Vacation rentals with outdoor seating in Oldham County

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Top-rated outdoor seating rentals in Oldham County

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Guest favorite

Home in La Grange

5.0 out of 5 average rating, 212 reviews

Your Romantic Cabin with Hot tub

This cabin is a completely renovated 1940's farm house 10 minutes from historic downtown LaGrange. Guests have the entire home with front and back porch overlooking the big backyard. The master bedroom has a queen bed and the second bedroom has a full bed. The kitchen is fully equipped and ready for some country cooking. The fire pit is located in the back yard ready for you or you can use the gas fire pit just steps from the hot tub. The hot tub is ready for guests with a view of stars!

Nov 26 – Dec 3

R3,314 ZAR per night

Guest favorite

Guest suite in Shelbyville

4.97 out of 5 average rating, 34 reviews

Spacious suite, country views, pool table, firepit

Escape to the tranquility of the countryside at Marshalls Creekside Haven. Our lower-level walkout guest suite, with own driveway and entrance, offers the perfect retreat, providing comfort and relaxation. Enjoy the warm glow of the fire pit or sway gently on the porch swing, taking in the breathtaking country views that surround you. Indoors enjoy a game of pool, darts or board games. Convenient to bourbon trail, wineries and quaint towns. Cell service is AT&T. Wi-Fi provided by Starlink.

Jun 8 – 15

R2,496 ZAR per night

Guest favorite

Guest suite in Louisville

4.98 out of 5 average rating, 122 reviews

Derby City Hideaway

Whiskey Hollow offers you a unique stay with our Bourbon-themed space. Your stay in Kentucky is sure to be memorable and cozy. Our newly renovated space offers a full kitchen, cozy living area, bedroom and full bath with a private patio. Local attractions include Churchill Downs, home of the Kentucky Derby, Kentucky Derby Museum. Louisville Slugger Museum, Kentucky Bourbon Trail, local city eats, 4th Street Live, horse farms, hiking, waterfalls, parks, shopping, local arts, and much more!

Feb 16 – 23

R2,011 ZAR per night

Guest favorite

Tiny home in La Grange

4.98 out of 5 average rating, 161 reviews

Brakeman's Cottage

"All Aboard the Brakeman's Cottage! Experience the charm of this tiny house listed on the National Register of Historic Buildings in LaGrange, Kentucky. Nestled just feet from the train tracks in the heart of downtown, it offers a unique experience. Situated across from the train observation tower and within walking distance of the best restaurants and quaint shops, our newly remodeled property features private off-street parking. Step into history with modern comforts at Brakeman's

Jul 18 – 25

R1,859 ZAR per night

Guest favorite

Apartment in Pewee Valley

5.0 out of 5 average rating, 22 reviews

Loft in Pewee Valley

Welcome to our charming Pewee Valley loft! This tastefully decorated 2-bedroom, 1 bathroom space is an inviting retreat for your next getaway. Nestled in a peaceful town, it offers a perfect blend of comfort and serenity. Lounge in the cozy living area or enjoy a cup of coffee on the private balcony. Conveniently located near local attractions and with easy access to nearby cities, this hidden gem is ready to make your stay unforgettable. Book now and experience the charm firsthand!

Jun 16 – 23

R2,495 ZAR per night

Guest favorite

Home in La Grange

4.93 out of 5 average rating, 74 reviews

Hot Tub-King Bed-Coffee Bar-Arcade-Fire Pit!

Centrally located in La Grange, the Kindness Capital of Kentucky. Welcome to the hallmark of small towns where the train rolls down Main Street over 30 times each day. Walk to locally owned donut and coffee shops, Farmer’s market, playground with splash pad, and restaurants. Spend your day on the Bourbon Trail or Churchill Downs before relaxing in the Hot Tub. Driving distance to the Creation Museum and Ark Encounter, The Slugger Museum, Falls of the Ohio, and Mega Caverns.

Aug 28 – Sep 4

R3,319 ZAR per night

Guest favorite

Home in La Grange

4.92 out of 5 average rating, 49 reviews

Caboose Cottage

Historic 3 bed, 1 bath farmhouse within walking distance of downtown LaGrange & The Railroad Museum. Secluded on a 1.5 acre lot with a fenced in backyard, fire pit, private patio & perfect view of the CSX train line rolling into Main Street. A few minutes walk to local gift shops, restaurants & coffeehouse. 25 minutes from Louisville International Airport & downtown Louisville. Less than 15 minutes to the home of Jefferson's Reserve Bourbon, Kentucky Artisan Distillery.

Aug 21 – 28

R2,790 ZAR per night

Guest favorite

Guest suite in Crestwood

4.95 out of 5 average rating, 63 reviews

Charming suite in Bourbon Country

A great base for bourbon tours, the Derby, Louisville and Central KY attractions. Easy access to I-71, 25 minutes from downtown Louisville. 5 minutes from distillery, brewery, and botanical gardens in scenic Oldham County. A beautiful spot off the beaten path to relax and recharge. Private two bedroom basement suite with natural light, dedicated entrance, and privacy. Shared outside covered deck and yard with mature trees. 1 queen, 2 twin beds, 1 queen air mattress.

Jul 16 – 23

R2,107 ZAR per night

Guest favorite

Guest suite in Prospect

4.97 out of 5 average rating, 172 reviews

Private Prospect Flat

Two bedroom apartment located on picturesque Covered Bridge Road in Prospect, KY. There is a separate entrance with plenty of parking. Beautiful views of Kentucky landscape from every window. Our property is four acres with a meandering stream, forest, and fields. There is a fully stocked kitchen including a dishwasher. The main bedroom includes a work space area and two closets. Feel free to grab a few eggs for breakfast if there are eggs in the nesting boxes.

Jun 21 – 28

R2,693 ZAR per night

Guest favorite

Guesthouse in Louisville

4.97 out of 5 average rating, 112 reviews

The City Cottage…quiet, peaceful, and convenient!

A quaint, cozy, and private space close to everything Louisville has to offer. Located on the Northeast side of Louisville, The City Cottage is near the highways for quick access to destinations in and around Louisville. This newly completed space is fresh, clean and created for guests in mind. Are you a couple traveling or a business person wanting more room and comfort than a typical hotel? The City Cottage is for you! (Three night minimum during Derby time.)

Jun 30 – Jul 7

R2,930 ZAR 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.

Aug 11 – 18

R6,465 ZAR per night

Guest favorite

Loft in Charlestown

4.93 out of 5 average rating, 43 reviews

Cozy hideaway on Yankee creek.

In the country, yet close to the city. You’ll love our cozy hideaway in the beautiful Indiana farmland. Situated in between the small towns of Charlestown and New Washington.You’ll be only minutes away from beautiful hiking at Charlestown State Park or head up the Ohio river scenic by-way (HWY 62) to Clifty Falls State Park in Madison, Indiana. This area is about 20 minutes to the east bridge(Lewis and Clark bridge)to Louisville, Kentucky.

Jan 27 – Feb 3

R2,010 ZAR per night