Highland Holiday Rentals
House
- St. Louis
- ·
- Glen Carbon
- 1.39 mi to center
10.0Exceptional
(35 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
CA $286/Night
7 Nights - CA $2,001
House
- St. Louis
- ·
- Edwardsville
- 1.69 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
9 Guests
1700.7 ft²
- Parking
Internet
Pet Friendly
Sports/Activities
CA $395/Night
7 Nights - CA $2,764
Hotel
- Illinois
- ·
- Collinsville
- 1.64 mi to center
9.6Exceptional
(1016 Reviews)
1 Bath
Breakfast- Parking
Pool- Kitchen
CA $177/Night
7 Nights - CA $1,238
Apartment
- Collinsville
- ·
- Shiloh
- 1.33 mi to center
10.0Exceptional
(18 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $127/Night
7 Nights - CA $889
Bed & Breakfast
- Carlyle Lake
- ·
- Breese
- 0.21 mi to center
9.8Exceptional
(9 Reviews)
4 Bedrooms
4 Baths
8 Guests
454.77 ft²
- Parking
- Balcony/Terrace
View- Air Conditioner
CA $223/Night
7 Nights - CA $1,563
Apartment
- Collinsville
- ·
- Shiloh
- 1.40 mi to center
10.0Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $289/Night
7 Nights - CA $2,023
Apartment
- Carlyle Lake
- ·
- Highland
- 1.44 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $514/Night
7 Nights - CA $3,596
House
- Collinsville
- ·
- Lebanon
- 0.31 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $307/Night
7 Nights - CA $2,151
Villa
- Collinsville
- ·
- Lebanon
- 1.24 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $311/Night
7 Nights - CA $2,176
Luxury Holiday Rentals in Highland
Over 129+ Luxury Holiday Rentals in or Near Highland
House
9.0Exceptional
(14 Reviews)
4 Bedrooms
4 Baths
10 Guests
6000 ft²
Hot Tub- Parking
Spa
Ocean View
CA $936/Night
7 Nights - CA $6,553
House
- Carlyle Lake
- ·
- Highland
- 1.23 mi to center
10.0Exceptional
(13 Reviews)
4 Bedrooms
2 Baths
11 Guests
3000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $808/Night
7 Nights - CA $5,653
House
- Carlyle Lake
- ·
- Highland
- 1.58 mi to center
10.0Exceptional
(83 Reviews)
6 Bedrooms
3 Baths
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $746/Night
7 Nights - CA $5,222
House
- St. Louis
- ·
- Glen Carbon
- 0.28 mi to center
8.6Fabulous
(8 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $645/Night
7 Nights - CA $4,518
House
- Illinois
- ·
- Collinsville
- 1.98 mi to center
9.6Exceptional
(99 Reviews)
3 Bedrooms
2 Baths
12 Guests
2056 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $632/Night
7 Nights - CA $4,428
Hotel
7.5Very Good
(115 Reviews)
3 Baths
301.39 ft²
Private Pool- Parking
- Pool
- Kitchen
CA $618/Night
7 Nights - CA $4,329
Apartment
- Carlyle Lake
- ·
- Highland
- 1.54 mi to center
10.0Exceptional
(9 Reviews)
3 Bedrooms
1 Bath
6 Guests
1400 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $551/Night
7 Nights - CA $3,858
House
- Carlyle Lake
- ·
- Highland
- 1.53 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $547/Night
7 Nights - CA $3,827
House
- St. Louis
- ·
- Edwardsville
- 1.69 mi to center
9.8Exceptional
(32 Reviews)
3 Bedrooms
2 Baths
9 Guests
1700 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $529/Night
7 Nights - CA $3,705
Top-Rated Holiday Rentals with a Pool in Highland
Over 46+ The Best Private Villas and Holiday Rentals in Highland with a Pool
Hotel
- Collinsville
- ·
- O'Fallon
- 2.03 mi to center
9.7Exceptional
(32 Reviews)
3 Baths
466.43 ft²
- Private Pool
Oceanfront- Breakfast
EV Charge Station
CA $186/Night
7 Nights - CA $1,301
Hotel
- Collinsville
- ·
- O'Fallon
- 2.28 mi to center
9.6Exceptional
(1009 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
CA $201/Night
7 Nights - CA $1,407
Hotel
- Illinois
- ·
- Collinsville
- 1.59 mi to center
9.4Exceptional
(571 Reviews)
12 Baths
322.02 ft²
- Private Pool
- Parking
- Pool
- Kitchen
CA $158/Night
7 Nights - CA $1,104
Hotel
- St. Louis
- ·
- Edwardsville
- 3.78 mi to center
9.2Exceptional
(884 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
CA $183/Night
7 Nights - CA $1,281
Hotel
- Collinsville
- ·
- O'Fallon
- 1.87 mi to center
9.2Exceptional
(863 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
CA $189/Night
7 Nights - CA $1,326
Hotel
9.2Exceptional
(803 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
CA $158/Night
7 Nights - CA $1,107
Hotel
- Collinsville
- ·
- Mascoutah
- 6.38 mi to center
9.0Exceptional
(1001 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
CA $180/Night
7 Nights - CA $1,260
Hotel
- St. Louis
- ·
- Edwardsville
- 3.94 mi to center
9.0Exceptional
