Condo
10.0(231 Reviews)
2 Bedrooms
9 Guests
Hot Tub
Parking
Balcony/Terrace
Kitchen
£345/Night
7 Nights - £2,418
West Side Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in West Side
10.0
Apartment
10.0(4 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
View
Air Conditioner
£260/Night
7 Nights - £1,821
Bed & Breakfast
9.8(219 Reviews)
1 Bedroom
Breakfast- Kitchen
- Air Conditioner
Internet
£216/Night
7 Nights - £1,512
Condo
10.0(219 Reviews)
1 Bedroom
5 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
£223/Night
7 Nights - £1,562
House
10.0(3 Reviews)
5 Bedrooms
16 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- View
£1,683/Night
7 Nights - £11,783
Apartment
10.0(89 Reviews)
1 Bedroom
3 Guests
- Hot Tub
- Parking
Spa- Balcony/Terrace
£188/Night
7 Nights - £1,313
House
10.0(75 Reviews)
2 Bedrooms
5 Guests
Oceanfront- Parking
Ocean View- Balcony/Terrace
£368/Night
7 Nights - £2,574
Condo
10.0(32 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£241/Night
7 Nights - £1,689
Apartment
10.0(29 Reviews)
1 Bedroom
4 Guests
- Kitchen
- Air Conditioner
- Internet
Child Friendly
£194/Night
7 Nights - £1,360
Luxury Holiday Rentals in West Side
Over 1601+ Luxury Holiday Rentals in or Near West Side
Bed & Breakfast
8 Bedrooms
16 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
£3,162/Night
7 Nights - £22,135
House
9.4(16 Reviews)
4 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
£2,548/Night
7 Nights - £17,840
House
10 Bedrooms
22 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
£2,179/Night
7 Nights - £15,255
New
Apartment
13 Bedrooms
32 Guests
- Hot Tub
- Parking
Pool- Balcony/Terrace
£1,954/Night
7 Nights - £13,679
Apartment
10.0(1 Review)
9 Bedrooms
21 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
£1,573/Night
7 Nights - £11,009
House
3.0(1 Review)
7 Bedrooms
18 Guests
- Balcony/Terrace
- View
- Air Conditioner
- Internet
£1,569/Night
7 Nights - £10,981
House
6 Bedrooms
20 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
£1,534/Night
7 Nights - £10,740
Apartment
9 Bedrooms
22 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£1,301/Night
7 Nights - £9,107
House
9.8(15 Reviews)
5 Bedrooms
23 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
£1,289/Night
7 Nights - £9,025
Top-Rated Holiday Rentals with a Pool in West Side
Over 245+ The Best Private Villas and Holiday Rentals in West Side with a Pool
Apartment
10.0(12 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
£382/Night
7 Nights - £2,676
Apartment
10.0(3 Reviews)
3 Bedrooms
7 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
£460/Night
7 Nights - £3,218
Apartment
10.0(2 Reviews)
3 Bedrooms
7 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
£493/Night
7 Nights - £3,453
Apartment
10.0(2 Reviews)
3 Bedrooms
7 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
£459/Night
7 Nights - £3,212
Apartment
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
£326/Night
7 Nights - £2,283
Apartment
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
£326/Night
7 Nights - £2,283
Apartment
10.0(1 Review)
6 Bedrooms
14 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
£1,074/Night
7 Nights - £7,520
Hotel
10.0(1 Review)
- Parking
- Pool
- Balcony/Terrace
- Kitchen
£629/Night
7 Nights - £4,405
Hotel
10.0(1 Review)
- Parking
- Pool
- Balcony/Terrace
- Kitchen
£411/Night
7 Nights - £2,874
Pet-Friendly Holiday Rentals in West Side
Over 658+ Pet-Friendly Holiday Rentals in or Near West Side
House
10.0(13 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
£478/Night
7 Nights - £3,346
Apartment
10.0(2 Reviews)
4 Bedrooms
14 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
£228/Night
7 Nights - £1,598
Apartment
9.6(345 Reviews)
1 Bedroom
3 Guests
- Kitchen
- Air Conditioner
- Internet
Pet Friendly
£95/Night
7 Nights - £665
Apartment
10.0(6 Reviews)
1 Bedroom
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£324/Night
7 Nights - £2,269
Apartment
10.0(1 Review)
3 Bedrooms
8 Guests
- Spa
- Air Conditioner
- Internet
- Pet Friendly
£478/Night
7 Nights - £3,345
Apartment
10.0(4 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
£442/Night
7 Nights - £3,092
Apartment
10.0(4 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£289/Night
7 Nights - £2,022
Apartment
10.0(4 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£252/Night
7 Nights - £1,764
Apartment
10.0(3 Reviews)
2 Bedrooms
8 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
£290/Night
7 Nights - £2,028
Large Holiday Rentals and Private Villas in West Side
Over 234+ Large Holiday Rentals and Private Villas in or Near West Side
Apartment
9.6(8 Reviews)
1 Bedroom
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
£624/Night
7 Nights - £4,368
Apartment
10.0(3 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
£529/Night
7 Nights - £3,701
Apartment
3 Bedrooms
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
£233/Night
7 Nights - £1,630
New
Apartment
1 Bedroom
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£636/Night
7 Nights - £4,450
Apartment
10.0(2 Reviews)
5 Bedrooms
14 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
£417/Night
7 Nights - £2,919
Apartment
1 Bedroom
14 Guests
- Hot Tub
- Kitchen
- Air Conditioner
- Internet
£229/Night
7 Nights - £1,606
Apartment
10.0(28 Reviews)
4 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
£547/Night
7 Nights - £3,828
Condo
10.0(14 Reviews)
4 Bedrooms
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
£465/Night
7 Nights - £3,258
Apartment
10.0(11 Reviews)
5 Bedrooms
24 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
£582/Night
7 Nights - £4,071
Wheelchair Accessible Holiday Homes in West Side
Over 466+ Wheelchair Accessible Holiday Homes in or Near West Side
Apartment
10.0(10 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
£108/Night
7 Nights - £756
Apartment
10.0(1 Review)
2 Bedrooms
6 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
£305/Night
7 Nights - £2,136
Apartment
9.8(7 Reviews)
