Oakland Holiday Rentals
Apartment
- Chicago
- ·
- Armour Square
- 0.77 mi to center
10.0Exceptional
(22 Reviews)
4 Bedrooms
1 Bath
11 Guests
1100 ft²
Kitchen
Parking
Internet
Child Friendly
د.إ.1,643/Night
7 Nights - د.إ.11,499
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.46 mi to center
9.7Exceptional
(18 Reviews)
2 Bedrooms
2 Baths
8 Guests
1001.04 ft²
Pet Friendly- Parking
Air Conditioner- Internet
د.إ.1,098/Night
7 Nights - د.إ.7,687
House
- Chicago
- ·
- Bronzeville
- 0.16 mi to center
8.4Excellent
(88 Reviews)
1 Bedroom
1 Bath
Fireplace/Heating
Balcony/Terrace- Kitchen
- Parking
د.إ.698/Night
7 Nights - د.إ.4,888
Apartment
- Chicago
- ·
- North Kenwood
- 0.10 mi to center
10.0Exceptional
(18 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,113/Night
7 Nights - د.إ.7,789
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.64 mi to center
9.0Exceptional
(1 Review)
1 Bedroom
1 Bath
6 Guests
1496.18 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
د.إ.551/Night
7 Nights - د.إ.3,856
House
10.0Exceptional
(17 Reviews)
5 Bedrooms
4 Baths
8 Guests
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
د.إ.2,558/Night
7 Nights - د.إ.17,907
Condo
10.0Exceptional
(16 Reviews)
4 Bedrooms
2 Baths
20 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,896/Night
7 Nights - د.إ.13,269
Apartment
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
2 Guests
Oceanfront
Spa- Fireplace/Heating
- Ocean View
د.إ.1,178/Night
7 Nights - د.إ.8,245
Condo
10.0Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
6 Guests
1600 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.3,195/Night
7 Nights - د.إ.22,366
Luxury Holiday Rentals in Oakland
Over 1114+ Luxury Holiday Rentals in or Near Oakland
New
Hotel
- Chicago
- ·
- Near South Side
- 0.81 mi to center
2 Baths
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
Unlock the Best Price
Hotel
9.1Exceptional
(220 Reviews)
4 Baths
349.83 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
د.إ.8,568/Night
7 Nights - د.إ.59,976
New
Hotel
- Chicago
- ·
- Near South Side
- 0.34 mi to center
5 Baths
1575.84 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
د.إ.8,263/Night
7 Nights - د.إ.57,842
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
5 Bedrooms
4 Baths
12 Guests
2303.48 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
د.إ.8,071/Night
7 Nights - د.إ.56,494
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
9.0Exceptional
(1 Review)
5 Bedrooms
3 Baths
12 Guests
2723.27 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
د.إ.7,925/Night
7 Nights - د.إ.55,477
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
5 Bedrooms
3 Baths
12 Guests
1851.39 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
د.إ.7,782/Night
7 Nights - د.إ.54,474
Hotel
- Chicago
- ·
- Near South Side
- 0.37 mi to center
8.2Excellent
(825 Reviews)
13 Baths
423.11 ft²
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Parking
د.إ.5,490/Night
7 Nights - د.إ.38,433
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
9.8Exceptional
(9 Reviews)
3 Bedrooms
2 Baths
8 Guests
2368.06 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
د.إ.5,384/Night
7 Nights - د.إ.37,687
New
Apartment
- Chicago
- ·
- Prairie District
- 0.05 mi to center
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
د.إ.4,612/Night
7 Nights - د.إ.32,289
Top-Rated Holiday Rentals with a Pool in Oakland
Over 49+ The Best Private Villas and Holiday Rentals in Oakland with a Pool
House
- Chicago
- ·
- Bronzeville
- 0.38 mi to center
9.4Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
6 Guests
1500 ft²
Private Pool- Fireplace/Heating
Pool- Balcony/Terrace
د.إ.1,253/Night
7 Nights - د.إ.8,774
Hotel
- Chicago
- ·
- Near South Side
- 0.41 mi to center
9.2Exceptional
(811 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
د.إ.482/Night
7 Nights - د.إ.3,375
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
9.0Exceptional
(1008 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
د.إ.569/Night
7 Nights - د.إ.3,985
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
8.7Fabulous
(285 Reviews)
1 Bath
301.39 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
د.إ.1,068/Night
7 Nights - د.إ.7,474
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
8.6Fabulous
(1006 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
د.إ.590/Night
7 Nights - د.إ.4,132
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
8.6Fabulous
(751 Reviews)
1 Bath
333.68 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
د.إ.679/Night
7 Nights - د.إ.4,752
House
- Chicago
- ·
- Grand Boulevard
- 0.32 mi to center
8.3Excellent
(12 Reviews)
6 Bedrooms
5 Baths
15 Guests
3196.88 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
د.إ.2,412/Night
7 Nights - د.إ.16,882
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
7.7Very Good
(346 Reviews)
1 Bath
333.68 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
د.إ.594/Night
7 Nights - د.إ.4,161
House
6.0Good
(2 Reviews)
4 Bedrooms
3 Baths
4 Guests
