Lakeview Holiday Rentals
Apartment
10.0Exceptional
(172 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
R6,841/Night
7 Nights - R47,880
Apartment
- Chicago
- ·
- Lake View East
- 0.30 mi to center
10.0Exceptional
(14 Reviews)
1 Bedroom
1 Bath
2 Guests
699.65 ft²
Internet
Child Friendly
R4,199/Night
7 Nights - R29,394
House
10.0Exceptional
(26 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Parking
R8,710/Night
7 Nights - R60,969
New
Apartment
10.0Exceptional
(2 Reviews)
3 Bedrooms
1 Bath
8 Guests
1250 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R7,416/Night
7 Nights - R51,915
Apartment
- Chicago
- ·
- Lake View East
- 0.18 mi to center
10.0Exceptional
(4 Reviews)
6 Bedrooms
2 Baths
20 Guests
3498.27 ft²
Private Beach- Fireplace/Heating
Ocean View- Balcony/Terrace
R15,129/Night
7 Nights - R105,896
New
Apartment
9.6Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
Air Conditioner- Internet
Laundry
R3,764/Night
7 Nights - R26,359
Apartment
8.8Fabulous
(70 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,765/Night
7 Nights - R26,359
Apartment
- Chicago
- ·
- Wrigleyville
- 0.16 mi to center
10.0Exceptional
(51 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R11,628/Night
7 Nights - R81,391
Condo
10.0Exceptional
(36 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
R6,082/Night
7 Nights - R42,565
Luxury Holiday Rentals in Lakeview
Over 504+ Luxury Holiday Rentals in or Near Lakeview
House
4 Bedrooms
2 Baths
10 Guests
2497.23 ft²
- Parking
- Internet
- Child Friendly
Security/Safety
R62,097/Night
7 Nights - R434,674
House
- Chicago
- ·
- Wrigleyville
- 0.22 mi to center
7.4Very Good
(3 Reviews)
9 Bedrooms
4 Baths
22 Guests
4200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R42,846/Night
7 Nights - R299,925
Apartment
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R40,199/Night
7 Nights - R281,390
House
10.0Exceptional
(59 Reviews)
6 Bedrooms
5 Baths
17 Guests
5000 ft²
Oceanfront- Hot Tub
Spa- Fireplace/Heating
R35,723/Night
7 Nights - R250,061
Apartment
- Chicago
- ·
- Wrigleyville
- 0.20 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
2497.23 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
R30,619/Night
7 Nights - R214,335
Apartment
- Chicago
- ·
- Wrigleyville
- 0.20 mi to center
10.0Exceptional
(8 Reviews)
5 Bedrooms
3 Baths
10 Guests
2302 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R30,215/Night
7 Nights - R211,514
House
10.0Exceptional
(62 Reviews)
4 Bedrooms
2 Baths
10 Guests
4000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R29,985/Night
7 Nights - R209,890
House
10.0Exceptional
(6 Reviews)
5 Bedrooms
3 Baths
13 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R28,882/Night
7 Nights - R202,181
House
10.0Exceptional
(16 Reviews)
6 Bedrooms
3 Baths
15 Guests
3000 ft²
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
R26,100/Night
7 Nights - R182,694
Top-Rated Holiday Rentals with a Pool in Lakeview
Over 20+ The Best Private Villas and Holiday Rentals in Lakeview with a Pool
Apartment
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
13 Guests
Private Pool- Hot Tub
Pool- Kitchen
R14,977/Night
7 Nights - R104,847
Condo
9.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
7 Guests
1200 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
R6,963/Night
7 Nights - R48,749
Apartment
7.8Very Good
(10 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
R1,575/Night
7 Nights - R11,023
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
2 Bedrooms
2 Baths
4 Guests
1214 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
R3,838/Night
7 Nights - R26,868
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
2 Bedrooms
2 Baths
4 Guests
1214 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
R3,624/Night
7 Nights - R25,359
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
2 Bedrooms
2 Baths
4 Guests
1214 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
R3,502/Night
7 Nights - R24,522
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
1 Bedroom
1 Bath
2 Guests
850 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
R3,109/Night
7 Nights - R21,767
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
1 Bedroom
1 Bath
2 Guests
850 ft²
- Pool
- Kitchen
- Air Conditioner
- Child Friendly
R2,575/Night
7 Nights - R18,027
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
1 Bedroom
1 Bath
2 Guests
850 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
R2,569/Night
7 Nights - R17,977
Pet-Friendly Holiday Rentals in Lakeview
Over 195+ Pet-Friendly Holiday Rentals in or Near Lakeview
Apartment
- Chicago
- ·
- Wrigleyville
- 0.22 mi to center
10.0Exceptional
(7 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R9,462/Night
7 Nights - R66,235
Apartment
- Chicago
- ·
- Wrigleyville
- 0.22 mi to center
10.0Exceptional
(4 Reviews)
4 Bedrooms
2 Baths
10 Guests
1205.56 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
R6,780/Night
7 Nights - R47,453
Bed & Breakfast
8.0Excellent
(657 Reviews)
1 Bedroom
1 Bath
- Pet Friendly
