1629+ Private Villas and Holiday Rentals in Logan Square |
Logan Square Holiday Rentals
Apartment
10.0Exceptional
(172 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $417/Night
7 Nights - US $2,919
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
US $413/Night
7 Nights - US $2,893
Bed & Breakfast
9.8Exceptional
(404 Reviews)
1 Bedroom
1 Bath
Spa- Fireplace/Heating
- Balcony/Terrace
Breakfast
US $184/Night
7 Nights - US $1,289
Apartment
- Chicago
- ·
- Wicker Park
- 0.14 mi to center
10.0Exceptional
(11 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
Internet
US $668/Night
7 Nights - US $4,673
House
- Chicago
- ·
- Sheffield Neighbors
- 0.18 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
1001.04 ft²
- Balcony/Terrace
- Pet Friendly
- Parking
- Air Conditioner
US $832/Night
7 Nights - US $5,827
New
House
- Chicago
- ·
- Smith Park
- 0.20 mi to center
10.0Exceptional
(8 Reviews)
4 Bedrooms
2 Baths
10 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $363/Night
7 Nights - US $2,542
Apartment
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $347/Night
7 Nights - US $2,428
New
Apartment
10.0Exceptional
(2 Reviews)
3 Bedrooms
1 Bath
8 Guests
1250 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $452/Night
7 Nights - US $3,165
Apartment
- Chicago
- ·
- Near West Side
- 1.05 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $375/Night
7 Nights - US $2,627
Luxury Holiday Rentals in Logan Square
Over 1620+ Luxury Holiday Rentals in or Near Logan Square
Bed & Breakfast
- Chicago
- ·
- East Village
- 0.24 mi to center
8 Bedrooms
8 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $5,106/Night
7 Nights - US $35,741
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
House
9.4Exceptional
(14 Reviews)
4 Bedrooms
6 Baths
12 Guests
6000 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $3,490/Night
7 Nights - US $24,433
New
House
10 Bedrooms
7 Baths
32 Guests
3700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $2,808/Night
7 Nights - US $19,659
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
US $2,612/Night
7 Nights - US $18,285
Apartment
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $2,451/Night
7 Nights - US $17,155
Apartment
- Chicago
- ·
- Pulaski Park
- 0.33 mi to center
7 Bedrooms
5 Baths
16 Guests
4004.17 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $2,412/Night
7 Nights - US $16,882
House
- Chicago
- ·
- North Center
- 0.50 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
10 Guests
5000 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
US $2,283/Night
7 Nights - US $15,979
House
- Chicago
- ·
- Wicker Park
- 0.38 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
4 Baths
16 Guests
4004.17 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
US $2,234/Night
7 Nights - US $15,637
Top-Rated Holiday Rentals with a Pool in Logan Square
Over 37+ The Best Private Villas and Holiday Rentals in Logan Square with a Pool
Bed & Breakfast
- Chicago
- ·
- Roscoe Village
- 0.04 mi to center
9.8Exceptional
(103 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Fireplace/Heating
Pool- Balcony/Terrace
- Kitchen
US $430/Night
7 Nights - US $3,007
Apartment
9.8Exceptional
(24 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $224/Night
7 Nights - US $1,565
Hotel
- Chicago
- ·
- Wicker Park
- 0.14 mi to center
9.2Exceptional
(1001 Reviews)
1 Bath
- Spa
- Pool
- Balcony/Terrace
- Breakfast
US $552/Night
7 Nights - US $3,866
Apartment
- Chicago
- ·
- River North
- 0.81 mi to center
9.2Exceptional
(17 Reviews)
4 Bedrooms
4 Baths
8 Guests
1103.3 ft²
- Pool
- Parking
- Air Conditioner
- Internet
US $1,691/Night
7 Nights - US $11,837
Hotel
9.0Exceptional
(879 Reviews)
1 Bath
- Hot Tub
- Spa
- Pool
- Balcony/Terrace
US $415/Night
7 Nights - US $2,903
Hotel
- Chicago
- ·
- Belmont Cragin
- 0.15 mi to center
9.0Exceptional
(2 Reviews)
1 Bath
567 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $327/Night
7 Nights - US $2,288
Resort
8.9Fabulous
(166 Reviews)
2 Baths
6 Guests
344.45 ft²
Private Pool
Oceanfront- Hot Tub
- Spa
US $440/Night
7 Nights - US $3,081
Hotel
- Chicago
- ·
- Wicker Park
- 0.14 mi to center
8.8Fabulous
(249 Reviews)
14 Baths
377.5 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $423/Night
7 Nights - US $2,963
Hotel
1 Bath
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $415/Night
7 Nights - US $2,904
Pet-Friendly Holiday Rentals in Logan Square
Over 596+ Pet-Friendly Holiday Rentals in or Near Logan Square
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
550 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $287/Night
7 Nights - US $2,010
Apartment
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
904.17 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $194/Night
7 Nights - US $1,355
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $186/Night
7 Nights - US $1,304
New
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
