Holiday rentals with beach access in West Side

Find and book unique rentals with beach access on Airbnb

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Popular amenities for rentals with beach access in West Side

Apartment rentals with beach access

Guest favourite
Flat in Chicago
4.92 out of 5 average rating, 37 reviews

Sheridan Beach Apartment

RanceRating, 5 stars3 weeks ago
Amy was an excellent host, very responsive to email, and offered flexible check-in times. The location is only a few blocks from the train and an easy ride to Wrigley. Many good restaurants in the area. The unit was very clean and well cared for with modern amenities. Overall, an easy choice to stay here again.
Guest favourite
Flat in Chicago
4.83 out of 5 average rating, 167 reviews

The Posh Apt. Mins to Downtown & Hyde Park

VijayRating, 5 stars1 month ago
We had a most wonderful stay at Kayode's apartment which was very clean and matched all the descriptions in the listing and it was perfectly located for our purpose which was to be close to Hyde Park. Kayode was the perfect host and was extremely responsive and even when had a minor issue, he responded within minutes and had the issue resolved within the hour. Highly recommend Kayode as a host if you need an apartment in the Hyde Park area
Guest favourite
Flat in Chicago
4.78 out of 5 average rating, 9 reviews

3 Bed 3 Bath Lakefront Oasis, Parking Included

Robert MasonRating, 5 stars4 weeks ago
Very nice place right on the lake. Roomy, top of the line appliances. Two en suite baths. Conveniently located between Rogers Park (Loyola) and Evanston (Northwestern). Grocery store close by. Very responsive owner - responded within 10 minutes every time I reached out, before and during our stay.
Guest favourite
Flat in Chicago
4.93 out of 5 average rating, 171 reviews

*Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D

KivlinaRating, 5 stars1 month ago
Spacious and well appointed with everything we needed to feel right at home. Good quality linens and furnishings, thick toilet paper and exactly as the photos showed. VERY walkable. We walked to the river/lake everyday and enjoyed boat tours, the theatre and sightseeing. It is a very urban stay so there is a lot of city noise, that’s not a critique, just the reality of staying in a large city.
Top guest favourite
Flat in Chicago
4.96 out of 5 average rating, 93 reviews

Andersonville Bicycle Studio

RebeccaRating, 5 stars1 week ago
I had a wonderful stay at this lovely Airbnb! The decor was so thoughtful and definitely matched the bicycle studio vibes. The space was really cozy and welcoming. I especially appreciated the small details that showed how much care went into setting up the home. The host also left a kind handwritten note, which was such a warm and personal touch. It made me feel right at home from the moment I arrived. It was great being back in my old neighborhood for a visit and this space was in the perfect location. Highly recommend staying here!
Top guest favourite
Flat in Chicago
4.98 out of 5 average rating, 198 reviews

Beautiful Hollywood-Ridge Suite in Edgewater

BillRating, 5 stars1 week ago
Dorothy was very welcoming and communicative, and the bagels and snacks were an extra nice touch. The rental is as described, if not better, and provided a quiet and comfortable place to stay. The location is well centered between Andersonville and the Bryn Mayr red line station with easy access to all of the locations in Edgewater. There is currently some road construction that blocks off close by roads, however, the streets are open to local traffic and it actually makes walking easier.
Guest favourite
Flat in Chicago
4.97 out of 5 average rating, 33 reviews

Comfy Garden Suite in Andersonville

JoseRating, 5 stars7 months ago
This was a great little apartment. It was clean and there were plenty of staples in the kitchen, which helps on the first day before having a chance to go to the market. Mark was very proactive and available when needed. He gave recommendations on Thursday for fun on the weekend. The neighborhood is perfect. It was very walkable and the houses were beautiful. The place is close to a Main Street with plenty of shops and close to the red line train and other buses which take you straight to downtown. I had no problem getting around the city on public transportation. I plan on going back! It was one of my favorite AirBnB experiences thus far. Thanks Mark!!!
Superhost
Flat in Chicago
4.83 out of 5 average rating, 63 reviews

Fuzzy Master Bedroom (Entire Apt)

MegRating, 5 stars2 weeks ago
Great apartment in Wrigleyville with an incredible location. Very walkable with nearby fun things to do and great restaurants. Neighborhood felt safe and really enjoyed the street parking - would recommend and stay again.