- Parking
- Internet
- Security/Safety
R2,753/Night
7 Nights - R19,273
Condo
9.6Exceptional
(25 Reviews)
2 Bedrooms
2 Baths
4 Guests
1070 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R4,004/Night
7 Nights - R28,032
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
20 Guests
2497.23 ft²
- Private Beach
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R10,209/Night
7 Nights - R71,467
Apartment
9.6Exceptional
(11 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R4,048/Night
7 Nights - R28,328
Apartment
- Chicago
- ·
- Lake View East
- 0.27 mi to center
9.2Exceptional
(17 Reviews)
1 Bedroom
1 Bath
3 Guests
404 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
R4,418/Night
7 Nights - R30,936
Apartment
6.0Good
(1 Review)
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R3,303/Night
7 Nights - R23,128
Apartment
1 Bedroom
1 Bath
2 Guests
700 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
R7,266/Night
7 Nights - R50,865
Large Holiday Rentals and Private Villas in Lakeview
Over 71+ Large Holiday Rentals and Private Villas in or Near Lakeview
Condo
10.0Exceptional
(121 Reviews)
3 Bedrooms
3 Baths
10 Guests
2200 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R8,956/Night
7 Nights - R62,692
New
Apartment
- Chicago
- ·
- Wrigleyville
- 0.23 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
12 Guests
23680.6 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Air Conditioner
R16,706/Night
7 Nights - R116,936
Apartment
10.0Exceptional
(109 Reviews)
4 Bedrooms
3 Baths
16 Guests
2300 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R16,799/Night
7 Nights - R117,592
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
9.5Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
20 Guests
2497.23 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
R7,332/Night
7 Nights - R51,324
House
10.0Exceptional
(95 Reviews)
3 Bedrooms
3 Baths
20 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R12,741/Night
7 Nights - R89,182
Apartment
- Chicago
- ·
- Wrigleyville
- 0.15 mi to center
10.0Exceptional
(65 Reviews)
5 Bedrooms
2 Baths
11 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R17,568/Night
7 Nights - R122,972
Apartment
- Chicago
- ·
- Lake View East
- 0.14 mi to center
10.0Exceptional
(51 Reviews)
4 Bedrooms
2 Baths
20 Guests
2300 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R9,636/Night
7 Nights - R67,448
House
- Chicago
- ·
- Lake View East
- 0.28 mi to center
10.0Exceptional
(49 Reviews)
6 Bedrooms
2 Baths
20 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R16,212/Night
7 Nights - R113,491
House
- Chicago
- ·
- Lake View East
- 0.15 mi to center
10.0Exceptional
(32 Reviews)
4 Bedrooms
2 Baths
20 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R10,433/Night
7 Nights - R73,042
Wheelchair Accessible Holiday Homes in Lakeview
Over 59+ Wheelchair Accessible Holiday Homes in or Near Lakeview
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
2 Bedrooms
2 Baths
4 Guests
1208 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R6,003/Night
7 Nights - R42,024
Apartment
7.6Very Good
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
548.96 ft²
- Air Conditioner
- Internet
Wheelchair Accessible
R1,115/Night
7 Nights - R7,808
Hotel
- Chicago
- ·
- Wrigleyville
- 0.20 mi to center
9.6Exceptional
(1002 Reviews)
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Parking
R6,143/Night
7 Nights - R42,992
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
1 Bedroom
1 Bath
2 Guests
655 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,920/Night
7 Nights - R27,442
Apartment
6.3Good
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
548.96 ft²
- Air Conditioner
- Internet
- Wheelchair Accessible
R1,083/Night
7 Nights - R7,578
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
2 Bedrooms
2 Baths
4 Guests
958 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,821/Night
7 Nights - R19,749
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
2 Bedrooms
2 Baths
4 Guests
1025 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,666/Night
7 Nights - R18,666
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
1 Bedroom
1 Bath
2 Guests
475 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
R1,626/Night
7 Nights - R11,384
Apartment
- Chicago
- ·
- Lake View East
- 0.09 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R3,879/Night
7 Nights - R27,163
Lakeview Private Villas and Holiday Homes Under $200
Over 142+ Lakeview Private Villas and Holiday Homes Under $200
Condo
- Chicago
- ·
- Lake View East
- 0.29 mi to center
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,353/Night
7 Nights - R16,468
Apartment
- Chicago
- ·
- Lake View East
- 0.13 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
505.9 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
R2,802/Night
7 Nights - R19,618
New
Apartment
3 Bedrooms
1 Bath
9 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
R2,532/Night
7 Nights - R17,731
Apartment
9.8Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
