Beachfront vacation rentals in Oak Street Beach

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Oak Street Beach

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Evanston

4.94 out of 5 average rating, 113 reviews

Historic Coach House in Evanston Near Beach & Town

Stay in the Coach House of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire coach house which is renovated and includes a large bedroom with king bed and desk, a sun-filled living room/dining room, a full bath with claw-foot soaking tub and shower and a kitchen with amenities. The space can be equipped with an air mattress for an extra guest. Also available is a 3rd floor guest suite in the main house . Extra

Rental unit in Evanston

4.71 out of 5 average rating, 104 reviews

Modern|Aesthetic|2BR|Evanston|Near Beach

Welcome to this beautifully remodeled 2 bedroom, 1 bathroom unit in the highly sought-after neighborhood of Evanston! With an abundance of natural light flooding in, this unit boasts a warm and inviting atmosphere that will make you feel right at home. Our apartment is located right next to the beach and a very nice path along the lake. Hot water in shower takes 10 minutes to warm up. For those sensitive to noise, the building environment has been described as being noisy by previous guests.

Guest favorite

Rental unit in Chicago

4.92 out of 5 average rating, 214 reviews

Stone Mansion Sleeps 10-20 Free parking & TV

Giant, 4 bedroom, 2,300 square feet apartment on 2nd floor, near Red Line Train, bars, cafe's, shopping, restaurants, Lakefront and everything else Chicago has to offer. Large living room with bar area, TV and fridge for socializing before hitting the town. Dining room has a large table and 8 chairs. 4 bedrooms with 2 private rooms with king beds and one with a double bed. 4 futons for in the living room for extra sleeping space two (2) parking spots in the west facing garage on premises.

Superhost

Condo in Chicago

4.88 out of 5 average rating, 179 reviews

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

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

Guest favorite

Private room in Chicago

4.98 out of 5 average rating, 41 reviews

Sunny,Comfortable,CleanTop Location at Lake,Beach

Comfortable, large, sunny bedroom. Perfect for relaxation, work, study. Many amenities: wifi, desk, tv, coffee maker, small refrigerator. Private bathroom with shower/tub. Friendly hosts will welcome you. Fabulous location, fifteen minutes from downtown Chicago. Within 1/2 block of public transportation, Lake Michigan, beach, park, tennis courts. Six blocks to Loyola University. 3.5 miles to Northwestern U. Wonderful neighborhood, stores, restaurants, theaters, coffee shops, grocery.

Superhost

Private room in Chicago

4.75 out of 5 average rating, 151 reviews

Basic accomodation equipped for short terms stays.

I am renting out my extra bedroom in my 2 bed apartment for 1 guest only. Guests have access to their bedroom and bathroom only. No kitchen or living room access. My space is not luxury, but it's sanitized and clean, the neighborhood is cute/safe where you can feel calm/ peaceful. I have a lovely park across the street you can lounge. I am in an area where there are good restaurants within walking distance. Apartment 1W edit: Do not book my place for someone else under your profile.

Rental unit in Chicago

4.56 out of 5 average rating, 114 reviews

Home in heart of Lincoln Park & Lake Sea and beach

This home is located In the heart of Lincoln Park near Old Town Triangle and near the beach in the core of Chicago. Ideal people who want to stay in the vibrant beautiful city. Close to parks, beach, lake, subway station, shops, restaurants and night life! Entire one bedroom apartment with spacious (850 sqft) and beautiful interior design. As you can pick up the key from self check-in box, you can check in and out anytime. Check in time is 2pm and check out is 11am. R22000082349

Villa in Chicago

4.6 out of 5 average rating, 47 reviews

Rooftop | Villa | Parking

Meet up with group at this gorgeous designer space, a mini Villa but large throughout making it light, bright, airy with feelings of calm and tranquility. Indoor features Luminaire Chandeliers, 10 feet ceilings, Grand Piano, Music Box etc. Huge backyard offer spaces to entertain. Guest can view cameras of all entrances; Roof deck, Front, Back & Alley via Monitor (HDMI-1) 24/7 record You’re booking a separate entry: 3 levels of home and is exclusive to your guests/party.

Guest favorite

Rental unit in Chicago

5 out of 5 average rating, 39 reviews

Gold Coast Pristine Paradise 3BR/2BA. Free Parking

FREE GARAGE PARKING!! Step into luxury in this modern loft with 3 bedrooms, 2 bathrooms and a private patio with an amazing view. Experience the feeling of being at home in a bright and spacious haven amidst Chicago's most sought-after neighborhood "Gold Coast" This centrally located gem is situated within walking distance of much of Chicago Downtown's exquisite dining, upscale boutiques, popular tourist destinations, and just a stone's throw away from Oak Beach.

Superhost

Rental unit in Chicago

4.82 out of 5 average rating, 51 reviews

Woodlawn Oasis

Welcome to Woodlawn Oasis! Come and enjoy the charm and warmth of this fully remodeled and furnished apartment with original artwork! Just 5 minutes from our beautiful Chicago lakefront, the prestiges University of Chicago, and soon to be Tiger Woods golf course and President Obama library. Also, 10 minutes from Chicago museums, Soldier Field (Chicago Bears), Guaranteed Rate Field (Chicago White Sox) and the fabulous night life of Downtown Chicago!

Home in Chicago

4.84 out of 5 average rating, 32 reviews

Only Urban Beach House in Chicago

Why stay in a hotel or dorm when you can have your own house! The Urban Beach House of Rogers Park, Chicago’s only urban beach house, has 4 bedrooms, 3 full baths, and is loaded with features that make it the perfect place for vacationers, students, faculty, family and gatherings of all kinds. Steps from the sandy beaches of Lake Michigan, walking distance from dozens of restaurants and shops, and minutes from 3 train stations and a Divvy bike station.

Guest favorite

Private room in Evanston

4.83 out of 5 average rating, 65 reviews

1 Room for up to 3, Near NU & Old Orchard Mall

Close to fabulous shopping at Old Orchard. Avoid the traffic! Walk or jump on the bus for OO, NU. Can host 1 couple or up to 3 people in one room. Charming art-filled Tudor home, beautiful garden setting near NU, lake, downtown Evanston. Large private room, queen bed + twin, updated bathroom. Free street parking. Perfect spot for visiting NU, many North Shore sights, local retirement communities. Easy access to trains to city. Great restaurants!