Owner Direct Vacation
Rentals in Near North Side

The Best Owner Direct Vacation Rentals in Near North Side. Explore thousands of vacation home rentals, large cabins, and villas near Near North Side

Explore the Best Near North Side Vacation Homes

Looking for the perfect place to stay in Near North Side? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Near North Side character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.

  • vacation rentals
  • luxury villas
  • beachfront homes
  • pet-friendly rentals
  • condos
|
10 (1 Review)
Apartment
3BR Luxury Modern Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
US
View Availability
|
10 (1 Review)
Apartment
3BR Luxury Modern Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
US
View Availability
|
9.6 (192 Reviews)
Apartment
Kasa River North Chicago
  • Air Conditioner
  • Pet Friendly
  • Pool
US
View Availability
|
7.6 (12 Reviews)
Apartment
River North Deltee
  • Air Conditioner
  • Parking
  • Pet Friendly
US
View Availability

Why Travelers Love Using
Owner Direct to
Find Near North Side Vacation Rentals

What makes our vacation homes stand out?

check-mark

Verified Properties

Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

check-mark

Value You Can Trust

Compare a range of properties and find fair, transparent pricing—no hidden fees.

check-mark

Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

More Places to Stay Near Near North Side

|
10 (4 Reviews)
Hotel
ENVITAE Hotel | 2 Bedroom Luxury Apartments
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility
US
View Availability
|
10 (1 Review)
Apartment
3BR Luxury Modern Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
US
View Availability

Popular Neighborhoods for Near North Side Vacation Rentals

What are the best areas to stay in Near North Side

Discover the top neighborhoods in Near North Side and choose a place that suits your stay.

Wednesday May 13

Near North Side, Chicago

Wed
weather icon
11.8°C
Thu
weather icon
11.1°C
Fri
weather icon
14.2°C
Sat
weather icon
18.7°C
Sun
weather icon
13.8°C
Mon
weather icon
19.4°C
Tue
weather icon
12.7°C

More Vacation Rentals You May Like Near Near North Side

How to Reserve Your Near North Side Vacation Rental

Booking Made Simple

Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.

search-icon

SEARCH PROPERTIES

Use filters for location, amenities, and budget.

compare-icon

VIEW DETAILS

Check photos, reviews, and features for your top picks.

bed-icon

BOOK SECURELY

Confirm your stay safely through our trusted travel partners.

Near North Side Vacation Rental FAQs

What are the top vacation rentals in Near North Side?
How many vacation rentals have private pools in Near North Side?

There are 28 vacation rentals with private pools near Near North Side. Top-rated homes that have access to a swimming pool include:

Which vacation homes in Near North Side are best for families?

If you are looking for a family-friendly vacation home in Near North Side, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Near North Side:

How many vacation rentals are available in Near North Side?

Currently, the total number of properties listed in 2026 is over 1319 in the Near North Side area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Near North Side.