Holiday houses in Woodlawn

PRIVATE 2-bedroom 1.5 bath w/ living room

Next to University of Chicago campus. Private entry to 2-bedroom/1.5-bath apartment: back half is our separate craft space and front half is your private Airbnb suite. No proper kitchen, but there is a large fridge, microwave, etc. This Airbnb is in our 4-unit apt building next to our house where we've had a 5-star Airbnb room for 10+ years as a Super Host. The other tenants are long-term lease-holders and wonderful people whom we're happy to call our neighbors on this quiet tree-lined street.

UChicago Luxurious King Suite Lakefront

Sink into a pillowtop king size bed in a sunny, spacious bedroom suite w/twin bed, comfy love seat. Spacious 1,000 s.f. condo luxury, kitchens /bath with granite counters, office space, 3rd-flr. unit, private entrance gated and on-street parking. 1 min walk to beach, trails, golf course and bike rental. 1 block from Express bus (15 minutes) to Univ of Chicago/Hyde Park, Obama Presidential Center and Museum of Science and Industry, 20 minutes to Soldier Field, Grant Park, Downtown, Navy Pier

You are my Muse!

Allow the Muse to be your home away from home. It provides luxury and comfort. Its unique decor was chosen with you in mind. The Muse is filled with energy that captures your artistic eye. Each room tells a story. Each piece was carefully selected. It sleeps 4-6 and has space to entertain. The Muse is nestled in the heart of Woodlawn. The expansive unit, has one full and two half baths. Each has a spa-like feel; especially the full bath that is easily accessible through the masons.

University Retreat

Lovely 3 bedroom apartment in Hyde Park location. Within one block of the U of Chicago; close to the science museum, Metra, restaurants, parks, and less than 1 mile from the proposed Obama Library and the lake. Updated unit has nearly 1,300 SF of livable space to enjoy: vintage hardwood floors throughout, separate living/dining rooms, kitchen with new stainless steel appliances, new furnace, new hot water tank, and a new porch with large fenced yard. Permit parking for guests only!

*Hyde Park *2 Masters *2 Living Rooms *Courtyard

Welcome to our newly renovated retreat, The Urban Oasis in Hyde Park. Embrace the artful decor throughout the spacious house only a 10 minute walk to the nearest beach. Rent a bike for a scenic ride to nearby attractions like University of Chicago, Obama Library, Museums, the Natural Walkway Nature Park and the lake. Conveniently located near Hyde Park central to downtown Chicago, this is the perfect stay for families and small groups as you explore everything Chicago has to offer.

South Shore Dr Retreat

Enjoy easy access to everything from this perfectly located home base. Walking distance to a 9 hole golf course, beach, and famous Lake Michigan lakefront bike and walking path. Commuters dream with easy access to Chicago bus line and Metra train station. You are close to the following Chicago locations: Lake Michigan lakefront path La Rabida Children’s Hospital 63rd Street Beach Museum of Science and Industry Obama Museum(opening June 19, 2026) University of Chicago Hyde Park

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.

Cheerful 3 Bedroom, City Oasis

Take it easy at this unique and tranquil getaway located in the Woodlawn neighborhood within walking distance of the University of Chicago campus ( 1 mile) and the Obama Presidential Center (1 mile). This house has plenty of charm with three uniquely themed bedrooms, two full bathrooms, finished basement with ping pong table and washer/dryer. Enjoy this home to experience the best of the Chicago’s South Side with its balance of history, academics, and culture.

Beautiful Penthouse (Near Obama Center, UChicago)

This is 3BR/2B condo located in Woodlawn on the confluence of Hyde Park, walking distance to the University of Chicago and a 15 min drive from downtown! The condo includes modern and new appliances, fireplace, In-unit washer/dryer, walk-in closet, double vanities in bathrooms, and a rear deck. Couch is also a pull-out bed for living accommodations. One designated parking space is available for Airbnb guests, with free street parking also available.

Modern Eco Stay • UChicago • Parking • Backyard

Relax in this eco-friendly South Side retreat designed for comfort, style, and convenience. Located minutes from UChicago, Hyde Park, Jackson Park, the Museum of Science & Industry, and the lakefront, this unit is perfect for families, medical visits, students, and anyone exploring Chicago. With a private entrance, free parking, and a large fenced backyard, this modern space gives you privacy and peace in the city.

Luxe Loft vibe | King Suite |4BR 3Ba

Stay in style near Chicago’s best! This luxe 4BR, 3BA loft is perfect for families, professionals, or UChicago guests. Enjoy a king suite with jacuzzi, 3 queen bedrooms with desks, and an open layout with smart TVs, exposed ducts, and dining for 10. Walk to the Obama Presidential Center, Museum of Science & Industry, and lakefront. Adjacent to Hyde Park with quick downtown transit—just 50 min to Indiana Dunes!

South Shore Oasis | Lakefront Suite Near Hyde Park

Thoughtfully renovated garden-level guest suite with private entrance in Chicago’s historic South Shore, just outside Hyde Park. Ideal for visitors to the University of Chicago, Jackson Park, the Obama Presidential Center, and the lakefront. A peaceful home base with easy access to public transit and downtown. Perfect for guests visiting family, attending local events, or exploring Chicago’s South Side.