6 Guests
947.22 ft²
- Oceanfront
- Ocean View
- View
- Pet Friendly
R2,185/Night
7 Nights - R15,287
Condo
3 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R3,050/Night
7 Nights - R21,356
Apartment
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R1,766/Night
7 Nights - R12,368
Apartment
- Chicago
- ·
- Wrigleyville
- 0.08 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
650 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
R3,011/Night
7 Nights - R21,078
Condo
9.2Exceptional
(20 Reviews)
1 Bedroom
1 Bath
4 Guests
5382 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Internet
R2,622/Night
7 Nights - R18,355
Instantly Bookable Holiday Homes in Lakeview
Over 259+ Instantly Bookable Holiday Homes in or Near Lakeview
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
R8,634/Night
7 Nights - R60,444
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
R3,056/Night
7 Nights - R21,389
Condo
9.6Exceptional
(33 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R9,169/Night
7 Nights - R64,184
Apartment
9.4Exceptional
(32 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Kitchen
- Air Conditioner
- Internet
R3,386/Night
7 Nights - R23,702
Apartment
6.8Good
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R6,220/Night
7 Nights - R43,533
Apartment
- Chicago
- ·
- Wrigleyville
- 0.18 mi to center
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R9,057/Night
7 Nights - R63,397
New
Apartment
2 Bedrooms
1 Bath
4 Guests
754 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R8,276/Night
7 Nights - R57,935
New
Apartment
2 Bedrooms
1 Bath
5 Guests
849 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Internet
R8,145/Night
7 Nights - R57,016
Apartment
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R6,471/Night
7 Nights - R45,305
Book a Last Minute Place to Stay in Lakeview
About Casai's Private Villas and Holiday Rentals in Lakeview
Discover more than 513 vacation rentals available in Lakeview. 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 Lakeview.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Lakeview, 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 Lakeview. On average, places to stay near Lakeview offer 957.33 ft², with nightly prices averaging R9,696.
With Casai, finding and comparing holiday rentals in Lakeview 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 Lakeview
| Type | Count |
|---|---|
| Holiday Apartments | 379 |
| Vacation Homes | 47 |
Use these Quick Filters to Find a Holiday Rental in Lakeview
★ 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 Lakeview.
Weather in Lakeview, IL
View the weather forecast for Lakeview before booking your Lakeview 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 Lakeview, IL
Frequently Asked Questions About Lakeview?
What are the top holiday rentals in Lakeview?
With numerous options available in Lakeview, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Lakeview:
- Single Family Home! Sleeps 8 Lincoln Park/Lakeview
- Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
- Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
- Dramatic Wrigley Loft +PRIVATE Rooftop, Center of Wrigley, Ranked GUEST FAVORITE
- Wrigley Field/Lakeview -Entire Home- Large Groups!
- 5 Bedroom Wrigleyville experience right by stadium
- PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME! ABSOLUTELY NO PARTIES!
- Luxurious Four-Level Home with Personal Touches Everywhere
- Wrigleyville Private Guesthouse
- Wrigley Field Rooftop Apartment! - CUBS SEASON OPEN
Which holiday homes in Lakeview are best for families?
If you're searching for a family-friendly holiday home in Lakeview, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Lakeview:
- Stylish Two Bedroom - A block from Wrigley Field
- Modern 3BR Apt in Boystown, 12-min walk to Wrigley - Stratford 1S
- Best Western Plus Hawthorne Terrace Hotel
How many Casai.co.za holiday rentals are available in Lakeview?
As of 2026, Casai boasts over 513 properties listed in the Lakeview area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Lakeview.
Nearby Neighborhood (13)
| Neighborhood | Property Count |
|---|---|
| Lincoln Park Vacation Rentals in Chicago, Illinois | 59 |
| Lake View East Vacation Rentals in Chicago, Illinois | 27 |
| Wrigleyville Vacation Rentals in Chicago, Illinois | 1585 |
| North Center Vacation Rentals in Chicago, Illinois | 1840 |
| Uptown Vacation Rentals in Chicago, Illinois | 1232 |
| Sheffield and DePaul Vacation Rentals in Chicago, Illinois | 3794 |
| Park West Vacation Rentals in Chicago, Illinois | 3594 |
| Wrightwood Neighbors Vacation Rentals in Chicago, Illinois | 3480 |
| Ravenswood Vacation Rentals in Chicago, Illinois | 1332 |
| Roscoe Village Vacation Rentals in Chicago, Illinois | 1990 |
| Boystown Vacation Rentals in Chicago, Illinois | 1706 |
| West Lakeview Vacation Rentals in Chicago, Illinois | 2270 |
| West DePaul Vacation Rentals in Chicago, Illinois | 3258 |
People Also Ask
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