Find Vacation Rentals in Near South Side

We have 3,369 properties to choose from
Near South Side
Anytime
Guests
Near South Side
Anytime
Guests

Popular Near South Side Vacation Rentals

Find the perfect Near South Side vacation rental

Condo Near South Side
$305 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding (16 ratings)
Near South Side, Chicago, Illinois, United States
Details
Vrbo
Details
Details
Apartment Near South Side
$694 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
4.6
Excellent (5 ratings)
Near South Side, Chicago, Illinois, United States
Details
Vrbo
Details
Details
Apartment Near South Side
$857 per night
Apartment ∙ 12 guests ∙ 4 bedrooms
4.8
Outstanding (17 ratings)
Near South Side, Chicago, Illinois, United States
Details
Vrbo
Details
Details
Apartment Near South Side
$410 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding (37 ratings)
Near South Side, Chicago, Illinois, United States
Details
Vrbo
Details
Details
Apartment Near South Side
$420 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding (47 ratings)
Near South Side, Chicago, Illinois, United States
Details
Vrbo
Details
Details
Apartment Near South Side
$666 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (130 ratings)
Near South Side, Chicago, Illinois, United States
Details
Vrbo
Details
Details
Apartment Near South Side
$222 per night
Apartment ∙ 5 guests ∙ 3 bedrooms
4.9
Outstanding (17 ratings)
Near South Side, Chicago, Illinois, United States
Details
Vrbo
Details
Details
House Near South Side
$427 per night
House ∙ 10 guests ∙ 4 bedrooms
4.8
Outstanding (10 ratings)
Near South Side, Chicago, Illinois, United States
Details
Vrbo
Details
Details
Apartment Near South Side
$198 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
3.8
Good (8 ratings)
Near South Side, Chicago, Illinois, United States
Details
Vrbo
Details
Details
View more

Recommended Rentals With Pools

Aparthotel  Near South Side
$171 per night
Aparthotel ∙ 8 guests ∙ 1 bedroom
4.6
Excellent (402 ratings)
Near South Side, Chicago, Illinois, United States
Pool
Details
Expedia
Details
Details
Condo  Near South Side
$704 per night
Condo ∙ 7 guests ∙ 2 bedrooms
5.0
Outstanding (6 ratings)
Near South Side, Chicago, Illinois, United States
Pool
Details
Vrbo
Details
Details
Apartment  Near South Side
$179 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Near South Side, Chicago, Illinois, United States
Pool
Details
Vrbo
Details
Details
View more

Pet-Friendly Homes and Apartments

Apartment  Near South Side
$436 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding (31 ratings)
Near South Side, Chicago, Illinois, United States
Pet-friendly
Details
Vrbo
Details
Details
Apartment  Near South Side
$429 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (10 ratings)
Near South Side, Chicago, Illinois, United States
Pet-friendly
Details
Vrbo
Details
Details
Apartment  Near South Side
$432 per night
Apartment ∙ 12 guests ∙ 3 bedrooms
4.8
Outstanding (38 ratings)
Near South Side, Chicago, Illinois, United States
Pet-friendly
Details
Vrbo
Details
Details
View more

Best vacation rentals with a balcony

Apartment  Near South Side
$404 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding (27 ratings)
Near South Side, Chicago, Illinois, United States
Balcony
Details
Vrbo
Details
Details
Condo  Near South Side
$461 per night
Condo ∙ 10 guests ∙ 3 bedrooms
4.5
Excellent (15 ratings)
Near South Side, Chicago, Illinois, United States
Balcony
Details
Vrbo
Details
Details
Apartment  Near South Side
$181 per night
Apartment ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding (21 ratings)
Near South Side, Chicago, Illinois, United States
Balcony
Details
Vrbo
Details
Details
View more

Frequently Asked Questions

How much does it cost to book a vacation rental in Near South Side?

In Near South Side, vacation rentals start at $46 per night.

Can I see all vacation rentals that are available in Near South Side?

You can find and compare 3,369 offers in Near South Side and book an ideal place for your next getaway.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Near South Side

Looking for a vacation rental in Near South Side? Tripping.com has 100 vacation rental homes available in Near South Side. You'll find 4 studios, 58 1-bedroom, 34 2-bedroom and 4 rentals with 3 or more bedrooms ranging from $43 a night. For extra convenience, many of these vacation homes can be booked directly online. The average price of a nightly rental in Near South Side is $249 while the average price of a weekly rental is $25. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Near South Side home is $25. Wondering if you can bring your dog or cat along with you? There are 6 pet-friendly vacation rentals available in Near South Side. In addition to accommodating pets, Near South Side rentals offer a variety of amenities. In particular, 81 rentals have Internet and WiFi, 79 have TV and/or cable and 18 have a pool or hot tub. Search properties from 5 vacation rental sites in Near South Side where the top providers in that area are HomeAway, Booking.com, and Expedia. There are 38 HomeAway rentals, 24 Booking.com short term rentals and 18 Expedia vacation rentals.

Popular Day Trips Near Near South Side

Show more
image-tag