Lakeview Holiday Rentals
Apartment
10.0Exceptional
(169 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $360/Night
7 Nights - US $2,519
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
US $256/Night
7 Nights - US $1,792
House
10.0Exceptional
(25 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Parking
US $531/Night
7 Nights - US $3,717
Condo
- Chicago
- ·
- Lake View East
- 0.17 mi to center
10.0Exceptional
(62 Reviews)
2 Bedrooms
2 Baths
6 Guests
1500 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $542/Night
7 Nights - US $3,793
Apartment
10.0Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
914.93 ft²
- Fireplace/Heating
- Pet Friendly
Air Conditioner- Internet
US $618/Night
7 Nights - US $4,329
Condo
10.0Exceptional
(53 Reviews)
2 Bedrooms
2 Baths
5 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $463/Night
7 Nights - US $3,243
Apartment
- Chicago
- ·
- Wrigleyville
- 0.16 mi to center
10.0Exceptional
(50 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,014/Night
7 Nights - US $7,095
Apartment
10.0Exceptional
(49 Reviews)
2 Bedrooms
1 Bath
5 Guests
900 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $531/Night
7 Nights - US $3,718
Condo
10.0Exceptional
(36 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $390/Night
7 Nights - US $2,728
Luxury Holiday Rentals in Lakeview
Over 530+ Luxury Holiday Rentals in or Near Lakeview
House
4 Bedrooms
2 Baths
10 Guests
2497.23 ft²
- Parking
- Internet
- Child Friendly
Security/Safety
US $3,786/Night
7 Nights - US $26,500
Apartment
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $2,457/Night
7 Nights - US $17,200
House
10.0Exceptional
(57 Reviews)
6 Bedrooms
5 Baths
17 Guests
5000 ft²
Oceanfront- Hot Tub
Spa- Fireplace/Heating
US $2,172/Night
7 Nights - US $15,205
House
- Chicago
- ·
- Wrigleyville
- 0.22 mi to center
7.4Very Good
(3 Reviews)
9 Bedrooms
4 Baths
20 Guests
30139 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $2,150/Night
7 Nights - US $15,051
Apartment
- Chicago
- ·
- Wrigleyville
- 0.27 mi to center
10.0Exceptional
(1 Review)
9 Bedrooms
5 Baths
16 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $1,923/Night
7 Nights - US $13,459
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
US $1,867/Night
7 Nights - US $13,067
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
US $1,694/Night
7 Nights - US $11,855
House
10.0Exceptional
(6 Reviews)
5 Bedrooms
3 Baths
13 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,689/Night
7 Nights - US $11,823
Apartment
- Chicago
- ·
- Wrigleyville
- 0.16 mi to center
10.0Exceptional
(14 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,688/Night
7 Nights - US $11,816
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
US $913/Night
7 Nights - US $6,392
Condo
9.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
7 Guests
1200 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
US $425/Night
7 Nights - US $2,972
Apartment
7.8Very Good
(10 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $96/Night
7 Nights - US $672
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
2 Bedrooms
2 Baths
4 Guests
1214 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
US $234/Night
7 Nights - US $1,638
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
2 Bedrooms
2 Baths
4 Guests
1214 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
US $221/Night
7 Nights - US $1,546
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
2 Bedrooms
2 Baths
4 Guests
1214 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
US $214/Night
7 Nights - US $1,495
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
1 Bedroom
1 Bath
2 Guests
850 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
US $190/Night
7 Nights - US $1,327
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
1 Bedroom
1 Bath
2 Guests
850 ft²
- Pool
- Kitchen
- Air Conditioner
- Child Friendly
US $157/Night
7 Nights - US $1,099
Apartment
- Chicago
- ·
- Lake View East
- 0.33 mi to center
1 Bedroom
1 Bath
2 Guests
850 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
US $157/Night
7 Nights - US $1,096
Pet-Friendly Holiday Rentals in Lakeview
Over 213+ Pet-Friendly Holiday Rentals in or Near Lakeview
Apartment
- Chicago
- ·
- Lake View East
- 0.22 mi to center
10.0Exceptional
(13 Reviews)
1 Bedroom
1 Bath
2 Guests
404 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $610/Night
7 Nights - US $4,270
Apartment
- Chicago
- ·
- Lake View East
- 0.18 mi to center
10.0Exceptional
(3 Reviews)
6 Bedrooms
2 Baths
20 Guests
3498.27 ft²
Private Beach- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $645/Night
7 Nights - US $4,515
Bed & Breakfast
7.8Very Good
(641 Reviews)
1 Bedroom
1 Bath
- Pet Friendly
- Parking
- Internet
- Security/Safety
US $154/Night
7 Nights - US $1,075
Apartment
- Chicago
- ·
- Wrigleyville
- 0.22 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $499/Night
7 Nights - US $3,492
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
US $1,040/Night
7 Nights - US $7,280
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
6 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $307/Night
7 Nights - US $2,149
Apartment
- Chicago
- ·
- Wrigleyville
- 0.27 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
6 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $344/Night
7 Nights - US $2,408
Condo
9.6Exceptional
(25 Reviews)
2 Bedrooms
2 Baths
4 Guests
1070 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $361/Night
7 Nights - US $2,529
Apartment
9.6Exceptional
(11 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $256/Night
7 Nights - US $1,794
Large Holiday Rentals and Private Villas in Lakeview
Over 73+ Large Holiday Rentals and Private Villas in or Near Lakeview
Apartment
9.2Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
10 Guests
969 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $341/Night
7 Nights - US $2,385
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
US $447/Night
7 Nights - US $3,129
Condo
10.0Exceptional
(117 Reviews)
3 Bedrooms
3 Baths
10 Guests
2200 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $587/Night
7 Nights - US $4,111
Apartment
- Chicago
- ·
- Lake View East
- 0.15 mi to center
