Holiday rentals near Oak Street Beach

We found 3,032 holiday rentals — enter your dates for availability

Choose the perfect private holiday rental within close proximity to Oak Street Beach. Holiday rentals provide the amenities that you need and want for your stay with friends, family or just your pet, such as air conditioning and Wi-Fi. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Oak Street Beach

Showing deals for:29 May - 5 June

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Frequently asked questions

What are the best holiday rentals near Oak Street Beach?
The best holiday rentals near Oak Street Beach are primarily located in Downtown Chicago, offering superb access to the city's attractions and the beach itself. You will find a wide array of options, mostly comprising stylish apartments and modern condos, many with stunning city or lake views. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties. You will find the best holiday rentals near Oak Street Beach here, providing both convenience and comfort.

Many of these homes feature amenities ideal for a comfortable stay, such as in-unit laundry facilities, shared fitness facilities, and access to a shared pool. Given Oak Street Beach is pet-friendly, many rentals also permit pets, which is great for guests travelling with animals. These homes are ideal for solo travellers, couples or small families looking for a convenient city break.
Are there any cheap holiday rentals near Oak Street Beach?
There are several affordable holiday rentals near Oak Street Beach, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around AU$230 per night in areas like Downtown Chicago. Some stays even drop below this price in February and March during the off-season, making it a great option for guests looking to experience the area without overspending. These rentals often include free amenities such as WiFi, toiletries, and self-parking, and can range from cosy studio apartments to modest family homes, providing a clean, comfortable base for adventure.

To get the best value, consider staying slightly outside major hubs. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. With a little planning, it is absolutely possible to find a comfortable stay near Oak Street Beach while keeping costs down.

*Pricing data are based on past 12 months data.
What are the best pet-friendly holiday rentals near Oak Street Beach?
There are hundreds of pet-friendly holiday rentals near Oak Street Beach, with over 800 properties available, primarily apartments and private holiday houses. These rentals, found throughout Downtown Chicago, offer amenities such as dedicated pet-friendly policies (Permitted for pets, service animals, dogs only, cats only, or dogs and cats), alongside essential comforts like fully equipped kitchens and Wi-Fi, ensuring a comfortable stay for both guests and their animal companions.

When searching for the best pet-friendly holiday rentals near Oak Street Beach, it is important to review specific house rules, size restrictions, and any additional fees. Oak Street Beach welcomes pets to enjoy the beach area, providing ample space for them to roam.
What are the top holiday rentals with pools near Oak Street Beach?
There are approximately 594 holiday rentals near Oak Street Beach that offer access to swimming pools, primarily featuring shared indoor pools within apartment and condo buildings. These properties are concentrated in Downtown Chicago, providing convenient access to the beach and city attractions. Many of these homes come with standard amenities like fully equipped kitchens, Wi-Fi, and comfortable living areas, making them suitable for families, groups, or solo travellers seeking a comfortable stay.

When selecting a rental, consider whether a shared indoor pool meets your preferences, as these are the most common type in the area. Shared pools often include access to other building facilities, enhancing your stay. Given Chicago's climate, indoor pools are a fantastic option year-round, ensuring guests can enjoy a swim regardless of the weather.
What are the best family holiday rentals near Oak Street Beach?
There are over 436 family-friendly holiday homes available in the areas surrounding Oak Street Beach, providing ample space and comfort for groups. These properties often feature multiple bedrooms and bathrooms, fully equipped kitchens for meal preparation, and outdoor play areas like yards or patios. Many also provide entertainment options such as games and video games, ensuring there's something for everyone.

When selecting a holiday rental, consider properties that offer separate spaces for adults and children, and practical amenities like highchairs and travel cribs if travelling with infants. Staying close to Oak Street Beach means less travel time and more opportunities to enjoy the local attractions.
Are there any luxury holiday rentals near Oak Street Beach?
Near Oak Street Beach, there are several luxury holiday rentals that combine stunning lake scenery with modern comfort. These properties often feature amenities such as private pools, heated pools, designer toiletries, and gourmet kitchens with private chef services. Many homes also offer lake views, premium bedding, and fireplaces.

These homes are ideal for families or larger groups, providing conveniences like air conditioning and spacious interiors. Many of these exceptional properties are managed by highly rated Stayz hosts, ensuring a professional and premium experience.
How much is a holiday rental near Oak Street Beach?
Holiday rentals near Oak Street Beach offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties, such as simple apartments, typically start around AU$230 per night, providing an affordable option. Mid-range rentals, including private homes, are generally around AU$590 per night, offering more comfort and privacy. Upscale options can cost AU$935 or more per night, especially during peak seasons.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.

*Pricing data are based on past 12 months data.
Where should I stay when visiting Oak Street Beach?
When planning your stay near Oak Street Beach, several areas offer excellent holiday rental options. The Gold Coast neighbourhood is a top choice, featuring elegant properties within a short walk of Oak Street Beach. This area is known for its beautiful architecture, upscale boutiques, and fine dining, providing a sophisticated backdrop to your stay.

Alternatively, Streeterville offers a dynamic urban experience with its proximity to cultural attractions and entertainment venues. Properties here are a convenient distance from Oak Street Beach and provide easy access to the Magnificent Mile for shopping and various museums.
What is the cheapest month to stay near Oak Street Beach?
The cheapest time to find holiday rentals near Oak Street Beach is typically during the late Winter to early Spring (February to March). February is frequently the cheapest month, often providing various savings on properties and homes. Guests can often find lower rates during these months, along with greater availability, with prices often 15-20% less compared to the peak summer season.
Are there any lakefront holiday rentals near Oak Street Beach
Lakefront holiday rentals near Oak Street Beach are primarily found along the shores of Lake Michigan itself. These properties are a short drive from Oak Street Beach, offering convenient access to water activities such as swimming, paddleboating, fishing, or relaxing by the shore with stunning lake views.

These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups. Guests can enjoy the beauty of the lake year-round, from summer boating and swimming to enjoying the winter scenery.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz customer service and Stayz™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare customer service is available 24/7 to support you every step of the way.

Stayz also offers support via live chat through our Help Centre, 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 Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive.

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