Vacation rentals in Oakwood Beach

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Top-rated vacation rentals in Oakwood Beach

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Guest favorite

A vibrant living area showcases eclectic décor, featuring a colorful mural with artistic motifs on one wall. A round coffee table sits in the center, surrounded by cream-colored sofas adorned with green cushions. A wet bar with wooden stools is visible in the background.

Apartment in South Side

4.89 out of 5 average rating, 176 reviews

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TV, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles), Navy Pier, Obama Library, Millennium Park, Beach (1 mile), Museum, & Sports arenas.

Guest favorite

A spacious living area features high ceilings with a skylight and large windows, offering ample natural light. A comfortable green sofa and a black armchair are positioned near a coffee table. A fireplace and a television are visible, with scenic views seen through the glass doors.

Apartment in South Side

4.96 out of 5 average rating, 71 reviews

Sunny Penthouse - Oakwood Beach

Bright top-floor 2-bedroom, 2-bath condo in the heart of Bronzeville with soaring ceilings and abundant natural light. Relax in the in-unit jacuzzi jetted tub after a day exploring Chicago. The fully equipped kitchen has everything you need to cook at home, or enjoy nearby restaurants. 🌊 Just a 18-minute walk to Oakwood Beach & the lakefront. Within a 20-minute drive of Downtown, Soldier Field, Guaranteed Rate Field, the Field Museum, the Art Institute, Chinatown, Hyde Park, Pilsen & more!

Guest favorite

A modern living space is illuminated by natural light from large windows, showcasing a stylish dining table accompanied by upholstered chairs. A comfortable seating area features a sectional sofa and decorative accents. A classic game table adds an engaging element to the room's design.

Home in South Side

4.96 out of 5 average rating, 91 reviews

Oakwood Beach Lake & SkylineViews+CuldeSac+Parking

Modern luxury awaits you in this Urban Oasis in North Kenwood/ McCormick area. New construction with all new finishes and stylish decor. Great natural light, free parking, views of Lake Michigan and the Chicago Skyline, nestled on a culdesac. Take advantage of many attractions that the Windy City has to offer. A few minutes from Obama Presidential Center, Navy Pier, Downtown, White Sox Stadium, Museum Campus, University of Chicago, 31st and Oakwood Beach Perfect for photos and filming!

Top guest favorite

A multifunctional space is featured with a queen-size Murphy bed tucked into the wall, a mounted television, and a cozy seating area with two armchairs. Natural light is welcomed through the entrance door, and a minimalist design enhances the overall simplicity.

Guesthouse in South Side

4.92 out of 5 average rating, 130 reviews

Guesthouse | Near public transit and Lake front

A unique 400 sqft loft with bright open concept, large windows, full kitchen, and private access located in the historic Kenwood/Hyde Park area. Public Transit - 5 min walk Lake - 10 min walk Obama Presidential Library - 1.8 miles University of Chicago - 2 miles Museum of Science and Industry - 2.8 miles McCormick Place 3.4 miles Millennium Park - 6 miles Navy Pier - 6.7 miles Hyde Park restaurants! Perfect for individuals or couples, access to expressways to get anywhere in the city.

Guest favorite

Apartment in South Side

5.0 out of 5 average rating, 8 reviews

Simply Sleek & Uneek: Mins To/Fr D'Town Chicago

Simple Sleek Minimalist 1-BDR Condo at the Crossroads of Bronzeville, Kenwood & Hyde Park: Situated at the intersection of historic Bronzeville, elegant Kenwood, & culturally rich Hyde Park, this 1-BDR, condo offers a peaceful retreat just minutes from downtown Chicago & the Lake. Featuring a large living room, fully equipped kitchen, & private bathroom; designed with your comfort & convenience in mind. It's an ideal home base whether you’re visiting for work/business, school, or a getaway.

