Beachfront holiday rental in Oak Street Beach
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Top-rated beachfront accommodation in Oak Street Beach
Guests agree: These beachfront homes are highly rated for location, cleanliness and more.
Holiday 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
Room in Chicago
4.77 out of 5 average rating, 129 reviewsBasic accomodation equipped for short terms stays.
3 – 10 July
Apartment in Chicago
4.94 out of 5 average rating, 85 reviews420 at Cheltenham 4BR
15 – 22 Sept
Apartment in Chicago
4.86 out of 5 average rating, 100 reviewsRock Star Beach Pad on Lake Michigan with parking
30 Mar – 6 Apr
Apartment in Chicago
4.91 out of 5 average rating, 183 reviewsStone Mansion Sleeps 10-20 Free parking & TV
15 – 22 Nov
Apartment in Chicago
4.88 out of 5 average rating, 86 reviewsCannabis Condo 4BR
19 – 26 Oct
Apartment in Chicago
4.94 out of 5 average rating, 124 reviewsExecutive Apartment on Lake Michigan with parking
25 Mar – 1 Apr
Condo in Chicago
4.69 out of 5 average rating, 16 reviewsModern Duplex Condo With Advanced 4K LED TV’s/PS5
24 Nov – 1 Dec
Apartment in Chicago
New place to stayLovely & spacious 1B by the lake
3 – 10 Oct
Private beachfront home rentals
Condo in Chicago
4.9 out of 5 average rating, 235 reviewsMAG MILE 2/2 Gold Coast Gem (+Parking/Rooftop)
10 – 15 May
Condo in Chicago
4.87 out of 5 average rating, 242 reviewsMAG MILE 2/2 w/ Lake VIEWS! (+Rooftop)
17 – 24 June
Apartment in Chicago
4.86 out of 5 average rating, 50 reviewsLakeview/Boystown/Wrigleyville Paradise Haven
29 July – 5 Aug
Apartment in Evanston
4.98 out of 5 average rating, 42 reviewsNew renovation|1BR|Stylish|Modern|Next to the Lake
9 – 16 Oct
Guest suite in Evanston
4.85 out of 5 average rating, 86 reviewsHistoric Manor House Private Guest Suite Evanston
12 – 19 June
Apartment in Evanston
4.8 out of 5 average rating, 83 reviewsModern|Aesthetic|2BR|Evanston|Near Beach
30 Oct – 6 Nov
Apartment in Evanston
4.71 out of 5 average rating, 113 reviews✨Chic|Luxurious|2BR|Trendy|Evanston Next To Beach✨
23 – 30 Sept
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