Owner Direct Vacation
Rentals in The Loop
The Best Owner Direct Vacation Rentals in The Loop. Explore thousands of vacation home rentals, large cabins, and villas near The Loop
GUESTS
Explore the Best The Loop Vacation Homes
Looking for the perfect place to stay in The Loop? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic The Loop 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 The Loop 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 The Loop
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- TV
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- Wheelchair Accessible
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- View
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- View
- Air Conditioner
- Pet Friendly
- Pool
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Popular Neighborhoods for The Loop Vacation Rentals
What are the best areas to stay in The Loop
Discover the top neighborhoods in The Loop and choose a place that suits your stay.
Sunday Feb 8
The Loop, Chicago
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our The Loop vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near The Loop
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How to Reserve Your The Loop 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.
The Loop Vacation Rental FAQs
1. What are the top vacation rentals in The Loop?
There are a lot of options in The Loop. If you plan on staying in the The Loop area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in The Loop:
- 52nd Floor MagMile Penthouse Views Fireplace Pool
- 55th Floor Penthouse with Award-Winning Views
- 53 Floor MagMile Penthouse Views, Balcony, Pool
- 51st Floor MagMile Penthouse Views Balcony Pool
- 2-Story Penthouse Views, Fireplace, Pool, Gym
- Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
- 52nd Floor Penthouse with Skyline Views & Pool
- 50th Floor Mag Mile VIEWS, Balcony, Pool, Gym
- Smart Home in Logan Square by the 606 Trail
- Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
2. How many vacation rentals have private pools in The Loop?
There are 23 vacation rentals with private pools near The Loop. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in The Loop are best for families?
If you are looking for a family-friendly vacation home in The Loop, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in The Loop:
4. How many vacation rentals are available in The Loop?
Currently, the total number of properties listed in 2026 is over 1099 in the The Loop area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in The Loop.