Scroll through and discover holiday rentals within easy reach of Historic Frankfort Avenue that can be your home away from home. Whether you're going on holiday with family or friends, holiday homes have the amenities that you need and want for your stay, such as parking and air conditioning. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Showing deals for:12 Feb - 19 Feb
Image gallery for Castle St Matthews
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Castle St Matthews
Louisville
8% off
Price is S$11,785
S$11,785
for 7 nights, 1 home
S$1,684 per night
includes taxes & fees
Image gallery for Spacious 5BR Getaway – Pool, Patios & Fun
9.49.4 out of 10, Exceptional, (26 reviews)
Exceptional
(26 reviews)
Spacious 5BR Getaway – Pool, Patios & Fun
Louisville
8% off
Price is S$9,831
S$9,831
for 7 nights, 1 home
S$1,404 per night
includes taxes & fees
Image gallery for Large Home - Bar - Hot Tub - Private Back Yard
1010 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Large Home - Bar - Hot Tub - Private Back Yard
Louisville
8% off
Price is S$9,281
S$9,281
for 7 nights, 1 home
S$1,326 per night
includes taxes & fees
Image gallery for Riverfront | Hot Tub, Sauna & Theater
1010 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)
Riverfront | Hot Tub, Sauna & Theater
Jeffersonville
8% off
Price is S$11,350
S$11,350
for 7 nights, 1 home
S$1,621 per night
includes taxes & fees
Image gallery for Luxury Derby Mansion | Speakeasy & Games
1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Luxury Derby Mansion | Speakeasy & Games
Louisville
15% off
Price is S$7,109
S$7,109
for 7 nights, 1 home
S$1,016 per night
includes taxes & fees
Image gallery for Lovely Gem in the Vibrant Highlands close to it all!
8.88.8 out of 10, Excellent, (10 reviews)
Excellent
(10 reviews)
Lovely Gem in the Vibrant Highlands close to it all!
Louisville
8% off
Price is S$8,224
S$8,224
for 7 nights, 1 home
S$1,175 per night
includes taxes & fees
Image gallery for Beautiful views and sunrises overlooking the water. Spacious home with elevator.
9.89.8 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Beautiful views and sunrises overlooking the water. Spacious home with elevator.
Jeffersonville
16% off
Price is S$5,308
S$5,308
for 7 nights, 1 home
S$758 per night
includes taxes & fees
Image gallery for Luxury Victorian | Speakeasy & Hot Tub
1010 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Luxury Victorian | Speakeasy & Hot Tub
Louisville
15% off
Price is S$7,252
S$7,252
for 7 nights, 1 home
S$1,036 per night
includes taxes & fees
Image gallery for NuLu 5BR | Walk to Bourbon Trail | Sleeps 12
1010 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)
NuLu 5BR | Walk to Bourbon Trail | Sleeps 12
Louisville
12% off
Price is S$6,460
S$6,460
for 7 nights, 1 home
S$923 per night
includes taxes & fees
Image gallery for Safe, scenic, and convenient. Bordering a State Park!
1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Safe, scenic, and convenient. Bordering a State Park!
Louisville
13% off
Price is S$4,916
S$4,916
for 7 nights, 1 home
S$702 per night
includes taxes & fees
Image gallery for ❤️Stay at Peppermint Cottage - Norton Commons -Walk eat & shop- free breakfast
1010 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)
❤️Stay at Peppermint Cottage - Norton Commons -Walk eat & shop- free breakfast
Prospect
16% off
Price is S$3,636
S$3,636
for 7 nights, 1 home
S$519 per night
includes taxes & fees
Image gallery for Historic Whiskey Row Loft | 5BR Skyline Views
9.49.4 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Historic Whiskey Row Loft | 5BR Skyline Views
Louisville
12% off
Price is S$6,677
S$6,677
for 7 nights, 1 apartment
S$954 per night
includes taxes & fees
Image gallery for New Modern Construction Home Near Everything!
1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
New Modern Construction Home Near Everything!
