Holiday rentals in Briarwood

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Top-rated holiday rentals in Briarwood

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Home in Prospect

LUX Waterside Retreat|Geo Dome+Outdoor Fire Table

✅Climate controlled GeoDome w/movie screen ✅Fire Table ✅Family+baby friendly👶 ✅Not in a Neighborhood Tucked away on two private acres along Harrods Creek, this beautifully remodeled historic home offers rare privacy, creekside charm, and easy access to Louisville's best attractions. No crowded neighborhoods - just open space, creek views, and boats drifting by. Perfect for bourbon tours, concerts, and Derby weekends, you can explore the area, then return to your own peaceful creekside retreat.

4.98 out of 5 average rating, 130 reviews
Guest favourite
Home in Jeffersontown

Bourbon Trail Estate | 3 Epic Acres | 7 Bed 6 Bath

Welcome to your ultimate Louisville getaway! 🏡 This private 5BR retreat blends space, comfort, and style with unbeatable access to the Bourbon Trail, dining, and attractions—perfect for families or groups. ✨ Spacious 5BR, 5.5BA Retreat – 7 beds (5 Kings) 🛏️ 🍳 3 Full Kitchens + Bar 🎬 Entertainment Room w/ Media System – Perfect for Game Night 🎮 🌳 Private Backyard for Dining & Relaxing 🥃 Quiet setting just minutes from Bourbon Trail, Shopping & Top Attractions A serenity-meets-convenienc

4.93 out of 5 average rating, 14 reviews
Guest favourite
Home in Jeffersonville

Mins to Louisville•2024 Home•Fire Pit•Ping Pong!

Welcome to Your PRIME Stay! in Jeffersonville, minutes from Louisville, Big Four Bridge, Waterfront Park, Churchill Downs, Falls of the Ohio & downtown Jeffersonville. Perfect for Derby travel, concerts, sports, festivals, family trips & exploring the Ohio River with easy access to Louisville dining entertainment & attractions. Home Highlights: ✓ 2024 Home ✓ Private Backyard + Fire Pit ✓ Ping Pong + Cornhole ✓ King Primary Suite ✓ 2-Car Garage ✓ Sleeps Up to 7 ✓ 2 Full Bathrooms ✓ Hulu/Disney+

4.95 out of 5 average rating, 19 reviews
Top guest favourite
Home in Louisville

Newly Renovated 5BR • 2 Living Rooms • Sleeps 10

Stay in a newly renovated 5BR, 3BA Louisville home for up to 10 guests. Enjoy two large living rooms, a dining room that seats 10, and a cozy sitting room that opens to a covered porch for morning coffee or evening chats. A bright walk-out basement adds extra space and light. In a quiet, walkable neighborhood with sidewalks, you’re 1 min to highways, 10 min to Downtown & Churchill Downs, and close to the Bourbon Trail plus the Expo Center/Fairgrounds. Fast Wi-Fi, smart TV, and laundry included.

4.97 out of 5 average rating, 36 reviews
Top guest favourite
A colorful living area is furnished with a patterned sectional sofa and a round glass coffee table. Natural light enters through multiple windows, illuminating the artful wall decor. A kitchenette area with modern appliances is visible in the background, enhancing the space's functionality.
Guest suite in Louisville

Hide away close to everything

Recently remodeled in law suite. We just upgraded the bed to a queen size. Very private, detached garage getaway. A cozy sitting area 60" CableTV with HBO SHOWTIME and STARZ. Wet bar with fridge, ice maker, coffee maker, microwave, hot plate, dishes and some cookware. Private bath has shower and a walk in closet. This private apt. is above the garage. Outside has fenced in yard for your furry friend, outdoor fire pit and sitting area. Close to the interstate and minutes from downtown.

4.95 out of 5 average rating, 330 reviews
Guest favourite
Home in Prospect

Iconic Lighthouse Estate on Scenic Ohio River!

