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Chicago, IL holiday homes
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772 Villa rentals in Chicago, IL

Best Chicago, IL villas and holiday homes with a pool

Among the 772 accommodations in Chicago, IL, here are the 4 best villas and holiday homes with a pool

102 M² House ∙ 3 Bedrooms ∙ 6 Guests - Chicago, IL
No reviews

102 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Des Plaines
House listing for up to 6 people. Your accommodation will be located in Des Plaines.
Services and facilities: a garden, a washing machine and a terrace. Take a dip in the pool of this house in Des Plaines!
Extended Stay: Walk To Uic Campus & Train! - Chicago, IL
No reviews

Extended Stay: Walk To Uic Campus & Train!

house, Chicago
This Chicago flat is located near the University of Illinois Chicago (UIC) campus, offering convenient access within 3.4 kilometres of Willis Tower and 4 kilometres of Union Station.
This 116 square metre apartment accommodates up to seven guests with two bedrooms and two bathrooms, featuring air conditioning, a fully equipped kitchen, complimentary Wi-Fi, and an outdoor swimming pool.
Sleeps7 • 2br • Coffee Station • Backyard W/ Grill - Chicago, IL
No reviews

Sleeps7 • 2br • Coffee Station • Backyard W/ Grill

apartment, Chicago
This Chicago detached house is located approximately 12 kilometres from the United Centre and 12.2 kilometres from Lincoln Park Zoo, offering straightforward access to several key city attractions.
This detached house provides accommodation for up to 7 guests across 2 bedrooms, featuring a fully equipped kitchen with an oven and microwave, complimentary WiFi, and a backyard with a grill, all within a 1000 square metre floor area.
Forest Park Oasis - Dog Friendly - Parks - The "L" - Chicago, IL
9.9 29 reviews

Forest Park Oasis - Dog Friendly - Parks - The "L"

house, Forest Park
This newly renovated Forest Park townhouse is situated directly opposite Forest Park, Roos Recreation Centre, tennis courts and a swimming pool, and a 0.8 km walk from the Harlem Blue Line station, offering easy access to downtown Chicago and O'Hare Airport.
The two-bedroom, one-bathroom property sleeps four, features a fully equipped kitchen with a bean-to-cup coffee machine, smart TVs, a dedicated workspace, a fenced yard with a pet door, and includes board games; free on-street parking supplements the designated parking space.

Best family friendly Chicago, IL villas and holiday home

Among the 772 accommodations in Chicago, IL, here are the 4 best family friendly villas and holiday homes

Sleeps 26 • Modern Multi-unit • Gym • Workspaces - Chicago, IL
No reviews

Sleeps 26 • Modern Multi-unit • Gym • Workspaces

house, Chicago
This property offers a spacious seven-bedroom dwelling in Chicago, located less than 1 kilometre from Millennium Park, under 3 kilometres from Navy Pier, and within 5 kilometres of Lincoln Park Zoo.
This family-friendly accommodation provides space for up to 26 guests with modern furnishings, an indoor gym, free Wi-Fi, and multiple parking options, making it ideal for larger groups seeking convenient access to the city's attractions.
Lovely Central Oak Park Th W/parking & On Green El - Chicago, IL
10 240 reviews

Lovely Central Oak Park Th W/parking & On Green El

house, Oak Park
This charming house is located in a central Oak Park neighbourhood, just a short walk from the Green Line, Metra, and the Oak Park Farmers Market. It has received excellent ratings for location, cleanliness and user experience.
The property has two bedrooms and two bathrooms, making it ideal for families or groups of up to five people. It comes equipped with a kitchen, a garden, parking, and laundry facilities, as well as air conditioning and internet access.
Spacious Home With Modern Amenities - Charming Group Getaway - Chicago, IL
No reviews

Spacious Home With Modern Amenities - Charming Group Getaway

house, Berwyn
This detached house in Berwyn, Illinois, is situated a convenient 32 kilometres from downtown Chicago, with easy access to local amenities and Midway Airport.
The property offers accommodation for up to eight guests in four bedrooms and two bathrooms, featuring a fully equipped kitchen, a living room with a smart TV, on-site laundry, private garden, and garage parking, all supported by fast Wi-Fi.
Charming & Comfy Gem ~ 10 Mins To Downtown ~Patio! - Chicago, IL
9.5 109 reviews

Charming & Comfy Gem ~ 10 Mins To Downtown ~Patio!

apartment, Chicago
This four-bedroom Chicago house, situated less than 6.4 km from the city centre, offers easy access to major attractions.
The spacious property sleeps ten guests, boasting a fully equipped kitchen, six 55" Smart TVs, a private patio with Solostove and smoker, and free on-street parking; breed restrictions and fees apply for pets.