550 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $271/Night
7 Nights - US $1,895
Apartment
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
14 Guests
1797.57 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $1,134/Night
7 Nights - US $7,938
Apartment
- Chicago
- ·
- Smith Park
- 0.11 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
8 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,141/Night
7 Nights - US $7,989
Apartment
9.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
14 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $658/Night
7 Nights - US $4,606
New
Apartment
8.8Fabulous
(70 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $230/Night
7 Nights - US $1,607
New
Apartment
3 Bedrooms
3 Baths
6 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $357/Night
7 Nights - US $2,498
Large Holiday Rentals and Private Villas in Logan Square
Over 263+ Large Holiday Rentals and Private Villas in or Near Logan Square
New
Apartment
- Chicago
- ·
- Ukrainian Village
- 0.36 mi to center
4 Bedrooms
4 Baths
10 Guests
1600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,128/Night
7 Nights - US $7,897
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
House
- Chicago
- ·
- Wicker Park
- 0.38 mi to center
5 Bedrooms
3 Baths
16 Guests
4000 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Balcony/Terrace
US $719/Night
7 Nights - US $5,036
House
- Chicago
- ·
- Wrightwood Neighbors
- 0.25 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
5 Baths
16 Guests
3003.13 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $1,501/Night
7 Nights - US $10,505
House
- Chicago
- ·
- Wicker Park
- 0.46 mi to center
4 Bedrooms
3 Baths
15 Guests
3100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $635/Night
7 Nights - US $4,446
New
House
- Chicago
- ·
- Wicker Park
- 0.10 mi to center
3 Bedrooms
3 Baths
14 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $457/Night
7 Nights - US $3,196
Apartment
- Chicago
- ·
- West Bucktown
- 0.32 mi to center
10.0Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $596/Night
7 Nights - US $4,172
Condo
10.0Exceptional
(121 Reviews)
3 Bedrooms
3 Baths
10 Guests
2200 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $546/Night
7 Nights - US $3,822
Apartment
10.0Exceptional
(109 Reviews)
4 Bedrooms
3 Baths
16 Guests
2300 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,024/Night
7 Nights - US $7,169
Wheelchair Accessible Holiday Homes in Logan Square
Over 121+ Wheelchair Accessible Holiday Homes in or Near Logan Square
Condo
- Chicago
- ·
- Roscoe Village
- 0.44 mi to center
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
US $168/Night
7 Nights - US $1,173
Bed & Breakfast
9.5Exceptional
(161 Reviews)
11 Bedrooms
11 Baths
30 Guests
190.81 ft²
- Spa
- Fireplace/Heating
- Balcony/Terrace
- View
US $271/Night
7 Nights - US $1,897
Bed & Breakfast
- Chicago
- ·
- Lincoln Park
- 0.23 mi to center
9.4Exceptional
(121 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Kitchen
US $269/Night
7 Nights - US $1,881
Apartment
- Chicago
- ·
- River North
- 0.83 mi to center
1 Bedroom
1 Bath
2 Guests
438 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $152/Night
7 Nights - US $1,064
Apartment
- Chicago
- ·
- Ukrainian Village
- 0.41 mi to center
7.7Very Good
(7 Reviews)
2 Bedrooms
1 Bath
4 Guests
1001.04 ft²
- Air Conditioner
- Internet
Wheelchair Accessible
US $70/Night
7 Nights - US $490
Apartment
- Chicago
- ·
- River North
- 0.83 mi to center
1 Bedroom
1 Bath
2 Guests
438 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $132/Night
7 Nights - US $924
Apartment
- Chicago
- ·
- River North
- 0.83 mi to center
1 Bedroom
1 Bath
2 Guests
438 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $88/Night
7 Nights - US $613
Apartment
- Chicago
- ·
- River North
- 0.83 mi to center
1 Bedroom
1 Bath
2 Guests
438 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $82/Night
7 Nights - US $574
Apartment
- Chicago
- ·
- River North
- 0.83 mi to center
1 Bedroom
1 Bath
2 Guests
366 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $80/Night
7 Nights - US $557
Logan Square Private Villas and Holiday Homes Under $200
Over 511+ Logan Square Private Villas and Holiday Homes Under $200
Condo
- Chicago
- ·
- Wrightwood Neighbors
- 0.16 mi to center
9.6Exceptional
(135 Reviews)
3 Bedrooms
1 Bath
5 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $188/Night
7 Nights - US $1,316
Apartment
- Chicago
- ·
- East Garfield Park
- 0.40 mi to center
9.9Exceptional
(19 Reviews)
4 Bedrooms
2 Baths
12 Guests
1302.43 ft²
- Fireplace/Heating
- Pet Friendly
- Child Friendly
Sports/Activities
US $178/Night
7 Nights - US $1,246
House
7.0Very Good
(102 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $135/Night
7 Nights - US $943
Apartment
- Chicago
- ·
- Irving Park
- 0.22 mi to center
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $143/Night
7 Nights - US $1,001
House
9.9Exceptional
(7 Reviews)
1 Bedroom
1 Bath
