143+ Private Villas and Holiday Rentals in Highland |
Highland Holiday Rentals
10.0
Exceptional
(29 Reviews)
- St. Louis
- Glen Carbon
- 1.37 mi to center
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R3,626/Night
For 7 Nights R25,384
10.0
Exceptional
(1 Review)
1700.7 ft²
9 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Pet Friendly
- Parking
R4,800/Night
For 7 Nights R33,600
9.6
Exceptional
(1016 Reviews)
- Collinsville
- O'Fallon
- 2.28 mi to center
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Pool
- Breakfast
R2,049/Night
For 7 Nights R14,350
10.0
Exceptional
(18 Reviews)
- Collinsville
- Shiloh
- 1.33 mi to center
400 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
R1,498/Night
For 7 Nights R10,483
9.6
Exceptional
(11 Reviews)
454.77 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- View
R2,683/Night
For 7 Nights R18,784
10.0
Exceptional
(6 Reviews)
- Collinsville
- Shiloh
- 1.40 mi to center
1100 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R2,483/Night
For 7 Nights R17,384
10.0
Exceptional
(5 Reviews)
- Carlyle Lake
- Highland
- 1.44 mi to center
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
R5,225/Night
For 7 Nights R36,584
10.0
Exceptional
(5 Reviews)
- Collinsville
- Lebanon
- 0.31 mi to center
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R2,679/Night
For 7 Nights R18,750
10.0
Exceptional
(3 Reviews)
- Carlyle Lake
- Highland
- 1.35 mi to center
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
R5,667/Night
For 7 Nights R39,667
Luxury Holiday Rentals in Highland
Over 134+ Luxury Holiday Rentals in or Near Highland
6.5
Good
(77 Reviews)
- St. Louis
- Glen Carbon
- 2.48 mi to center
204.51 ft²
1 Bathroom
Ocean View
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
R9,133/Night
For 7 Nights R63,934
9.6
Exceptional
(97 Reviews)
- Illinois
- Collinsville
- 1.98 mi to center
22131 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R8,727/Night
For 7 Nights R61,084
9.0
Exceptional
(14 Reviews)
6000 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Hot Tub
- Spa
- Fireplace/Heating
R8,373/Night
For 7 Nights R58,601
8.5
Fabulous
(204 Reviews)
283.45 ft²
1 Bathroom
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Parking
R8,250/Night
For 7 Nights R57,751
9.4
Exceptional
(6 Reviews)
- St. Louis
- Glen Carbon
- 0.28 mi to center
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R8,109/Night
For 7 Nights R56,767
7.5
Very Good
(115 Reviews)
301.39 ft²
3 Bathrooms
Hotel
- Private Pool
- Fireplace/Heating
- Pool
R7,433/Night
For 7 Nights R52,034
10.0
Exceptional
(11 Reviews)
- Carlyle Lake
- Highland
- 1.23 mi to center
3000 ft²
11 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R7,154/Night
For 7 Nights R50,084
7.0
Very Good
(188 Reviews)
290.63 ft²
4 Bathrooms
Free Cancellation
Hotel
- Private Pool
- Fireplace/Heating
- Pool
R6,283/Night
For 7 Nights R43,984
10.0
Exceptional
(73 Reviews)
- Carlyle Lake
- Highland
- 1.64 mi to center
14 Guests
7 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R6,010/Night
For 7 Nights R42,067
Top-Rated Holiday Rentals with a Pool in Highland
Over 46+ The Best Private Villas and Holiday Rentals in Highland with a Pool
9.6
Exceptional
(1003 Reviews)
- Illinois
- Collinsville
- 1.64 mi to center
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
R2,127/Night
For 7 Nights R14,883
9.6
Exceptional
(33 Reviews)
- Collinsville
- O'Fallon
- 2.03 mi to center
466.43 ft²
3 Bathrooms
Ocean View
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
R2,633/Night
For 7 Nights R18,434
9.4
Exceptional
(750 Reviews)
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
R2,164/Night
For 7 Nights R15,150
9.4
Exceptional
(571 Reviews)
- Illinois
- Collinsville
- 1.59 mi to center
322.02 ft²