1 Bedroom
1 Guest
- Kitchen
- Internet
- Child Friendly
Wheelchair Accessible
£312/Night
7 Nights - £2,183
Apartment
10.0(8 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
£262/Night
7 Nights - £1,832
Apartment
10.0(1 Review)
2 Bedrooms
3 Guests
- Parking
- Air Conditioner
- Internet
- Wheelchair Accessible
£58/Night
7 Nights - £406
Apartment
10.0(6 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
£332/Night
7 Nights - £2,324
Apartment
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£182/Night
7 Nights - £1,275
Apartment
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£303/Night
7 Nights - £2,120
Apartment
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£291/Night
7 Nights - £2,039
West Side Private Villas and Holiday Homes Under $200
Over 631+ West Side Private Villas and Holiday Homes Under $200
Apartment
10.0(4 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
£116/Night
7 Nights - £815
Apartment
9.7(25 Reviews)
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
£141/Night
7 Nights - £986
£142/Night
7 Nights - £995
Apartment
10.0(3 Reviews)
1 Bedroom
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
£147/Night
7 Nights - £1,029
Apartment
9.5(103 Reviews)
3 Bedrooms
6 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
£130/Night
7 Nights - £907
Apartment
10.0(3 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£131/Night
7 Nights - £914
Apartment
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
£122/Night
7 Nights - £851
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
£112/Night
7 Nights - £781
Apartment
10.0(1 Review)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
£109/Night
7 Nights - £763
Instantly Bookable Holiday Homes in West Side
Over 885+ Instantly Bookable Holiday Homes in or Near West Side
Apartment
10.0(26 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
£319/Night
7 Nights - £2,235
Apartment
1 Bedroom
- Pool
- Kitchen
- Air Conditioner
- Internet
£115/Night
7 Nights - £805
Condo
10.0(22 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
£233/Night
7 Nights - £1,631
Apartment
10.0(17 Reviews)
2 Bedrooms
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
£216/Night
7 Nights - £1,513
Condo
10.0(14 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
£319/Night
7 Nights - £2,235
Apartment
10.0(12 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£293/Night
7 Nights - £2,050
Apartment
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£186/Night
7 Nights - £1,304
Apartment
10.0(4 Reviews)
1 Bedroom
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
£262/Night
7 Nights - £1,833
Apartment
10.0(4 Reviews)
2 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
£161/Night
7 Nights - £1,130
Book a Last Minute Place to Stay in West Side
About Casai's Private Villas and Holiday Rentals in West Side
Discover more than 1610 vacation rentals available in West 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 West Side.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in West 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 West Side. On average, places to stay near West Side offer 842.55 ft², with nightly prices averaging £264.
With Casai, finding and comparing holiday rentals in West 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 West Side, IL
There are 1610 West Side, IL Holiday Rentals
- Prices for a holiday home in West Side start at £5
- Top rated vacation home in West Side is 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- Most popular short term in West Side is Hyatt House Chicago Medical/University District
- Cheapest place to stay in West Side is Homan Square
- Most expensive holiday rental in West Side is Your Own 8 Bedroom Private Inn and Event Space, Urban Garden Included
Frequently Asked Questions About West Side?
What are the top holiday rentals in West Side?
With numerous options available in West Side, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in West Side:
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- NEW LUXURY PENTHOUSE CONDO
- NEW LUXURY CONDO WITH PATIO DECK
- 1F Chicago's Little italy Graystone nearDowntown
- Entire Below Level Studio w/Private Sauna
- Private Historic Coach House Wicker Park
- Ukrainian Village 3BR/3BA Private Patio, Parking
- Vibrant 3BR Pilsen Stay Free Parking Near Downtown
- Trendy West Town Flat - 2 bed/1.5 bath with parking
- Luxury Modern home minutes from Downtown Chicago
How many holiday rentals have private pools in West Side?
Discover a selection of holiday rentals with private pools near West 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 West Side are best for families?
If you're searching for a family-friendly holiday home in West Side, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in West Side:
How many Casai.uk holiday rentals are available in West Side?
As of 2026, Casai boasts over 1610 properties listed in the West Side area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in West Side.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1403 |
| The Loop Vacation Rentals in Chicago, Illinois | 633 |
| Near North Side Vacation Rentals in Chicago, Illinois | 586 |
| River North Vacation Rentals in Chicago, Illinois | 351 |
| Near West Side Vacation Rentals in Chicago, Illinois | 315 |
| West Town Vacation Rentals in Chicago, Illinois | 307 |
| West Loop Vacation Rentals in Chicago, Illinois | 184 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 129 |
| University Village / Little Italy Vacation Rentals in Chicago, Illinois | 87 |
| Logan Square Vacation Rentals in Chicago, Illinois | 53 |
| Wicker Park Vacation Rentals in Chicago, Illinois | 35 |
| Belmont Cragin Vacation Rentals in Chicago, Illinois | 31 |
| Austin Vacation Rentals in Chicago, Illinois | 24 |
| Little Village Vacation Rentals in Chicago, Illinois | 462 |
| Bucktown Vacation Rentals in Chicago, Illinois | 3138 |
| North Lawndale Vacation Rentals in Chicago, Illinois | 640 |
