Owner Direct Vacation
Rentals in Streeterville
The Best Owner Direct Vacation Rentals in Streeterville. Explore thousands of vacation home rentals, large cabins, and villas near Streeterville
GUESTS
Explore the Best Streeterville Vacation Homes
Looking for the perfect place to stay in Streeterville? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Streeterville character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Streeterville Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Streeterville
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- Wheelchair Accessible
- Accessibility
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- Pet Friendly
- Pool
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- Pet Friendly
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Popular Neighborhoods for Streeterville Vacation Rentals
Discover the top neighborhoods in Streeterville and choose a place that suits your stay.
Thursday May 28
Streeterville, Chicago
More Vacation Rentals You May Like Near Streeterville
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How to Reserve Your Streeterville Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Streeterville Vacation Rental FAQs
There are a lot of options in Streeterville. If you plan on staying in the Streeterville area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Streeterville:
- Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
- Downtown Guild #3 Mag Mile Gold Coast The Lake!
- Rooms for the Crew | 3 units | Steps to Mag Mile| Navy Pier | 24-hour Gym
- City Center Luxury, Double Queen - The Chicago Hotel Collection Mag Mile
- Shop Chicago and Relax by The Bean | City Viwes | 24-hour Gym | 2 Units
- Lovely Streeterville Studio w/Gym, Pool, near Navy Pier, by Blueground
- Spacious 2 Bed Downtown Chicago with Housekeeping and Laundry. Dogs Welcome.
- Trendy Streeterville Studio w/Pool & Gym, nr Navy Pier, by Blueground
- Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
- Guild #2 | Gold Coast Mag Mile Best Location
There are 5 vacation rentals with private pools near Streeterville. Top-rated homes that have access to a swimming pool include:
If you are looking for a family-friendly vacation home in Streeterville, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Streeterville:
Currently, the total number of properties listed in 2026 is over 320 in the Streeterville area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Streeterville.