12 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
R2,633/Night
For 7 Nights R18,434
9.2
Exceptional
(849 Reviews)
- St. Louis
- Edwardsville
- 3.78 mi to center
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
R2,990/Night
For 7 Nights R20,934
9.2
Exceptional
(831 Reviews)
- Collinsville
- O'Fallon
- 1.87 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
R1,891/Night
For 7 Nights R13,233
9.0
Exceptional
(1001 Reviews)
- Collinsville
- Mascoutah
- 6.38 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
R2,081/Night
For 7 Nights R14,567
9.0
Exceptional
(199 Reviews)
- St. Louis
- Edwardsville
- 3.94 mi to center
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
R3,526/Night
For 7 Nights R24,684
9.0
Exceptional
(138 Reviews)
- Collinsville
- O'Fallon
- 2.03 mi to center
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
R2,358/Night
For 7 Nights R16,500
Pet-Friendly Holiday Rentals in Highland
Over 34+ Pet-Friendly Holiday Rentals in or Near Highland
9.6
Exceptional
(7 Reviews)
- Collinsville
- Shiloh
- 0.85 mi to center
930 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R1,798/Night
For 7 Nights R12,583
8.7
Fabulous
(372 Reviews)
365.97 ft²
1 Bathroom
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
R1,976/Night
For 7 Nights R13,833
7.8
Very Good
(1003 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
R1,257/Night
For 7 Nights R8,800
9.4
Exceptional
(51 Reviews)
- Collinsville
- Caseyville
- 1.49 mi to center
700 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R3,177/Night
For 7 Nights R22,234
8.6
Fabulous
(199 Reviews)
- Collinsville
- O'Fallon
- 1.87 mi to center
301.39 ft²
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Pool
- Pet Friendly
R2,317/Night
For 7 Nights R16,217
10.0
Exceptional
(7 Reviews)
- Carlyle Lake
- Highland
- 1.54 mi to center
1400 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
R5,917/Night
For 7 Nights R41,417
9.8
Exceptional
(27 Reviews)
- St. Louis
- Edwardsville
- 1.69 mi to center
1700 ft²
9 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
R5,125/Night
For 7 Nights R35,884
9.6
Exceptional
(113 Reviews)
- Illinois
- Collinsville
- 1.98 mi to center
1100 ft²
9 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R3,735/Night
For 7 Nights R26,150
10.0
Exceptional
(2 Reviews)
- Collinsville
- Caseyville
- 1.06 mi to center
1000 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R1,772/Night
For 7 Nights R12,400
Large Holiday Rentals and Private Villas in Highland
Over 7+ Large Holiday Rentals and Private Villas in or Near Highland
10.0
Exceptional
(2 Reviews)
- Collinsville
- Lebanon
- 1.31 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R2,826/Night
For 7 Nights R19,784
New
- Carlyle Lake
- Greenville
- 1.41 mi to center
10 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Parking
- Air Conditioner
R3,134/Night
For 7 Nights R21,934
10.0
Exceptional
(177 Reviews)
- Collinsville
- Lebanon
- 0.36 mi to center
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Villa
- Fireplace/Heating
- Kitchen
- Parking
R2,385/Night
For 7 Nights R16,684
10.0
Exceptional
(19 Reviews)
- Carlyle Lake
- Breese
- 0.22 mi to center
3000 ft²
8 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R5,520/Night
For 7 Nights R38,634
7.0
Very Good
(8 Reviews)
- Collinsville
- New Baden
- 3.62 mi to center
10 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pet Friendly
R5,482/Night
For 7 Nights R38,384
10.0
Exceptional
(1 Review)
- Illinois
- Clinton County
- 5.78 mi to center
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Bed & Breakfast
- Child Friendly
R4,583/Night
For 7 Nights R32,084
New
- Carlyle Lake
- Highland
- 1.62 mi to center
12 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
House
- Child Friendly
R6,667/Night
For 7 Nights R46,667
