Condo
10.0(15 Reviews)
2 Bedrooms
4 Guests
Balcony/Terrace
Kitchen
Air Conditioner
Internet
£280/Night
7 Nights - £1,963
South Side Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in South Side
10.0
House
10.0(2 Reviews)
1 Bedroom
8 Guests
View- Air Conditioner
- Internet
Pet Friendly
£291/Night
7 Nights - £2,035
Hotel
9.6(1003 Reviews)
Breakfast
Parking- Kitchen
- Air Conditioner
£359/Night
7 Nights - £2,511
House
10.0(13 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£668/Night
7 Nights - £4,676
Apartment
10.0(2 Reviews)
3 Bedrooms
8 Guests
EV Charge Station- Parking
- Air Conditioner
- Internet
£262/Night
7 Nights - £1,833
Apartment
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£132/Night
7 Nights - £922
Apartment
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£121/Night
7 Nights - £844
Apartment
10.0(5 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£105/Night
7 Nights - £733
Apartment
10.0(4 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£119/Night
7 Nights - £833
Luxury Holiday Rentals in South Side
Over 577+ Luxury Holiday Rentals in or Near South Side
New
Apartment
6 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
£3,762/Night
7 Nights - £26,332
New
Apartment
5 Bedrooms
12 Guests
- EV Charge Station
- Parking
- Balcony/Terrace
- Air Conditioner
£3,436/Night
7 Nights - £24,051
Apartment
7.4(17 Reviews)
2 Bedrooms
13 Guests
- Parking
- Air Conditioner
- Internet
Child Friendly
£2,019/Night
7 Nights - £14,133
Apartment
5 Bedrooms
12 Guests
- EV Charge Station
- Parking
- Air Conditioner
- Internet
£1,661/Night
7 Nights - £11,629
Apartment
9.0(1 Review)
5 Bedrooms
12 Guests
- EV Charge Station
- Parking
- Air Conditioner
- Internet
£1,631/Night
7 Nights - £11,420
Apartment
5 Bedrooms
12 Guests
- EV Charge Station
- Parking
- Air Conditioner
- Internet
£1,602/Night
7 Nights - £11,214
Apartment
9.4(16 Reviews)
3 Bedrooms
8 Guests
- EV Charge Station
- Parking
- Air Conditioner
- Internet
£1,108/Night
7 Nights - £7,758
Apartment
7.0(2 Reviews)
6 Bedrooms
12 Guests
- EV Charge Station
- Parking
- Air Conditioner
- Internet
£925/Night
7 Nights - £6,476
Apartment
9.0(2 Reviews)
6 Bedrooms
12 Guests
- EV Charge Station
- Parking
- Air Conditioner
- Internet
£893/Night
7 Nights - £6,250
Top-Rated Holiday Rentals with a Pool in South Side
Over 72+ The Best Private Villas and Holiday Rentals in South Side with a Pool
Hotel
9.2(942 Reviews)
- Breakfast
- Parking
Pool- Balcony/Terrace
£132/Night
7 Nights - £922
£144/Night
7 Nights - £1,011
Hotel
8.8(2178 Reviews)
- Breakfast
- Parking
- Pool
- Balcony/Terrace
£186/Night
7 Nights - £1,300
Hotel
8.6(1006 Reviews)
- Breakfast
- Parking
- Pool
- Balcony/Terrace
£143/Night
7 Nights - £1,002
Hotel
8.6(269 Reviews)
Private Pool- Parking
- Pool
- Balcony/Terrace
£220/Night
7 Nights - £1,538
Hotel
8.5(730 Reviews)
- Private Pool
- Parking
- Pool
- Balcony/Terrace
£173/Night
7 Nights - £1,213
Hotel
8.0(359 Reviews)
- Private Pool
- Parking
- Pool
- Balcony/Terrace
£122/Night
7 Nights - £857
Hotel
7.9(868 Reviews)
- Private Pool
Hot Tub- Breakfast
- Parking
£342/Night
7 Nights - £2,397
Hotel
7.9(483 Reviews)
- Private Pool
- Hot Tub
- Breakfast
- Parking
£129/Night
7 Nights - £903
Pet-Friendly Holiday Rentals in South Side
Over 133+ Pet-Friendly Holiday Rentals in or Near South Side
Condo
9.8(54 Reviews)
2 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
£288/Night
7 Nights - £2,015
Apartment
10.0(1 Review)
2 Bedrooms
8 Guests
- EV Charge Station
- Parking
- Air Conditioner
- Internet
£219/Night
7 Nights - £1,533
Apartment
9.8(38 Reviews)
2 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
£275/Night
7 Nights - £1,925
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
£140/Night
7 Nights - £979
Condo
9.8(34 Reviews)
2 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
£277/Night
7 Nights - £1,938
Condo
9.8(30 Reviews)
