Apartment
10.0(13 Reviews)
2 Bedrooms
4 Guests
Kitchen
Air Conditioner
Internet
Laundry
R2,831/Night
7 Nights - R19,818
Middlesboro, KY Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Middlesboro
10.0
House
10.0(7 Reviews)
1 Bedroom
21 Guests
Parking
View- Air Conditioner
- Internet
R4,240/Night
7 Nights - R29,685
Hotel
9.6(749 Reviews)
Breakfast- Parking
Pool
Balcony/Terrace
R3,840/Night
7 Nights - R26,885
House
9.6(43 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,664/Night
7 Nights - R25,651
Apartment
9.5(4 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R2,359/Night
7 Nights - R16,518
House
9.0(8 Reviews)
1 Bedroom
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R6,559/Night
7 Nights - R45,919
House
10.0(35 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,822/Night
7 Nights - R26,751
House
8.0(3 Reviews)
1 Bedroom
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R6,522/Night
7 Nights - R45,652
House
8.0(1 Review)
1 Bedroom
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R5,568/Night
7 Nights - R38,969
Luxury Holiday Rentals in Middlesboro
Over 26+ Luxury Holiday Rentals in or Near Middlesboro
House
1 Bedroom
10 Guests
- Internet
Pet Friendly
Security/Safety
R5,389/Night
7 Nights - R37,719
House
7.4(3 Reviews)
1 Bedroom
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R5,389/Night
7 Nights - R37,719
House
9.8(103 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R4,893/Night
7 Nights - R34,252
House
10.0(19 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R4,869/Night
7 Nights - R34,085
Villa
1 Bedroom
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R3,354/Night
7 Nights - R23,485
House
8.0(5 Reviews)
1 Bedroom
8 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
R3,146/Night
7 Nights - R22,018
R2,943/Night
7 Nights - R20,601
Cottage
9.4(51 Reviews)
2 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R2,803/Night
7 Nights - R19,618
Apartment
9.8(32 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R2,496/Night
7 Nights - R17,468
Top-Rated Holiday Rentals with a Pool in Middlesboro
Over 7+ The Best Private Villas and Holiday Rentals in Middlesboro with a Pool
Hotel
8.8(126 Reviews)
- Breakfast
- Parking
- Pool
- Balcony/Terrace
R2,361/Night
7 Nights - R16,534
R1,585/Night
7 Nights - R11,101
R1,335/Night
7 Nights - R9,351
R1,466/Night
7 Nights - R10,267
R1,314/Night
7 Nights - R9,200
R1,555/Night
7 Nights - R10,884
R1,538/Night
7 Nights - R10,767
Pet-Friendly Holiday Rentals in Middlesboro
Over 6+ Pet-Friendly Holiday Rentals in or Near Middlesboro
House
9.0(43 Reviews)
1 Bedroom
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R1,833/Night
7 Nights - R12,834
Hotel
9.0(305 Reviews)
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
R1,702/Night
7 Nights - R11,917
House
8.8(25 Reviews)
5 Bedrooms
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R10,139/Night
7 Nights - R70,970
House
9.8(6 Reviews)
4 Bedrooms
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R4,547/Night
7 Nights - R31,835
House
4.9(17 Reviews)
3 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
R2,950/Night
7 Nights - R20,651
House
5.0(1 Review)
8 Bedrooms
22 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Pet Friendly
R16,668/Night
7 Nights - R116,673
Large Holiday Rentals and Private Villas in Middlesboro
Over 1+ Large Holiday Rentals and Private Villas in or Near Middlesboro
House
5.0(5 Reviews)
5 Bedrooms
12 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
R8,334/Night
7 Nights - R58,336
Middlesboro Private Villas and Holiday Homes Under $200
Over 2+ Middlesboro Private Villas and Holiday Homes Under $200
House
3 Bedrooms
7 Guests
- Air Conditioner
- Internet
Bedding/Linens
Designated Smoking Area
R2,326/Night
7 Nights - R16,284
R1,850/Night
7 Nights - R12,951
Book a Last Minute Place to Stay in Middlesboro
About Casai's Private Villas and Holiday Rentals in Middlesboro
Discover more than 35 vacation rentals available in Middlesboro. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Middlesboro.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Middlesboro, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Middlesboro. On average, places to stay near Middlesboro offer 2028.26 ft², with nightly prices averaging R4,004.
With Casai, finding and comparing holiday rentals in Middlesboro is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Middlesboro, KY
There are 35 Middlesboro, KY Holiday Rentals
- Prices for a holiday home in Middlesboro start at R1,314
- Top rated vacation home in Middlesboro is 4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
- Most popular short term in Middlesboro is Sleep Inn & Suites Middlesboro
- Cheapest place to stay in Middlesboro is Boone trail inn
- Most expensive holiday rental in Middlesboro is Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Recently Booked Holiday Rentals in Middlesboro
Frequently Asked Questions About Middlesboro?
What are the top holiday rentals in Middlesboro?
With numerous options available in Middlesboro, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Middlesboro:
- 4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
- Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU
- Mountain Views - LMU 1 1/2
- Minutes from LMU, ARH, and Cumberland Gap National Historic Park, Laurel Cove Music Festival, and Pine Mountain State Resort Park
- 1928 Home in the heart of Cumberland Gap
- Luxury Brooklyn St APT - Near LMU & Nat’l Park
- Holiday Inn Express Middlesboro by IHG
- Blissful Bungalow across from LMU campus
- Mountain View Retreat 5 min to LMU
- Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Which holiday homes in Middlesboro are best for families?
If you're searching for a family-friendly holiday home in Middlesboro, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Middlesboro:
How many Casai.co.za holiday rentals are available in Middlesboro?
As of 2026, Casai boasts over 35 properties listed in the Middlesboro area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Middlesboro.
