Near South Side holiday rentals

We found 1,422 holiday rentals — enter your dates for availability
Discover a selection of 8 homes and other holiday rentals in Near South Side that are perfect for your trip. Holiday rentals provide the amenities that you need and want for you and your friends, family or even pets, such as cable TV and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Near South Side

Showing deals for:15 Jan - 22 Jan

Terrace/patio
Exterior
Living area
Room
Exceptional
(41 reviews)

Chicago Gold Coast Luxury Private Mansion

Chicago

6% off
S$27,974
for 7 nights, 1 home
S$3,996 per night
includes taxes & fees
Chicago Gold Coast Luxury Private Mansion
Dining
Our downtown Townhouse is in an amazing location
It is huge! With lots of areas for relaxing and entertaining
Room
Exceptional
(93 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
S$6,423
for 7 nights, 1 home
S$918 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
Bedroom 1
Private kitchen
Exterior
Living area
Wonderful
(25 reviews)

Chicago Grand Retreat - 6BR Near Downtown

Chicago

7% off
S$5,118
for 7 nights, 1 home
S$731 per night
includes taxes & fees
Chicago Grand Retreat - 6BR Near Downtown
French Bistro and Wine Bar - right downstairs
River North Luxury Living
Outdoors at night
The building
Exceptional
(107 reviews)

River North's Rock N' Roll - In The Heart of the City

Chicago

7% off
S$4,254
for 7 nights, 1 apartment
S$608 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Upstairs queen bedroom 2
Downstairs living area
Downstairs living room
Fun Mirror Wall Upstairs
Exceptional
(101 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
S$13,101
for 7 nights, 1 apartment
S$1,872 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Room
Living area
Private kitchen
Interior
Wonderful
(9 reviews)

The En Bronze ~ 7mins To Dining & Downtown Chicago

Chicago

7% off
S$5,296
for 7 nights, 1 apartment
S$757 per night
includes taxes & fees
The En Bronze ~ 7mins To Dining & Downtown Chicago
Private kitchen
Property grounds
Room
Interior
Exceptional
(8 reviews)

3bed/1 bath Retreat - 10 min from Downtown

Chicago

8% off
S$2,732
for 7 nights, 1 apartment
S$390 per night
includes taxes & fees
3bed/1 bath Retreat - 10 min from Downtown
Well stocked kitchen with Keurig coffee maker, microwave, water filter and more
Living area
Close to the beautiful Ping Tom Park and a short water taxi ride to downtown
Interior
Exceptional
(22 reviews)

1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

Chicago

7% off
S$4,668
for 7 nights, 1 apartment
S$667 per night
includes taxes & fees
1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Bedroom #1 with 2 double beds and an in-suite bathroom
5 minutes drive to McCormick Place (0.9 miles)
Upscale kitchen with an equally spacious dining room
Upscale kitchen with an equally spacious dining room
Wonderful
(9 reviews)

23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown

Chicago

7% off
S$3,013
for 7 nights, 1 apartment
S$430 per night
includes taxes & fees
23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
Property grounds
Living area
Dining
Room
Wonderful
(9 reviews)

Great Location. 5min to McCormick place. Downtown. Chinatown

Chicago

7% off
S$2,633
for 7 nights, 1 apartment
S$376 per night
includes taxes & fees
Great Location. 5min to McCormick place. Downtown. Chinatown
Exterior
Living area
Room
Living area
Exceptional
(14 reviews)

Cozy apartment near zoo, DePaul, Oz Park and much more!

Chicago

7% off
S$4,103
for 7 nights, 1 apartment
S$586 per night
includes taxes & fees
Cozy apartment near zoo, DePaul, Oz Park and much more!