Guest favorite

Home in South Side

4.85 out of 5 average rating, 62 reviews

Lux Home Chicago 7mins Downtown

Come stay at our luxurious 2-story newer construction home in Chicago. This centrally located, gated, 4 Bedroom, 5Beds, 3 1/2 bath home is ideal for family vacation, work or leisure trips. It comes with a full upscale gourmet kitchen and a spacious fully furnished basement with gym equipment. It is just a 7mins drive to the best attractions in Chicago, including the beach and museums; close to numerous restaurants, nightlife, and major highways for easy travel and access around the city.

Superhost

A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.

Apartment in Downtown Chicago

4.81 out of 5 average rating, 1031 reviews

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Guest favorite

Apartment in South Side

4.83 out of 5 average rating, 69 reviews

West Loop Urban Chic Coach House

Welcome to this historic neighborhood in Chicago, a cultural tapestry, rich in history and bursting with energy. Enjoy strolling along the streets lined with historic buildings, savor diverse culinary delights. Bronzeville is not just a place to stay; it is a community experience Enjoy, this one-bedroom, full bathroom historic coach house with a full kitchen, smart TV, and dedicated living space. Unwind in comfort with an in-unit washer/dryer. Plenty of street parking available.

Guest favorite

An inviting living area features hardwood flooring and large windows allowing natural light. A plush sofa with dark cushions is complemented by a unique accent chair. A contemporary chandelier hangs from the ceiling, and a mirror is mounted on the wall, reflecting the cozy ambiance.

Condo in South Side

4.94 out of 5 average rating, 67 reviews

UChicago Condo | 2 Baths, Private Parking & Entry

Enjoy the convenience of a dedicated private parking space with direct access to your own private entrance. This upgraded and spacious 1-bedroom, 2-bathroom condo near the University of Chicago features hardwood floors, stainless steel appliances, in-unit laundry, two Smart TVs, a cozy reading nook, and a large outdoor patio. Conveniently located near Hyde Park, Lake Michigan, Jackson Park, and the Obama Presidential Center. Perfect for extended stays and remote work.

Guest favorite

Apartment in South Side

5.0 out of 5 average rating, 26 reviews

Stylish Hyde Park/Kenwood Brownstone Garden Apt

Enjoy a stylish experience in Chicago's historic Hyde Park/Kenwood neighborhood in this updated brownstone garden apartment. You'll have an entire tastefully designed speakeasy chic 2-bedroom/1.5-bathroom unit with a separate entrance to yourself. Great location off South DuSable Lakeshore Drive- you're minutes away from Lake Michigan's scenic lakefront, the University of Chicago, McCormick Place and downtown Chicago.

Guest favorite

A cozy front room features a light gray sofa adorned with decorative cushions. A sleek glass table is positioned beside the sofa, while a large wall-mounted TV is visible above. Natural light enters through a small window with blinds, and a colorful area rug adds warmth to the space.

Apartment in South Side

4.91 out of 5 average rating, 44 reviews

Comfy Near Downtown Chicago

Keep it simple at this peaceful and centrally-located place. Near the University of Chicago and only ten minutes from Downtown Chicago. Located in the Bronzeville neighborhood on a cute and quiet block. Spacious one bedroom unit with a newly remodeled bathroom and Jacuzzi tub. Big screen TV in the cozy and comfy front room. And nice kitchen with the setup ready for meals and entertainment.

Superhost

A modern living area features a curved sofa and two armchairs, arranged around a circular, striped rug. A flat-screen TV is mounted on the wall above a sleek fireplace. Natural light enters through large windows, complementing a dining area with a round table and multiple chairs.

Home in South Side

4.89 out of 5 average rating, 83 reviews

CasaNova Modern City Living

Sprawling 4 Bedroom, 2.5 Bath 3 story house nestled on private cul de sac in a residential area. Chicago’s North Kenwood/Bronzeville neighborhood walking distance to the lakefront and 10min drive to city’s loop. Features open floor plan with hardwood floors, fireplace in living room, washer dryer, with outdoor space on each floor. Large patio available to enjoy Chicago's city and lake views!