The Gap holiday lettings
Find spaces that suit your style
Find the best place to stay - The Gap
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Photo gallery for New 3BR Residence Adjacent to Wrigley Field - Outdoor Patio - BBQ Grill
New 3BR Residence Adjacent to Wrigley Field - Outdoor Patio - BBQ Grill
Photo gallery for Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location!
Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location!
Photo gallery for Home away from home. Perfect for remote workers.
Home away from home. Perfect for remote workers.
Photo gallery for Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
Photo gallery for Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
- 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, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental accommodation in The Gap?
Condos are the most popular kind of holiday rental in The Gap, according to our data. Even if you have something else in mind, Vrbo has properties in loads of sizes and shapes. Filter our options to find your perfect fit.
How much does it cost to rent a holiday rental in The Gap?
The average price for a holiday home in The Gap is determined by several factors, like property type, length of stay and time of year. Whether you're thinking about a sprawling villa with space for extended family or a cosy condo that's perfect for two, just add your dates of travel to find stays with amazing value.
How much does it cost to rent a beach house in The Gap?
The average price for a holiday home near the beach in The Gap will depend on when you're going and the size and style of property you want. Find prices easily on Vrbo by entering your destination and travel dates. Then use our filters to choose the number of bedrooms and amenities that you prefer, such as air conditioning, WiFi and a hot tub.
Are there pet-friendly holiday rentals in The Gap?
Pack a travel bag for your puppy dog because The Gap has two properties that throw open their doors to pets. Let your four-legged buddy enjoy the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your destination and dates, then check the "Pets allowed" filter box.
What are popular rental amenities in The Gap?
When it comes to rental amenities that people are searching for in The Gap, nearby museums, a barbecue grill and off-street parking options rank highest. With Vrbo holiday homes, you'll enjoy choices to match your taste and style, whether you're going away with your partner, family members or even pets.
Are there large group holiday rentals in The Gap?
With two The Gap holiday homes that can accommodate five or more people, you can bring a few extra family members or buddies along. Whether you're planning a casual gathering or a birthday party, we'll help you book the perfect space to fit the occasion.
Are there holiday rentals in The Gap that welcome kids?
With two family-friendly holiday properties to select from in The Gap, now is the perfect time to introduce your children to the wonders of travel. Check our "Properties good for families" filter box to view stays that feature amenities ideal for holidaying families, like multiple bedrooms, private pools, bunk beds and hot tubs.
What are the top attractions for families in The Gap?
Keeping the kids happy during your The Gap holiday is simple with these cool family-friendly attractions:
- Navy Pier
- Chicago Riverwalk
- Shedd Aquarium
How can I find holiday rentals with air conditioning in The Gap?
Pick your dates and then use the filters to view holiday rentals with ac in The Gap on Vrbo. With two air-conditioned properties to choose from here, you can enjoy a comfy and cool stay.
How old do you have to be to rent a holiday rental in The Gap?
We recommend checking with the Gap holiday home you're considering on Vrbo as the minimum age differs. However, normally it's 16, 18 or 21.
How long can I rent a holiday rental in The Gap for?
The amount of time you can rent a The Gap holiday rental for is down to the property. Simply put in your travel dates to view available options offering longer term stays. They come with all you require to make your extended trip more enjoyable and comfortable, like air conditioning and laundries. Some properties might also offer discounted weekly or monthly prices, so you can stick around for longer for less.