Streeterville holiday lettings

We found 673 holiday rentals — enter your dates for availability
Discover a selection of 60 apartments and other holiday rentals in Streeterville that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more
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Why visit Streeterville

  • Scenic waterfront: Enjoy breathtaking views along Lake Michigan, perfect for leisurely strolls and outdoor activities.
  • Cultural attractions: Discover engaging museums and historic buildings that showcase the rich heritage of the area.
  • Streeterville Art Fair: Experience the vibrant local art scene at this annual event, featuring talented artists and unique artworks.
  • Diverse dining options: Indulge in a variety of eateries offering everything from casual bites to fine dining experiences.
  • Family-friendly activities: Engage in numerous outdoor adventures suitable for all ages, making it a perfect family destination.

Popular types of accommodation around Streeterville

Streeterville, a vibrant neighbourhood in Chicago, Illinois, offers a captivating blend of urban excitement and scenic beauty. Visitors can explore iconic landmarks, enjoy waterfront views, and indulge in diverse dining options. The area features a variety of vacation rentals, including stylish apartments, private homes, and modern condos. Whether you're seeking a studio apartment or a spacious family retreat, Streeterville promises an unforgettable experience in the heart of the Windy City.

  • Apartments: These are the most sought-after lodging options in Streeterville, offering modern amenities and convenient locations for your stay.
  • Houses: A fantastic choice for those seeking a more personal and spacious environment, these homes provide privacy and comfort.
  • Condos: Ideal for short-term stays, condos combine hotel-like services with the comforts of home, perfect for exploring the area.
  • Villas: These luxurious options offer ample space and upscale features, making them perfect for families or groups.
  • Cottages: Charming and quaint, cottages provide a cosy escape with a homey feel, perfect for relaxation.**

Top attractions near Streeterville

Streeterville, Chicago, is a vibrant neighbourhood perfect for family outings and outdoor adventures. Visitors can admire stunning skyscrapers, explore urban parks, and discover historic buildings. Highlights include engaging museums and cultural attractions, making it an ideal spot for family experiences and city-themed holidays. The annual Streeterville Art Fair adds a unique local flavour, showcasing artistic talent amidst the urban landscape. Streeterville truly offers a delightful blend of culture and city life for all travellers.

  • Michigan Avenue: Known as the Magnificent Mile, this bustling street is lined with high-end shops, restaurants, and iconic architecture, offering a vibrant urban atmosphere perfect for leisurely strolls and shopping.
  • Navy Pier: A popular destination with stunning views of Lake Michigan, Navy Pier features attractions like rides, gardens, and dining options, creating a friendly and scenic environment for all visitors.
  • Millennium Park: This urban oasis is home to impressive art installations, beautiful gardens, and outdoor concerts, making it a perfect spot for families and those seeking a relaxing outdoor experience.

Things to do recommended for couples

Seeking a romantic escape in Streeterville? Enjoy a leisurely walk along the picturesque Lakefront Trail, or indulge in a sunset boat cruise on the Chicago River. Don’t forget to explore the charming cafés and intimate restaurants that offer delightful dining experiences for couples.

Things to do recommended for families

Families will delight in the interactive exhibits at the Chicago Children's Museum, explore the wonders of the Shedd Aquarium, or enjoy a leisurely stroll along the scenic Lakefront Trail. Don't miss the iconic Navy Pier for rides and entertainment suitable for all ages.

Things to do recommended for groups

Groups visiting Streeterville can enjoy a scenic stroll along the Chicago Riverwalk, take an architectural boat tour to admire the city’s skyline, and indulge in a group dining experience at the renowned Navy Pier, where entertainment and local cuisine await.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Streeterville

If you're planning a trip with friends, family, pets, or seeking extended stays, it's essential to filter your options based on your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Streeterville with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options, and many more, on Vrbo.
  • Traveling to Streeterville with young kids: Travelling with young children can present its challenges. It’s important to prioritise their comfort and safety, as well as access to suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Streeterville: For many, a family holiday isn’t truly complete without their furry companion by their side. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Streeterville: If you’re seeking holiday rentals that offer discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include additional features in your search, such as a parking space, a well-equipped kitchen, or a private pool.

Where to stay near Streeterville

Streeterville, a vibrant neighbourhood in Chicago, offers an exciting blend of urban charm and scenic views. Visitors can explore the stunning waterfront along Lake Michigan, marvel at iconic landmarks, and enjoy family-friendly activities in the area. With its friendly atmosphere and plethora of dining options, Streeterville provides an ideal setting for outdoor adventures and urban exploration, making it a perfect destination for travellers seeking an unforgettable experience in the heart of the Windy City.

