Roseland Holiday Rentals

Compare Villas, Resorts, & Rentals in Roseland, Chicago, Illinois, USA

New Family-Friendly Home with Style & Space
New
4 Bedrooms 8 Guests
From ZA R1,989 per night
|
10.0 (4 Reviews)
1 Bedroom 6 Guests
From ZA R1,537 per night
7.2 (228 Reviews)
1 Bedroom 2 Guests
8.9 (12 Reviews)
5 Bedrooms 10 Guests
From ZA R1,556 per night
3.8 (45 Reviews)
1 Bedroom 2 Guests
New City Romance Retreat Private Experience for Two
New
1 Bedroom 2 Guests
From ZA R3,289 per night
8.6 (14 Reviews)
1 Bedroom 2 Guests
New 4/20 Friendly 12PM Check Out 1 Bedroom Basement
New
1 Bedroom 3 Guests
From ZA R2,755 per night
8.4 (40 Reviews)
3 Bedrooms 9 Guests
From ZA R3,979 per night
10.0 (2 Reviews)
1 Bedroom 2 Guests
|
8.2 (5 Reviews)
3 Bedrooms 7 Guests
9.6 (13 Reviews)
2 Bedrooms 6 Guests
|
7.6 (7 Reviews)
4 Bedrooms 12 Guests
5.1 (18 Reviews)
72 Bedrooms 6 Guests
9.0 (28 Reviews)
2 Bedrooms 6 Guests
From ZA R1,389 per night
|
3.3 (47 Reviews)
2 Bedrooms 4 Guests
9.0 (2 Reviews)
1 Bedroom 6 Guests
New
1 Bedroom 3 Guests
8.0 (1 Review)
2 Bedrooms 4 Guests
From ZA R1,908 per night
New
1 Bedroom 3 Guests
From ZA R1,871 per night
New
2 Bedrooms 6 Guests
From ZA R1,809 per night
New
1 Bedroom 2 Guests
10.0 (5 Reviews)
3 Bedrooms 8 Guests
10.0 (4 Reviews)
3 Bedrooms 8 Guests
10.0 (2 Reviews)
3 Bedrooms 6 Guests
From ZA R6,429 per night
10.0 (1 Review)
4 Bedrooms 13 Guests
9.8 (7 Reviews)
3 Bedrooms 6 Guests
9.6 (5 Reviews)
4 Bedrooms 10 Guests
From ZA R10,678 per night
9.6 (4 Reviews)
4 Bedrooms 14 Guests
9.0 (22 Reviews)
4 Bedrooms 7 Guests
8.8 (6 Reviews)
4 Bedrooms 11 Guests
2.0 (1 Review)
4 Bedrooms 4 Guests
New
3 Bedrooms 12 Guests
From ZA R4,548 per night
New
3 Bedrooms 10 Guests
New
3 Bedrooms 6 Guests
From ZA R4,421 per night
New
5 Bedrooms 12 Guests
New
4 Bedrooms 8 Guests
10.0 (2 Reviews)
2 Bedrooms 4 Guests
From ZA R4,486 per night
7.0 (12 Reviews)
4 Bedrooms 10 Guests
7.0 (2 Reviews)
4 Bedrooms 10 Guests
6.8 (3 Reviews)
4 Bedrooms 8 Guests
6.0 (3 Reviews)
2 Bedrooms 5 Guests
5.0 (2 Reviews)
2 Bedrooms 6 Guests
From ZA R3,484 per night
4.6 (8 Reviews)
2 Bedrooms 5 Guests
4.3 (3 Reviews)
2 Bedrooms 6 Guests

About Casai's Private Villas and Holiday Rentals in Roseland

Discover more than 120 vacation rentals available in Roseland. 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 Roseland.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Roseland, 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 Roseland. On average, places to stay near Roseland offer 351.71 ft², with nightly prices averaging ZA R5,209.

With Casai, finding and comparing holiday rentals in Roseland is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Frequently Asked Questions About Roseland?

What are the top holiday rentals in Roseland?

How many Casai.co.za holiday rentals are available in Roseland?

As of 2026, Casai boasts over 120 properties listed in the Roseland area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Roseland.

Nearby Neighborhood (2)

Neighborhood Property Count
Washington Heights Vacation Rentals in Chicago, Illinois 112
Princeton Park Vacation Rentals in Chicago, Illinois 144