
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.
0 of 0 items showing
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Oakwood Beach beachfront rentals
Private beachfront home rentals
Superhost

Apartment in Chicago
4.84 out of 5 average rating, 55 reviewsWoodlawn 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 reviewsExecutive 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 reviewsPristine 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 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

Condo in Chicago
4.87 out of 5 average rating, 195 reviews2BD/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 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
Guest favorite

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.
Luxury beachfront home rentals
Superhost

Condo in Chicago
4.87 out of 5 average rating, 195 reviews2BD/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 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.

Home in Chicago
4.84 out of 5 average rating, 32 reviewsOnly 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 reviewsGold 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 reviewsHistoric 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
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- West Side Vacation rentals
- North Side Vacation rentals
- South Bend Vacation rentals
- South Haven Vacation rentals
- South Side Vacation rentals
- Saugatuck Vacation rentals
- Lake Michigan Beach Vacation rentals
- Evanston Vacation rentals
- Chicago Vacation rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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
- Flossmoor Golf Club