2087 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
د.إ.808/Night
7 Nights - د.إ.5,652
Pet-Friendly Holiday Rentals in Oakland
Over 382+ Pet-Friendly Holiday Rentals in or Near Oakland
Apartment
- Chicago
- ·
- East Hyde Park
- 0.30 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
د.إ.960/Night
7 Nights - د.إ.6,721
Apartment
- Chicago
- ·
- Bridgeport
- 0.63 mi to center
3 Bedrooms
1 Bath
7 Guests
1001.04 ft²
- Pet Friendly
- Parking
- Internet
- Child Friendly
د.إ.1,241/Night
7 Nights - د.إ.8,689
Condo
- Chicago
- ·
- Grand Boulevard
- 0.49 mi to center
1 Bedroom
1 Bath
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
د.إ.661/Night
7 Nights - د.إ.4,624
Apartment
- Chicago
- ·
- East Hyde Park
- 0.31 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
د.إ.822/Night
7 Nights - د.إ.5,751
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(3 Reviews)
6 Bedrooms
4 Baths
12 Guests
1851.39 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
د.إ.4,171/Night
7 Nights - د.إ.29,200
Apartment
10.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
12 Guests
2400 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
د.إ.3,161/Night
7 Nights - د.إ.22,123
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.1,907/Night
7 Nights - د.إ.13,346
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.1,013/Night
7 Nights - د.إ.7,092
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
د.إ.836/Night
7 Nights - د.إ.5,850
Large Holiday Rentals and Private Villas in Oakland
Over 140+ Large Holiday Rentals and Private Villas in or Near Oakland
House
10.0Exceptional
(6 Reviews)
4 Bedrooms
4 Baths
10 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.2,940/Night
7 Nights - د.إ.20,577
Apartment
- Chicago
- ·
- Near South Side
- 0.71 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
1937.5 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
د.إ.2,835/Night
7 Nights - د.إ.19,846
Apartment
- Chicago
- ·
- Near South Side
- 0.12 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
10 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,926/Night
7 Nights - د.إ.13,482
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(1 Review)
6 Bedrooms
3 Baths
12 Guests
2723.27 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
د.إ.4,337/Night
7 Nights - د.إ.30,361
Apartment
- Chicago
- ·
- Prairie District
- 0.13 mi to center
10.0Exceptional
(4 Reviews)
6 Bedrooms
4 Baths
12 Guests
1850 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.3,808/Night
7 Nights - د.إ.26,655
House
- Chicago
- ·
- Near South Side
- 0.39 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
10 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.2,141/Night
7 Nights - د.إ.14,987
Apartment
- Chicago
- ·
- Near South Side
- 0.37 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
12 Guests
1850 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.3,386/Night
7 Nights - د.إ.23,702
Apartment
- Chicago
- ·
- Near South Side
- 0.43 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
1120 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,819/Night
7 Nights - د.إ.12,733
Apartment
- Chicago
- ·
- Near South Side
- 0.57 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.2,332/Night
7 Nights - د.إ.16,321
Wheelchair Accessible Holiday Homes in Oakland
Over 370+ Wheelchair Accessible Holiday Homes in or Near Oakland
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,713/Night
7 Nights - د.إ.11,987
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Air Conditioner
د.إ.1,621/Night
7 Nights - د.إ.11,344
Hotel
9.6Exceptional
(1003 Reviews)
1 Bath
- Breakfast
- Kitchen
- Parking
- Air Conditioner
د.إ.556/Night
7 Nights - د.إ.3,893
Apartment
- Chicago
- ·
- Near South Side
- 0.41 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
8 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,637/Night
7 Nights - د.إ.11,458
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
د.إ.1,287/Night
7 Nights - د.إ.9,012
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
8 Guests
950 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,558/Night
7 Nights - د.إ.10,904
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,521/Night
7 Nights - د.إ.10,650
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
1250 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,802/Night
7 Nights - د.إ.12,611
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,333/Night
7 Nights - د.إ.9,335
Oakland Private Villas and Holiday Homes Under $200
Over 338+ Oakland Private Villas and Holiday Homes Under $200
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.52 mi to center
9.6Exceptional
(76 Reviews)
2 Bedrooms
1 Bath
8 Guests
1600 ft²
- Fireplace/Heating
- Ocean View
- View
- Kitchen
د.إ.623/Night
7 Nights - د.إ.4,363
Apartment
5.0Average
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
861.11 ft²
- Air Conditioner
- Internet
- Child Friendly
د.إ.305/Night
7 Nights - د.إ.2,134
House
- Chicago
- ·
- Bronzeville
- 0.35 mi to center
7.6Very Good
(57 Reviews)
1 Bedroom