9.3Exceptional
(3 Reviews)
4 Bedrooms
2 Baths
20 Guests
2002.09 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
US $360/Night
7 Nights - US $2,520
Apartment
10.0Exceptional
(106 Reviews)
4 Bedrooms
3 Baths
16 Guests
2300 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,200/Night
7 Nights - US $8,403
House
10.0Exceptional
(93 Reviews)
3 Bedrooms
3 Baths
20 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $853/Night
7 Nights - US $5,968
Apartment
- Chicago
- ·
- Wrigleyville
- 0.15 mi to center
10.0Exceptional
(64 Reviews)
5 Bedrooms
2 Baths
11 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $922/Night
7 Nights - US $6,456
House
10.0Exceptional
(59 Reviews)
4 Bedrooms
2 Baths
10 Guests
4000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,679/Night
7 Nights - US $11,754
House
- Chicago
- ·
- Lake View East
- 0.28 mi to center
10.0Exceptional
(48 Reviews)
6 Bedrooms
2 Baths
20 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $988/Night
7 Nights - US $6,919
Wheelchair Accessible Holiday Homes in Lakeview
Over 63+ 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
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $593/Night
7 Nights - US $4,148
Apartment
7.6Very Good
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
548.96 ft²
- Air Conditioner
- Internet
Wheelchair Accessible
US $68/Night
7 Nights - US $476
Hotel
- Chicago
- ·
- Wrigleyville
- 0.20 mi to center
9.6Exceptional
(1005 Reviews)
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Parking
US $292/Night
7 Nights - US $2,046
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
US $496/Night
7 Nights - US $3,472
Apartment
6.3Good
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
548.96 ft²
- Air Conditioner
- Internet
- Wheelchair Accessible
US $66/Night
7 Nights - US $462
Apartment
- Chicago
- ·
- Lake View East
- 0.13 mi to center
1 Bedroom
1 Bath
4 Guests
500 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $418/Night
7 Nights - US $2,925
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
US $387/Night
7 Nights - US $2,709
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
US $239/Night
7 Nights - US $1,673
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
US $193/Night
7 Nights - US $1,351
Lakeview Private Villas and Holiday Homes Under $200
Over 147+ Lakeview Private Villas and Holiday Homes Under $200
Apartment
1 Bedroom
1 Bath
2 Guests
700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $184/Night
7 Nights - US $1,291
Apartment
9.8Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
6 Guests
947.22 ft²
- Oceanfront
- Ocean View
- View
- Pet Friendly
US $133/Night
7 Nights - US $932
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
US $174/Night
7 Nights - US $1,218
Apartment
8.4Excellent
(12 Reviews)
5 Bedrooms
1 Bath
10 Guests
645.83 ft²
- Balcony/Terrace
- Pet Friendly
- Parking
- Air Conditioner
US $95/Night
7 Nights - US $665
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $172/Night
7 Nights - US $1,201
Condo
- Chicago
- ·
- Lake View East
- 0.29 mi to center
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $143/Night
7 Nights - US $1,004
Apartment
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $98/Night
7 Nights - US $685
Condo
3 Bedrooms
2 Baths
6 Guests
2600 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $173/Night
7 Nights - US $1,210
Instantly Bookable Holiday Homes in Lakeview
Over 260+ Instantly Bookable Holiday Homes in or Near Lakeview
Condo
10.0Exceptional
(33 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $490/Night
7 Nights - US $3,433
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $186/Night
7 Nights - US $1,304
Apartment
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
647 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $476/Night
7 Nights - US $3,331
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $549/Night
7 Nights - US $3,846
House
- Chicago
- ·
- Wrigleyville
- 0.17 mi to center
9.8Exceptional
(89 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,030/Night
7 Nights - US $7,208
Apartment
9.8Exceptional
(32 Reviews)
2 Bedrooms
1 Bath
4 Guests
754 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $401/Night
7 Nights - US $2,807
Apartment
9.8Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $389/Night
7 Nights - US $2,723
Apartment
9.8Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $481/Night
7 Nights - US $3,368
Condo
9.6Exceptional
(32 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $547/Night
7 Nights - US $3,826
Book a Last Minute Place to Stay in Lakeview
About Casai's Private Villas and Holiday Rentals in Lakeview
Discover more than 539 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 1070.75 ft², with nightly prices averaging US $589.
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 | 401 |
| 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
- EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
- PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME! ABSOLUTELY NO PARTIES!
- Luxurious Four-Level Home with Personal Touches Everywhere
- Wrigleyville Private Guesthouse
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
- Wrigleyville Suites
How many Casai.com holiday rentals are available in Lakeview?
As of 2026, Casai boasts over 539 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 | 133 |
| North Center Vacation Rentals in Chicago, Illinois | 56 |
| Lake View East Vacation Rentals in Chicago, Illinois | 53 |
| Wrigleyville Vacation Rentals in Chicago, Illinois | 47 |
| Sheffield and DePaul Vacation Rentals in Chicago, Illinois | 38 |
| Uptown Vacation Rentals in Chicago, Illinois | 35 |
| Ravenswood Vacation Rentals in Chicago, Illinois | 28 |
| Wrightwood Neighbors Vacation Rentals in Chicago, Illinois | 25 |
| Park West Vacation Rentals in Chicago, Illinois | 3584 |
| Roscoe Village Vacation Rentals in Chicago, Illinois | 1927 |
| Boystown Vacation Rentals in Chicago, Illinois | 1690 |
| West Lakeview Vacation Rentals in Chicago, Illinois | 2184 |
| West DePaul Vacation Rentals in Chicago, Illinois | 3258 |
People Also Ask
Finding the best prices in Lakeview
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