Holiday rentals with outdoor seating in Frankfort

4.98 out of 5 average rating, 251 reviews

A rustic cabin is nestled among trees, featuring a well-lit entryway and a front deck with two wooden lounge chairs. Soft evening light spills through the windows, creating a welcoming atmosphere. Stone stepping stones lead towards the doorway, enhancing the natural setting.

Cabin in Lawrenceburg

Romantic Cozy Cabin Getaway w/ Firepit & Hot Tub

Privately nestled on over 5 wooded acres & intentionally curated for your stay. Gain access to quiet, immerse yourself in nature, support your rejuvenation, & to tap into your creative flow. Amenities include on-site hiking trail, artist work space, wood burning stove, covered porch, hammocks, outdoor dining, fire pit, moon garden, salt-water hot tub, & outdoor shower. Close to Beaver Lake & located along the Bourbon Trail, just minutes from Wild Turkey & Four Roses distilleries. (Note:18+only)

5 out of 5 average rating, 117 reviews

Bourbon Central Waterfront Luxe near Buffalo Trace

This Ultra Luxe River Flat located in the heart of the Capital City of Frankfort, Ky offers 1600 square feet of step free luxurious, modern living within walking distance to everything downtown has to offer- 15+restaurants/pubs. 1.8 miles to Buffalo Trace, less than 10 miles to Woodford Reserve, Castle & Key and Whiskey Thief. -King Size Bed Suite -Heated floors in main bath -1 Gig Wifi -75" /55" Smart TVs/Direct TV/Apps - Coffee Station w/Decaf and tea - Piano, Guitar - Golden Tee Ms. Pac-Man

The exterior of the remodeled house is framed by lush trees, showcasing a welcoming deck with ambient lighting. A traditional barrel sauna is positioned nearby, blending with the natural surroundings. The inviting façade reflects warm tones, enhanced by the soft glow of the setting sun.

4.99 out of 5 average rating, 124 reviews

Bourbon Trail*River Views*Hot Tub*Sauna*EVSE*WiFi

Welcome to River Whisper. The remodeled riverfront house offers the perfect blend of organic modern decor and unparalleled comfort. Experience luxury with top-of-the-line features, a hot tub, and a barrel sauna, all overlooking the beautiful Kentucky River. Located in the heart of Bourbon Trail, with easy access to many renowned distilleries, including Buffalo Trace and Woodford Reserve. Explore historic downtown Frankfort, Cove Spring Park, river boat tours, kayaking, fishing, hiking and more.

4.99 out of 5 average rating, 121 reviews

Backyard Bourbon Retreat

Your family will be close to everything when you stay at this centrally-located place. This is a beautiful two bedroom two full bath home packed with a ton of amenities! Only minutes from several distilleries such as Buffalo Trace, Jim Beam, Woodford Reserve, Ancient Age and Four Roses just to name a few! There is a fully fenced in yard with a deck looking into a 1/4 acre landscaped backyard. Great for sitting back and relaxing with a Kentucky beverage. Welcome to the Backyard Bourbon Retreat!

5 out of 5 average rating, 234 reviews

A well-equipped kitchen features dark wooden cabinetry and granite countertops. Four barstools with cushioned seats are arranged around a large island. Stainless steel appliances, including a refrigerator and oven, are visible alongside natural light streaming through a window.

Cabin in Frankfort

On The Rocks

Ultimate in privacy, yet two minutes from downtown Frankfort! This cabin-style home (think Gatlinburg!) sits on three wooded acres. Long, rambling decks on three sides (one covered, one fully screened, one open air). Our adjacent farm surrounds the property, making it even more private. This home sits high on a bluff above downtown Frankfort & the Kentucky River (our farm borders on the river). Just three miles to Buffalo Trace Distillery (if you could fly, it's way closer than that!)

The exterior of the home features a welcoming porch with rocking chairs framed by neatly trimmed hedges. A manicured lawn with shrubs enhances the inviting approach to the entrance. Surrounding trees provide a natural backdrop, contributing to the overall charm of the property.