House rentals with beach access

Top guest favourite
Home in Chicago
5 out of 5 average rating, 27 reviews

Gold Coast Home|Rooftop |PoolTable |Parking |Views

RikkiRating, 5 stars3 days ago
Great home and location. Safe neighborhood, walkable to restaurants, shopping, beach. Home was clutter free, clean and well maintained. Beds were comfortable and we had plenty of supplies for duration of stay (fresh towels, blankets, paper products, soap, shampoo, conditioner, etc.) Rooftop deck with nice view. Host was very responsive with any questions and communicated well. House was perfect size for our group of 6. We appreciate Rasheed making our stay perfect! Will stay here again in the future.
Guest favourite
Home in Skokie
4.93 out of 5 average rating, 85 reviews

Quiet and welcoming house.

SupatchaRating, 5 stars6 days ago
We had a great stay at Tsegie’s beautiful home. The house was not only very clean and well-maintained, but also tastefully decorated and comfortable. It’s located in a quiet, safe residential neighborhood with friendly neighbors — perfect for those who have a car, as there’s plenty of free street parking available. Tsegie is a professional and responsive host — very kind and easy to communicate with. We especially appreciated the spacious basement, which was great for indoor activities without disturbing anyone. Our toddler loved the front lawn — it became his favorite play area during the stay. If you're visiting Chicago with a car and prefer a peaceful, suburban atmosphere, this is a wonderful option. I was traveling with a young child and felt very safe and comfortable here. We’d love to stay in this area again on our next trip.
Guest favourite
Home in Chicago
5 out of 5 average rating, 18 reviews

Amazing historic campus mansion!

ArunaRating, 5 stars2 weeks ago
Caryl was extremely helpful with a check in process and she introduced us the property as well as surrounding local attractions. We felt the place was warm and very spacious for our group and we had a pleasant stay.
Superhost
Home in Chicago
4.92 out of 5 average rating, 142 reviews

House 5BED/3BATH/1PARKING close to Downtown & Lake

JenniferRating, 5 stars1 month ago
This is great, quiet little neighborhood; it doesn’t feel like you’re in a big city. It was nice to go to a couple Cubs games, hang out in the city, enjoy the amazing food, and then head back to a quiet space. Specifically, Junni was very responsive and friendly. We had a couple little snafus that were all me but Junni was there to help and that’s unusual in my experience. I highly recommend and will do it again!
Guest favourite
Home in Chicago
4.88 out of 5 average rating, 51 reviews

CasaNova Modern City Living

HelenRating, 5 stars3 weeks ago
Beautiful home layout and very spacious! Location was a quick drive to the city, which was convenient. Host was also very kind and attentive. Thank you Ms. Lilly for our stay!
Guest favourite
Home in Skokie
4.86 out of 5 average rating, 96 reviews

Luxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |

TaniaRating, 5 starstoday
Words can’t describe how beautiful and clean the property and neighborhood is! The house is very spacious and modern. The basement is new, has a big room and bathroom with shower. The masters bedroom has a living room and GORGEOUS bathroom! The host provided cleaning supplies and even personal bathroom supplies for men and woman. The host was very nice and friendly 🥰 We had an incident with our previous AIRBNB and we had to rent this one last minute- The host responded at 1am letting us checked in at 1am. If you plan on staying here, please take care of it lol It’s such a lovely house! 100% Recommend!
Superhost
Home in Chicago
4.83 out of 5 average rating, 122 reviews

Woodlawn Oasis: 5-15 Mins from Food, Fun, Dining

HaliRating, 5 stars3 weeks ago
This was a fantastic find! My whole party loved the place. It was clean and wonderfully located in a peaceful neighborhood close enough to transport to walk but far enough from the noise and bustle of downtown. Shawn was very responsive to any questions I had and was super kind and friendly! I absolutely would stay here again!!
Top guest favourite
Home in Chicago
4.94 out of 5 average rating, 71 reviews

Cheryl's on Sheffield! 3 bedroom in Lincoln Park.

