Holiday rentals near Rupp Arena
We found 674 holiday rentals — enter your dates for availability
If you'd like to stay close to Rupp Arena, take a look at private holiday rentals to find the perfect one for your trip. Whether you're staying in a holiday rental with your children and pets or just with friends, you'll find the amenities that you need and want, including parking and a TV. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Rupp Arena
Showing deals for:3 Oct - 10 Oct
Image gallery for Handcrafted Rustic Cabin on the Bourbon Trail
1010 out of 10 rating
Exceptional
(16 reviews)
Handcrafted Rustic Cabin on the Bourbon Trail
Versailles, KY
8% off
Price is AU$2,160
AU$2,160
AU$309 per night
includes taxes & fees
Image gallery for Fully Renovated | Finished Basement | Luxury Beds | Games
1010 out of 10 rating
Exceptional
(64 reviews)
Fully Renovated | Finished Basement | Luxury Beds | Games
Lexington, KY
7% off
Price is AU$7,230
AU$7,230
AU$1,033 per night
includes taxes & fees
Image gallery for Cozy updated home mins to Keeneland & Lexington. Championship Golf Course Views
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Cozy updated home mins to Keeneland & Lexington. Championship Golf Course Views
Nicholasville, KY
8% off
Price is AU$8,056
AU$8,056
AU$1,151 per night
includes taxes & fees
Image gallery for Pool | Hot Tub | Covered Porch | Patio | Game Room
9.89.8 out of 10 rating
Exceptional
(110 reviews)
Pool | Hot Tub | Covered Porch | Patio | Game Room
Lexington, KY
8% off
Price is AU$16,933
AU$16,933
AU$2,419 per night
includes taxes & fees
Image gallery for New 2-bedroom farmhouse on 23 acres of pasture, part of a working horse farm.
1010 out of 10 rating
Exceptional
(21 reviews)
New 2-bedroom farmhouse on 23 acres of pasture, part of a working horse farm.
Cynthiana, KY
13% off
Price is AU$2,867
AU$2,867
AU$410 per night
includes taxes & fees
Image gallery for Peaceful Chevy Chase Retreat
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Peaceful Chevy Chase Retreat
Lexington, KY
8% off
Price is AU$7,646
AU$7,646
AU$1,092 per night
includes taxes & fees
Image gallery for Happy Moo's Fink Family Farm, where cows & guests are free to enjoy our 50 acres
1010 out of 10 rating
Exceptional
(6 reviews)
Happy Moo's Fink Family Farm, where cows & guests are free to enjoy our 50 acres
Versailles, KY
23% off
Price is AU$6,542
AU$6,542
AU$935 per night
includes taxes & fees
Image gallery for Firepit | Outdoor Deck | Great Location
1010 out of 10 rating
Exceptional
(76 reviews)
Firepit | Outdoor Deck | Great Location
Lexington, KY
7% off
Price is AU$5,980
AU$5,980
AU$854 per night
includes taxes & fees
Image gallery for Entire Home in Hamburg!
1010 out of 10 rating
Exceptional
(22 reviews)
Entire Home in Hamburg!
Lexington, KY
7% off
Price is AU$3,520
AU$3,520
AU$503 per night
includes taxes & fees
Image gallery for Bourbon n Horses themed 3B/2Ba home in beautiful Chevy Chase neighborhood!
1010 out of 10 rating
Exceptional
(32 reviews)
Bourbon n Horses themed 3B/2Ba home in beautiful Chevy Chase neighborhood!
Lexington, KY
8% off
Price is AU$4,478
AU$4,478
AU$640 per night
includes taxes & fees
Image gallery for Hot Tub | Great Location | Patio | Grill | Ping Pong
1010 out of 10 rating
Exceptional
(59 reviews)
Hot Tub | Great Location | Patio | Grill | Ping Pong
Lexington, Kentucky
7% off
Price is AU$10,415
AU$10,415
AU$1,488 per night
includes taxes & fees
Image gallery for 🏇🏼Equestrian & Bourbon Central🥃 👑The Kingston👑 Near Fasig-Tipton & KYSHP🐴
1010 out of 10 rating
Exceptional
(13 reviews)
🏇🏼Equestrian & Bourbon Central🥃 👑The Kingston👑 Near Fasig-Tipton & KYSHP🐴
Lexington, KY
6% off
Price is AU$3,980
AU$3,980
AU$569 per night
includes taxes & fees
Image gallery for World Class Horse Farm Minutes To Keeneland, Bluegrass Airport, Bourbon Trail
9.89.8 out of 10 rating
Exceptional
(94 reviews)
World Class Horse Farm Minutes To Keeneland, Bluegrass Airport, Bourbon Trail
Lexington, KY
15% off
Price is AU$4,888
AU$4,888
AU$698 per night
includes taxes & fees
Image gallery for Great Location | Patio | Grill | Tempurpedic Beds
9.89.8 out of 10 rating
Exceptional
(29 reviews)
Great Location | Patio | Grill | Tempurpedic Beds
Lexington, Kentucky
7% off
Price is AU$3,344
AU$3,344
AU$478 per night
includes taxes & fees
Image gallery for Lexington Fun Zone! Pool! HotTub! Arcade! Games!
