
Beachfront holiday rentals in Oakwood Beach
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Oakwood Beach
Guests agree: these beachfront homes are highly rated for location, cleanliness and more.
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Popular amenities for beachfront rentals in Oakwood Beach
Pet-friendly beachfront home rentals
Guest favourite

Townhouse in Chicago
4.84 out of 5 average rating, 206 reviewsHistoric 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.
Superhost

Flat in Chicago
4.89 out of 5 average rating, 176 reviewsExecutive Apartment on Lake Michigan with parking
JoshuaRating, 5 stars2 weeks ago
Man this place was awesome! It was so relaxing and peaceful. Everything was the way it was described. Definitely coming back!
Guest favourite

Flat in Chicago
4.9 out of 5 average rating, 101 reviewsCannabis Condo 4BR
JenniferRating, 5 stars1 month ago
Shomari was a great host, very friendly and gave great recommendations. We had all the towels and he had toiletry items in the bathroom and cooking items (spices, extra drinks) in the kitchen. My girls and I didn’t feel unsafe in the area, although finding street parking on the block can be tough, depending on the time of day. His place is a 25-30 min drive to downtown, soldier field and McCormick place, it can be less or more depending on the traffic. It was a great stay and I would recommend.
Guest favourite

Flat in Chicago
4.92 out of 5 average rating, 236 reviewsStone Mansion Sleeps 10-20 Free parking & TV
FionaRating, 5 stars2 weeks ago
We had a great stay! The location is great and Will was incredibly responsive.
Private beachfront home rentals
Superhost

Flat in Chicago
4.84 out of 5 average rating, 56 reviewsWoodlawn Oasis
KimberlyRating, 5 stars1 week ago
Excellent communication. Easy access to the apartment. Located in a safe building and a quiet neighborhood. I would both recommend the Oaklawn Oasis and stay here again.
Guest favourite

Flat in Evanston
4.9 out of 5 average rating, 91 reviewsNew renovation|1BR|Stylish|Modern|Next to the Lake
AmyRating, 5 stars1 month ago
Clean, comfortable, and beautifully appointed apt. Emily and Roya are helpful and communicative, and all the instructions and photos made things very easy. Would happily stay there again!
Superhost

Flat in Chicago
4.89 out of 5 average rating, 176 reviewsExecutive Apartment on Lake Michigan with parking
JoshuaRating, 5 stars2 weeks ago
Man this place was awesome! It was so relaxing and peaceful. Everything was the way it was described. Definitely coming back!
Superhost

Flat in Chicago
4.85 out of 5 average rating, 92 reviewsPristine Lakeview| Boystown |Wrigley Haven |Beach
JonathanRating, 5 stars1 week 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

Flat in Evanston
4.85 out of 5 average rating, 67 reviewsModern|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

Apartment in Chicago
4.87 out of 5 average rating, 195 reviews2BD/2BA MAG MILE MASTERPIECE (+Rooftop)
LeannRating, 5 stars3 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!

Flat 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 favourite

Guest house in Evanston
4.94 out of 5 average rating, 120 reviewsHistoric 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
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Moraine Hills State Park