink or meal in one of the neighborhood’s hip local eateries and bars. Plan your next journey.

Top guest favorite

A cozy seating area features a modern sofa and a small side table, positioned on a patterned rug. Natural light filters through sheer curtains, illuminating the dark walls. Nearby, a door leads to the exterior, while colorful artwork decorates the walls.

Guest suite in Shelby Park

4.98 out of 5 average rating, 635 reviews

Eco+ guest suite in the center of all the fun

Hip modern amenities meet historic home in Shelby Park. A quick drive to everything in the urban core - Downtown, Nulu, Old Louisville, the Highlands, Germantown, and more. Easy access to the airport, to boot! We are pet friendly home, but require your pets be registered on the booking. We want your pets (and ours) to be as safe and comfortable as you are, and the fee covers additional costs to complete allergen level sanitization.

Guest favorite

A spacious living area is equipped with a large sectional sofa and a wooden coffee table, providing a comfortable gathering space. The modern kitchen features stainless steel appliances and dark cabinetry, while an open layout invites natural light from the adjacent windows.

Home in Germantown

4.94 out of 5 average rating, 141 reviews

The Caldwell Highlands/Germantown

Welcome to The Caldwell, a Germantown/Highland area home that includes three bedrooms, one and half bathrooms and sleeps up to five people. The home is within walking distance of several restaurants, bars, retail and vintage stores, and entertainment venues including the Germantown Gables, Logan Street Market and Old Forester’s Paristown Hall. The home features a covered deck, a fenced-in yard as well as home gym.