Wheelchair Accessible Holiday Homes in Highland
Over 32+ Wheelchair Accessible Holiday Homes in or Near Highland
4.5
Average
(2 Reviews)
- Collinsville
- O'Fallon
- 2.69 mi to center
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- View
- Kitchen
- Air Conditioner
R2,917/Night
For 7 Nights R20,417
8.9
Fabulous
(108 Reviews)
519.74 ft²
14 Bathrooms
Ocean View
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
R3,733/Night
For 7 Nights R26,134
8.6
Fabulous
(686 Reviews)
- St. Louis
- Edwardsville
- 3.90 mi to center
1 Bathroom
Family Friendly
Hotel
- Balcony/Terrace
- Breakfast
- Kitchen
R2,664/Night
For 7 Nights R18,650
8.7
Fabulous
(145 Reviews)
- St. Louis
- Edwardsville
- 3.81 mi to center
328.3 ft²
10 Bathrooms
Ocean View
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
R2,623/Night
For 7 Nights R18,367
8.4
Excellent
(591 Reviews)
- Collinsville
- O'Fallon
- 2.17 mi to center
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
R2,257/Night
For 7 Nights R15,800
8.2
Excellent
(129 Reviews)
301.39 ft²
12 Bathrooms
Hotel
- Private Pool
- Oceanfront
- Spa
R2,233/Night
For 7 Nights R15,634
8.4
Excellent
(432 Reviews)
- Carlyle Lake
- Greenville
- 2.90 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
R1,740/Night
For 7 Nights R12,183
8.1
Excellent
(242 Reviews)
- Litchfield
- Staunton
- 2.13 mi to center
363.28 ft²
4 Bathrooms
Free Cancellation
Hotel
- Fireplace/Heating
- Pet Friendly
- Parking
R1,472/Night
For 7 Nights R10,300
7.9
Very Good
(82 Reviews)
322.92 ft²
8 Bathrooms
Hotel
- Private Pool
- Fireplace/Heating
- Pool
R2,087/Night
For 7 Nights R14,617
Highland Private Villas and Holiday Homes Under $200
Over 75+ Highland Private Villas and Holiday Homes Under $200
9.8
Exceptional
(14 Reviews)
- Collinsville
- Lebanon
- 0.25 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
R2,508/Night
For 7 Nights R17,567
8.2
Excellent
(63 Reviews)
- Carlyle Lake
- Greenville
- 2.16 mi to center
150.69 ft²
3 Bathrooms
Family Friendly
Hotel
- Parking
- Air Conditioner
- Internet
R825/Night
For 7 Nights R5,783
8.8
Fabulous
(22 Reviews)
- Carlyle Lake
- Pocahontas
- 0.88 mi to center
1 Bathroom
Family Friendly
Hotel
- Parking
- Internet
- Child Friendly
R1,505/Night
For 7 Nights R10,533
9.8
Exceptional
(8 Reviews)
- Collinsville
- Shiloh
- 1.19 mi to center
1 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R1,451/Night
For 7 Nights R10,150
7.9
Very Good
(39 Reviews)
- St. Louis
- Edwardsville
- 3.96 mi to center
426.97 ft²
6 Bathrooms
Family Friendly
Hotel
- Private Pool
- Pool
- Pet Friendly
R3,022/Night
For 7 Nights R21,150
New
- St. Louis
- Edwardsville
- 2.80 mi to center
700 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
R1,984/Night
For 7 Nights R13,883
New
- St. Louis
- Edwardsville
- 2.80 mi to center
700 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
R1,692/Night
For 7 Nights R11,833
New
- St. Louis
- Edwardsville
- 2.80 mi to center
700 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
R1,593/Night
For 7 Nights R11,150
New
- Carlyle Lake
- Greenville
- 2.16 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Kitchen
R1,830/Night
For 7 Nights R12,817
Instantly Bookable Holiday Homes in Highland
Over 29+ Instantly Bookable Holiday Homes in or Near Highland
New
- Carlyle Lake
- Greenville
- 2.16 mi to center
3 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Kitchen
R5,077/Night
For 7 Nights R35,534
New
- Carlyle Lake
- Greenville
- 2.16 mi to center
3 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Kitchen
R5,042/Night
For 7 Nights R35,300
New
- Carlyle Lake
- Greenville
- 2.16 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Kitchen
R1,681/Night
For 7 Nights R11,767
10.0
Exceptional
(16 Reviews)
- Collinsville
- Shiloh
- 1.32 mi to center
