Oakland Holiday Rentals
Apartment
- Chicago
- ·
- Near South Side
- 0.41 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
12 Guests
Fireplace/Heating
Kitchen
Air Conditioner
Internet
US $909/Night
7 Nights - US $6,366
Apartment
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
Parking- Air Conditioner
- Internet
Child Friendly
US $834/Night
7 Nights - US $5,840
House
- Chicago
- ·
- Bronzeville
- 0.16 mi to center
8.4Excellent
(88 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
Balcony/Terrace- Kitchen
- Parking
US $190/Night
7 Nights - US $1,331
Apartment
9.4Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $527/Night
7 Nights - US $3,688
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
US $1,136/Night
7 Nights - US $7,951
New
Apartment
- Chicago
- ·
- Near South Side
- 0.41 mi to center
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $1,407/Night
7 Nights - US $9,850
Apartment
- Chicago
- ·
- Near South Side
- 0.41 mi to center
4 Bedrooms
2 Baths
10 Guests
2497 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $1,005/Night
7 Nights - US $7,037
New
Apartment
- Chicago
- ·
- Near South Side
- 0.41 mi to center
5 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $808/Night
7 Nights - US $5,656
Apartment
- Chicago
- ·
- Near South Side
- 0.41 mi to center
4 Bedrooms
2 Baths
8 Guests
2110 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $710/Night
7 Nights - US $4,970
Luxury Holiday Rentals in Oakland
Over 1110+ Luxury Holiday Rentals in or Near Oakland
Hotel
9.1Exceptional
(220 Reviews)
4 Baths
349.83 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $2,333/Night
7 Nights - US $16,331
New
Hotel
- Chicago
- ·
- Near South Side
- 0.34 mi to center
5 Baths
1575.84 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $2,250/Night
7 Nights - US $15,750
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
US $2,198/Night
7 Nights - US $15,383
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
US $2,158/Night
7 Nights - US $15,106
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
US $2,119/Night
7 Nights - US $14,833
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
US $1,495/Night
7 Nights - US $10,465
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
US $1,466/Night
7 Nights - US $10,262
Apartment
- Chicago
- ·
- Prairie District
- 0.13 mi to center
10.0Exceptional
(3 Reviews)
6 Bedrooms
4 Baths
12 Guests
1850 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,408/Night
7 Nights - US $9,857
Apartment
- Chicago
- ·
- Near South Side
- 0.42 mi to center
6.0Good
(2 Reviews)
6 Bedrooms
3 Baths
12 Guests
2609 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,380/Night
7 Nights - US $9,661
Top-Rated Holiday Rentals with a Pool in Oakland
Over 49+ The Best Private Villas and Holiday Rentals in Oakland with a Pool
Apartment
- Chicago
- ·
- Near South Side
- 0.38 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
Hot Tub- Fireplace/Heating
Pool- Balcony/Terrace
US $501/Night
7 Nights - US $3,506
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
US $341/Night
7 Nights - US $2,389
Hotel
- Chicago
- ·
- Near South Side
- 0.41 mi to center
9.2Exceptional
(811 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $131/Night
7 Nights - US $919
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
9.0Exceptional
(1008 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $155/Night
7 Nights - US $1,085
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
8.7Fabulous
(283 Reviews)
1 Bath
301.39 ft²
- Private Pool
Oceanfront- Fireplace/Heating
- Pool
US $291/Night
7 Nights - US $2,035
Hotel
- Chicago
- ·
- Near South Side
- 0.40 mi to center
8.6Fabulous
(1006 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $161/Night
7 Nights - US $1,125
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
US $185/Night
7 Nights - US $1,294
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
US $657/Night
7 Nights - US $4,597
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
US $162/Night
7 Nights - US $1,133
Pet-Friendly Holiday Rentals in Oakland
Over 382+ Pet-Friendly Holiday Rentals in or Near Oakland
New
Apartment
- Chicago
- ·
- Lower West Side
- 1.59 mi to center
2 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $327/Night
7 Nights - US $2,291
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
8 Guests
796.53 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $434/Night
7 Nights - US $3,041
Condo
- Chicago
- ·
- Grand Boulevard
- 0.49 mi to center
1 Bedroom
1 Bath
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $180/Night
7 Nights - US $1,259
Condo
10.0Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $358/Night
7 Nights - US $2,505
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
US $772/Night
7 Nights - US $5,404
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
US $236/Night
7 Nights - US $1,650
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
US $224/Night
7 Nights - US $1,566
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $276/Night
7 Nights - US $1,931
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $204/Night
7 Nights - US $1,429
Large Holiday Rentals and Private Villas in Oakland
Over 136+ Large Holiday Rentals and Private Villas in or Near Oakland
Apartment
- Chicago
- ·
- Back of the Yards
- 0.61 mi to center
1 Bedroom
1 Bath
16 Guests
- Air Conditioner
- Child Friendly
Security/Safety
US $167/Night
7 Nights - US $1,171
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
US $1,181/Night
7 Nights - US $8,267
House
10.0Exceptional
(17 Reviews)
5 Bedrooms
4 Baths
8 Guests
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
US $697/Night
7 Nights - US $4,876
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
10 Guests
1194.79 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $516/Night
7 Nights - US $3,612
Condo
10.0Exceptional
(16 Reviews)
4 Bedrooms
2 Baths
20 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $516/Night
7 Nights - US $3,613
