Condo
10.0(231 Reviews)
2 Bedrooms
9 Guests
Hot Tub
Parking
Balcony/Terrace
Kitchen
US $458/Night
7 Nights - US $3,209
West Side Holiday Rentals
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Compare Villas, Resorts, & Rentals in West Side
10.0
Apartment
10.0(4 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
View
Air Conditioner
US $354/Night
7 Nights - US $2,475
Bed & Breakfast
9.8(217 Reviews)
1 Bedroom
Breakfast- Kitchen
- Air Conditioner
Internet
US $305/Night
7 Nights - US $2,138
Condo
10.0(217 Reviews)
1 Bedroom
5 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $294/Night
7 Nights - US $2,060
House
10.0(3 Reviews)
5 Bedrooms
16 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- View
US $2,234/Night
7 Nights - US $15,637
Apartment
10.0(89 Reviews)
1 Bedroom
3 Guests
- Hot Tub
- Parking
Spa- Balcony/Terrace
US $249/Night
7 Nights - US $1,743
Condo
10.0(32 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $322/Night
7 Nights - US $2,251
Apartment
10.0(29 Reviews)
1 Bedroom
4 Guests
- Kitchen
- Air Conditioner
- Internet
Child Friendly
US $258/Night
7 Nights - US $1,805
Apartment
10.0(26 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $424/Night
7 Nights - US $2,966
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
US $4,197/Night
7 Nights - US $29,376
House
9.4(16 Reviews)
4 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $3,382/Night
7 Nights - US $23,675
House
10 Bedrooms
22 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $2,892/Night
7 Nights - US $20,245
New
Apartment
13 Bedrooms
32 Guests
- Hot Tub
- Parking
Pool- Balcony/Terrace
US $2,593/Night
7 Nights - US $18,153
Apartment
10.0(1 Review)
9 Bedrooms
21 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $2,087/Night
7 Nights - US $14,610
House
3.0(1 Review)
7 Bedrooms
18 Guests
- Balcony/Terrace
- View
- Air Conditioner
Pet Friendly
US $2,082/Night
7 Nights - US $14,573
House
6 Bedrooms
20 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $2,036/Night
7 Nights - US $14,253
Apartment
9 Bedrooms
22 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,727/Night
7 Nights - US $12,086
New
House
6 Bedrooms
16 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $1,546/Night
7 Nights - US $10,822
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(11 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $463/Night
7 Nights - US $3,241
Apartment
10.0(3 Reviews)
3 Bedrooms
7 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $609/Night
7 Nights - US $4,263
Apartment
10.0(2 Reviews)
3 Bedrooms
7 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $609/Night
7 Nights - US $4,263
Apartment
10.0(2 Reviews)
3 Bedrooms
7 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $581/Night
7 Nights - US $4,068
Apartment
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $433/Night
7 Nights - US $3,030
Apartment
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $433/Night
7 Nights - US $3,030
Apartment
10.0(1 Review)
6 Bedrooms
14 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $1,426/Night
7 Nights - US $9,980
Hotel
10.0(1 Review)
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $835/Night
7 Nights - US $5,846
Hotel
10.0(1 Review)
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $545/Night
7 Nights - US $3,814
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
US $634/Night
7 Nights - US $4,440
Apartment
10.0(2 Reviews)
4 Bedrooms
14 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $303/Night
7 Nights - US $2,121
Apartment
9.6(338 Reviews)
1 Bedroom
3 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $126/Night
7 Nights - US $882
Apartment
10.0(6 Reviews)
1 Bedroom
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $430/Night
7 Nights - US $3,011
Apartment
10.0(1 Review)
3 Bedrooms
8 Guests
- Spa
- Air Conditioner
- Internet
- Pet Friendly
US $634/Night
7 Nights - US $4,439
Apartment
10.0(4 Reviews)
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $586/Night
7 Nights - US $4,104
Apartment
10.0(4 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $383/Night
7 Nights - US $2,684
Apartment
10.0(4 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $334/Night
7 Nights - US $2,341
Apartment
10.0(3 Reviews)
2 Bedrooms
8 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $384/Night
7 Nights - US $2,691
Large Holiday Rentals and Private Villas in West Side
Over 234+ Large Holiday Rentals and Private Villas in or Near West Side
Apartment
10.0(1 Review)
3 Bedrooms
12 Guests
Oceanfront
Ocean View- View
- Kitchen
US $194/Night
7 Nights - US $1,358
Apartment
10.0(2 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $702/Night
7 Nights - US $4,912
Apartment
3 Bedrooms
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $309/Night
7 Nights - US $2,163
Apartment
9.6(8 Reviews)
1 Bedroom
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $784/Night
7 Nights - US $5,486
Apartment
10.0(2 Reviews)
3 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $516/Night
7 Nights - US $3,612
Apartment
9.0(4 Reviews)
3 Bedrooms
12 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $355/Night
7 Nights - US $2,485
Apartment
