Vacation rentals in Pioneer Village

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Top-rated vacation rentals in Pioneer Village

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Guest favorite

A magazine featuring Louisville's landmarks is placed on a wooden floor. Above it, a succulent plant sits in a simple pot, adding a touch of greenery to the arrangement. The background is lightly textured, enhancing the overall aesthetic.

Tiny home in Shepherdsville

4.93 out of 5 average rating, 229 reviews

Tiny House Near Louisville

The tiny house is 200 square feet, but has everything you need for a cozy stay! It’s located inside our half acre fenced in backyard which is right off I-65 and is 15 minutes to downtown Louisville. Fast food, restaurants, gas stations, and laundry mat are less than a mile away. The backyard is a shared space with us, so there’s a small chance you see us or our friendly dogs out there. We built the tiny house ourselves, so we take pride in it and hope you choose to experience tiny house living!

Top guest favorite

The kitchen includes modern appliances, including a gas stove and an electric kettle. A large wood dining table is surrounded by metal chairs. A laundry area is visible, with washing and drying machines neatly arranged. Natural light filters in through a window.

Home in Fern Creek

4.99 out of 5 average rating, 178 reviews

"Call Me Old-Fashioned"in Derby & Bourbon Country!

Welcome to "Call Me Old-Fashioned" - a unique spin on Bourbon w/ a mix of new & vintage amenities! Located in a QUIET & SAFE neighborhood, this family-friendly home is located close to Downtown Louisville & Churchill Downs (18 min), Expo Center & airport (15 min). Bardstown, the Bourbon capitol, is 35 min away. We are also 5 min from Parklands @ Floyds Fork park system - home to 60 miles of hiking, biking & paddling trails & a big playground. Come make yourself at home in our cozy KY home!!

Guest favorite

A welcoming porch features a rustic wooden bench adorned with decorative pillows. An American flag flutters in the breeze, while a vintage lantern and baskets add character to the space, surrounded by towering trees and natural woodland scenery.

Cabin in Louisville

4.95 out of 5 average rating, 340 reviews

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.

Top guest favorite

A narrow staircase with wooden steps leads downward, flanked by a stone wall on one side. The natural texture of the stone contrasts with the smooth wood, while a black railing provides support. The descent opens to a light-colored doorway at the bottom.

Cabin in Louisville

5 out of 5 average rating, 213 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.

Guest favorite

The Gladys Airstream is showcased under a covered patio, featuring wooden support beams and string lights. Outdoor seating includes a picnic table and multiple chairs arranged around a fire pit. The surrounding area is landscaped with gravel and green grass.

Camper/RV in Louisville

5 out of 5 average rating, 129 reviews

The Gladys Airstream at Progress Park - Derby City

This is our Gladys Airstream! She is a 2011 International Serenity. She sleeps 4 adults comfortably possibly 5 depending on your comfort level. Theres a queen bed in back, dinette folds to a double and the couch to a F/Q. You'll have a private bath w/shower & a kitchen. You'll also have a covered patio with your own private firepit and grill. Progress Park has a total of 11 units ( 2 houses, 8 airstreams & a bunk house). *DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

Top guest favorite

Guesthouse in Hardinsburg

4.96 out of 5 average rating, 282 reviews

Once Upon a Time little Cabin in the Woods

Welcome to Always Ranch where this unique tiny cabin offers you a tranquil spot to relax. You will be surrounded by nature and off the beaten path. The cabin may look like a lean to but the inside is rustic and warming. We are located 20 minutes form Salem, 20 minutes from Paoli and Paoli Peak, and 35 minutes from Frenchlick Casino The kitchenette includes mini fridge, microwave, double hot plate and, grill on the outdoor firepit or grill. Boats are NOT available for guests at this time

Guest favorite

A uniquely designed sink showcases an ornate, colorful basin with floral patterns. The polished wooden countertop is complemented by a modern black faucet. A small dish containing soap and a towel are neatly arranged beside the sink, with glimpses of a bright and airy interior visible in the background.