House
10.0Exceptional
(11 Reviews)
5 Bedrooms
3 Baths
8 Guests
4000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $649/Night
7 Nights - US $4,540
House
10.0Exceptional
(6 Reviews)
4 Bedrooms
4 Baths
10 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $695/Night
7 Nights - US $4,868
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
US $578/Night
7 Nights - US $4,048
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
US $583/Night
7 Nights - US $4,081
Wheelchair Accessible Holiday Homes in Oakland
Over 373+ Wheelchair Accessible Holiday Homes in or Near Oakland
New
Apartment
- Chicago
- ·
- Near South Side
- 0.44 mi to center
2 Bedrooms
2 Baths
4 Guests
850 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $596/Night
7 Nights - US $4,169
House
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Air Conditioner
US $441/Night
7 Nights - US $3,089
Hotel
9.6Exceptional
(1003 Reviews)
1 Bath
- Breakfast
- Kitchen
- Parking
- Air Conditioner
US $151/Night
7 Nights - US $1,060
New
Apartment
- Chicago
- ·
- Near South Side
- 0.44 mi to center
3 Bedrooms
2 Baths
6 Guests
1033 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $587/Night
7 Nights - US $4,108
House
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $351/Night
7 Nights - US $2,454
New
Apartment
- Chicago
- ·
- Near South Side
- 0.44 mi to center
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $580/Night
7 Nights - US $4,058
Apartment
- Chicago
- ·
- Near South Side
- 0.44 mi to center
3 Bedrooms
1 Bath
6 Guests
883 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $569/Night
7 Nights - US $3,986
New
Apartment
- Chicago
- ·
- Near South Side
- 0.44 mi to center
3 Bedrooms
1 Bath
6 Guests
883 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $559/Night
7 Nights - US $3,910
New
Apartment
- Chicago
- ·
- Near South Side
- 0.44 mi to center
1 Bedroom
2 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $549/Night
7 Nights - US $3,846
Oakland Private Villas and Holiday Homes Under $200
Over 338+ Oakland Private Villas and Holiday Homes Under $200
Condo
- Chicago
- ·
- North Kenwood
- 0.14 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $191/Night
7 Nights - US $1,339
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
9687.52 ft²
- Air Conditioner
- Internet
- Child Friendly
US $180/Night
7 Nights - US $1,260
House
- Chicago
- ·
- Bronzeville
- 0.35 mi to center
7.8Very Good
(56 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $125/Night
7 Nights - US $875
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $193/Night
7 Nights - US $1,352
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
495.14 ft²
- Ocean View
- View
- Air Conditioner
- Internet
US $54/Night
7 Nights - US $378
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.54 mi to center
9.8Exceptional
(101 Reviews)
1 Bedroom
1 Bath
5 Guests
1000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $170/Night
7 Nights - US $1,193
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
US $170/Night
7 Nights - US $1,188
Apartment
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $188/Night
7 Nights - US $1,314
Apartment
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Child Friendly
Laundry
US $176/Night
7 Nights - US $1,231
Instantly Bookable Holiday Homes in Oakland
Over 532+ Instantly Bookable Holiday Homes in or Near Oakland
New
Apartment
- Chicago
- ·
- Near South Side
- 0.44 mi to center
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $527/Night
7 Nights - US $3,687
Bed & Breakfast
- Chicago
- ·
- Bronzeville
- 0.16 mi to center
2.0Average
(1 Review)
1 Bedroom
1 Bath
2 Guests
237 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $194/Night
7 Nights - US $1,357
New
Apartment
- Chicago
- ·
- Near South Side
- 0.44 mi to center
3 Bedrooms
2 Baths
8 Guests
926 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $514/Night
7 Nights - US $3,595
New
Apartment
- Chicago
- ·
- Near South Side
- 0.44 mi to center
1 Bedroom
2 Baths
6 Guests
926 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $505/Night
7 Nights - US $3,533
New
Apartment
- Chicago
- ·
- Near South Side
- 0.44 mi to center
3 Bedrooms
2 Baths
6 Guests
937 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $502/Night
7 Nights - US $3,512
New
Apartment
- Chicago
- ·
- Near South Side
- 0.44 mi to center
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $493/Night
7 Nights - US $3,452
New
Apartment
- Chicago
- ·
- Near South Side
- 0.44 mi to center
3 Bedrooms
2 Baths
6 Guests
926 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $461/Night
7 Nights - US $3,226
New
Apartment
- Chicago
- ·
- Near South Side
- 0.44 mi to center
1 Bedroom
2 Baths
6 Guests
937 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $437/Night
7 Nights - US $3,059
New
Apartment
- Chicago
- ·
- Near South Side
- 0.44 mi to center
3 Bedrooms
2 Baths
6 Guests
937 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $406/Night
7 Nights - US $2,840
Book a Last Minute Place to Stay in Oakland
About Casai's Private Villas and Holiday Rentals in Oakland
Discover more than 1119 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 740.84 ft², with nightly prices averaging US $441.
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.
Show more
Show less
Top Accommodation Types in Oakland
| Type | Count |
|---|---|
| Holiday Apartments | 820 |
| Vacation Homes | 125 |
| 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:
- 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
- McCormick 3B/2Ba w optional parking/Up to 8 guests
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:
- Spacious 3BR Retreat Near McCormick Place
- Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront
- Stylish Apartment near Chicago Downtown
How many Casai.com holiday rentals are available in Oakland?
As of 2026, Casai boasts over 1119 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 |
People Also Ask
Finding the best prices in Oakland
Map
