Grand Boulevard vacation rentals
We found 104 vacation rentals — enter your dates for availability
Discover a selection of 12 homes, 20 apartments, and other vacation rentals in Grand Boulevard that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation homes have the best amenities for hanging out with the people that matter most, which might include WiFi and a pool. You'll be able to choose a rental that has what everyone needs, including places that are non-smoking or accessible.
Vacation rentals with weekly discounts - Grand Boulevard
Showing deals for:Nov 14 - Nov 21
Image gallery for Cheerful 4 bedroom smart home w/ indoor fireplace
8.08.0 out of 10 rating
Very good
(14 reviews)
Cheerful 4 bedroom smart home w/ indoor fireplace
Chicago, IL
5% off
Price is CA $399
CA $399
CA $4,363 total
CA $4,363 total
includes taxes & fees
Image gallery for Lakefront property , minutes from McCormick Place and Downtown Chicago.
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Lakefront property , minutes from McCormick Place and Downtown Chicago.
Chicago, IL
15% off
Price is CA $585
CA $585
CA $5,929 total
CA $5,929 total
includes taxes & fees
Image gallery for 1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
1010 out of 10 rating
Exceptional
(62 reviews)
1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
Chicago, IL
10% off
Price is CA $434
CA $434
CA $4,291 total
CA $4,291 total
includes taxes & fees
Image gallery for Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
8.68.6 out of 10 rating
Excellent
(13 reviews)
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
Chicago, IL
10% off
Price is CA $237
CA $237
CA $2,472 total
CA $2,472 total
includes taxes & fees
Image gallery for 3BR Prime Hyde Park Location Near University of Chicago and Dining
1010 out of 10 rating
Exceptional
(7 reviews)
3BR Prime Hyde Park Location Near University of Chicago and Dining
Chicago, IL
7% off
Price is CA $314
CA $314
CA $3,246 total
CA $3,246 total
includes taxes & fees
Image gallery for Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
Chicago, IL
19% off
Price is CA $582
CA $582
CA $6,120 total
CA $6,120 total
includes taxes & fees
Image gallery for Lux Home in Chicago 7mins Downtown
9.89.8 out of 10 rating
Exceptional
(23 reviews)
Lux Home in Chicago 7mins Downtown
Chicago, IL
10% off
Price is CA $682
CA $682
CA $6,850 total
CA $6,850 total
includes taxes & fees
Image gallery for Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
9.69.6 out of 10 rating
Exceptional
(72 reviews)
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
Chicago, IL
10% off
Price is CA $132
CA $132
CA $1,352 total
CA $1,352 total
includes taxes & fees
Image gallery for Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
8.08.0 out of 10 rating
Very good
(8 reviews)
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
Chicago, IL
20% off
Price is CA $165
CA $165
CA $1,760 total
CA $1,760 total
includes taxes & fees
Image gallery for Spacious 4 Bedroom (5 queen beds) 2 Bath in the kenwood neighborhood
9.49.4 out of 10 rating
Exceptional
(41 reviews)
Spacious 4 Bedroom (5 queen beds) 2 Bath in the kenwood neighborhood
Chicago, IL
10% off
Price is CA $381
CA $381
CA $3,918 total
CA $3,918 total
includes taxes & fees
Image gallery for Spacious apartment in awesome Chicago with WiFi, AC- 4 Bedrooms
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Spacious apartment in awesome Chicago with WiFi, AC- 4 Bedrooms
Chicago, IL
21% off
Price is CA $327
CA $327
CA $3,271 total
CA $3,271 total
includes taxes & fees
Image gallery for Toca Bella ~ 7mins to Downtown
9.89.8 out of 10 rating
Exceptional
(15 reviews)
Toca Bella ~ 7mins to Downtown
Chicago, IL
10% off
Price is CA $155
CA $155
CA $1,708 total
CA $1,708 total
includes taxes & fees
Image gallery for Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
Chicago, IL
10% off
Price is CA $551
CA $551
CA $5,919 total
CA $5,919 total
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Grand Boulevard
Just Minutes from Downtown Chicago
Sleeps 6 · 1 bedroom · 1+ bathroom
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
Just Minutes from Downtown Chicago
Sleeps 6 · 1 bedroom · 1+ bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
Sleeps 6 · 3 bedrooms · 2 bathrooms
8.68.6 out of 10
Excellentexcellent
13 reviews(13 reviews)
Modern & Spacious Stay in Historic Bronzeville
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Bronzeville Manor walking distance to hospitals
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Toca Bella ~ 7mins to Downtown
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
Top rated rentals - Grand Boulevard
Hidden Jem.