1010 out of 10 rating
Exceptional
(9 reviews)
Lexington Fun Zone! Pool! HotTub! Arcade! Games!
Lexington, KY
8% off
Price is AU$8,806
AU$8,806
AU$1,258 per night
includes taxes & fees
Image gallery for Cozy, Comfortable & Convenient
9.49.4 out of 10 rating
Exceptional
(36 reviews)
Cozy, Comfortable & Convenient
Lexington, KY
7% off
Price is AU$3,311
AU$3,311
AU$473 per night
includes taxes & fees
Image gallery for Shipping Container Cabin - The Tuck
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Shipping Container Cabin - The Tuck
Lexington, KY
7% off
Price is AU$1,334
AU$1,334
AU$191 per night
includes taxes & fees
Image gallery for Historic Paris Livery Home of Kentucky's Covered Bridge Tour
8.68.6 out of 10 rating
Excellent
(7 reviews)
Historic Paris Livery Home of Kentucky's Covered Bridge Tour
Paris, KY
8% off
Price is AU$2,306
AU$2,306
AU$329 per night
includes taxes & fees
Image gallery for Bourbon Chaser- Horse Park 12min, Ark 30min, Hot Tub, 4 Bedrooms, Walk Downtown
1010 out of 10 rating
Exceptional
(24 reviews)
Bourbon Chaser- Horse Park 12min, Ark 30min, Hot Tub, 4 Bedrooms, Walk Downtown
Georgetown, KY
8% off
Price is AU$3,974
AU$3,974
AU$568 per night
includes taxes & fees
Image gallery for NEW! Fire Pit, Downtown, Walkable, King Bed, Pet-Friendly, Near Horse Park.
1010 out of 10 rating
Exceptional
(5 reviews)
NEW! Fire Pit, Downtown, Walkable, King Bed, Pet-Friendly, Near Horse Park.
Georgetown, KY
16% off
Price is AU$7,530
AU$7,530
AU$1,076 per night
includes taxes & fees
Image gallery for "The Meridian" Modern Stay near Downtown / Airport
9.89.8 out of 10 rating
Exceptional
(27 reviews)
"The Meridian" Modern Stay near Downtown / Airport
Lexington, KY
8% off
Price is AU$4,976
AU$4,976
AU$711 per night
includes taxes & fees
Image gallery for KY Family Comfort Stay
8.88.8 out of 10 rating
Excellent
(24 reviews)
KY Family Comfort Stay
Georgetown, KY
8% off
Price is AU$3,223
AU$3,223
AU$460 per night
includes taxes & fees
Image gallery for Kentucky Dream! 4BR, 3BA, 2Car-G/Covered Backyard Stage, 1-Mile from Rupp!
1010 out of 10 rating
Exceptional
(8 reviews)
Kentucky Dream! 4BR, 3BA, 2Car-G/Covered Backyard Stage, 1-Mile from Rupp!
Lexington, KY
8% off
Price is AU$31,688
AU$31,688
AU$4,527 per night
includes taxes & fees
Image gallery for 3 BR 2 bath 5 beds! sleeps 8. Pool, hot tub oasis in LEX
9.49.4 out of 10 rating
Exceptional
(15 reviews)
3 BR 2 bath 5 beds! sleeps 8. Pool, hot tub oasis in LEX
Lexington, KY
7% off
Price is AU$5,224
AU$5,224
AU$746 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Rupp Arena
Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
95 reviews(95 reviews)
Location, Location, Location
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
Large Two Bedroom Apartment in Downtown Lexington near Rupp Arena
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
Nature Escape! Unit Near Attractions in GuestHouse Lexington, Parking, Pool!
Sleeps 4 · 1 bedroom · 1 bathroom
8.68.6 out of 10
Excellentexcellent
4 reviews(4 reviews)
This house is a 4 bedroom(s), 3 bathrooms, located in Lexington, KY.
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
72 reviews(72 reviews)
This house is a 3 bedroom(s), 2.5 bathrooms, located in Lexington, KY.
Sleeps 6 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
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