Settle into this spacious 2,200-square-foot Prospect retreat along the Ohio River, accommodating up to 10 guests across a king suite, bunk room, and flexible loft. The home features 2.5 bathrooms, a full galley kitchen with dishwasher and Keurig, a bar family room, and a living room with a smart TV. A private in-home elevator connects the two levels — a rare touch that sets this retreat apart. Five dedicated parking spaces, whole-home Wi-Fi, and in-home laundry complete the package.

4.8 out of 5 average rating, 5 reviews
Guest favourite
A cozy living room is presented with a dark sofa facing a white-brick fireplace. Above the fireplace, a flat-screen television is mounted. Two armchairs flank the fireplace, while a small ottoman completes the seating arrangement. Light-colored drapes frame the windows, and artwork decorates the walls.
Home in Louisville

Private EAST END gem, minutes to everything!

Cozy, East End cottage just minutes from Top Golf, shopping malls, restaurants, entertainment, and other amenities. Easy access to the expressway. Home is well appointed with granite countertops, stainless appliances, hardwood floors, and more. A seasonal creek across from the house can be heard giving the impression of a cabin in the woods with privacy and seclusion, with the convenience of city living at your fingertips. There is also a beautiful park steps away from the house.

4.88 out of 5 average rating, 243 reviews
Guest favourite
Home in Louisville

Louisville Getaway

Escape to a peaceful 3 bedroom, 2 bath home surrounded by woods, ponds, and a creek on one acre of land . Enjoy two spacious living rooms, a full kitchen, and a large backyard with patio perfect for relaxing or entertaining. Bike trails and quiet surroundings make it an ideal getaway for families, friends, or anyone seeking serenity. A 2 car garage adds extra convenience, and you’re just minutes from malls, shopping centers, and great restaurants

4.96 out of 5 average rating, 27 reviews
Top guest favourite
The bedroom features a spacious king-sized bed, adorned with decorative pillows, and a stylish ceiling fan above. A wooden chest sits at the foot of the bed, complemented by a desk and chair in the corner. Natural light enters through window treatments, illuminating the room.
Guest house in Louisville

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 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.)

4.97 out of 5 average rating, 150 reviews
Guest favourite
The entrance features a black door with an oval window, framed by decorative brick. Two potted topiaries are placed alongside the door, while a wicker chair with a patterned cushion sits to one side. Warm outdoor lighting is provided by wall-mounted lanterns.
Home in Louisville

...Happy Trails House in Derby City

4 bedroom, 2 full baths, 1 half bath, ( bedrooms on 2nd floor, none on 1st floor ). Our home is on a dead end street steps away to a walking trail, fenced yard, 2 patios, charcoal grill. Only 15 to 20 min. drive to Downtown, Churchill Downs, Hospitals, Airport, close to major highways. Near restaurants, shopping centers, grocery, liquor store etc. pets welcome with $10 fee per pet per night. Washer/dryer and dishwasher

4.93 out of 5 average rating, 112 reviews
Guest favourite
A colorful living area features a striking red ceiling and vibrant wall art depicting a circus theme. Seating includes a gray sofa, a round dining table, and unique patterned chairs. Large windows allow natural light to fill the space, enhancing the playful decor.
Home in Prospect

CIRCO LOCO - uNCommon Stay

Circo Loco is a fun getaway where any idea is welcome, there is not one too wild. Circo Loco invites you to come embark on a circus adventure of a lifetime. With free access to beautiful community pools, countless parks, and an endless number of unique opportunities in the Norton Commons & Louisville area- we promise you won't be disappointed staying here. This unique place has a style all its own.

4.99 out of 5 average rating, 69 reviews
Top guest favourite
A modern kitchen features white cabinetry and a spacious island with seating for five. The countertops are finished in light stone, complemented by a neutral backsplash. Large windows provide natural light, and stainless steel appliances are neatly integrated into the design.
Flat in Prospect

Cozy Getaway at Norton Commons!

Welcome! This place can accommodate up to 8-10 (or more people). Our aim is to provide a space thats is relaxing and enjoyable. We have all the necessary equipments and utilities including a laundry room, a private garage, a fully equipped kitchen, and so much more! Please contact us for more information to better assist with your stay!

5.0 out of 5 average rating, 32 reviews

Popular amenities for Briarwood holiday rentals