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Chicago vacation
1010 out of 10
Exceptionalexceptional
62 reviews(62 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of vacation rental in Grand Boulevard?
In Grand Boulevard, apartments are the most popular type of vacation rental, with about 25 available throughout the area. These apartments typically feature modern amenities such as fully equipped kitchens, spacious living areas, and access to communal facilities like fitness centres or swimming pools. Many are conveniently located near local attractions and dining options, making them ideal for both short and long stays.
Are there any beach house rentals in Grand Boulevard?
In Grand Boulevard, Illinois, there are several beach house rentals available, primarily found along the shores of Lake Michigan. These properties typically offer spacious interiors with multiple bedrooms, allowing for comfortable accommodation for families or groups. Most rentals come equipped with modern amenities, such as fully equipped kitchens, large living areas, and outdoor decks or patios that provide stunning views of the lake. The neighbourhood is known for its vibrant atmosphere and proximity to local attractions, making it an appealing choice for travellers seeking a relaxing getaway by the water.
How much does it cost to rent a vacation home in Grand Boulevard?
Prices for vacation rentals in Grand Boulevard vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Grand Boulevard to more spacious homes.
Are there any discounts for Grand Boulevard vacation house rentals?
You can find great discounts on house rentals in Grand Boulevard on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Grand Boulevard?
In Grand Boulevard, popular rental amenities include fully equipped kitchens, superb for those who enjoy preparing their own meals. Many rentals feature additional conveniences such as coffee and tea makers, allowing guests to enjoy a warm beverage at their leisure. Blenders are also commonly found, suiting those who like to whip up smoothies or other blended drinks. Onsite parking is another sought-after amenity, providing ease of access for those travelling by car. Additionally, many properties offer kitchen islands, which serve as great gathering spots for meals or casual conversations.
Are there any family house rentals in Grand Boulevard?
In Grand Boulevard, Illinois, there are numerous family-friendly house rentals available, with around 18 options to choose from. This vibrant community offers spacious homes that cater to families, featuring amenities such as well-equipped kitchens, ample living areas for relaxation, and outdoor spaces great for children to play. Many properties also provide conveniences like Wi-Fi and laundry facilities, ensuring a comfortable stay for all visitors.
Can I rent a vacation home with a pool or hot tub in Grand Boulevard?
In Grand Boulevard, Illinois, there are several vacation homes available for rent that feature pools and hot tubs. This suburban area offers a peaceful setting with easy access to local amenities and attractions. Many of the properties include spacious outdoor areas, superb for relaxation, as well as fully equipped kitchens to cater to family meals or entertaining guests. Expect amenities such as private pools, hot tubs, and well-furnished patios, providing a great environment for both leisure and social gatherings.
Are there any Grand Boulevard vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Grand Boulevard with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there pet-friendly vacation rentals in Grand Boulevard?
In Grand Boulevard, there are several pet-friendly vacation rentals available for travellers. The area features a range of accommodations, including modern apartments and charming homes equipped with amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can play.
Can I find long-stay vacation rentals in Grand Boulevard?
A long-stay vacation rental in Grand Boulevard is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any remote work vacation rentals in Grand Boulevard?
In Grand Boulevard, Illinois, there are ample options for remote work vacation rentals, with around 35 available in the area. These properties typically offer a variety of amenities tailored to meet the needs of remote workers. Expect to find features such as high-speed Wi-Fi, dedicated office spaces, desks with ergonomic chairs, and even computer monitors in some accommodations, allowing for a productive work environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Grand Boulevard vacation rental?
Book your Grand Boulevard vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.
*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Grand Boulevard home rental booking on Vrbo?
To find Grand Boulevard vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Grand Boulevard vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.