Casa Playa Comforts - Vacation Rentals in Historic South Hill

Lexington Family Home about 2 Miles to UK Campus! From US $136
         

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9.3 (3 Reviews)
House
  • Parking
  • Wheelchair Accessible
  • Child Friendly
Chez Lyndon Manor From US $219
         

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9.6 (122 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
3 Bedroom Downtown Townhouse, Close to All! From US $193
         

Town home with private garage From US $198
         

9.8 (58 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Cozy Downtown Apartment - Steps to UK and Downtown! From US $91
         

Luxury Places to Stay in Historic South Hill

Over 638+ Luxury Places to Stay in or Near Historic South Hill
Historic Mansion in Heart of Downtown Lexington From US $4,016
         

LUX - Downtown Oasis - Pool Table! Free Parking! From US $3,197
         

5.5 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Hot Tub | Close to Downtown | Game Room | Fire Pit | From US $2,351
         

10.0 (72 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Napa Hous - 7BD, 7.5 BA, Bar - Downtown From US $1,524
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Gratz Park Place-Historic District- Walk Downtown From US $1,480
         

10.0 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Upper's Historic Pink Oasis From US $1,402
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Botherum Carriage House, Garden Lovers Delight From US $1,351
         

9.4 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Historic South Hill

Over 51+ Top-Rated Vacation Rentals with a Pool in or Near Historic South Hill
Pool | Hot Tub | Covered Porch | Patio | Game Room From US $796
         

10.0 (121 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Condo downtown Lexington! From US $370
         

9.8 (7 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Hampton Inn Lexington Medical Center From US $141
         

9.4 (1001 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Everhome Suites Lexington - Horse Park From US $108
         

9.4 (495 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Residence Inn by Marriott Lexington City Center From US $223
         

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9.2 (293 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Historic South Hill

Over 253+ Pet-Friendly Vacation Rentals in or Near Historic South Hill
Firepit | Outdoor Deck | Great Location From US $478
         

10.0 (94 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Steps from Downtown UK / Transylvania University From US $154
         

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7.7 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
This apartment is a 2 bedroom(s), 2 bathrooms, located in Lexington, KY. From US $411
         

Hot Tub | Great Location | King Beds | Grill & Patio From US $807
         

10.0 (90 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Golf Simulator | Hot Tub | Game Room | Pool Table From US $1,039
         

10.0 (72 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Hot Tub | Great Location | Patio | Grill | 6 BR From US $708
         

10.0 (69 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Hot Tub | 7 Beds | Fire Pit | Patio & Grill From US $443
         

10.0 (63 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Golf Simulator | Hot Tub | Game Room | Downtown | Patio & Firepit From US $782
         

Large Vacation Homes & Villas in Historic South Hill

Over 73+ Large Vacation Homes & Villas in or Near Historic South Hill
7 Bedrooms | 6.5 Bathrooms | Hot Tub | 10 Beds From US $1,001
         

10.0 (45 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Second Street's Queen Ann From US $866
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Golf Simulator | Hot Tub | Downtown | Game Room | From US $879
         

10.0 (30 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern Cheerful Bluegrass Beauty From US $794
         

10.0 (21 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The Stadium Getaway From US $858
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Historic South Hill

Over 93+ Wheelchair Accessible Vacation Homes in or Near Historic South Hill
Penthouse @ 175 LEX -Walk to Rupp Arena on Main St From US $553
         

10.0 (14 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Candlewood Suites - Lexington - Medical District by IHG From US $107
         

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9.2 (335 Reviews)
Hotel
  • Air Conditioner
  • Pet Friendly
  • TV
The Manchester From US $288
         

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9.6 (1205 Reviews)
Hotel
  • Parking
  • TV
  • Wheelchair Accessible
Bourbon Condo Downtown Lexington From US $258
         

10.0 (12 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Comfort meets luxury in this city condo! From US $508
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Best Downtown Lexington location! + free parking From US $360
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
175 LEX - Walkable Downtown Lexington Condo From US $226
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Historic South Hill Vacation Rentals and Airbnb Places to Stay Under $200

Over 251+ Historic South Hill Vacation Rentals and Airbnb Places to Stay Under $200
Private One Bedroom Apartment in Downtown Lexington near Rupp Arena From US $138
         

10.0 (163 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Elwood Hotel & Suites From US $113
         

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9.4 (1046 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Treetops Solar Sanctuary From US $166
         

10.0 (87 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Graffiti Art Haus - Walk to Central Bank Arena From US $198
         

10.0 (41 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Location location location-#15015318-1 From US $122
         

10.0 (33 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Solar Sanctuarynnn From US $136
         

10.0 (10 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Modern Loft - Parking Included, Walk to Downtown From US $197
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

Instantly Bookable Vacation Homes in Historic South Hill

Over 366+ Instantly Bookable Vacation Homes in or Near Historic South Hill
Lexington Home ~ 2 Mi to University of Kentucky! From US $217
         

Newly Renovated 2BR Apartment w/Free Parking in Downtown From US $377
         

Southern Charm - 2BR - BBQ - Walk to Kroger Field From US $278
         

Charming Kentucky Cottage From US $321
         

10.0 (43 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Historic South Hill Vacation Rentals

With more than 647 Historic South Hill vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Casaplayacomforts 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 Historic South Hill.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Casaplayacomforts Historic South Hill, 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 Historic South Hill. Places to stay near Historic South Hill are 634.2 ft² on average, with prices averaging $322 a night.

Casaplayacomforts makes it easy and safe to find and compare vacation rentals in Historic South Hill 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 Historic South Hill

Type Count
Vacation Homes 364
Holiday Apartments 149
Hotels with Suites 59
B&B 5
Cottages 5
Others 2

Use these Quick Filters to Find a Vacation Rental in Historic South Hill

Pro Tip: Casaplayacomforts makes it easy to compare the best listings on Casaplayacomforts homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Casaplayacomforts 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 Historic South Hill.

Weather in Historic South Hill

View the weather forecast for Historic South Hill before booking your Historic South Hill 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

Historic South Hill Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Historic South Hill?
How many vacation rentals are available in Historic South Hill?

Currently, the total number of properties listed in 2026 is over 647 in the Historic South Hill area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Historic South Hill.