2 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
£284/Night
7 Nights - £1,988
Condo
9.8(17 Reviews)
2 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
£225/Night
7 Nights - £1,575
Apartment
9.4(28 Reviews)
2 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
£273/Night
7 Nights - £1,912
Condo
2 Bedrooms
3 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
£248/Night
7 Nights - £1,734
Large Holiday Rentals and Private Villas in South Side
Over 80+ Large Holiday Rentals and Private Villas in or Near South Side
Apartment
9.4(30 Reviews)
2 Bedrooms
13 Guests
- Kitchen
- Air Conditioner
- Internet
Laundry
£130/Night
7 Nights - £907
Apartment
10.0(2 Reviews)
3 Bedrooms
10 Guests
- EV Charge Station
- Parking
Spa- Air Conditioner
£211/Night
7 Nights - £1,473
Condo
10.0(20 Reviews)
4 Bedrooms
20 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£471/Night
7 Nights - £3,295
Apartment
9.5(2 Reviews)
3 Bedrooms
10 Guests
- EV Charge Station
- Parking
- Air Conditioner
- Internet
£313/Night
7 Nights - £2,191
House
10.0(1 Review)
4 Bedrooms
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
£442/Night
7 Nights - £3,092
House
9.8(16 Reviews)
4 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£430/Night
7 Nights - £3,008
New
Apartment
9.6(14 Reviews)
6 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£335/Night
7 Nights - £2,342
New
Apartment
9.6(7 Reviews)
5 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£285/Night
7 Nights - £1,998
Apartment
9.6(5 Reviews)
3 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£200/Night
7 Nights - £1,402
Wheelchair Accessible Holiday Homes in South Side
Over 314+ Wheelchair Accessible Holiday Homes in or Near South Side
Apartment
10.0(3 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£170/Night
7 Nights - £1,187
House
8.5(2 Reviews)
1 Bedroom
8 Guests
- Air Conditioner
- Internet
- Pet Friendly
Wheelchair Accessible
£265/Night
7 Nights - £1,855
£340/Night
7 Nights - £2,381
Apartment
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£141/Night
7 Nights - £989
House
1 Bedroom
8 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Wheelchair Accessible
£326/Night
7 Nights - £2,280
Apartment
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£132/Night
7 Nights - £922
Apartment
10.0(1 Review)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£142/Night
7 Nights - £996
Apartment
10.0(1 Review)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£132/Night
7 Nights - £922
Apartment
10.0(1 Review)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£126/Night
7 Nights - £882
South Side Private Villas and Holiday Homes Under $200
Over 182+ South Side Private Villas and Holiday Homes Under $200
Apartment
10.0(1 Review)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£126/Night
7 Nights - £882
Apartment
5.5(2 Reviews)
2 Bedrooms
8 Guests
- EV Charge Station
- Parking
- Air Conditioner
- Internet
£125/Night
7 Nights - £873
£143/Night
7 Nights - £999
Apartment
10.0(1 Review)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£126/Night
7 Nights - £882
Apartment
5.5(2 Reviews)
3 Bedrooms
7 Guests
- Air Conditioner
- Internet
- Child Friendly
Accessibility
£122/Night
7 Nights - £857
Apartment
9.6(4 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£134/Night
7 Nights - £934
Apartment
9.2(26 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£132/Night
7 Nights - £922
Apartment
9.2(9 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£126/Night
7 Nights - £882
Apartment
9.0(17 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£132/Night
7 Nights - £922
Instantly Bookable Holiday Homes in South Side
Over 356+ Instantly Bookable Holiday Homes in or Near South Side
Condo
9.2(26 Reviews)
2 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£223/Night
7 Nights - £1,559
Apartment
1 Bedroom
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£259/Night
7 Nights - £1,816
Apartment
