Beachfront vacation rentals in Oak Street Beach
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Oak Street Beach
Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Oak Street Beach beachfront rentals
Pet-friendly beachfront home rentals
Apartment in Chicago
New place to stayLovely & spacious 1B by the lake
Aug 26 – Sep 2
$217 per night
Room in Chicago
4.77 out of 5 average rating, 130 reviewsBasic accomodation equipped for short terms stays.
Jul 12 – 19
$52 per night
Guest favorite
Apartment in Chicago
4.94 out of 5 average rating, 85 reviews420 at Cheltenham 4BR
Jul 8 – 15
$273 per night
Apartment in Chicago
4.86 out of 5 average rating, 101 reviewsRock Star Beach Pad on Lake Michigan with parking
Apr 28 – May 5
$306 per night
Private beachfront home rentals
Superhost
Condo in Chicago
4.89 out of 5 average rating, 169 reviews2BD/2BA MAG MILE MASTERPIECE (+Rooftop)
Jul 10 – 17
$447 per night
Guest favorite
Apartment in Chicago
4.86 out of 5 average rating, 50 reviewsLakeview/Boystown/Wrigleyville Paradise Haven
Jun 6 – 13
$255 per night
Guest favorite
Apartment in Evanston
4.95 out of 5 average rating, 43 reviewsNew renovation|1BR|Stylish|Modern|Next to the Lake
Aug 8 – 15
$233 per night
Guest favorite
Guest suite in Evanston
4.85 out of 5 average rating, 86 reviewsHistoric Manor House Private Guest Suite Evanston
Jul 15 – 22
$328 per night
Apartment in Evanston
4.71 out of 5 average rating, 113 reviews✨Chic|Luxurious|2BR|Trendy|Evanston Next To Beach✨
Nov 14 – 21
$221 per night
Apartment in Evanston
4.78 out of 5 average rating, 85 reviews🌟Elegant|Brand New Remodeled|1BR|Next to beach🌟🏖
Oct 13 – 20
$222 per night
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