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Best Chicago, IL villas and holiday homes with parking

King Bed L Cta L United Center L Near Kasama L Patio - Chicago, IL
No reviews

King Bed L Cta L United Center L Near Kasama L Patio

house, Chicago
This Chicago residence is situated 2.6 kilometres from the United Center and within 4.5 kilometres of the Chicago Water Tower and Union Station, offering convenient access to downtown attractions.
This property provides accommodation for up to 9 guests across 2 bedrooms, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, complimentary Wi-Fi, air conditioning, a private patio, and parking, with a floor area of 15 square meters.
82 M² House ∙ 4 Bedrooms ∙ 8 Guests - Chicago, IL
No reviews

82 M² House ∙ 4 Bedrooms ∙ 8 Guests

house, Oak Park
House for 8 guests. This accommodation is based in Oak Park.
Services and facilities include an iron, a kitchen and a fridge. Take advantage of the Free Parking with this accommodation.
Private, Charming, Coach House Loft In Andersonville - Chicago, IL
9.8 447 reviews

Private, Charming, Coach House Loft In Andersonville

house, Chicago
This meticulously renovated Chicago loft, ideal for couples, offers a unique blend of Midwest farmhouse and industrial styles and is situated in a residential area with easy street parking, though its precise distance from specific Chicago landmarks requires further clarification.
The 1-bathroom apartment features an open-plan kitchen with modern appliances (fridge, microwave, dishwasher), secure keyless entry, and accommodates two guests; nearby attractions and activities will depend on its exact location within the city.
2 Newly Built Luxury Condos With Private Roofdeck - Chicago, IL
9.0 1 review

2 Newly Built Luxury Condos With Private Roofdeck

house, Chicago
This newly built luxury condominium in Chicago offers a private roof deck and is a mere 1.76-kilometre walk from the Museum of Contemporary Art, with Oak Street Beach and Water Tower Chicago also within easy reach.
This expansive 279-square-metre residence features six air-conditioned bedrooms and six bathrooms, accommodating up to 31 guests with a fully equipped kitchen, complimentary Wi-Fi, and outdoor seating.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL villas and holiday homes with a garden

Stunning Condo #2 - Downtown River North - Chicago, IL
8.5 34 reviews

Stunning Condo #2 - Downtown River North

house, Chicago
This River North apartment is ideally located 2.4km from Ohio Street Beach and 2.9km from North Avenue Beach, offering easy access to Chicago's downtown attractions including the Water Tower and the Museum of Contemporary Art.
The 167 square metre, three-bedroom condo sleeps 27 guests and features a fully equipped kitchen, private patio, in-unit laundry, and free Wi-Fi; enjoy nearby beaches and city exploration.
Upscale 4-bedroom Townhouse W/garage - Location - Chicago, IL
9.7 146 reviews

Upscale 4-bedroom Townhouse W/garage - Location

house, Chicago
This stylish townhouse is situated in Chicago's River West neighbourhood, just a short walk from the vibrant West Loop, River North, and the Loop, offering easy access to the city's best restaurants, bars, and attractions. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The property is spread across three floors, offering four bedrooms and five beds, comfortably accommodating up to 10 guests. The townhouse features a modern design, a private patio, a fully equipped kitchen, and a private garage, ensuring a comfortable and convenient stay.
A Pleasant Stay In Oak Park - Chicago, IL
10 75 reviews

A Pleasant Stay In Oak Park

house, Oak Park
This Oak Park townhouse, situated in a residential neighbourhood, is a short walk (less than 0.16 km) from the Chicago ‘L’ train station, 0.32 km from the Oak Park Arts District, and 0.16 km from Barrie Park.
The self-catering property sleeps six guests in two bedrooms and one bathroom, featuring a king-size bed, modern kitchen with dishwasher, three smart TVs, free high-speed Wi-Fi, a washer/dryer, off-street parking and a private garden.
Spacious Roscoe Village Getaway - Chicago, IL
9.7 7 reviews

Spacious Roscoe Village Getaway

house, Chicago
This Roscoe Village detached house is situated within easy walking distance of numerous eateries, shops, and a Starbucks, with the Brown Line train station a mere 500-meter stroll away for convenient access to downtown Chicago.
This residence offers two floors of living space, accommodating up to six guests with flexible bedding, and boasts a chef's kitchen, a spacious deck, and a grass yard complete with a full-size barbecue.
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