(210 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
CA $303/Night
7 Nights - CA $2,120
Hotel
- Collinsville
- ·
- O'Fallon
- 2.03 mi to center
9.0Exceptional
(151 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
CA $497/Night
7 Nights - CA $3,479
Pet-Friendly Holiday Rentals in Highland
Over 34+ Pet-Friendly Holiday Rentals in or Near Highland
House
- Collinsville
- ·
- Shiloh
- 0.85 mi to center
9.6Exceptional
(7 Reviews)
1 Bedroom
1 Bath
2 Guests
930 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $204/Night
7 Nights - CA $1,430
Hotel
- Collinsville
- ·
- Mascoutah
- 6.37 mi to center
8.8Fabulous
(378 Reviews)
1 Bath
365.97 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
CA $178/Night
7 Nights - CA $1,248
Hotel
7.8Very Good
(1005 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
CA $111/Night
7 Nights - CA $775
Apartment
- Collinsville
- ·
- Caseyville
- 1.49 mi to center
9.4Exceptional
(51 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $316/Night
7 Nights - CA $2,213
Hotel
- Collinsville
- ·
- O'Fallon
- 1.87 mi to center
8.6Fabulous
(201 Reviews)
1 Bath
301.39 ft²
- Private Pool
- EV Charge Station
- Parking
- Pool
CA $208/Night
7 Nights - CA $1,453
House
- Collinsville
- ·
- Caseyville
- 1.06 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $147/Night
7 Nights - CA $1,032
Cottage
- St. Louis
- ·
- Glen Carbon
- 1.89 mi to center
2 Bedrooms
1 Bath
3 Guests
788 ft²
- Air Conditioner
- Internet
- Pet Friendly
Child Friendly
CA $235/Night
7 Nights - CA $1,643
House
- St. Louis
- ·
- Edwardsville
- 1.60 mi to center
10.0Exceptional
(26 Reviews)
3 Bedrooms
3 Baths
6 Guests
2050 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $650/Night
7 Nights - CA $4,548
House
- Collinsville
- ·
- Shiloh
- 1.13 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $330/Night
7 Nights - CA $2,310
Large Holiday Rentals and Private Villas in Highland
Over 5+ Large Holiday Rentals and Private Villas in or Near Highland
New
Other
- Litchfield
- ·
- Staunton
- 2.29 mi to center
3 Bedrooms
2 Baths
13 Guests
- Internet
- Child Friendly
Laundry
Bedding/Linens
CA $394/Night
7 Nights - CA $2,757
House
- Carlyle Lake
- ·
- Greenville
- 1.41 mi to center
3 Bedrooms
2 Baths
10 Guests
- Parking
- Air Conditioner
- Internet
- Laundry
CA $297/Night
7 Nights - CA $2,083
House
- Collinsville
- ·
- New Baden
- 3.62 mi to center
7.0Very Good
(8 Reviews)
5 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Air Conditioner
- Internet
- Pet Friendly
CA $456/Night
7 Nights - CA $3,193
Bed & Breakfast
- Illinois
- ·
- Clinton County
- 5.78 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
12 Guests
- Child Friendly
CA $381/Night
7 Nights - CA $2,669
CA $555/Night
7 Nights - CA $3,883
Wheelchair Accessible Holiday Homes in Highland
Over 29+ Wheelchair Accessible Holiday Homes in or Near Highland
Condo
- Collinsville
- ·
- O'Fallon
- 2.69 mi to center
4.5Average
(2 Reviews)
2 Bedrooms
2 Baths
- View
- Kitchen
- Air Conditioner
- Internet
CA $243/Night
7 Nights - CA $1,699
Hotel
8.8Fabulous
(113 Reviews)
14 Baths
519.74 ft²
- Private Pool
- Oceanfront
- Breakfast
- EV Charge Station
CA $311/Night
7 Nights - CA $2,174
Hotel
- St. Louis
- ·
- Edwardsville
- 3.90 mi to center
8.6Fabulous
(723 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
CA $158/Night
7 Nights - CA $1,105
Hotel
- St. Louis
- ·
- Edwardsville
- 3.81 mi to center
8.7Fabulous
(145 Reviews)
10 Baths
328.3 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
CA $195/Night
7 Nights - CA $1,364
Hotel
- Carlyle Lake
- ·
- Greenville
- 2.90 mi to center
8.4Excellent
(455 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
CA $158/Night
7 Nights - CA $1,105
Hotel
- St. Louis
- ·
- Edwardsville
- 3.90 mi to center
8.5Fabulous
(204 Reviews)
1 Bath
283.45 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
CA $230/Night
7 Nights - CA $1,608
Hotel
8.2Excellent
(1003 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
CA $111/Night
7 Nights - CA $775
Hotel
8.2Excellent
(150 Reviews)
12 Baths
301.39 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
CA $186/Night
7 Nights - CA $1,301
Hotel
- Litchfield
- ·
- Staunton
- 2.13 mi to center
8.1Excellent
(209 Reviews)
4 Baths
363.28 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
CA $114/Night
7 Nights - CA $799
Highland Private Villas and Holiday Homes Under $200
Over 73+ Highland Private Villas and Holiday Homes Under $200
House
- Collinsville
- ·
