Far Southeast Side Vacation Rentals

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Our top choices for Far Southeast Side vacation rentals

Chic Retreat, Chic Retreat "Your Urban Getaway"

Chic Retreat, Chic Retreat "Your Urban Getaway"
Roseland
6.0 out of 10, (4 reviews)
"The host was excellent and she responded to all my questions in an excellent manner. The home was beautiful as pictured. I wouldn’t mind staying there again on my next visit! I parked my car out in front and was no problems the 3 days we were there! "
United States
Keiona W.
$403 nightly
The price is $422
Jun 1 - Jun 2
Total with taxes and fees
Chic Retreat, Chic Retreat "Your Urban Getaway"

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,160 reviews)
"Spacious apartment with stunning view. A great stay!!"
United States
Tina
$174 nightly
The price is $204
May 26 - May 27
Total with taxes and fees
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (477 reviews)
"Love the amenities. Great location too"
United States
Paul
$225 nightly
The price is $264
May 26 - May 27
Total with taxes and fees
Level Chicago – Old Town

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
$205 nightly
The price is $231
May 25 - May 26
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
$238 nightly
The price is $269
May 25 - May 26
Total with taxes and fees
West Loop Living – Bright 1BR

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
$238 nightly
The price is $269
May 25 - May 26
Total with taxes and fees
Sunlit 1BR Apartment | Warm & Welcoming Space

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
$520 nightly
The price is $595
May 26 - May 27
Total with taxes and fees
River North Rooftop With In and Out Parking 3

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
$354 nightly
The price is $437
May 27 - May 28
Total with taxes and fees
Modern 3BR Apartment Near North Ave Shops

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
$192 nightly
The price is $227
May 20 - May 21
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 2BR

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
$524 nightly
The price is $576
May 20 - May 21
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 3

Smart Home, direct Beach Dunes Nat’l Park access, luxury amenities

Smart Home, direct Beach Dunes Nat’l Park access, luxury amenities
Miller Beach
8.0 out of 10, Very Good, (22 reviews)
"Short drive to National Park and State Park hikes! Short walk to very nice beach area! Wonderful place to stay, fully stocked and plenty of room for 2 adults and 2 teens… and a dog!"
United States
Erica R.
$543 nightly
The price is $596
May 18 - May 19
Total with taxes and fees
Smart Home, direct Beach Dunes Nat’l Park access, luxury amenities

Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.8 out of 10, Excellent, (25 reviews)
"The cabin was cute and cozy and the host was very welcoming. "
United States
Deric D.
$103 nightly
The price is $115
May 17 - May 18
Total with taxes and fees
Beautiful Rustic Cabin for Two!

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
$206 nightly
The price is $243
May 27 - May 28
Total with taxes and fees
LIVN West Loop Chicago King Studio

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (17 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
$389 nightly
The price is $480
May 20 - May 21
Total with taxes and fees
Spacious 4BR Central Apartment w/ Skyline Views

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Clean spacious great location easy to get everywhere "
United States
Melissa M.
$286 nightly
The price is $325
May 26 - May 27
Total with taxes and fees
Chicago-Themed 1BR in a Central Spot near Downtown

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Miller Beach
8.6 out of 10, Excellent, (46 reviews)
"Awesome place!"
United States
Justin M.
$503 nightly
The price is $552
May 20 - May 21
Total with taxes and fees
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"Host was amazing, very responsive. VRBO was spotless! Great location! Would definitely stay here again."
United States
Amy L.
$374 nightly
The price is $415
May 19 - May 20
Total with taxes and fees
River North Rooftop With In and Out Parking 6

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.8 out of 10, Excellent, (3 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$231 nightly
The price is $260
May 19 - May 20
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry

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.
Robertsdale
9.8 out of 10, Exceptional, (26 reviews)
"I had a fun stay "
United States
Jusu K.
$178 nightly
The price is $199
May 18 - May 19
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago
Hyde Park
9.8 out of 10, Exceptional, (10 reviews)
"Room was clean, check in was easy, and the owner was very communicative."
United States
David
$161 nightly
The price is $180
May 19 - May 20
Total with taxes and fees
Cozy Charm Studio Apt in Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Far Southeast Side Hotel Reviews

Find out more about Far Southeast Side

Everything you need to know about Far Southeast Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Far Southeast Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Far Southeast Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Far Southeast Side vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Far Southeast Side. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Far Southeast Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $208 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Far Southeast Side rentals

At Expedia, we put the best Far Southeast Side vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Far Southeast Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Far Southeast Side vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Far Southeast Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.