
Beachfront vacation 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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Vacation rentals for every style
Get the amount of space that is right for you.
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 reviews1 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 reviewsExecutive 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 reviewsCannabis 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 reviewsStone 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.
Private beachfront home rentals

Apartment in Evanston
4.67 out of 5 average rating, 158 reviews✨Chic|Luxurious|2BR|Trendy|Evanston Next To Beach✨
JayRating, 5 stars2 weeks ago
great location. well back from street so quiet. dedicated free parking a big bonus in this area.

Apartment in Evanston
4.72 out of 5 average rating, 120 reviewsModern|Aesthetic|2BR|Evanston|Near Beach
ShiyuanRating, 5 stars4 days ago
Demitri is really friendly and the house is clean. It’s an enjoyable stay.
Guest favourite

Apartment in Evanston
4.92 out of 5 average rating, 86 reviewsNew renovation|1BR|Stylish|Modern|Next to the Lake
AyseRating, 5 stars4 days ago
It was a cozy clean and cute place. thank you so much. i will definetely come back again !
Superhost

Apartment in Chicago
4.88 out of 5 average rating, 88 reviewsPristine Lakeview| Boystown |Wrigley Haven |Beach.
WarrenRating, 5 stars1 week ago
Great location for being in the Northalsted (Boystown) area and being able to catch the bus to go downtown.
Luxury beachfront home rentals
Superhost

Condo in Chicago
4.87 out of 5 average rating, 193 reviews2BD/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 reviewsOnly 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 reviewsGold 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 reviewsHistoric 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.
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Six Flags Great America
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park Zoo
- Flossmoor Golf Club
- Museum of Science and Industry
- Willis Tower
- Lincoln Park
- Wicker Park
- Chicago History Museum
- Skokie Country Club
- Illinois Beach State Park
- Washington Park Zoo
- Promontory Point
- Brookfield Zoo