South Side vacation rentals

We found 430 vacation rentals — enter your dates for availability

Select from 114 homes, 10 cottages, and other vacation rentals in South Side to find one that's perfect for your trip. Whether you're staying in a vacation rental with friends, family, or just with your pet, you'll have the amenities you expect and more, which might include a garden and pool. You'll be able to choose a rental to meet everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - South Side

Showing deals for:May 15 - May 22

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Frequently asked questions

What is the most popular type of vacation rental in South Side?
In South Side, vacation houses are the most popular accommodation choice, with around 110 available in the area. These properties are typically spacious and suitable for families or larger groups, featuring amenities like fully equipped kitchens, multiple bedrooms, and outdoor spaces for relaxation. Additionally, there are about 10 cottages available, which offer a more rustic charm, often set in serene environments. While there are several apartments, they are less common compared to the vacation houses.
Are there any beach house rentals in South Side?
In South Side, Michigan, there are approximately 151 beach house vacation rentals available, providing a variety of options for travelers. These beach houses are typically situated close to the shoreline, allowing easy access to the beautiful beaches and stunning Lake Michigan views. Most rentals come equipped with essential amenities such as fully stocked kitchens, spacious living areas, and outdoor patios or decks for enjoying the fresh air. Many properties also feature multiple bedrooms, making them suitable for families or groups looking for a relaxing getaway by the water.
How much does it cost to rent a vacation home in South Side?
Prices for vacation rentals in South Side 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in South Side to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for South Side vacation house rentals?
You can find great discounts on house rentals in South Side 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 South Side?
In South Side, popular vacation rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, as well as outdoor decks or patios for enjoying fresh air and socializing. Onsite parking is another sought-after feature, making it convenient for those traveling by car. Additionally, many rentals offer coffee and tea makers, ensuring that guests can enjoy their favorite beverages at their leisure.
Can I find family house rentals in South Side?
In South Side, Michigan, there are numerous family-friendly house rentals available, totaling around 112 options. This area is known for its vibrant neighborhoods, which provide an inviting space for families. Many of these homes feature spacious living areas, fully equipped kitchens great for preparing family meals, and cozy outdoor spaces where children can play and enjoy the fresh air.

Visitors can also explore nearby parks and recreational facilities, offering plenty of opportunities for outdoor activities. Local attractions, including community centers and family-friendly restaurants, are easily accessible, making it convenient for families to enjoy their stay.
Can I rent a vacation home with a pool or hot tub in South Side?
In South Side, Michigan, there are several vacation homes available for rent that come equipped with pools and hot tubs, with around 18 options featuring pools and 20 options with hot tubs. This vibrant area offers a variety of amenities, allowing travelers to enjoy a comfortable and relaxing stay. Many of these properties include outdoor spaces great for lounging, fully equipped kitchens for meal preparation, and cozy living areas for family gatherings. Additionally, some rentals may provide barbecue grills and patios, ideal for entertaining or enjoying warm summer evenings.
Are there any South Side vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in South Side with parking available—perfect for families or travelers 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.
Can I book pet-friendly vacation rentals in South Side?
In the South Side of Chicago, travelers can find a variety of pet-friendly vacation rentals, with approximately 44 options available. This vibrant area offers a mix of accommodations, including modern apartments and cozy houses, many of which come equipped with amenities such as fully stocked kitchens, spacious living rooms, and outdoor spaces where pets can enjoy fresh air.

South Side is home to several parks that are great for pets, such as Washington Park and Jackson Park, both of which provide ample open space for walks and playtime. Additionally, the area boasts pet-friendly cafes and shops, ensuring that you and your furry friends will have enjoyable outings during your stay.
Can I find long-stay vacation rentals in South Side?
A long-stay vacation rental in South Side is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit South Side for a vacation rental?
The best time to book a vacation rental in South Side, Michigan, is during the peak season from June to August. This vibrant period attracts travelers eager to immerse themselves in the area's lively summer atmosphere. With warm temperatures typically ranging from the low 60s to the mid-80s Fahrenheit, it's an ideal time for outdoor activities, local festivals, and exploring parks.

July stands out as the most popular month, where families and friends flock to enjoy community events, outdoor dining, and scenic strolls along the lakeshore. The energy is palpable, making it great for those who thrive in a bustling environment filled with opportunities for socializing and engaging in recreational activities.

For travelers seeking a more budget-friendly experience, November presents a unique charm, offering a quieter, more reflective atmosphere. This month is great for those who appreciate the beauty of changing seasons and enjoy a peaceful retreat. Exploring the local sights, such as cultural landmarks and parks, can be particularly enjoyable without the crowds.

Ultimately, the choice of when to visit South Side will depend on your preference for a lively summer experience filled with activities or a serene autumn getaway that allows for a more relaxed pace.
Are there any remote work vacation rentals in South Side?
In the South Side of Michigan, there are ample options for remote work vacation rentals, with around 119 properties available. Travelers can expect rentals equipped with essential amenities tailored for productivity, including dedicated office spaces, desks, and high-speed internet or Wi-Fi, ensuring a conducive work environment. Many of these rentals also provide comfortable living areas that allow for relaxation after a day of work.

This area boasts a vibrant setting with access to local parks, cafes, and shops, making it a great location for those seeking a blend of work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a South Side vacation rental?
Book your South Side 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.
What are the top attractions in South Side, Michigan, United States of America?
In South Side, Michigan, visitors can explore a variety of attractions that showcase the area's rich history and natural beauty. The neighborhood is known for its vibrant community and numerous parks. The nearby Lake Michigan shoreline offers picturesque views and recreational activities, making it a great spot for outdoor enthusiasts.

For those interested in cultural experiences, the area is home to several local art galleries and community events that highlight local talent. The South Side is also conveniently located near the historic downtown area, where travelers can discover charming shops, cafes, and dining options that reflect the local cuisine.

Additionally, the nearby Indiana Dunes National Park provides opportunities for hiking, birdwatching, and enjoying sandy beaches, appealing to nature lovers looking for a scenic getaway.
Can I change or cancel my South Side home rental booking on Vrbo?
To find South Side 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the South Side 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

Frequently asked questions

Can I find a vacation rental in South Side?
Yes, we offer vacation rentals near well known local attractions in South Side, or you can choose a more secluded option if you want a relaxing place to stay.
How many vacation rentals will I find in South Side?
With 114 Expedia vacation rentals, you're sure to find just the right place for your South Side stay.
What can I see and do in South Side?
While exploring the area, visit family-friendly sights like Michigan Maritime Museum, or get outside and enjoy nature at South Beach. Southside Municipal Marina and South Haven Lighthouse are a couple of places you'll find in the larger area.
What are vacation rentals like in South Side?
Vacation rentals are private accommodations you can stay in for several days or more in South Side. Vacation rentals offer extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.