Oakland Rentals By Owner

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

• Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
• Large historic home minutes from downtown Chicago and the lakefront.
• Gather, relax, enjoy— in chic luxury home near Lake Michigan & McCormick Center
• Spacious unit in historic gem
• The Brown House - A luxurious UChicago Campus stay
• 2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, & Conv Ct
• Modern & Spacious Stay in Historic Bronzeville
• Spacious 6BR Luxury Suite Perfect for Groups Near McCormick Place and Soldier Field
• Cozy 2BR South Loop Condo with Optional Parking and Gym Near McCormick Place, Public Transit & City Hotspots
• Large 4BR Cozy Stay Near Field Museum & McCormick

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

• 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
• Luxurious Stay at Modern Apartment with Self Check-in Mins Frm Downtown
• Villa Dubois Guest House
• Penthouse, Lux stay near Downtown, McComick & Lake

Yes, there are 938 self-catering vacation homes in Oakland that have hot tubs, swimming pools, & other amenities.

There are more than 938 luxury villas and vacation homes in or near Oakland. Filter by price to compare find the most expensive places to stay on Maimonbeach.

Yes, there are 938 pet friendly vacation homes and places to stays that are available in or near Oakland that you may consider.