
House holiday rentals in Darien
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Top-rated house rentals in Darien
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Holiday rentals for every style
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Popular amenities for Darien house rentals
House rentals with a pool

2-Acre Highland Park Retreat with Heated Pool ~ 5*
We had a great stay overall. From start to finish, Kailash was extremely helpful, friendly and responsive. We needed a long-term stay with 2 big dogs, and this house worked great for us. We didn't get to use the pool much because the weather didn't cooperate, but the pool and patio area are gorgeous. The location is great, close to everything - grocery stores, restaurants, etc. There is a trail behind the house (accessible through a gate in the back yard), and it leads to a beautiful and huge forest preserve - beautiful for walks/hikes in the woods! The kitchen was a great space for us, and it had everything we might need for cooking, etc. The house was very comfortable for our family, and we would come again. Thank you, Kailash!

Cozy house in Schererville
Very well thought through place for every detail, with a mix of 70s wood style and some higher tech upgrades like the main bathroom mirror with light and anti fog, or sensor lights. Kate was very responsive and accommodating for the 1 baby & 1 toddler we asked for. The place was stocked with all necessary items especially in the kitchen with appliances and cutlery, coffee, tea. There were 2 hairdryers, nice shampoo and conditioner, shower gel.

Rosemont 4BD2BA house with Pool
Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!

Now Open: Heated Pool with Entire House
Moizs was an amazing host. Very accommodating, quick response, had some great recommendations for local restaurants, shopping, etc. Bloomingdale is a cute and nice suburb of Chicago. We had a great trip and we will definitely be back.

Schaumburg Oasis:Private Pool & Enchanted Garden
They were a fantastic host, very responsive to every question and anything we needed. The location is quiet and amazing, great place to relax and enjoy time. love the pool! Will definitely stay again. 100% recommend!

Relaxing Spanish style Home (w/inground pool)
Stayed here the night before my wedding with my siblings who stayed the night of the wedding. We hosted our getting ready portion here for the morning of the wedding and Olinka and Daniel were gracious enough to allow us to stay in their beautiful home. Made for gorgeous pictures and a comfortable stay both nights. Thank you!!

In Ground Pool, Full Ranch Home
Great place and easy to work with.

Bayless Dune Lodge at West Beach - Indiana Dunes!
We had a great weekend getaway from Chicago and it was less than an hour (without traffic) away! Peaceful, quiet, near the beach. Cullen was an awesome host!
Weekly house rentals

Island Time - Murals and more
Great little house for a quick stay! We needed a 1 night stay, and this was a good fit. Cozy little home with live houseplants, fresh cut flowers, a nice patio and landscaping, an attentive host, coffees, teas, drink mixes and some chocolate chip cookies with a personalized note! Lots of positives for sure! If you're a light sleeper and plan on extra pillow time, the Metra train through a crossing a few blocks away sounding its horn, not a big deal to us, just a note if it might affect you.

Stylish Convenient House Peaceful Retreat 4BR 2BTH
We booked Son’s place for a 4-day business trip to Chicago. The house looks exactly like what he advised on the platform. We have total of 4 people, and the 4 bedrooms is just perfect for us all. We enjoyed the morning coffee before heading to work, worked together at dining table and discuss some business detail at the second living room(entertainment room). My managers are very picky, but they both gave this place a thumbs up! Plus the price is absolutely fair compare to hotels. Thank you for providing us such great place for our short stay in Chicago. If I ever had a chance to re-visit Chicago, I will definitely book this place again.

Lofty Urban Retreat
Needed a space for my family visiting my Dad who's been ill, so finding a quiet location with the space being so clean and efficiently stocked with supplies and extra towel + linens was so appreciative. Bart was so responsive from day 1 up to the end. I would definitely recommend this airbnb with the highest 2 thumbs up. Thank you for making this trip a good memory.

Bolingbrook 4B 2ba Sleeps 8| LCP Collection
Dawn’s house was great. My family traveled to town and the space was what we expected. The beds were comfortable and the kitchen had what we needed. Dawn was very responsive with anything we needed.

Spacious Home in Chicago Suburbs
We enjoyed our stay very much and felt right at home. The hosts were very communicative and helpful. They were very flexible with check in and check out times. The home was fully stocked with lots of extra linens. Simple check out. Very beautiful home! I would 10/10 recommend! 🤩

Cozy getaway in the city.
Juan was not only a great communicator but his home was beautiful and centrally located. If ever in the Chicago/Burbank area would definitely love to rent.

Stylish 1970s Home for Vintage Getaway!
Beautiful spacious home in a lovely neighborhood. close to great parks and markets. would stay again!

Grand Retreat/5Brs/Game Room
Very nice, comfortable house with room for family to spread out. Very clean w good amenities (plus a few welcoming chocolates)! Grandkids enjoyed the PAC Man game in the game room as well as shooting baskets!
Private house rentals

Little house on the river
Beautiful view! The house was cute and clean and very comfortable. The pictures don’t do it justice! Also, the Fox River Trail is right out the back door. It’s great for walking, biking or running along the river.

Family Friendly Stylish Villa Park Home!
I had an excellent stay at Jabeen’s house in Villa Park. The home was exactly as described, spotlessly clean, very comfortable, and well-equipped with everything I needed. The location was peaceful and quiet, perfect for a restful weekend. What truly made the experience stand out was the combination of thoughtful amenities and top-notch communication. I especially appreciated the fast Wi-Fi, well-stocked kitchen, reliable AC, and relaxing patio. When I mentioned that the blender wasn’t working, Jabeen immediately replaced it—an example of her responsiveness and attention throughout my stay. I highly recommend this place for families looking for a comfortable and hassle-free stay in the area. Would definitely return!

Hazelton's Wheaton Gem | Walk2 Starbucks & Target
This is an outstanding property. Located across the street from a pond and meadow and an easy walk to Target, this is a peaceful and convenient location. The property has the prettiest decor I’ve seen at an Airbnb. Consistent, stylish, cozy, bright aesthetic. Fully updated house, with everything expertly coordinated, from the art to the plumbing fixtures to the toaster. Great deck with a fenced yard. Friendly, responsive host. Highly recommend!

New!Fully renovated/King bed/Free Wi-Fi
We really enjoyed ourselves at this Chicago gem. The mattress was wonderful and the entire space was very clean.

Evergreen Retreat
Spectacular place with so much to offer. Was pleasantly surprised with the outdoor setting. We were in town for a family wedding and the property was selected based on proximity to the venue. After this experience, we're considering scheduling a family reunion since the accommodations were so great!

Modern River Cabin
Nicolas is always accommodating and makes me feel at home.

Westmont,Il 4/3 on the Lake
We had seven people in town for a family wedding, three couples and a single. They all had their own bedrooms and with bathrooms, no one was waiting to do business, so to speak. The lake and water toys were great. The back deck was very relaxing. Also, compared to most airbnbs, Shon had a lot of things available, such as aluminum foil, Saran wrap and more things in the kitchen. Shon was very responsive when we had questions. If I ever have another reason to visit the area and have a big group, I'd want to use Shon's place again. Oh, one other thing. You're right off Ogden, which has everything you'd need ... groceries, drug store, tons of restaurants and more.

Cosmos Cozy Home, Hot Tub, King Beds, Jacuzzi
We had a good weekend at Gracielas place. It has enough space indoors and outdoors for hosting a large-ish group which was nice. it's also decorated very nicely and on theme! Graciela was kind enough to let us check in a little early as well as we got into town earlier than expected.
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- The 606
- The Beverly Country Club
- Moraine Hills State Park
- Flossmoor Golf Club