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental accommodation in Near South Side?
Apartments are the most popular style of holiday rental in Near South Side, according to our data. Even if you have something different in mind, Vrbo has properties in a variety of shapes and sizes. Look over our options to find your ideal fit.
How much does it cost to rent a holiday rental in Near South Side?
Length of stay, season and property type are some of the conditions that can influence the price of a holiday home. Simply enter your dates of travel to find your dream escape. From cosy country cottages to expansive luxury villas, all Vrbo holiday rentals offer incredible value.
How much does it cost to rent a beach house in Near South Side?
The average price for a holiday rental close to the beach in Near South Side depends on when you're visiting the area and the style and size of property you want. Find prices quickly and easily on Vrbo by entering your preferred travel dates. Then use the filters to select the number of bedrooms and amenities that you prefer, such as WiFi, air conditioning and a hot tub.
Are there pet-friendly holiday rentals in Near South Side?
Yes. There are. You'll have your pick of 90 holiday rentals that cater to pets in Near South Side. Several of our pet-friendly holiday rentals even have a garden for your four-legged fur baby to run around in, complimentary treats, doggie beds and proximity to parks or green space. Apply the "Pets allowed" filter to find a pad that'll set tails wagging on Vrbo.
Can I rent a house with a pool in Near South Side?
Add an extra element of fun to your getaway by booking your crew into one of the 31 houses with a private pool in Near South Side. Use our handy search filter to find the kind of property you want on Vrbo, and then spend carefree days splashing about in a swimming pool that's all your own.
What are popular rental amenities in Near South Side?
The most popular rental amenities guests are looking for in Near South Side include nearby museums, a lake view and a nearby river. Whether you're holidaying with family, buddies or even pets, Vrbo holiday properties provide the best amenities for chilling out with the people you cherish the most.
Are there large group holiday rentals in Near South Side?
With 36 Near South Side holiday homes that can host five or more people, you can bring a few extra family members or pals along. Whether you're planning an informal gathering or a birthday party, Vrbo will help you find a comfy space to match the occasion.
Are there holiday rentals in Near South Side that welcome kids?
With 90 family-friendly holiday rentals to choose from in Near South Side, now is a great time to introduce your children to the joys of travel. Just check our "Properties good for families" filter box to browse stays packed with amenities ideal for families on the move, such as multiple bedrooms, swimming pools, hot tubs and entertainment areas.
What are the top attractions for families in Near South Side?
Keep your kids entertained at these popular family-friendly attractions in Near South Side:
  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium
Are there one-bedroom holiday rentals in Near South Side?
Yes, you can take your pick from 30 one-bedroom rentals in Near South Side. Whether you're on the lookout for a cosy chalet or a cabin, Vrbo's one-bedroom properties are just right if you don't need lots of space. One of the major perks of having your own digs? You'll never need to share your trip with strangers.
Can I find two-bedroom holiday rentals in Near South Side?
You can select from 34 two-bedroom holiday homes in Near South Side. Put the kids in the second room or maybe fill it with a couple of your nearest and dearest friends. There's a comfy spot for whoever's fortunate enough to be coming along.
Are there holiday rentals with WiFi in Near South Side?
Near South Side has 31 holiday rentals with WiFi, so you'll be able to stay connected during your holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with the family to scrolling social media, these Vrbo homes will keep you online.
How can I find holiday rentals with air conditioning in Near South Side?
You'll find 85 holiday rentals with air conditioning in Near South Side giving you that cooling breeze and extra comfort level. Just enter your preferred travel dates and then make use of our filters to help you book stays with air conditioning.
How old do you have to be to rent a holiday rental in Near South Side?
We recommend you check with the Near South Side holiday property you want on Vrbo as the minimum age differs. However, it's generally 16, 18 or 21.
How long can I rent a holiday rental in Near South Side for?
The length of time you can rent a holiday rental in Near South Side depends on the property. Just enter your desired travel dates to view a list of options offering extended stays. With many amenities like air conditioning and full kitchens, as well as some offering discounted weekly or monthly prices, you're sure to find the perfect place to call your home away from home in Near South Side.

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