1 Bath
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.459/Night
7 Nights - د.إ.3,213
Apartment
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
د.إ.690/Night
7 Nights - د.إ.4,826
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.60 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
9687.52 ft²
- Air Conditioner
- Internet
- Child Friendly
د.إ.661/Night
7 Nights - د.إ.4,627
Apartment
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Child Friendly
Laundry
د.إ.627/Night
7 Nights - د.إ.4,389
Apartment
- Chicago
- ·
- Bridgeport
- 0.29 mi to center
8.6Fabulous
(16 Reviews)
1 Bedroom
1 Bath
4 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.648/Night
7 Nights - د.إ.4,536
Apartment
8.0Excellent
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
د.إ.690/Night
7 Nights - د.إ.4,826
House
7.8Very Good
(6 Reviews)
2 Bedrooms
1 Bath
5 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.676/Night
7 Nights - د.إ.4,730
Instantly Bookable Holiday Homes in Oakland
Over 520+ Instantly Bookable Holiday Homes in or Near Oakland
Apartment
- Chicago
- ·
- Near South Side
- 0.37 mi to center
10.0Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
8 Guests
1150 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.1,790/Night
7 Nights - د.إ.12,531
Apartment
- Chicago
- ·
- Near South Side
- 0.41 mi to center
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.2,012/Night
7 Nights - د.إ.14,084
Apartment
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.843/Night
7 Nights - د.إ.5,902
House
- Chicago
- ·
- Bronzeville
- 0.40 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.2,492/Night
7 Nights - د.إ.17,448
House
- Chicago
- ·
- Grand Boulevard
- 0.20 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
د.إ.1,397/Night
7 Nights - د.إ.9,780
Apartment
- Chicago
- ·
- Near South Side
- 0.37 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
1200 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.2,055/Night
7 Nights - د.إ.14,382
Apartment
- Chicago
- ·
- Near South Side
- 0.37 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
1100 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.1,869/Night
7 Nights - د.إ.13,085
Condo
- Chicago
- ·
- Washington Park
- 0.31 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.1,519/Night
7 Nights - د.إ.10,632
Apartment
- Chicago
- ·
- Prairie District
- 0.03 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
550 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,262/Night
7 Nights - د.إ.8,832
Book a Last Minute Place to Stay in Oakland
About Casai's Private Villas and Holiday Rentals in Oakland
Discover more than 1123 vacation rentals available in Oakland. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Oakland.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Oakland, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Oakland. On average, places to stay near Oakland offer 747.02 ft², with nightly prices averaging د.إ.1,636.
With Casai, finding and comparing holiday rentals in Oakland is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Oakland
| Type | Count |
|---|---|
| Holiday Apartments | 820 |
| Vacation Homes | 127 |
| Villas | 2 |
| Cottages | 1 |
Use these Quick Filters to Find a Holiday Rental in Oakland
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Oakland.
Weather in Oakland, IL
View the weather forecast for Oakland before booking your Oakland Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Other Places to Stay in Oakland, IL
Frequently Asked Questions About Oakland?
What are the top holiday rentals in Oakland?
With numerous options available in Oakland, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Oakland:
- 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
- Penthouse, Lux stay near Downtown, McComick & Lake
- Gorgeous historic mansion on UChicago campus. Renovation with original detail.
- 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Large historic home minutes from downtown Chicago and the lakefront.
- Modern Apt Near U of Chicago!
- The Landmark; a comfy suite near McCormick Place
- Gather, relax, enjoy— in chic luxury home near Lake Michigan & McCormick Center
- Spacious 3BR on UChicago Campus & Hospitals Free Street Parking
Which holiday homes in Oakland are best for families?
If you're searching for a family-friendly holiday home in Oakland, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Oakland:
- 1-bedroom apartment in charming Chicago with AC and free street parking
- The Brown House - A luxurious UChicago Campus stay
- Stylish Apartment near Chicago Downtown
How many Casai.ae holiday rentals are available in Oakland?
As of 2026, Casai boasts over 1123 properties listed in the Oakland area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Oakland.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Bronzeville Vacation Rentals in Chicago, Illinois | 74 |
| North Kenwood Vacation Rentals in Chicago, Illinois | 763 |
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