Apartment
10.0(12 Reviews)
2 Bedrooms
6 Guests
Hot Tub
Parking
Pool
Balcony/Terrace
US $507/Night
7 Nights - US $3,552
West Loop Holiday Rentals
We compare holiday rentals from owners across Booking.com, Vrbo and Expedia.
- Up-front pricing
- No markup
- Trusted partners
Compare Holiday Rentals, Villas & Resorts in West Loop
10.0
Apartment
10.0(3 Reviews)
4 Bedrooms
10 Guests
- Parking
Air Conditioner
Internet
Child Friendly
US $702/Night
7 Nights - US $4,912
Bed & Breakfast
9.8(219 Reviews)
1 Bedroom
Breakfast
Kitchen- Air Conditioner
- Internet
US $287/Night
7 Nights - US $2,006
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(2 Reviews)
1 Bedroom
2 Guests
- Air Conditioner
- Internet
- Child Friendly
Accessibility
US $509/Night
7 Nights - US $3,563
Apartment
10.0(6 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $441/Night
7 Nights - US $3,084
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(2 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $402/Night
7 Nights - US $2,814
Luxury Holiday Rentals in West Loop
Over 311+ Luxury Holiday Rentals in or Near West Loop
Apartment
13 Bedrooms
32 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $2,593/Night
7 Nights - US $18,153
Apartment
9 Bedrooms
22 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,727/Night
7 Nights - US $12,086
Apartment
2.0(1 Review)
8 Bedrooms
20 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,518/Night
7 Nights - US $10,628
Hotel
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $1,266/Night
7 Nights - US $8,861
Apartment
8.4(10 Reviews)
2 Bedrooms
6 Guests
Private Pool- Hot Tub
- Parking
- Pool
US $1,247/Night
7 Nights - US $8,732
Apartment
6 Bedrooms
15 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,227/Night
7 Nights - US $8,592
Apartment
9.8(5 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $1,123/Night
7 Nights - US $7,858
Apartment
6 Bedrooms
15 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,105/Night
7 Nights - US $7,737
Apartment
9.5(50 Reviews)
13 Bedrooms
32 Guests
- Parking
- Pool
- Balcony/Terrace
View
US $896/Night
7 Nights - US $6,272
Top-Rated Holiday Rentals with a Pool in West Loop
Over 171+ The Best Private Villas and Holiday Rentals in West Loop with a Pool
Apartment
10.0(2 Reviews)
3 Bedrooms
7 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $655/Night
7 Nights - US $4,582
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
Apartment
10.0(1 Review)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $463/Night
7 Nights - US $3,241
Hotel
10.0(1 Review)
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $374/Night
7 Nights - US $2,621
Hotel
10.0(1 Review)
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $303/Night
7 Nights - US $2,118
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $128/Night
7 Nights - US $893
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $105/Night
7 Nights - US $734
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $94/Night
7 Nights - US $655
Pet-Friendly Holiday Rentals in West Loop
Over 181+ Pet-Friendly Holiday Rentals in or Near West Loop
Apartment
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $387/Night
7 Nights - US $2,706
Apartment
9.7(3 Reviews)
1 Bedroom
6 Guests
- Air Conditioner
- Internet
Pet Friendly- Accessibility
US $261/Night
7 Nights - US $1,826
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Pool
- Kitchen
- Air Conditioner
- Internet
US $84/Night
7 Nights - US $588
Apartment
9.4(10 Reviews)
2 Bedrooms
6 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Accessibility
US $349/Night
7 Nights - US $2,443
Apartment
9.8(6 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $398/Night
7 Nights - US $2,788
Apartment
9.8(6 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $387/Night
7 Nights - US $2,706
Apartment
2.0(1 Review)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $387/Night
7 Nights - US $2,706
Apartment
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $459/Night
7 Nights - US $3,211
Apartment
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $402/Night
7 Nights - US $2,814
Large Holiday Rentals and Private Villas in West Loop
Over 24+ Large Holiday Rentals and Private Villas in or Near West Loop
Apartment
9.6(8 Reviews)
1 Bedroom
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $828/Night
7 Nights - US $5,797
Bed & Breakfast
9.4(38 Reviews)
11 Bedrooms
22 Guests
- Parking
- Air Conditioner
- Internet
Wheelchair Accessible
US $298/Night
7 Nights - US $2,089
Apartment
10.0(28 Reviews)
4 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $726/Night
7 Nights - US $5,080
Apartment
9.3(6 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Wheelchair Accessible
US $354/Night
7 Nights - US $2,476
Apartment
10.0(11 Reviews)
5 Bedrooms
24 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $772/Night
7 Nights - US $5,403
Apartment
9.8(32 Reviews)
3 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $357/Night
7 Nights - US $2,501
Apartment
9.6(11 Reviews)
4 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $737/Night
7 Nights - US $5,158
Apartment
9.4(15 Reviews)
4 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $859/Night
7 Nights - US $6,013
Apartment
9.4(8 Reviews)
4 Bedrooms
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $352/Night
7 Nights - US $2,467
Wheelchair Accessible Holiday Homes in West Loop
Over 194+ Wheelchair Accessible Holiday Homes in or Near West Loop
Apartment
9.6(23 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $321/Night
7 Nights - US $2,249
Apartment
9.3(3 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $253/Night
7 Nights - US $1,769
US $566/Night
7 Nights - US $3,960
Apartment
9.4(12 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $288/Night