Camper/RV in Louisville

4.82 out of 5 average rating, 261 reviews

Pastel Tiny Home • Romantic Retreat on 15 Acres

💖 Escape to your own pastel paradise—perfect for couples or solo dreamers. This periwinkle 200 sq ft Polly Pocket-inspired tiny home sits on 15 private acres in Louisville. Sip coffee at the bar table, cozy up with AC/heat, and stargaze by the fire pit 🔥 on your private deck with glowing lights ✨ Pet-friendly, peaceful, and totally unique—this is more than a stay. It’s a magical escape made for connection, rest, and unforgettable memories. 🌙🌿

Top guest favorite

Dome in Mount Washington

4.98 out of 5 average rating, 169 reviews

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

Guest favorite

An open living space features a wall-mounted TV opposite a sectional sofa. A bar-height dining table with seating for four is positioned beside the sofa. Light walls and large windows contribute to a bright atmosphere, while decorative wall art adds visual interest.

Home in Louisville

4.93 out of 5 average rating, 177 reviews

Parkside Pad - Iroquois Park

Central Location! One bedroom & One Bath Home. This newly updated home offers a 5 minute walk to wonderful Iroquois Park and the charming Beechmont Neighborhood. Short 5 minute drives to Churchill Downs and the University of Louisville, 10 minute drives to the Airport and Fairgrounds/Exposition Center, and 15 minute drives to trendy NuLu, Highlands, and Germantown neighborhoods. This space will offer the best of what Louisville has to offer.

Top guest favorite

The exterior of a brick apartment is displayed, featuring a gabled roof and two prominent windows on the upper level. A two-car garage is visible beneath a covered entryway, with lush greenery framing the structure and partly cloudy skies overhead.

Apartment in Mount Washington

4.95 out of 5 average rating, 201 reviews

“Crossroads” connecting Louisville and Bardstown

This apartment is good for couples, solo adventurer and business travelers. It is 10 miles south of Louisville, 18 miles north of Bardstown, 18 miles west of Taylorsville Lake and 1 hr away from Lexington. It is close to a very cool park, The Parklands, where you can hike, bike and kayak. The apartment is centrally located in the “crossroads” of several really cool communities in horse country, Kentucky.

Superhost

The entrance features a covered porch with a welcoming sign, providing space for seating and relaxation. Large windows allow natural light, while a basketball hoop mounted in the corner adds recreational options. A charcoal grill is available for outdoor cooking.

Guesthouse in Mount Washington

4.77 out of 5 average rating, 432 reviews

Kentucky Derby Guest House

The Kentucky Derby guest house is an affordable place to stay that’s comfortable with plenty of room. Sleeps 6 comfortably with 3 queen beds w/ linens but there is plenty of room for more guests with SELF SUPPLIED air mattresses and bedding, we do not supply them. Great for an overnight stay on a road trip , or a multi day getaway while you’re in Kentucky visiting the Bourbon Trail.

Top guest favorite

A spacious living area features a black leather sectional sofa and a wooden bar with stools. Tile flooring extends throughout the room, which is illuminated by ceiling lights. Walls are decorated with framed artwork, and there are double doors leading to a closet.

Apartment in Shepherdsville

4.91 out of 5 average rating, 126 reviews

For the ones who serve

We decorated and dedicated this place in honor of my father who served in WW2 as a Marine. He passed March of 2020. We have all type of military things along with other unique pieces. We plan on always coming up with more things to change it around. This is a part of a duplex which sits on the property with our wedding venue. Check out our guide book for local attractions and mileage

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Popular amenities for Pioneer Village vacation rentals

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Other great vacation rentals in Pioneer Village

The covered entrance features a white door with a circular window, flanked by a wall of light brown brick. A wooden bench with decorative pillows faces the door, while a colorful nutcracker figure adds a festive touch. A welcome mat is positioned on the concrete walkway.

Home in Louisville

4.79 out of 5 average rating, 77 reviews

2-Bedroom Home, Quiet Area

JaredRating, 5 stars1 month ago

We stayed for 4 months while I completed an internship. My wife, two young children, and I felt very comfortable and at home here. The neighbors were nice. The backyard was convenient and there is a park close enough to walk to. Walmart is about 10 minutes away. If you’re looking for a family friendly place to live away from the big city, but close enough to enjoy visiting, this is a great option.

Top guest favorite

A bright kitchen features white cabinetry and blue accents. The countertop includes modern appliances, with a black stove and a microwave. Natural light enters through a window, highlighting the cooking space. A small dining table is set nearby, and glass doors lead to the outside deck.

Apartment in Brooks

5 out of 5 average rating, 6 reviews

Cozy Studio in Brooks

CRating, 5 stars1 week ago

Wonderful place with a full kitchen, parking spot in right front of the house, and deck area to enjoy. Ron was very responsive and we had a great stay.