9.2(9 Reviews)
2 Bedrooms
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£280/Night
7 Nights - £1,963
Apartment
9.0(7 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£124/Night
7 Nights - £870
Apartment
9.0(6 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£126/Night
7 Nights - £882
Apartment
9.0(6 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£98/Night
7 Nights - £688
House
9.0(4 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£147/Night
7 Nights - £1,029
Apartment
9.0(2 Reviews)
2 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
£154/Night
7 Nights - £1,076
Apartment
9.0(2 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£141/Night
7 Nights - £987
Book a Last Minute Place to Stay in South Side
About Casai's Private Villas and Holiday Rentals in South Side
Discover more than 586 vacation rentals available in South Side. 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 South Side.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in South Side, 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 South Side. On average, places to stay near South Side offer 858.26 ft², with nightly prices averaging £308.
With Casai, finding and comparing holiday rentals in South Side 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 South Side, IL
There are 586 South Side, IL Holiday Rentals
- Prices for a holiday home in South Side start at £61
- Top rated vacation home in South Side is 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Most popular short term in South Side is Best Western Grant Park Hotel
- Cheapest place to stay in South Side is Chinatown Hotel Chicago
- Most expensive holiday rental in South Side is McCormick 6B/4Ba Luxury Suite w Jacuzzi/Group stay
Recently Booked Holiday Rentals in South Side
Frequently Asked Questions About South Side?
What are the top holiday rentals in South Side?
With numerous options available in South Side, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in South Side:
- 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Cozy Downtown MICH AVE #7 | gym+rooftop
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Townhome 3 bedroom 2 bath with Parking - near McCormick Place , Chinatown Sox
- McCormick Patio skyline view 2b/2b with optional Parking/sleep 6
- McCormick Place Patio skyline 2b/2b with optional Parking for up to 6 people
- Luxury Studio Apartment Near McCormick Place & Soldier Field
- Bright & Stylish 2BR Family Unit Near McCormick Place & Grant Park
- McCormick Place 2b/2b family unit with optional parking for up to 8 guests
- Stylish 3BR Gem in Prime Location
How many holiday rentals have private pools in South Side?
Discover a selection of holiday rentals with private pools near South Side 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.
Which holiday homes in South Side are best for families?
If you're searching for a family-friendly holiday home in South Side, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in South Side:
How many Casai.uk holiday rentals are available in South Side?
As of 2026, Casai boasts over 586 properties listed in the South Side area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in South Side.
Nearby Neighborhood (11)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1406 |
| The Loop Vacation Rentals in Chicago, Illinois | 634 |
| Near West Side Vacation Rentals in Chicago, Illinois | 316 |
| South Loop Vacation Rentals in Chicago, Illinois | 295 |
| Near South Side Vacation Rentals in Chicago, Illinois | 276 |
| Prairie District Vacation Rentals in Chicago, Illinois | 214 |
| West Loop Vacation Rentals in Chicago, Illinois | 184 |
| Lower West Side Vacation Rentals in Chicago, Illinois | 56 |
| Printers Row Vacation Rentals in Chicago, Illinois | 4161 |
| Chinatown Vacation Rentals in Chicago, Illinois | 3261 |
| Chicago Museum Campus Vacation Rentals in Chicago, Illinois | 3413 |
