Winters Vacations Rentals - Vacation Rentals in Southside

Derby and Downtown From US $233
         

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10.0 (11 Reviews)
House
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  • Parking
  • View
5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo From US $545
         

Bourbon House 1 | Walk to Expo Center From US $371
         

10.0 (48 Reviews)
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  • Air Conditioner
  • Parking
  • TV
Cozy, historic, pet-friendly home! From US $236
         

10.0 (31 Reviews)
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  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Southside

Over 330+ Luxury Places to Stay in or Near Southside
6 Spacious Units Close to Downtown & Expo Center From US $7,650
         

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New
Apartment
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5 Spacious Units Close to Downtown & Expo Center From US $7,633
         

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New
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Southern Parkway Retreat Near Downtown Louisville From US $7,617
         

Spacious 6BR, 10 bed Derby House. Walk to the track. From US $5,228
         

Short Walk to Churchill Downs! From US $2,089
         

New
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  • Pet Friendly
Blue Moon Over My Amy From US $1,515
         

9.8 (18 Reviews)
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  • TV

Top-Rated Vacation Rentals with a Pool in Southside

Over 33+ Top-Rated Vacation Rentals with a Pool in or Near Southside
Homewood Suites By Hilton Louisville Airport From US $126
         

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9.4 (519 Reviews)
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  • Pool
Close to Everything in Louisville! From US $258
         

9.4 (36 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
TownePlace Suites by Marriott Louisville Airport From US $148
         

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9.1 (21 Reviews)
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  • Pet Friendly
Crowne Plaza Louisville Airport Expo Ctr by IHG From US $85
         

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8.8 (1008 Reviews)
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  • Pool
Springhill Suites by Marriott Louisville Airport From US $111
         

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8.8 (1003 Reviews)
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  • Pool
Holiday Inn Louisville Airport South by IHG From US $86
         

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8.8 (774 Reviews)
Hotel
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  • Pool
Residence Inn by Marriott Louisville Airport From US $109
         

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8.8 (688 Reviews)
Hotel
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  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Southside

Over 86+ Pet-Friendly Vacation Rentals in or Near Southside
Stunning Newly Renovated 3BD Loft By Churchill From US $278
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Bedding/Linens
Walk to Churchill Downs Central Louisville Home! From US $203
         

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10.0 (2 Reviews)
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  • Pet Friendly
  • Accessibility
Red Roof Inn Louisville Expo Airport From US $67
         

6.2 (1004 Reviews)
Hotel
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  • Parking
  • Pet Friendly
Cozy Home | Walk to Churchill & Cardinal Stadium! From US $248
         

10.0 (1 Review)
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  • Pet Friendly
2BD Charming Ideally Located Bungalow From US $241
         

10.0 (1 Review)
House
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  • Parking
  • Pet Friendly
Wanderhaus - Eclectic Digs in Louisville From US $199
         

9.8 (47 Reviews)
House
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  • Pet Friendly
  • TV
Lush 3BD Newly Renovated 1st FL By Churchill From US $258
         

9.8 (14 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Sports/Activities
The Camp Taylor Cottage Close to Airport/Downtown From US $192
         

9.6 (46 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Southside

Over 46+ Large Vacation Homes & Villas in or Near Southside
Great Location-5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo From US $422
         

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9.6 (19 Reviews)
House
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  • Parking
  • Balcony/Terrace
Great Location-5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo From US $606
         

The Yellow Door! 5 BR! Near the EXPO & Airport! From US $469
         

10.0 (3 Reviews)
House
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  • Security/Safety
  • Bedding/Linens
Awesome Location for Louisville or Expo Stay! From US $209
         

Prime Derby Location - Firepit - Yard From US $387
         

9.6 (9 Reviews)
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  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Southside

Over 53+ Wheelchair Accessible Vacation Homes in or Near Southside
FRONTDESK The Marshall Campus Apts Louisville From US $229
         

3.8 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Derby City Gaming & Hotel - A Churchill Downs Property From US $140
         

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9.4 (1660 Reviews)
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  • Parking
  • TV
Frontdesk | 2 BR Apt near Churchill Downs From US $773
         

5.0 (1 Review)
Apartment
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  • TV
  • Wheelchair Accessible
Frontdesk | 2 BR Apt near Highland Festival Ground From US $78
         

4.3 (3 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Frontdesk | 2 BR Apt near Cardinal Stadium From US $797
         

4.0 (2 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Frontdesk | 2 BR Apt near The Speed Art Museum From US $718
         

4.0 (2 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Frontdesk | 2 BR Apt near Kentucky Kingdom From US $72
         

3.6 (7 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Southside Varoom and Airbnb Places to Stay Under $200

Over 163+ Southside Varoom and Airbnb Places to Stay Under $200
Room Near Downtown UofL,Airport&ExpoCenter From US $164
         

10.0 (2 Reviews)
House
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  • Parking
  • Pet Friendly
Top Floor Apt Near Churchill Downs & Expo Center From US $170
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
Staybridge Suites Louisville Expo Center by IHG From US $114
         

2BR/1BA Bourbon Bungalow - Expo Center From US $143
         

⭐Close to Churchill Downs, Expo center, Broadbent⭐ From US $106
         

U of L football and horse racing; Walkable! From US $197
         

9.6 (10 Reviews)
House
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  • Parking
  • Security/Safety
Pet-Friendly Louisville Home: Near Distilleries! From US $197
         

9.0 (16 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Walk to Churchill Downs: Central Louisville Home! From US $183
         

8.8 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Southside

Over 121+ Instantly Bookable Vacation Homes in or Near Southside
2BR Home with 3 beds! From US $271
         

New
House
  • Air Conditioner
  • TV
  • Wellness Facilities
Minutes from U of L & Expo Center I Cozy I Updated From US $233
         

The Lucky Horseshoe From US $228
         

10.0 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
4 Mi to Churchill Downs: Updated Retreat w/Deck! From US $269
         

2 Spacious Units Close to Downtown & Expo Center From US $278
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety

About Southside Vacation Rentals

With more than 339 Southside vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Wintersvacationsrentals and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Southside.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Wintersvacationsrentals Southside, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Southside. Places to stay near Southside are 744.44 ft² on average, with prices averaging $382 a night.

Wintersvacationsrentals makes it easy and safe to find and compare vacation rentals in Southside with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Southside

Type Count
Vacation Homes 201
Holiday Apartments 65
Hotels with Suites 59
Villas 2
B&B 1
Cabin Rentals 1
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Southside

Pro Tip: Wintersvacationsrentals makes it easy to compare the best listings on Wintersvacationsrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Wintersvacationsrentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Southside.

Weather in Southside

View the weather forecast for Southside before booking your Southside Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F