AdriaRating, 5 stars5 days ago
Wow! I can’t say enough good things about Cheryl’s hosting! She and her husband went above and beyond for us. They are so responsive and friendly and even went so far as buying a pack and play for us last minute and jumping our car battery when it died! Talk about amazing! The place had everything we needed and the location was lovely. Would definitely stay here again!

Apartment rentals with beach access

Top guest favourite
Apartment in Chicago
5 out of 5 average rating, 16 reviews

Entire condo steps from lake, dining + shopping

AliRating, 5 stars2 weeks ago
We loved everything about this place! David, Ben, Andy and Emily really nailed it—super welcoming, thoughtful and incredibly intentional. We walked in to fresh flowers and homemade cookies, which totally set the tone. The house itself is beautifully curated, filled with vintage pieces that only a true collector could have chosen. It’s a space with real character—charming, stylish, and filled with personality. It’s also impeccably stocked, down to the smallest detail. Kitchen had everything we needed (and then some), beds were comfy with layers for the weird weather, and the lighting made every room feel special. Neighborhood was awesome—great vibes and even better food. Calo’s fried chicken = a must. And don’t skip the scallion pancakes at Jin Ju. In a nutshell, JUST BOOK IT. You’ll thank yourself later. David, Ben, Andy and Emily thank you for sharing such a special place!!!
Guest favourite
Apartment in Chicago
4.87 out of 5 average rating, 237 reviews

A Stones Throw from U Chicago South Campus!

BrendaRating, 5 stars3 weeks ago
Everything was great! The location was perfect—close to most of the attractions we visited during our stay. We really appreciated how well everything was set up. The honey was a lovely touch, and we especially enjoyed the peaceful, quiet atmosphere away from the city. Thank you for a wonderful experience!
Top guest favourite
Apartment in Chicago
4.99 out of 5 average rating, 174 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

PeggyRating, 5 stars3 days ago
I stay in a lot of Airbnbs. At least 3 a year, most of them in Lakeview. This was the best one! I’m originally from Lakeview and have been disappointed how commercialized and impersonal Airbnb has become. This was the opposite of that. It was so homey, I felt like I’d lived there my whole life. Would definitely stay again.
Top guest favourite
Apartment in Chicago
4.98 out of 5 average rating, 108 reviews

The Ramblers Inn, Northside NEW Reno w/parking!

KerryRating, 5 stars4 weeks ago
Easy check in and close to LUC which is what we needed. Clean and comfortable. Bonus that it included parking.
Top guest favourite
Apartment in Chicago
4.97 out of 5 average rating, 59 reviews

Jarvis Gardens - 1BR/BEACH/Wine patio/fire pit

TammyRating, 5 stars1 week ago
Chip and Lito's place is a dream! Spacious, clean, quiet, and convenient to restaurants, the "L", and the beach. Apartment is very well appointed, yet not cluttered. The shower is awesome! It was very nice to have a full kitchen, with coffee makers and dishwasher. I definitely plan to stay here the next time I visit Chicago!
Superhost
Apartment in Chicago
4.74 out of 5 average rating, 156 reviews

Charming Apt. Near Beach, Train & Private Parking

LindaRating, 5 stars2 weeks ago
The location was a five minute walk to the beautiful Loyola Park along Lakr Michigan. Lots of walkable stores and restaurants. Would stay there again and recommend to others.
Top guest favourite
Apartment in Chicago
4.99 out of 5 average rating, 286 reviews

Cozy 3BR on Chicago's North Side & Free Parking

BethRating, 5 stars2 weeks ago
Beautifully decorated and comfortably furnished, a calm oasis in the urban landscape of Rogers Park. The kitchen was well stocked and thoughtfully laid out. There was easy access to many delicious restaurants and we were so thankful for our own parking space. Walking to and along the lake was was one of our top two highlights of our trip. Mark and Marcello were very responsive and helpful with our questions. We would definitely stay here again!
Superhost
Apartment 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!

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