The Gap Rentals By Owner

There are a lot of options in The Gap. If you plan on staying in the The Gap 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 Gap:

• Cozy Pilsen Depa
• 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
• Family Friendly 2-Bedroom w/Kitchen & Laundry
• Luxury Modern home minutes from Downtown Chicago
• Penthouse, Lux stay near Downtown, McComick & Lake
• Gorgeous historic mansion on UChicago campus. Renovation with original detail.
• Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
• Large historic home minutes from downtown Chicago and the lakefront.
• Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool
• The Landmark; a comfy suite near McCormick Place

There are many large, family-friendly vacation homes available in The Gap; however, here are the most popular family rentals listed on our site:

• Hamaline Luxury Guest House
• Villa Dubois Guest House Room 3
• Cozy Pilsen Depa
• Luxurious Stay at Modern Apartment with Self Check-in Mins Frm Downtown
• Mccormick Place Guest House
• 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena

Yes, there are 2 self-catering vacation homes in The Gap that have hot tubs, swimming pools, & other amenities.

There are more than 2 luxury villas and vacation homes in or near The Gap. Filter by price to compare find the most expensive places to stay on Castleinhawaii.

Yes, there are 2 pet friendly vacation homes and places to stays that are available in or near The Gap that you may consider.