Uptown Rentals By Owner

There are a lot of options in Uptown. If you plan on staying in the Uptown area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Uptown:

• Sunny Modern Loft Montrose Beach Rooftop WFH Gym
• Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered apts
• Designer 3BR with Balcony & Elevator on Clark! apts
• Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
• Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
• Elegant 2BR Apartment w/In-Unit Laundry
• Uptown studio apartment with breathing views
• Elite Studio Apartment in Uptown near Shops
• Pet Friendly! Can You Smell the Popcorn and Peanuts? One Mile from Wrigley Field and Room for All the Super Fans! by RedAwning
• PET FRIENDLY! Desirable Sheridan Park is a Safe, Vibrant, and Welcoming Area you are Sure to Love by AllSet Turnover

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

• Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
• Uptown Gem
• Chic apartment in marvelous Chicago with WiFi, AC
• Steps to the Lakefront! This Uptown Beauty is Everything You Need for a Perfect Chicago Getaway condo

Yes, there are 77 self-catering vacation homes in Uptown that have hot tubs, swimming pools, & other amenities.

There are more than 77 luxury villas and vacation homes in or near Uptown. Filter by price to compare find the most expensive places to stay on Cancunplayaluxuryrentals.

Yes, there are 77 pet friendly vacation homes and places to stays that are available in or near Uptown that you may consider.