Guest favorite

The kitchen features modern stainless steel appliances, including a convection oven and microwave, nestled within dark cabinetry. Gleaming granite countertops complement the sleek design, while a decorative plant adds a touch of natural warmth to the space.

Apartment in Mount Washington

4.88 out of 5 average rating, 26 reviews

The Getaway on Main

KhulanRating, 5 stars2 months ago

It was our first time in Kentucky and we loved it especially because of this place. The neighborhood was very safe and charming and the home itself was cute and cozy! Lori made our trip even more memorable.

Guest favorite

A modern bathroom is displayed, featuring a glass shower enclosure with a marble-patterned wall. A small black mat is positioned in front of the toilet, and white towels are neatly hung on a rack. Natural light enters through the window, enhancing the clean aesthetic.

Guesthouse in Louisville

4.85 out of 5 average rating, 13 reviews

Casita Linda

BrandonRating, 5 stars3 days ago

Place was clean. Justin was responsive when I messaged him. Full kitchen if you need it. It is attached to the house and not a separate building, but it's private and you don't share any space. Bed was comfortable. I bring my own anyway, but no toiletries provided.

A bright bathroom is depicted, featuring a light wood-paneled shower curtain with a vintage blue truck and floral design. Soft towels in green and a light blue rug create a welcoming atmosphere. A white toilet and sink with simple fixtures are also visible.

Home in Shepherdsville

4.67 out of 5 average rating, 3 reviews

Cozy Country House on Bates

JennyRating, 5 stars1 month ago

Kevin and Lisa were super hosts! The house was cozy, clean, and very welcoming. And Kevin is very responsive via the Airbnb messaging app. Also, we actually got to meet the hosts and have a nice conversation. So friendly and helpful! Plus, we were there for Derby weekend, and they took the time to put Derby decorations in the living room and kitchen. So fun and fabulous! The beds were super comfy, and the whole space was inviting and decorated with nice little homey touches. The neighborhood and surroundings were very peaceful and lovely. Plus, even though this Airbnb is slightly out of the way... easy driving distance to downtown Louisville and Churchill Downs. This place was a find! So happy with my stay here! Thank you, Kevin and Lisa!

Guest favorite

A gravel space is surrounded by six brown Adirondack chairs positioned around a fire pit. Flat stones are scattered around the area, enhancing the outdoor ambiance. A wooden shed and additional seating are visible in the background, framed by a wooden fence.

Home in Louisville

5 out of 5 average rating, 6 reviews

Bourbon Boho Bliss

RebeccaRating, 5 stars2 months ago

House was great! Jessica was very accommodating! Thank you for hosting us!

Top guest favorite

Cabin in Frankfort

5 out of 5 average rating, 80 reviews

Bourbon Trail Cabin!~hot tub~hiking~game shed!

JimRating, 5 stars2 days ago

The Bourbon Trail Cabin was perfect for us and our friends to meet halfway between our homes (different states). This was by far the best cabin rental we have ever had from any of the many different rental sites. The attention to detail and the extras made it a wonderful time. The kitchen had everything one could want or need to cook at "home" while staying in the cabin. The little extras is what stood out to us; hair ties, quality bath sundries and a huge assortment of games if you are forced to stay indoors. The attention to detail was excellent and the cleanliness was top notch.

Top guest favorite

A modern kitchen features gray cabinetry with a wooden countertop and stainless steel appliances. A black sink is positioned next to a microwave, and a glass sliding door provides natural light while leading outside.

Guesthouse in Louisville

5 out of 5 average rating, 57 reviews

Breakfast At Tiffany's

RobRating, 5 stars2 weeks ago

I stayed here for a week on a business trip and it was absolutely perfect. really easy to get to, nice quiet neighborhood and perfectly placed to get around the city and surrounding areas. I highly recommend checking out some of the trails and parks on the Louisville loop 😊 I feel like the place actually felt bigger than it looked in the pictures, it was lovely and clean, comfy bed and shower was hot with good water pressure. Tiffany and her husband (so sorry I forgot your name 😭) were great hosts. really responsive to queries and super friendly, but also kept to themselves when I didn't need them so it you prefer privacy then you will also be happy here. If I'm back in town again I will definitely stay here again and highly recommend to anyone who is considering it.

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Vacation rentals in Pioneer Village

Top-rated vacation rentals in Pioneer Village

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