4 Guests
850.35 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $160/Night
7 Nights - US $1,118
House
- Chicago
- ·
- North Austin
- 0.77 mi to center
10.0Exceptional
(8 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $148/Night
7 Nights - US $1,036
Apartment
- Chicago
- ·
- Albany Park
- 0.67 mi to center
10.0Exceptional
(7 Reviews)
2 Bedrooms
1 Bath
4 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $128/Night
7 Nights - US $898
Apartment
- Chicago
- ·
- Irving Park
- 0.63 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $169/Night
7 Nights - US $1,186
House
- Chicago
- ·
- Irving Park East
- 0.29 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $179/Night
7 Nights - US $1,253
Instantly Bookable Holiday Homes in Logan Square
Over 888+ Instantly Bookable Holiday Homes in or Near Logan Square
New
Apartment
9.6Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
Laundry
US $230/Night
7 Nights - US $1,607
House
- Chicago
- ·
- Belmont Cragin
- 1.07 mi to center
4 Bedrooms
3 Baths
9 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $653/Night
7 Nights - US $4,569
New
Apartment
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $218/Night
7 Nights - US $1,524
Hotel
2 Baths
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $353/Night
7 Nights - US $2,472
Condo
- Chicago
- ·
- Ukrainian Village
- 0.23 mi to center
10.0Exceptional
(217 Reviews)
2 Bedrooms
2 Baths
9 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $628/Night
7 Nights - US $4,396
Apartment
- Chicago
- ·
- Roscoe Village
- 0.17 mi to center
10.0Exceptional
(97 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $350/Night
7 Nights - US $2,447
Apartment
10.0Exceptional
(80 Reviews)
1 Bedroom
1 Bath
3 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Balcony/Terrace
US $263/Night
7 Nights - US $1,840
House
10.0Exceptional
(71 Reviews)
2 Bedrooms
1 Bath
5 Guests
880 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $432/Night
7 Nights - US $3,021
Apartment
- Chicago
- ·
- North Center
- 0.08 mi to center
10.0Exceptional
(53 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $510/Night
7 Nights - US $3,570
Book a Last Minute Place to Stay in Logan Square
About Casai's Private Villas and Holiday Rentals in Logan Square
Discover more than 1629 vacation rentals available in Logan Square. 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 Logan Square.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Logan Square, 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 Logan Square. On average, places to stay near Logan Square offer 752.77 ft², with nightly prices averaging US $467.
With Casai, finding and comparing holiday rentals in Logan Square 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 Logan Square
| Type | Count |
|---|---|
| Holiday Apartments | 1102 |
| Vacation Homes | 331 |
| Cottages | 2 |
| Villas | 1 |
Use these Quick Filters to Find a Holiday Rental in Logan Square
★ 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 Logan Square.
Weather in Logan Square, IL
View the weather forecast for Logan Square before booking your Logan Square 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 Logan Square, IL
Frequently Asked Questions About Logan Square?
What are the top holiday rentals in Logan Square?
With numerous options available in Logan Square, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Logan Square:
- NEW LUXURY PENTHOUSE CONDO
- 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
- Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6
- Wrigley Field/Lakeview -Entire Home- Large Groups!
- Entire Below Level Studio w/Private Sauna
- Private Historic Coach House Wicker Park
- Family-friendly, stylish Chicago Apartment in Logan Square
How many holiday rentals have private pools in Logan Square?
Discover a selection of holiday rentals with private pools near Logan Square with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Logan Square are best for families?
If you're searching for a family-friendly holiday home in Logan Square, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Logan Square:
- Welcome to our 2-Bed Apartment in West Town for 7!
- North Center Chicago - Walkable - Transit Accessible - King & Queen Beds
- Wicker Park Inn
How many Casai.nz holiday rentals are available in Logan Square?
As of 2026, Casai boasts over 1629 properties listed in the Logan Square area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Logan Square.
Nearby Neighborhood (5)
| Neighborhood | Property Count |
|---|---|
| West Bucktown Vacation Rentals in Chicago, Illinois | 2380 |
| Avondale Vacation Rentals in Chicago, Illinois | 1495 |
| Bucktown Vacation Rentals in Chicago, Illinois | 3118 |
| Palmer Square Vacation Rentals in Chicago, Illinois | 2024 |
| Hermosa Vacation Rentals in Chicago, Illinois | 876 |
People Also Ask
Finding the best prices in Logan Square
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