Lakeview Holiday Rentals
Apartment
10.0Exceptional
(176 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
R7,269/Night
7 Nights - R50,879
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
R4,160/Night
7 Nights - R29,120
House
10.0Exceptional
(28 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R8,629/Night
7 Nights - R60,402
Condo
- Chicago
- ·
- Lake View East
- 0.17 mi to center
10.0Exceptional
(63 Reviews)
2 Bedrooms
2 Baths
6 Guests
1500 ft²
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
R8,654/Night
7 Nights - R60,581
Apartment
- Chicago
- ·
- Wrigleyville
- 0.22 mi to center
10.0Exceptional
(5 Reviews)
4 Bedrooms
2 Baths
10 Guests
1205.56 ft²
- Parking
- Air Conditioner
- Internet
Pet Friendly
R7,802/Night
7 Nights - R54,617
Condo
10.0Exceptional
(63 Reviews)
2 Bedrooms
2 Baths
5 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,408/Night
7 Nights - R23,855
Apartment
10.0Exceptional
(57 Reviews)
2 Bedrooms
1 Bath
5 Guests
900 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
R7,920/Night
7 Nights - R55,446
Apartment
- Chicago
- ·
- Wrigleyville
- 0.16 mi to center
10.0Exceptional
(55 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R10,900/Night
7 Nights - R76,295
Apartment
10.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
6 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R6,637/Night
7 Nights - R46,459
Luxury Holiday Rentals in Lakeview
Over 511+ Luxury Holiday Rentals in or Near Lakeview
House
4 Bedrooms
2 Baths
10 Guests
2497.23 ft²
- Parking
- Internet
- Child Friendly
Security/Safety
R61,519/Night
7 Nights - R430,631
House
10.0Exceptional
(62 Reviews)
6 Bedrooms
5 Baths
17 Guests
5000 ft²
Oceanfront- Hot Tub
- Parking
Spa
R35,320/Night
7 Nights - R247,247
House
- Chicago
- ·
- Wrigleyville
- 0.22 mi to center
7.4Very Good
(3 Reviews)
9 Bedrooms
4 Baths
22 Guests
4200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R33,500/Night
7 Nights - R234,507
House
10.0Exceptional
(63 Reviews)
4 Bedrooms
2 Baths
10 Guests
4000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R29,452/Night
7 Nights - R206,167
Bed & Breakfast
5 Bedrooms
3 Baths
12 Guests
1200 ft²
Breakfast- Parking
- Balcony/Terrace
- Kitchen
R25,823/Night
7 Nights - R180,767
House
9.8Exceptional
(28 Reviews)
5 Bedrooms
3 Baths
16 Guests
- Oceanfront
- Parking
Ocean View
View
R24,850/Night
7 Nights - R173,959
Apartment
- Chicago
- ·
- Wrigleyville
- 0.27 mi to center
10.0Exceptional
(2 Reviews)
9 Bedrooms
5 Baths
16 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
R24,171/Night
7 Nights - R169,197
House
9.6Exceptional
(38 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
R23,607/Night
7 Nights - R165,248
Apartment
- Chicago
- ·
- Wrigleyville
- 0.23 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
12 Guests
2200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R21,150/Night
7 Nights - R148,056
Top-Rated Holiday Rentals with a Pool in Lakeview
Over 18+ 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
- Parking
Pool
R14,838/Night
7 Nights - R103,871
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
2 Bedrooms
2 Baths
4 Guests
1214 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
R3,803/Night
7 Nights - R26,618
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
2 Bedrooms
2 Baths
4 Guests
1214 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
R3,590/Night
7 Nights - R25,123
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
2 Bedrooms
2 Baths
4 Guests
1214 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
R3,469/Night
7 Nights - R24,294
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
1 Bedroom
1 Bath
2 Guests
850 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
R3,080/Night
7 Nights - R21,564
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
1 Bedroom
1 Bath
2 Guests
850 ft²
- Pool
- Kitchen
- Air Conditioner
- Child Friendly
R2,551/Night
7 Nights - R17,859
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
1 Bedroom
1 Bath
2 Guests
850 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
R2,545/Night
7 Nights - R17,810
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
1 Bedroom
1 Bath
2 Guests
850 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
R2,529/Night
7 Nights - R17,696
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
1 Bedroom
1 Bath
2 Guests
540 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
R2,291/Night
7 Nights - R16,039
Pet-Friendly Holiday Rentals in Lakeview
Over 199+ Pet-Friendly Holiday Rentals in or Near Lakeview
Apartment
- Chicago
- ·
- Wrigleyville
- 0.27 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
