
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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Popular amenities for Oak Street Beach beachfront rentals
Pet-friendly beachfront home rentals
Top guest favorite

Private room in Evanston
4.84 out of 5 average rating, 68 reviews1 Room for up to 3, Near NU & Old Orchard Mall
SakiRating, 5 stars4 months ago
We had an absolutely wonderful time. Nancy was truly kind and made various thoughtful arrangements to ensure our family felt comfortable. Her dog, Pepper, was also very friendly and played with my daughter. The room was impeccably clean and left nothing to be desired. The bathroom, in particular, was spotless, allowing us to relax in the bath with peace of mind. Thank you so much!
Superhost

Apartment in Chicago
4.89 out of 5 average rating, 166 reviewsExecutive Apartment on Lake Michigan with parking
DebraRating, 5 stars1 month ago
This was a beautiful place with an excellent view of Lake Michigan. Both rooms had comfortable beds and setup with everything you need. Kitchen is well stocked, but we mostly ordered Grub Hub, lol. Loved spending time here and great place to hangout and chat with friends. It is right on the water and we really enjoyed watching the waves crash against the barrier. It is on the 2nd floor, but the stairs are not bad at all. Felt very safe and having the parking space is a great perk. Very commutative and checked in with us to make sure everything was fine. Would definitely stay here again!
Guest favorite

Apartment in Chicago
4.9 out of 5 average rating, 98 reviewsCannabis Condo 4BR
Kristina LRating, 5 stars1 month ago
everything was perfect for my family of 8 house was clean and comfy felt like I was at home
Guest favorite

Apartment in Chicago
4.92 out of 5 average rating, 226 reviewsStone Mansion Sleeps 10-20 Free parking & TV
TylerRating, 5 stars3 days ago
Was a great place to stay. Will was very great to have as a host. Highly recommend!
Private beachfront home rentals
Superhost

Apartment in Chicago
4.82 out of 5 average rating, 51 reviewsWoodlawn Oasis
ZeeRating, 5 stars6 months ago
Super responsive host and I loved the candles they had! The place was super clean and is exactly how it is listed on the photos
Superhost

Apartment in Chicago
4.89 out of 5 average rating, 166 reviewsExecutive Apartment on Lake Michigan with parking
DebraRating, 5 stars1 month ago
This was a beautiful place with an excellent view of Lake Michigan. Both rooms had comfortable beds and setup with everything you need. Kitchen is well stocked, but we mostly ordered Grub Hub, lol. Loved spending time here and great place to hangout and chat with friends. It is right on the water and we really enjoyed watching the waves crash against the barrier. It is on the 2nd floor, but the stairs are not bad at all. Felt very safe and having the parking space is a great perk. Very commutative and checked in with us to make sure everything was fine. Would definitely stay here again!
Guest favorite

Apartment in Evanston
4.92 out of 5 average rating, 84 reviewsNew renovation|1BR|Stylish|Modern|Next to the Lake
GabbyRating, 5 stars1 month ago
This stay in Evanston was so convenient! It was a 15 minute walk from the Purple line, which made it easy to get to the city. The beach was also beautiful and it was only a 2 minute walk!
Guest favorite

Apartment in Chicago
4.88 out of 5 average rating, 85 reviewsPristine Lakeview| Boystown |Wrigley Haven |Beach.
MackenzieRating, 5 stars2 weeks ago
Wonderful stay in a beautiful part of Chicago! There's lot to do in the area and it's just a quick walk away from the lake shore. Would highly recommend for anyone looking for a clean and cozy place to stay in northern Chicago!
Guest favorite

Apartment in Chicago
4.9 out of 5 average rating, 98 reviewsCannabis Condo 4BR
Kristina LRating, 5 stars1 month ago
everything was perfect for my family of 8 house was clean and comfy felt like I was at home
Superhost

Apartment in Evanston
4.85 out of 5 average rating, 60 reviewsModern | Spacious | New Renovation | 1BR | Evanston
AmyRating, 5 stars1 month ago
Just stayed here for the second time and I highly recommend it!

Apartment in Evanston
4.67 out of 5 average rating, 157 reviews✨Chic|Luxurious|2BR|Trendy|Evanston Next To Beach✨
JayRating, 5 stars5 days ago
great location. well back from street so quiet. dedicated free parking a big bonus in this area.
Guest favorite

Guesthouse in Evanston
4.94 out of 5 average rating, 117 reviewsHistoric Coach House in Evanston Near Beach & Town
HeidiRating, 5 stars2 weeks ago
Janet was very easy to communicate with, and the accommodations were spotless, welcoming, and complete with all needed amenities. The walk to the lake was easy, and walking to restaurants, grocery stores, and shops was convenient. The accommodations fit the description, the photos were accurate, and Janet was as helpful as can be.
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