4.94 out of 5 average rating, 247 reviews

Wilkinson's Wheated Oasis/ 1.3 Mi to Buffalo Trace

Wake up & smell the mash! Located just steps away from Buffalo Trace Distillery. Enriched with history & tradition is where you will find Wilkinson. This historic home has recently undergone renovations & no expense was spared. Guests will enjoy the walkability to Downtown Frankfort & many of the local attractions. Featuring 2 bedrooms & 2 baths, guests are able to experience life like a local with all the modern-day amenities. We are also only a 7.2-mile drive to Castle & Key Distillery.

4.99 out of 5 average rating, 562 reviews

A red farmhouse tractor is positioned prominently in the foreground, with a vibrant red caboose labeled 'SOUTHERN X525' in the background. An outdoor pavilion with a gabled roof is partially visible, bordered by trees displaying autumn foliage.

Train in Lawrenceburg

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunkbeds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

4.95 out of 5 average rating, 244 reviews

A modern kitchen is showcased, featuring stainless steel appliances and white cabinetry. The spacious marble countertop is complemented by decorative elements, including teal accents. A cutting board rests on the counter while colorful artwork adorns the wall, adding a touch of vibrancy to the space.

Bungalow in Frankfort

Lil Bit O' History on Main- Historic Downtown!

Built in 1867, with original deed of 1813, this beautiful piece of Frankfort's history has been fully restored! This cozy shotgun home offers magnificent views of the State Capital in front and the Old Capital from the side! Located along the Bourbon Trail, it offers a short walk to BOM, local breweries, downtown coffee at Kentucky Coffee Tree, and all the shops of Broadway. The History Center is close, as is The Kentucky Military Museum. Buffalo Trace and Castle and Key are minutes away.

4.94 out of 5 average rating, 262 reviews

A cozy sleeping area features a spacious bed with crisp white linens. An inviting sitting area with a white couch rests next to a wooden wardrobe. Natural light filters through nearby windows, highlighting the room's soothing decor and warm atmosphere.

Guest house in Frankfort

The Carriage - Quaint Haven steps to the Capitol

Your perfect Kentucky getaway starts here. Tucked in Historic Frankfort, this charming Parisian-inspired retreat is minutes from 13 renowned bourbon distilleries, the Kentucky Capitol, and downtown favorites. Spend your days tasting, exploring, and discovering local history, then unwind with a glass of your perfect drink on your private bistro deck. Thoughtfully designed for comfort and relaxation, this cozy hideaway is the ideal home base for an unforgettable Bourbon Country escape.

4.93 out of 5 average rating, 317 reviews

Two outdoor bathtubs are positioned on a wooden deck, surrounded by trees and views of the creek. An Adirondack chair sits nearby, providing a space for relaxation while enjoying the natural surroundings.

Treehouse in Georgetown

KY’s #1 Wishlisted Stay-Treehouse and outdoor tubs

Escape to Kentucky’s 2026 most wishlisted Airbnb! A romantic treetop getaway with two outdoor tubs, twinkle lights, and a peaceful setting made for reconnecting. The treehouse features a large glass rolling garage door allowing stunning views of the sunset. The highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station ✔ Hot Water

4.97 out of 5 average rating, 143 reviews

A well-maintained backyard area is highlighted by a green hammock suspended between trees. The brick apartment is elevated with a wooden deck and stairs leading to the entrance. Surrounding the space, manicured shrubs and grass create a peaceful outdoor environment.

Guest house in Frankfort

Treetop Hideaway

Fully equipped apartment, only 5 blocks from the state Capitol in historic, tree-lined neighborhood. Kentucky Derby, Horse Park, and Bourbon Trail all close. Real pricing - no hidden fees! Downtown restaurants, entertainment, & distilleries are only minutes away by car or foot. Apartment includes everything for short-term or extended stays, including washer/dryer and fully-equipped kitchen. Separate building - totally separate entrance for privacy.

A charming exterior view of a two-story bungalow features blue-green siding and a welcoming front porch. American flags are displayed, while flower beds with various plants enhance the landscaped front yard. The stone walkway leads to the entrance, inviting visitors to approach the home.