
Holiday rentals in Shively
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Top-rated holiday rentals in Shively
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

4th Street Suites - Opulent King Bed Suite
Live the best of Louisville in this sleek 1‑bed, 1‑bath downtown retreat! Perfect for couples, families, or friends, it features a cozy king bed, pullout couch, a fully stocked kitchen, and a bright living area. Wake up to city sights, stroll to restaurants and bars, then relax by the pool or hot tub, play a round in the golf simulator, or unwind with a game of pool in the clubhouse. This is your launchpad for adventure—or a quiet, stylish escape when it’s time to rest. Come make it yours!

The House with the Orange Door
Located near Churchill Downs, UofL, downtown, the Convention Center and Fairgrounds, and a short distance to restaurants, bars and coffee shops. This single family home offers two bedrooms with queen beds and a pull-out couch in the living room. Enjoy coffee or a relaxing evening cocktail on the back deck. The kitchen is fully equipped and the open living space provides a great area for socializing. Locally made art and decor is on display, adding to the uniqueness of the space.

Bourbon City Loft - Free downtown parking!
If this loft is booked, please check out my other listings... https://www.airbnb.com/h/derby-city-loft https://www.airbnb.com/h/river-city-loft Spacious 950 sq. ft. loft located in the heart of downtown Louisville. Walking distance to shops, restaurants, bars and 1 block from 4th Street Live! You'll be 4 blocks from the YUM! Center, 2 blocks from the Kentucky International Convention Center, and less than 10 minutes from Churchill Downs! Free parking in a secured parking garage!

Limerick Carriage Company - Happy Fall, Ya'll!
The Carriage House is ready for your fall stay! Our Carriage House is warm and inviting to guests from all over. We are located close to downtown, Central Park, UofL, & the Bardstown Road corridor. There are many unique shops, restaurants, bars, & places to visit close by, and some are walkable in warmer weather. The Carriage House has undergone a complete renovation - we hope you love it as much as we do! Don’t let the outside fool you - the inside of our home is the treasure!

Basement Apartment in Germantown
Come stay in our rustic studio apartment with driveway parking in Schnitzelburg/Germantown, home to Monnik Beer Company, Nachbar, the Merryweather, and the Post. We’ve brought a little of our old home in East Tennessee to our new home in Louisville. This guest space features reclaimed wood from a barn Perry took down in Seymour, TN.; a stock tank shower; a refurbished farmhouse sink; a tobacco stake star wall hanging; and some Yee-haw Industries prints, straight from Knoxville.

DerbyLoft Louisville
Enjoy the best of Louisville in our second floor loft, a studs-up renovation with modern amenities, full kitchen, and a beautiful bathroom. We're in a central location from which guests can easily tour the heart of Louisville. Private entrance Free parking on street Free Wifi 10min (0.5mi) walk to Churchill Downs 25min (1.5mi) walk to Cardinal Stadium 5min (1.8mi) drive to historic Old Louisville 6min (1.9mi) drive to KY Expo Center 12min (3.2mi) drive to Louisville Airport

Bourbon Trail Spacious Backyard NEW HotTub Grill!
“A beautiful home to stay in. Very close to a lot of fun things and good places to eat!” Shannon Oct’24. “This home is gorgeous! The bed was extremely comfortable and the location was in a chill neighborhood that was quite walkable. This is a great spot to stay in Louisville!” Luke Oct ‘24 Highly recommended by guests! The house also features modern amenities, a cozy atmosphere, and easy access to public transportation, making it ideal for both short and long stays.

Delectable Delor
Private section of home. There are no shared spaces, so you have privacy, but I do live on the other side of the house which is divided by a locked door. You have your own entrance through the front door, and off street parking. My entrance is the back of the house through the gate, which is off limits. Please be aware that 2 cats live on my side of the house, for those of you with allergies, but they won't have access to your space when you’re there.

Parkside Pad - Iroquois Park
Central Location! One bedroom & One Bath Home. This 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.

Nulu/Butchertown 2 BR, along urban bourbon trail
Welcome to MARE on Washington, our Nulu/ Butchertown condo. We are located just steps away from the best food, drinks, and events in the derby city. We are located on a quiet street, only one block away from Main St. You can walk to breweries next door or even a soccer game at Lynn Family Stadium. The Yum Center is only a few blocks away, and we have one of the few properties located walking distance from Waterfront Park.

Germantown Carriage House w/garage
Germantown is a quaint neighborhood revitalized with restaurants, coffee shops and pubs. The carriage house has all the amenities for any length of stay, including garage parking with room for bikes. Only 2 miles from downtown Louisville, Germantown is nestled between the energetic and historic Highlands neighborhood, beautiful historic Old Louisville, and hipster NULU. Keyless entry makes for seamless check in and out.
Popular amenities for Shively holiday rentals
Other great holiday rentals in Shively

cellar hideaway

TINY WUNDERHAUS - A Fun, Hometown Experience

Iroquois Park Retreat Near Expo Center and Airport

Beautiful space with a garage.

✦ Near Expo ✦ Downtown ✦ Churchill ✦ Updated

Last Minute Booking for 1 or 2!

Adorable 2 BR - WALK to The Kentucky Derby!

Action City! Extravaganza at Bardstown Rd!
When is the best time to visit Shively?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $111 SGD | $124 SGD | $131 SGD | $144 SGD | $194 SGD | $124 SGD | $134 SGD | $124 SGD | $190 SGD | $169 SGD | $159 SGD | $159 SGD |
| Avg. temp | 2°C | 4°C | 9°C | 15°C | 20°C | 25°C | 27°C | 26°C | 22°C | 16°C | 9°C | 4°C |
Frequently Asked Questions
Where should I stay in Shively?
Make yourself at home in Shively by choosing from our most frequently booked neighborhoods. We have over 270 vacation rentals in St. Dennis, over 290 vacation rentals in Shively, and over 270 vacation rentals in Taylor Berry.
Do house rentals in Shively have wifi?
Absolutely! We offer over 20 house rentals with wifi in Shively. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Shively have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Shively. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Shively?
Experience the best of Shively with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Shively have free parking?
Absolutely! We offer over 20 house rentals with free parking in Shively. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Shively have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Shively. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Shively?
Shively has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Shively?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 20 homes with wifi, over 20 homes with air conditioning, over 20 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Shively

Total holiday rentals
Explore 30 holiday rentals in Shively

Nightly prices starting at
Shively holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 830 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Shively holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Shively rentals

4.8 Average rating
Shively stays are highly rated by guests – averaging 4.8 out of 5!
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- Kentucky Kingdom & Hurricane Bay
- Kentucky Derby Museum
- Valhalla Golf Club
- Muhammad Ali Center
- Angel's Envy Distillery
- Louisville Slugger Field
- Louisville Slugger Museum & Factory
- Heritage Hill Golf Club
- Charlestown State Park
- Falls of the Ohio State Park
- Turtle Run Winery
- Big Four Bridge
- Kentucky Science Center
- Waterfront Park
- River Run Family Water Park
- Frazier History Museum
- Big Spring Country Club
- Evan Williams Bourbon Experience
- Rising Sons Home Farm Winery
- Bruners Farm and Winery
- Best Vineyards
- McIntyre's Winery
- Hurstbourne Country Club




