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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

Private beachfront home rentals

Superhost
Apartment in Chicago
4.84 out of 5 average rating, 55 reviews

Woodlawn Oasis

MaryRating, 5 stars1 week ago
Nice residential neighborhood. Good easy parking. Very clean. Exactly as pictured on the listing. Perfect location for our Chicago vacation and to attend our daughter’s location from UChicago.
Superhost
Apartment in Chicago
4.9 out of 5 average rating, 175 reviews

Executive Apartment on Lake Michigan with parking

JoshuaRating, 5 stars1 week ago
Man this place was awesome! It was so relaxing and peaceful. Everything was the way it was described. Definitely coming back!
Superhost
Apartment in Chicago
4.85 out of 5 average rating, 92 reviews

Pristine Lakeview| Boystown |Wrigley Haven |Beach

JonathanRating, 5 stars4 days ago
What a fantastic time we had. It was spacious for the two of us. Comfortable bed and lounging. But the two big things that make this place a win: #1 Rasheed. He really goes above and beyond for his guests. He ensured we had what we needed and was on top of his messages. #2 Location. Everything you need is within reach. Transit options everywhere. Lots of good food, and close by grocery store. So many amazing bars. Great for our summertime adventure! Thanks Rasheed.
Superhost
Apartment in Evanston
4.85 out of 5 average rating, 67 reviews

Modern | Spacious | New Renovation | 1BR | Evanston

MadelineRating, 5 stars1 week ago
I loved this stay. The hosts were very responsive and friendly. The beach being nearby was so nice. We took nightly walks to the beach and it was very peaceful and beautiful. The apartment is spacious, cozy, has bright natural lighting during the day, and has all the amenities you’ll need. It felt luxurious and very homey. The bed was very comfortable and had a goose down blanket. It felt like I was sleeping on a marshmallow or a cloud! Only thing is parking can get a little complicated if you’re leaving and coming back often, but for the most part it was okay. Overall, I would stay here again and recommend this to anyone wanting to book!
Superhost
Condo in Chicago
4.87 out of 5 average rating, 195 reviews

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

LeannRating, 5 stars2 months 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!
Apartment in Evanston
4.66 out of 5 average rating, 165 reviews

✨Chic|Luxurious|2BR|Trendy|Evanston Next To Beach✨

CarolineRating, 5 stars1 week ago
Demitri was very thorough in description, comfort and location. The place was very comfortable and spacious. When I needed something, Dimitri responded immediately. I felt I was in very good hands, and I made a great choice for Evanston.
Top guest favorite
Guesthouse in Evanston
4.94 out of 5 average rating, 120 reviews

Historic Coach House in Evanston Near Beach & Town

MeganRating, 5 stars2 weeks ago
Janet was an amazing host and her carriage house was very lovely. Location was top notch a block from Lake Michigan. Janet had bikes available to ride on the lake front as well as seasonal beach passes. She was very accommodating to our 20 month old and made sure we had whatever we needed to feel at home. Highly recommend
Guest favorite
Townhouse in Chicago
4.84 out of 5 average rating, 206 reviews

Historic lux Townhouse on Chicago's Gold Coast

RobynRating, 5 stars2 weeks ago
The house was beautiful and in a very nice, safe neighborhood. There was some construction going on next door, but other than that, the place was everything we hoped it would be. We stayed here while we got married at a nearby venue in River North and it was able to accommodate our bridal party during our getting ready session and provide a quiet place to rest once our wedding was over.

Luxury beachfront home rentals

Superhost
Condo in Chicago
4.87 out of 5 average rating, 195 reviews

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

LeannRating, 5 stars2 months 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!
Guest favorite
Townhouse in Chicago
4.84 out of 5 average rating, 206 reviews

Historic lux Townhouse on Chicago's Gold Coast

RobynRating, 5 stars2 weeks ago
The house was beautiful and in a very nice, safe neighborhood. There was some construction going on next door, but other than that, the place was everything we hoped it would be. We stayed here while we got married at a nearby venue in River North and it was able to accommodate our bridal party during our getting ready session and provide a quiet place to rest once our wedding was over.
Home in Chicago
4.84 out of 5 average rating, 32 reviews

Only Urban Beach House in Chicago

TienRating, 5 stars11 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!
Top guest favorite
Apartment in Chicago
4.97 out of 5 average rating, 66 reviews

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

KimRating, 5 stars1 week ago
Great location for walking to the beach, shopping, and dining. We were able to check in a little early and leave our luggage while the cleaners were in the apt. Parking in the garage next door was super convenient. There are stairs to the unit, which wasn’t an issue for us, but Rasheed still helped get our luggage upstairs!
Superhost
Guest suite in Evanston
4.78 out of 5 average rating, 102 reviews

Historic Manor House Private Guest Suite Evanston

WilliamRating, 5 stars6 months ago
Great location. Janet was a great host and was extremely responsive for any questions we had. Definitely recommend for those looking to get a true taste of an Evanston residential neighborhood

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