6 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R5,658/Night
7 Nights - R39,602
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
EV Charge Station- Parking
- Ocean View
R7,826/Night
7 Nights - R54,779
Bed & Breakfast
8.0Excellent
(669 Reviews)
1 Bedroom
1 Bath
- Parking
- Internet
- Pet Friendly
- Security/Safety
R3,539/Night
7 Nights - R24,782
House
- Chicago
- ·
- Wrigleyville
- 0.23 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R6,385/Night
7 Nights - R44,688
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
- Parking
- Ocean View
- Balcony/Terrace
R10,114/Night
7 Nights - R70,802
Apartment
9.8Exceptional
(6 Reviews)
3 Bedrooms
1 Bath
12 Guests
1000 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R5,196/Night
7 Nights - R36,368
Condo
9.6Exceptional
(25 Reviews)
2 Bedrooms
2 Baths
5 Guests
1070 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R2,909/Night
7 Nights - R20,362
Apartment
9.6Exceptional
(20 Reviews)
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
R4,672/Night
7 Nights - R32,712
Apartment
9.6Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
10 Guests
1000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R7,051/Night
7 Nights - R49,352
Large Holiday Rentals and Private Villas in Lakeview
Over 71+ Large Holiday Rentals and Private Villas in or Near Lakeview
Condo
10.0Exceptional
(132 Reviews)
3 Bedrooms
3 Baths
10 Guests
2200 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R6,777/Night
7 Nights - R47,434
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
R12,987/Night
7 Nights - R90,904
Apartment
10.0Exceptional
(118 Reviews)
4 Bedrooms
3 Baths
16 Guests
2300 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R12,753/Night
7 Nights - R89,262
Apartment
10.0Exceptional
(1 Review)
4 Bedrooms
1 Bath
12 Guests
1700.7 ft²
- View
- Air Conditioner
- Internet
Sports/Activities
R20,557/Night
7 Nights - R143,896
Apartment
- Chicago
- ·
- Wrigleyville
- 0.15 mi to center
10.0Exceptional
(68 Reviews)
5 Bedrooms
2 Baths
11 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R18,487/Night
7 Nights - R129,417
Apartment
- Chicago
- ·
- Lake View East
- 0.14 mi to center
10.0Exceptional
(59 Reviews)
4 Bedrooms
2 Baths
20 Guests
2300 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
R5,290/Night
7 Nights - R37,034
House
- Chicago
- ·
- Lake View East
- 0.28 mi to center
10.0Exceptional
(53 Reviews)
6 Bedrooms
2 Baths
20 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R10,539/Night
7 Nights - R73,776
House
- Chicago
- ·
- Lake View East
- 0.15 mi to center
10.0Exceptional
(35 Reviews)
4 Bedrooms
2 Baths
20 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R5,260/Night
7 Nights - R36,823
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
10.0Exceptional
(34 Reviews)
4 Bedrooms
2 Baths
20 Guests
2500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R5,290/Night
7 Nights - R37,034
Wheelchair Accessible Holiday Homes in Lakeview
Over 56+ Wheelchair Accessible Holiday Homes in or Near Lakeview
Apartment
- Chicago
- ·
- Lake View East
- 0.13 mi to center
6.0Good
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
800 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
R4,460/Night
7 Nights - R31,217
Apartment
7.6Very Good
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
548.96 ft²
- Air Conditioner
- Internet
Wheelchair Accessible
R1,105/Night
7 Nights - R7,735
Hotel
- Chicago
- ·
- Wrigleyville
- 0.20 mi to center
9.6Exceptional
(1003 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Air Conditioner
R5,704/Night
7 Nights - R39,927
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
2 Bedrooms
2 Baths
4 Guests
1208 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
R3,704/Night
7 Nights - R25,935
Apartment
6.3Good
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
548.96 ft²
- Air Conditioner
- Internet
- Wheelchair Accessible
R1,073/Night
7 Nights - R7,508
Apartment
- Chicago
- ·
- Lake View East
- 0.13 mi to center
1 Bedroom
1 Bath
4 Guests
500 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
R3,585/Night
7 Nights - R25,090
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
2 Bedrooms
2 Baths
4 Guests
1025 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
R2,914/Night
7 Nights - R20,394
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
2 Bedrooms
2 Baths
4 Guests
958 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
R2,860/Night
7 Nights - R20,020
Apartment
- Chicago
- ·
- Lake View East
- 0.13 mi to center
1 Bedroom
1 Bath
2 Guests
500 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
