Streeterville holiday rentals
We found 693 holiday rentals — enter your dates for availability
Discover a selection of 81 homes, 59 apartments and other holiday rentals in Streeterville that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Streeterville
The Guild #3 Mag Mile, Gold Coast, Downtown 1bd/1ba
Sleeps 4 · 1 bedroom · 1 bathroom
10 out of 10
exceptional
(13 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, gardens and more
- More for lessMore space, more privacy, more amenities — more value