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Beachfront vacation rentals in Oakwood Beach

Find and book unique beachfront homes on Airbnb

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Popular amenities for Oakwood Beach beachfront rentals

Pet-friendly beachfront home rentals

Top guest favourite
Private room in Evanston
4.84 out of 5 average rating, 68 reviews

1 Room for up to 3, Near NU & Old Orchard Mall

SakiRating, 5 stars5 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, 167 reviews

Executive Apartment on Lake Michigan with parking

DevinRating, 5 stars1 week ago
me and my fiance stayed just a few days and I didn’t want to leave! The space was even better than expected. Having almost everything you’d need to cook, plenty of towels, clean bedding. It was so clean and beautiful inside and the view from the balcony was gorgeous. Felt just like home. The neighborhood was very nice and peaceful as well. We will 100% be back!
Guest favourite
Apartment in Chicago
4.9 out of 5 average rating, 99 reviews

Cannabis Condo 4BR

HeatherRating, 5 stars1 week ago
Great stay in Chicago. Parking was easy and getting inside was a breeze with the instructions provided. The unit was just as expected with added touches like extra towels and cold drinks in the fridge on arrival. We enjoyed our time and recommend Shomari’s place for a perfect weekend in Chicago with family and friends!
Guest favourite
Apartment in Chicago
4.92 out of 5 average rating, 227 reviews

Stone Mansion Sleeps 10-20 Free parking & TV

PennyRating, 5 stars1 week ago
Seven of us had a great stay at Will’s place! This is a spacious apartment that is in a quiet neighborhood, yet only two blocks from restaurants and bars. We walked just about every place we went, including to Wrigley Field for a game. The place had everything we could possibly need. The kitchen was well stocked, plenty of towels and linens. Very convenient to be able to drop our bags in the garage until check in time. Will is a very responsive host. We hope to come back some time.

Luxury beachfront home rentals

Superhost
Condo in Chicago
4.87 out of 5 average rating, 193 reviews

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)

LeannRating, 5 stars1 month ago
WWWWOOOWWW!! This host team was EXCEPTIONAL! I’ve stayed in plenty of AirBnBs, and I’ve NEVER encountered a host that was so EXTREMELY accommodating, responsive, and kind! Other hosts should take a page out of their book! The only thing I would change, and it’s not a bad thing (just a matter of preference); I would have some type of blinds or drapes over the living room windows. This will allow for privacy when you’re sitting in the living/dining room areas at night with the lights on inside. Hands down, we would without a doubt book with this team again! Thank you Wendy, Matt, and your co-hosts for helping to make our time in Chicago wonderful!
Home in Chicago
4.84 out of 5 average rating, 32 reviews

Only Urban Beach House in Chicago

TienRating, 5 stars9 months ago
This is a beautiful, old house right by the park and beach, plus a playground and adorable summer snack shack just a few minutes walk away. There's a lovely private back yard and deck for summer evenings. We especially appreciated the kitchen, which was well-stocked with all the dishes and equipment we needed to cook full meals for our large family. We stayed for an extended time, and whenever anything came up, our wonderful hosts were quick to respond and help. Thanks Keith for your hospitality!
Guest favourite
Apartment in Chicago
4.97 out of 5 average rating, 60 reviews

Gold Coast Pristine 3BD|2BR| Patio |Parking| Views

EllenRating, 5 stars4 days ago
Rasheed was a great host and went out of his way to make our stay comfortable. Thanks!
Superhost
Guest suite in Evanston
4.82 out of 5 average rating, 100 reviews

Historic Manor House Private Guest Suite Evanston

RebekahRating, 5 stars6 months ago
Charming and Historic. The house is on a quiet streat in a beautiful area. Janet's place is an easy drive to everything Chicago or a quick walk to the beach. Evanston has great restaurants and shops too.

Destinations to explore

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  5. Chicago
  6. Oakwood Beach
  7. Beachfront rentals