1100 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
R2,253/Night
For 7 Nights R15,767
9.6
Exceptional
(17 Reviews)
- St. Louis
- Edwardsville
- 1.62 mi to center
6 Guests
3 Bedrooms
1 Bathroom
Apartment
- Child Friendly
- Security/Safety
R2,744/Night
For 7 Nights R19,200
8.0
Excellent
(5 Reviews)
- St. Louis
- Glen Carbon
- 0.33 mi to center
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R4,565/Night
For 7 Nights R31,950
10.0
Exceptional
(3 Reviews)
- Carlyle Lake
- Greenville
- 1.41 mi to center
1860 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
R3,435/Night
For 7 Nights R24,050
10.0
Exceptional
(1 Review)
- Carlyle Lake
- Greenville
- 1.41 mi to center
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
R3,027/Night
For 7 Nights R21,184
New
- Carlyle Lake
- Greenville
- 2.16 mi to center
2 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Kitchen
R3,379/Night
For 7 Nights R23,650
Book a Last Minute Place to Stay in Highland
About Casai's Private Villas and Holiday Rentals in Highland
Discover more than 143 vacation rentals available in Highland. 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 Highland.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Highland, 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 Highland. On average, places to stay near Highland offer 521.87 ft², with nightly prices averaging R2,851.
With Casai, finding and comparing holiday rentals in Highland is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Highland
| Type | Count |
|---|---|
| Vacation Homes | 32 |
| Holiday Apartments | 23 |
| Cottages | 2 |
| Villas | 2 |
Use these Quick Filters to Find a Holiday Rental in Highland
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Highland.
Weather in Highland, IL
View the weather forecast for Highland before booking your Highland 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
Top Attractions Around Highland, IL
Casai offers a large selection of top attractions around Highland . Research things to do on your vacation before you visit Highland.
Other Places to Stay in Highland, IL
Frequently Asked Questions About Highland?
What are the top holiday rentals in Highland?
With numerous options available in Highland, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Highland:
- Quiet villa located one block from McKendree University in Lebanon Illinois.
- Craftsman styled home in the heart of downtown Highland
- Sunset Cottage - Entire home downtown Glen Carbon
- Walking distance to Breese Legion and Main st
- The Hangar - Healthcare/Military friendly!
- Skyline - Military/Family Friendly
- LARGE 3000 sq. ft Newly Renovated Upstairs Loft - Ideal Families & Friend
- The Loft on the Square
- The PanAm Flat - 2bed/2bath next to hospitals & Scott AFB
- The Swiss Post Apartment B
How many holiday rentals have private pools in Highland?
Discover a selection of holiday rentals with private pools near Highland with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Hilton Garden Inn St. Louis Shiloh/O'Fallon IL
- Super 8 by Wyndham Troy IL/St. Louis Area
- SureStay Hotel by Best Western Greenville
- Seasons Inn & Suites Highland
Which holiday homes in Highland are best for families?
If you're searching for a family-friendly holiday home in Highland, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Highland:
- Stay in the heart of downtown Highland in this spacious luxury loft!
- Urban Collective Boutique Hotel
- Super 8 by Wyndham Staunton
How many Casai.co.za holiday rentals are available in Highland?
As of 2026, Casai boasts over 143 properties listed in the Highland area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Highland.
People Also Ask
Finding the best prices in Highland
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