7 Nights - US $2,018
Apartment
5.5(2 Reviews)
4 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $682/Night
7 Nights - US $4,771
Apartment
2.0(1 Review)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $463/Night
7 Nights - US $3,241
Apartment
2.0(1 Review)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $275/Night
7 Nights - US $1,927
US $463/Night
7 Nights - US $3,241
Apartment
2 Bedrooms
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $226/Night
7 Nights - US $1,581
West Loop Private Villas and Holiday Homes Under $200
Over 163+ West Loop Private Villas and Holiday Homes Under $200
Apartment
2 Bedrooms
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $190/Night
7 Nights - US $1,328
Apartment
8.8(9 Reviews)
4 Bedrooms
2 Guests
- Air Conditioner
- Internet
- Child Friendly
- Accessibility
US $190/Night
7 Nights - US $1,332
US $189/Night
7 Nights - US $1,321
Apartment
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $182/Night
7 Nights - US $1,271
Apartment
2 Bedrooms
4 Guests
- Parking
- Pool
- Air Conditioner
- Internet
US $200/Night
7 Nights - US $1,400
Apartment
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $181/Night
7 Nights - US $1,268
Apartment
2 Bedrooms
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $173/Night
7 Nights - US $1,210
Apartment
2 Bedrooms
4 Guests
- Pool
- Kitchen
- Air Conditioner
- Internet
US $170/Night
7 Nights - US $1,193
Apartment
2 Bedrooms
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $170/Night
7 Nights - US $1,192
Instantly Bookable Holiday Homes in West Loop
Over 182+ Instantly Bookable Holiday Homes in or Near West Loop
Apartment
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $217/Night
7 Nights - US $1,518
Apartment
1 Bedroom
- Pool
- Kitchen
- Air Conditioner
- Internet
US $153/Night
7 Nights - US $1,068
Apartment
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $201/Night
7 Nights - US $1,407
Apartment
2 Bedrooms
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $201/Night
7 Nights - US $1,406
Apartment
2 Bedrooms
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $157/Night
7 Nights - US $1,096
Apartment
2 Bedrooms
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $156/Night
7 Nights - US $1,089
Apartment
1 Bedroom
2 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $154/Night
7 Nights - US $1,078
Apartment
2 Bedrooms
4 Guests
- Pool
- Kitchen
- Air Conditioner
- Internet
US $153/Night
7 Nights - US $1,068
Apartment
2 Bedrooms
4 Guests
- Pool
- Kitchen
- Air Conditioner
- Internet
US $148/Night
7 Nights - US $1,039
Book a Last Minute Place to Stay in West Loop
About Casai's Private Villas and Holiday Rentals in West Loop
Discover more than 320 vacation rentals available in West Loop. 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 Loop.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in West Loop, 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 Loop. On average, places to stay near West Loop offer 670.13 ft², with nightly prices averaging US $314.
With Casai, finding and comparing holiday rentals in West Loop 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 Loop, IL
There are 320 West Loop, IL Holiday Rentals
- Prices for a holiday home in West Loop start at US $84
- Top rated vacation home in West Loop is Modern West Loop Gem-City Views & Prime Location 6
- Most popular short term in West Loop is Hyatt House Chicago/West Loop-Fulton Market
- Cheapest place to stay in West Loop is Hip West Loop Studio w/Gym & Coworking, nr UIC, by Blueground
- Most expensive holiday rental in West Loop is 6 Luxe Apts, Perfect Group Solution, Sleeps 30
Recently Booked Holiday Rentals in West Loop
Frequently Asked Questions About West Loop?
What are the top holiday rentals in West Loop?
With numerous options available in West Loop, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in West Loop:
- Modern West Loop Gem-City Views & Prime Location 6
- Top Floor Views + Central Comfort
- Stunning Designer Loft in Fulton Market, Sleeps 24 | Featured In Architectural Digest
- Designer Loft in Fulton Market with Parking
- LIVN West Loop Chicago Classic Queen Studio
- LIVN West Loop Chicago King Studio
- West Loop - City Views With In & Out Parking 4
- West Loop Condo w/Parking + Gym - Walk to Fulton Market
- Prime 4BR Penthouse w/Skyline Views for Families
- Skyline Views in 3BR Apartment w/Top Amenities
How many holiday rentals have private pools in West Loop?
Discover a selection of holiday rentals with private pools near West Loop 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 Loop are best for families?
If you're searching for a family-friendly holiday home in West Loop, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in West Loop:
How many Casai.nz holiday rentals are available in West Loop?
As of 2026, Casai boasts over 320 properties listed in the West Loop area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in West Loop.
Nearby Neighborhood (12)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1403 |
| The Loop Vacation Rentals in Chicago, Illinois | 632 |
| Near North Side Vacation Rentals in Chicago, Illinois | 585 |
| River North Vacation Rentals in Chicago, Illinois | 351 |
| Near West Side Vacation Rentals in Chicago, Illinois | 317 |
| West Town Vacation Rentals in Chicago, Illinois | 308 |
| University Village / Little Italy Vacation Rentals in Chicago, Illinois | 87 |
| Lower West Side Vacation Rentals in Chicago, Illinois | 56 |
| West Loop Gate Vacation Rentals in Chicago, Illinois | 40 |
| Chinatown Vacation Rentals in Chicago, Illinois | 3296 |
| Greektown Vacation Rentals in Chicago, Illinois | 4566 |
| Fulton Market Vacation Rentals in Chicago, Illinois | 4292 |