R2,777/Night
7 Nights - R19,435
Lakeview Private Villas and Holiday Homes Under $200
Over 161+ Lakeview Private Villas and Holiday Homes Under $200
Apartment
9.6Exceptional
(17 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R2,589/Night
7 Nights - R18,119
Apartment
9.8Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
6 Guests
947.22 ft²
- Oceanfront
- Parking
- Ocean View
- View
R2,165/Night
7 Nights - R15,145
Hotel
8.4Excellent
(102 Reviews)
1 Bath
- Internet
Guest Services
R3,016/Night
7 Nights - R21,109
Apartment
9.4Exceptional
(19 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
Laundry
R2,785/Night
7 Nights - R19,500
Apartment
- Chicago
- ·
- Lake View East
- 0.13 mi to center
9.3Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
505.9 ft²
- Parking
- Spa
- Air Conditioner
- Internet
R2,824/Night
7 Nights - R19,760
Apartment
9.2Exceptional
(40 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Kitchen
- Air Conditioner
- Internet
R2,902/Night
7 Nights - R20,313
Apartment
9.0Exceptional
(79 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
R2,829/Night
7 Nights - R19,809
Apartment
8.8Fabulous
(38 Reviews)
2 Bedrooms
1 Bath
5 Guests
750 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R2,687/Night
7 Nights - R18,802
Apartment
8.4Excellent
(13 Reviews)
2 Bedrooms
1 Bath
5 Guests
800 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
R3,051/Night
7 Nights - R21,353
Instantly Bookable Holiday Homes in Lakeview
Over 258+ Instantly Bookable Holiday Homes in or Near Lakeview
Apartment
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
647 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
R5,713/Night
7 Nights - R39,992
Apartment
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Pet Friendly
- Child Friendly
R3,027/Night
7 Nights - R21,190
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
849 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
R4,532/Night
7 Nights - R31,720
Apartment
- Chicago
- ·
- Wrigleyville
- 0.18 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R4,401/Night
7 Nights - R30,810
Apartment
- Chicago
- ·
- Wrigleyville
- 0.19 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
R3,765/Night
7 Nights - R26,358
Apartment
9.8Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
R4,886/Night
7 Nights - R34,207
Apartment
9.8Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R4,278/Night
7 Nights - R29,949
Apartment
9.8Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
R4,314/Night
7 Nights - R30,193
Condo
9.6Exceptional
(38 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R4,547/Night
7 Nights - R31,834
Book a Last Minute Place to Stay in Lakeview
About Casai's Private Villas and Holiday Rentals in Lakeview
Discover more than 520 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 919.29 ft², with nightly prices averaging R8,685.
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 | 388 |
| Vacation Homes | 48 |
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:
- 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
- 5 Bedroom Wrigleyville experience right by stadium
- Wrigleyville Private Guesthouse
- PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME! ABSOLUTELY NO PARTIES!
- EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
- Chic Urban Retreat Near Wrigley Field w/Parking
- Luxurious Four-Level Home with Personal Touches Everywhere
- Stone Mansion Sleeps 10-20 Free Parking Near Lake, Red Line and Wrigley
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:
- Entire Apt in Heart of Chicago
- Modern 3BR Apt in Boystown, 12-min walk to Wrigley - Stratford 1S
- Dorothy's
How many Casai.co.za holiday rentals are available in Lakeview?
As of 2026, Casai boasts over 520 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 | 128 |
| North Center Vacation Rentals in Chicago, Illinois | 52 |
| Wrigleyville Vacation Rentals in Chicago, Illinois | 50 |
| Lake View East Vacation Rentals in Chicago, Illinois | 42 |
| Uptown Vacation Rentals in Chicago, Illinois | 38 |
| Sheffield and DePaul Vacation Rentals in Chicago, Illinois | 34 |
| Wrightwood Neighbors Vacation Rentals in Chicago, Illinois | 24 |
| Park West Vacation Rentals in Chicago, Illinois | 3572 |
| Ravenswood Vacation Rentals in Chicago, Illinois | 1368 |
| Roscoe Village Vacation Rentals in Chicago, Illinois | 1948 |
| West Lakeview Vacation Rentals in Chicago, Illinois | 2240 |
| Boystown Vacation Rentals in Chicago, Illinois | 1706 |
| West DePaul Vacation Rentals in Chicago, Illinois | 3258 |
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