
Far Southeast Side Vacation Rentals
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Our top choices for Far Southeast Side vacation rentals

1. Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park Trendy Studio Apartment in Good Spot
2. Wrigleyville Suites
Wrigleyville Suites
3. Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
Large Chicago Apt 3 BR - King Bed - 12 Min Downtown w/ Arcade
4. Great Area Logan Square Apt Games Pets - Sleeps 5
Great Area Logan Square Apt Games Pets - Sleeps 5
5. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
6. Cozy studio in Andersonville Chicago
Cozy studio in Andersonville Chicago
7. Flexhome East Village • Modern 2BR • Quiet Street
Flexhome East Village • Modern 2BR • Quiet Street
8. Chic Suite/Mins to L Train /Laundry/Free Parking
Chic Suite/Mins to L Train /Laundry/Free Parking
9. Flexhome Wicker Park • Stylish 2BR • Sleeps 6
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
10. Chic Urban Retreat Near Wrigley Field w/Parking
Chic Urban Retreat Near Wrigley Field w/Parking
11. Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
12. Private Workspace • Sleeps 4 • Modern and Stylish
Private Workspace • Sleeps 4 • Modern and Stylish
13. Kasa Lake Shore Chicago
Kasa Lake Shore Chicago
14. Beautiful Rustic Cabin for Two!
Beautiful Rustic Cabin for Two!
15. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
16. 3BR Complete and Spacious Apartment in Ideal Spot
3BR Complete and Spacious Apartment in Ideal Spot
17. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
18. 1BR/1BA City Comfort
1BR/1BA City Comfort
19. Sleeps 7 • Huge Projector • Designated Workspace
Sleeps 7 • Huge Projector • Designated Workspace
20. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.Find vacation rentals that suit your style
Top Far Southeast Side Hotel Reviews

The Royal Sonesta Chicago Downtown
Find out more about Far Southeast Side
You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Far Southeast Side. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.
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