  • Chicago: As a vibrant metropolis, Chicago is a treasure trove of experiences for travellers seeking family-friendly activities, outdoor adventures, and urban exploration. Nestled in the heart of the Windy City, Streeterville offers easy access to iconic attractions such as the Millennium Park, where you can enjoy outdoor concerts and art installations. Additionally, the nearby sports facilities and theatres provide a dynamic entertainment landscape, making it an ideal base for your Chicago visit.
  • Downtown Chicago: Located a mere 644m from Streeterville, Downtown Chicago is the bustling core of the city, brimming with life and excitement. This area is renowned for its spectacular shopping venues, theatres, and vibrant dining options, catering to all tastes. Attractions like the Chicago Riverwalk invite leisurely strolls, while sports facilities nearby offer thrilling game-day experiences. Whether you’re exploring the famous architecture or indulging in local cuisine, Downtown Chicago promises an unforgettable urban adventure.
  • Magnificent Mile: Just 161m from Streeterville, the Magnificent Mile is a shopper's paradise, featuring an array of world-class shops and boutiques. This lively neighbourhood combines culture and leisure, with educational attractions and entertainment venues, including theatres and concert halls. Stroll along the picturesque streets lined with stunning architecture, and take in the vibrant atmosphere. The Magnificent Mile is also home to beautiful urban parks, making it a perfect spot for families to relax and enjoy the scenery.

Best time to go to Streeterville

If you're planning a trip to Streeterville, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like January, August and November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyAverageSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageSlightly Low
April46.0°F (7.8°C)Light RainMostly SunnyAverageAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnySlightly HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighSlightly High
August73.0°F (22.8°C)Light RainMostly SunnySlightly LowSlightly High
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighAverage
October54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
November42.3°F (5.7°C)Light RainMostly SunnySlightly LowAverage
December33.1°F (0.6°C)Light RainMostly CloudyAverageAverage

Booking with Vrbo is a breeze

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a dedicated area for you to plan new trips, manage your existing arrangements, or review your bookings. The properties you’ve saved or reserved are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Streeterville?
Apartments are the most popular style of holiday rental in Streeterville, according to our data. Even if you've got something else in mind, Vrbo has holiday homes in many sizes and shapes. Explore our options to find your perfect match.
How much does it cost to rent a holiday rental in Streeterville?
Property type, length of stay and season are some things that can affect the price of a holiday home. Simply enter your dates of travel to find your ideal fit. From comfy cabins to sprawling villas, all Vrbo holiday rentals provide incredible value.
How much does it cost to rent a beach house in Streeterville?
Prices for beach houses in Streeterville may differ depending on the size and type of the property and when you're travelling. Simply enter your travel dates into Vrbo and how many guests to view available options and prices. From there you can use the filters to narrow your search by amenities, nearby activities, ratings and more.
Are there pet-friendly holiday rentals in Streeterville?
Pack a tug toy and treats for the pup in your life because Streeterville has 73 holiday rentals that roll out the welcome mat to pets. Let your happy hound get in on the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates and destination, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Streeterville?
Add a whole new level of fun to your adventure by booking one of the 30 houses with a private pool in Streeterville. Use our search filter to find the kind of property you want on Vrbo, and then spend your days splishing and splashing in a swimming pool that's for your use only.
What are popular rental amenities in Streeterville?
When it comes to rental amenities that people look for in Streeterville, a garden, a nearby waterfront and nearby museums rank highest. With Vrbo holiday rentals, you'll enjoy choices to match your style and taste, whether you're planning to get away with friends, relatives or even pets.
Are there large group holiday rentals in Streeterville?
Streeterville has three holiday homes that can cater to 10 or more guests. These stays come with the space and privacy you need to share good times with family and friends.
Are there holiday rentals in Streeterville that welcome kids?
Gather your whole family for an unforgettable adventure in Streeterville at one of our 73 family-friendly holiday homes. Many of these stays come with amenities that are great for trips with children, including kitchens, living rooms and private pools. Just click on the "Properties good for families" filter box and pick your favourite option.
What are the top attractions for families in Streeterville?
Keep the kids amused at these fun family-friendly attractions in Streeterville:
  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium
Are there one-bedroom holiday rentals in Streeterville?
Take your pick from 23 one-bedroom rentals in Streeterville. Whether you're looking for a cosy chalet or a fancy condo, Vrbo's one-bedroom rentals are just right if you don't need loads of space. One of the perks of having your own digs? You won't ever need to share your getaway with strangers.
Can I find two-bedroom holiday rentals in Streeterville?
Take off with your besties and enjoy total privacy and comfort in one of the 22 two-bedroom holiday homes Streeterville has to offer.
Are there holiday rentals with WiFi in Streeterville?
Streeterville has 12 holiday rentals with WiFi, so you'll be able to stay connected while travelling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with your family to posting pics on social media, these Vrbo homes will keep you online.
How can I find holiday rentals with air conditioning in Streeterville?
Streeterville has 73 holiday rentals where you can relax and recharge in air-conditioned comfort. To book a stay on Vrbo offering this amenity, enter your preferred travel dates and use the handy filters to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Streeterville?
Age restrictions can differ across properties on Vrbo, so look at the rules of the holiday home in Streeterville you're interested in. But in general, it's 16, 18 or 21.
How long can I rent a holiday rental in Streeterville for?
It really depends on the Streeterville property. To browse a list of options offering extended stays, just type your dates and guest number into Vrbo. Enjoy having the place to yourself, along with home comforts like a fully-equipped kitchen and an outdoor space where the kids can run and play. Keep an eye out for long-term stays that offer weekly or monthly discounts.

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