Photo by Eleonora Bertacchi
Vacation rentals near Oak Street
We found 2,808 vacation rentals — enter your dates for availability
Select the perfect vacation home within close proximity to Oak Street. Vacation rentals provide the best amenities for you and your friends, family, or even pets, such as WiFi and a hot tub. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.
Find spaces that suit your style
House
Condo/Apartment
Find properties near top attractions in Oak Street
Map Attractions
Find the best place to stay - Oak Street
Rare Gem! Indoor Pool, Rooftop Deck, Close to Magnificent Mile
Sleeps 2 · 1 bedroom · 1 bathroom
8.0 out of 10
very good
(65 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value