Jeffersonville
8% off
Price is S$3,833
S$3,833
for 7 nights, 1 villa
S$548 per night
includes taxes & fees
Image gallery for The Cozy Bungalow-Historic Highlands-Bardstown Rd
1010 out of 10, Exceptional, (131 reviews)
Exceptional
(131 reviews)
The Cozy Bungalow-Historic Highlands-Bardstown Rd
Louisville
8% off
Price is S$4,401
S$4,401
for 7 nights, 1 home
S$629 per night
includes taxes & fees
Image gallery for Churchill Downs, Music Festivals, U of L Sports; Walkable!
9.89.8 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)
Churchill Downs, Music Festivals, U of L Sports; Walkable!
Louisville
16% off
Price is S$2,577
S$2,577
for 7 nights, 1 home
S$368 per night
includes taxes & fees
Image gallery for 3-bedroom condo in Norton Commons
1010 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
3-bedroom condo in Norton Commons
Prospect
8% off
Price is S$3,157
S$3,157
for 7 nights, 1 apartment
S$451 per night
includes taxes & fees
Image gallery for Charming 4 bedroom home minutes from Downtown!
9.89.8 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Charming 4 bedroom home minutes from Downtown!
Jeffersonville
17% off
Price is S$2,610
S$2,610
for 7 nights, 1 home
S$373 per night
includes taxes & fees
Image gallery for Buddha's Bungalow above the Highlands
1010 out of 10, Exceptional, (31 reviews)
Exceptional
(31 reviews)
Buddha's Bungalow above the Highlands
Louisville
7% off
Price is S$2,397
S$2,397
for 7 nights, 1 apartment
S$342 per night
includes taxes & fees
Image gallery for River City Retreat
9.49.4 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)
River City Retreat
Jeffersonville
8% off
Price is S$2,273
S$2,273
for 7 nights, 1 home
S$325 per night
includes taxes & fees
Image gallery for Elegant Home Steps to Restaurant Row!
1010 out of 10, Exceptional, (175 reviews)
Exceptional
(175 reviews)
Elegant Home Steps to Restaurant Row!
Louisville
7% off
Price is S$2,085
S$2,085
for 7 nights, 1 home
S$298 per night
includes taxes & fees
Image gallery for Captain's Annex; close to Bourbon Trail and Churchill Downs, far from ordinary!
9.89.8 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)
Captain's Annex; close to Bourbon Trail and Churchill Downs, far from ordinary!
Louisville
6% off
Price is S$1,517
S$1,517
for 7 nights, 1 home
S$217 per night
includes taxes & fees
Image gallery for Waterfront Apartment, Directly on The Ohio River - 2nd floor unit
1010 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
Waterfront Apartment, Directly on The Ohio River - 2nd floor unit
Jeffersonville
8% off
Price is S$1,787
S$1,787
for 7 nights, 1 apartment
S$255 per night
includes taxes & fees
Image gallery for Big 4 Cottage
1010 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
Big 4 Cottage
Jeffersonville
8% off
Price is S$1,817
S$1,817
for 7 nights, 1 home
S$260 per night
includes taxes & fees
Image gallery for Minutes from Churchill Downs & Downtown Lou!
1010 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Minutes from Churchill Downs & Downtown Lou!
Louisville
8% off
Price is S$2,121
S$2,121
for 7 nights, 1 home
S$303 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Historic Frankfort Avenue
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Find the best place to stay - Historic Frankfort Avenue
Waterfront Romance | Hot Tub & Fireplace
Sleeps 4 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Highlands Lookout-3BR 3.5BA-Walk to Tons +Parking
Sleeps 10 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Equestrian Derby Escape
Sleeps 6 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Charming home walkable to bars & restaurants!
Sleeps 5 · 2 bedrooms · 1 bathroom
8.88.8 out of 10
Excellentexcellent
8 reviews(8 reviews)
Highlands Walkability- Top Restaurants, Nightlife, Shops- PacMan/King Bed
Sleeps 8 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
140 reviews(140 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value