- Lebanon
- 0.25 mi to center
9.8Exceptional
(21 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $270/Night
7 Nights - CA $1,887
House
- St. Louis
- ·
- Glen Carbon
- 1.39 mi to center
2 Bedrooms
1 Bath
4 Guests
1001.04 ft²
- Parking
- Air Conditioner
- Internet
- Laundry
CA $223/Night
7 Nights - CA $1,557
Hotel
- Carlyle Lake
- ·
- Pocahontas
- 0.88 mi to center
8.8Fabulous
(28 Reviews)
1 Bath
- Parking
- Internet
- Child Friendly
- Laundry
CA $128/Night
7 Nights - CA $893
Apartment
- Collinsville
- ·
- Shiloh
- 1.19 mi to center
9.8Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $140/Night
7 Nights - CA $979
Hotel
- St. Louis
- ·
- Edwardsville
- 1.97 mi to center
8.5Fabulous
(20 Reviews)
8 Baths
309.46 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
CA $250/Night
7 Nights - CA $1,750
Apartment
- St. Louis
- ·
- Edwardsville
- 2.80 mi to center
1 Bedroom
1 Bath
2 Guests
700 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $135/Night
7 Nights - CA $944
Apartment
- St. Louis
- ·
- Edwardsville
- 2.80 mi to center
1 Bedroom
1 Bath
2 Guests
700 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $133/Night
7 Nights - CA $930
New
Apartment
- St. Louis
- ·
- Edwardsville
- 2.80 mi to center
1 Bedroom
1 Bath
2 Guests
700 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $127/Night
7 Nights - CA $892
House
- Collinsville
- ·
- Shiloh
- 1.32 mi to center
9.8Exceptional
(18 Reviews)
3 Bedrooms
1 Bath
6 Guests
1100 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $246/Night
7 Nights - CA $1,725
Instantly Bookable Holiday Homes in Highland
Over 28+ Instantly Bookable Holiday Homes in or Near Highland
Apartment
- Carlyle Lake
- ·
- Highland
- 1.35 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $514/Night
7 Nights - CA $3,596
House
- St. Louis
- ·
- Edwardsville
- 1.78 mi to center
9.6Exceptional
(39 Reviews)
3 Bedrooms
2 Baths
8 Guests
2800 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $397/Night
7 Nights - CA $2,780
Apartment
- St. Louis
- ·
- Edwardsville
- 1.62 mi to center
9.6Exceptional
(21 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Child Friendly
Security/Safety
CA $290/Night
7 Nights - CA $2,030
House
- Carlyle Lake
- ·
- Greenville
- 1.41 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
1860 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $420/Night
7 Nights - CA $2,937
House
- Carlyle Lake
- ·
- Greenville
- 1.41 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $346/Night
7 Nights - CA $2,420
House
- Collinsville
- ·
- Lebanon
- 0.33 mi to center
10.0Exceptional
(42 Reviews)
2 Bedrooms
2 Baths
4 Guests
870 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $220/Night
7 Nights - CA $1,539
House
- St. Louis
- ·
- Edwardsville
- 2.35 mi to center
6.0Good
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $119/Night
7 Nights - CA $832
Apartment
- St. Louis
- ·
- Edwardsville
- 3.41 mi to center
2 Bedrooms
2 Baths
6 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
CA $361/Night
7 Nights - CA $2,524
Apartment
- St. Louis
- ·
- Edwardsville
- 2.80 mi to center
1 Bedroom
1 Bath
2 Guests
667 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $160/Night
7 Nights - CA $1,122
Book a Last Minute Place to Stay in Highland
About Casai's Private Villas and Holiday Rentals in Highland
Discover more than 138 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 423.9 ft², with nightly prices averaging CA $240.
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 | 34 |
| Holiday Apartments | 22 |
| Cottages | 1 |
| Villas | 1 |
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:
- Craftsman styled home in the heart of downtown Highland
- Sunset Cottage - 2 King beds! Downtown Glen Carbon
- The Hangar - Healthcare/Military 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
- Close to McKendree, Scott AFB & St. Louis
- Beautiful Historic Lebanon Illinois 2 Bedroom Villa
- The Swiss Post Apartment A
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
- Comfort Inn & Suites Greenville I-70
- TownePlace Suites by Marriott St. Louis Edwardsville, IL
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:
- Historic 4-bedroom house in Glen Carbon with AC
- Brick B&B - 3Bed 2Full Bath! Downtown Edwardsville
- Powhatan Motel
How many Casai.ca holiday rentals are available in Highland?
As of 2026, Casai boasts over 138 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.
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