8.0(4 Reviews)
4 Bedrooms
12 Guests
- Oceanfront
- Ocean View
- View
- Kitchen
US $237/Night
7 Nights - US $1,661
Apartment
1 Bedroom
14 Guests
- Hot Tub
- Kitchen
- Air Conditioner
- Internet
US $304/Night
7 Nights - US $2,131
Apartment
10.0(28 Reviews)
4 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $481/Night
7 Nights - US $3,369
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
US $143/Night
7 Nights - US $1,003
Apartment
10.0(1 Review)
2 Bedrooms
3 Guests
- Parking
- Air Conditioner
- Internet
Wheelchair Accessible
US $77/Night
7 Nights - US $539
Apartment
9.8(7 Reviews)
1 Bedroom
1 Guest
- Kitchen
- Internet
- Child Friendly
- Wheelchair Accessible
US $414/Night
7 Nights - US $2,897
Apartment
10.0(8 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $347/Night
7 Nights - US $2,431
Apartment
10.0(1 Review)
2 Bedrooms
6 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $405/Night
7 Nights - US $2,835
Apartment
10.0(6 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $441/Night
7 Nights - US $3,084
Condo
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $474/Night
7 Nights - US $3,318
Apartment
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $243/Night
7 Nights - US $1,701
Apartment
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $402/Night
7 Nights - US $2,814
West Side Private Villas and Holiday Homes Under $200
Over 626+ West Side Private Villas and Holiday Homes Under $200
Apartment
10.0(4 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $155/Night
7 Nights - US $1,082
Apartment
9.7(25 Reviews)
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $187/Night
7 Nights - US $1,309
US $151/Night
7 Nights - US $1,060
Apartment
10.0(3 Reviews)
1 Bedroom
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $195/Night
7 Nights - US $1,366
Apartment
9.5(103 Reviews)
3 Bedrooms
6 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $172/Night
7 Nights - US $1,204
Apartment
10.0(3 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $173/Night
7 Nights - US $1,213
Apartment
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $161/Night
7 Nights - US $1,129
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $151/Night
7 Nights - US $1,055
Apartment
10.0(1 Review)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $145/Night
7 Nights - US $1,012
Instantly Bookable Holiday Homes in West Side
Over 886+ Instantly Bookable Holiday Homes in or Near West Side
Condo
10.0(22 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $309/Night
7 Nights - US $2,165
Apartment
1 Bedroom
- Pool
- Kitchen
- Air Conditioner
- Internet
US $153/Night
7 Nights - US $1,068
Apartment
10.0(17 Reviews)
2 Bedrooms
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $287/Night
7 Nights - US $2,008
Condo
10.0(14 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $424/Night
7 Nights - US $2,966
Apartment
10.0(12 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $389/Night
7 Nights - US $2,720
Apartment
10.0(4 Reviews)
1 Bedroom
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $347/Night
7 Nights - US $2,432
Apartment
10.0(4 Reviews)
2 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $214/Night
7 Nights - US $1,499
House
10.0(3 Reviews)
1 Bedroom
2 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $290/Night
7 Nights - US $2,030
Apartment
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $284/Night
7 Nights - US $1,989
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 841.87 ft², with nightly prices averaging US $352.
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 near the West Side, IL
There are 1610 West Side, IL Holiday Rentals
- Prices for a holiday home in West Side start at US $7
- Top rated vacation home in West Side is Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- Most popular short term in West Side is Crowne Plaza Chicago West Loop by IHG
- 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:
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 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
- Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
- Entire Below Level Studio w/Private Sauna
- Private Historic Coach House Wicker Park
- Vibrant 3BR Pilsen Stay Free Parking Near Downtown
- Ukrainian Village 3BR/3BA Private Patio, Parking
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.com 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 | 1385 |
| The Loop Vacation Rentals in Chicago, Illinois | 620 |
| Near North Side Vacation Rentals in Chicago, Illinois | 580 |
| River North Vacation Rentals in Chicago, Illinois | 345 |
| Near West Side Vacation Rentals in Chicago, Illinois | 314 |
| West Town Vacation Rentals in Chicago, Illinois | 310 |
| West Loop Vacation Rentals in Chicago, Illinois | 183 |
| Lincoln Park Vacation Rentals in Chicago, Illinois | 127 |
| University Village / Little Italy Vacation Rentals in Chicago, Illinois | 85 |
| Logan Square Vacation Rentals in Chicago, Illinois | 56 |
| Wicker Park Vacation Rentals in Chicago, Illinois | 39 |
| Belmont Cragin Vacation Rentals in Chicago, Illinois | 30 |
| 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 |
