House holiday rentals in Oak Park

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Popular amenities for Oak Park house rentals

House rentals with a pool

Guest favourite
Home in Highland Park
4.91 out of 5 average rating, 145 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

MaryRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Munster
5 out of 5 average rating, 11 reviews

Munster hide away

ChristopherRating, 5 stars5 months ago
Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.
Superhost
Home in Des Plaines
5 out of 5 average rating, 4 reviews

Rosemont 4BD2BA house with Pool

HannahRating, 5 stars1 month ago
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!
Guest favourite
Home in Bloomingdale
4.92 out of 5 average rating, 51 reviews

Now Open: Heated Pool with Entire House

TaraRating, 5 stars1 month ago
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.
Superhost
Home in Lincoln Park
4.88 out of 5 average rating, 56 reviews

Luxury Loft with Private Pool and Movie Theater

RyanRating, 5 stars5 days ago
Damani was a great host, really responsive and easy to communicate with! The house was exactly as advertised and really nice! The pool was great!
Guest favourite
Home in Schaumburg
4.93 out of 5 average rating, 27 reviews

Schaumburg Oasis:Private Pool & Enchanted Garden

TeddyRating, 5 stars5 days ago
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!
Superhost
Home in Skokie
New place to stay

Luxury fenced in modern ranch

PatriciaRating, 5 stars4 days ago
It was a chaotic start to our vacation stemming off my daughter's graduation from Northwestern; however, Jennifer immediately took the stress off my shoulders and welcomed our family to a fabulous stay at her home. Words cannot express how grateful my family is and without Jennifer's help it would not have been as successfull. I highly recommend staying at any of her properties. She will go above and beyond to make sure you're stay is wonderful!
Guest favourite
Home in Carol Stream
4.86 out of 5 average rating, 7 reviews

Spacious 4 Bed/3.5 Bath Sleeps 8+

CarmenRating, 5 stars8 months ago
Beautiful house very clean and comfortable. We'll be back very soon

Weekly house rentals

Superhost
Home in Berwyn
4.91 out of 5 average rating, 33 reviews

European Custom Built Home

EmilyRating, 5 stars2 months ago
House is vast, clean, and absolutely beautiful inside and out. Easy to get with a car or local transit and a short walk. Pictures don't do the house justice it has lovely historical features and more room than it seems between the three floors (ground floor, basement and upstairs). With two usable balconies and a patio backyard there is more enough space to entertain a small group outside.
Guest favourite
Home in Austin
4.93 out of 5 average rating, 15 reviews

Spacious Designer Oasis: Game Room - Yard - Garage

Danielle GRating, 5 stars1 day ago
Rameez was an amazing host! Making the experience even more enjoyable with his quick responses & fast accommodations. The home is more spacious than it looks in the photos and it truly exceeded my expectations. I had a great stay for my birthday!
Top Guest favourite
Home in Norwood Park
4.97 out of 5 average rating, 32 reviews

Cheerful two bedroom home with patio/deck

EricRating, 5 stars3 months ago
Beautiful home in a quiet neighborhood with responsive and helpful hosts.
Top Guest favourite
Home in Forest Park
4.97 out of 5 average rating, 32 reviews

Walk to Oak Park From Our Large Sun-Soaked Home!

KarenRating, 5 stars6 months ago
Really beautiful place in great location for both Oak Park and Forest Park access. Very charming, clean and spacious. Highly recommend staying here!
Top Guest favourite
Home in Brookfield
4.97 out of 5 average rating, 29 reviews

Cozy Home in Brookfield

TomRating, 5 stars1 week ago
Juliana was a great host and we felt right at home. She was very friendly and helpful. The place was outstanding and the fenced in huge backyard was awesome. Our dogs loved it. I would highly recommend this place to anyone visiting the area.
Guest favourite
Home in Humboldt Park
4.95 out of 5 average rating, 63 reviews

Private Logan Square Garden Apt

TiffanyRating, 5 stars1 week ago
Was a very nice and relaxing place to stay after spending time in the city! Really close to multiple bus stops which made the public transport really easy to access. The inside was very clean and nice, the bed is extremely comfortable! Would stay again!
Guest favourite
Home in Chicago
4.95 out of 5 average rating, 22 reviews

Big house in the BEST Location!

JodiRating, 5 starstoday
The house is lovely! Better than the pictures, just as all of the reviews say. The showers are incredible. The master bathroom is a dream. We had everything we needed & more. We don’t have a single complaint. We definitely plan on booking here again.
Superhost
Home in Austin
4.83 out of 5 average rating, 71 reviews

Brand New Spacious Duplex

LillianRating, 5 stars1 week ago
I just wanna say thank to each other to host. It was nice and big. The bed downstairs was a little hard. The water stain around the basement floor area and it did smell like mold. Other than that. It was good value for your money. Parking was a challenge for us, but we figured it out. Have a great day if you stay.

Private house rentals

Top Guest favourite
Home in Northbrook
4.97 out of 5 average rating, 73 reviews

*King bed *Outdoor Living *Sought-After Area

TylerRating, 5 stars1 week ago
Beautiful home, clean and worked perfect for our family. Elisabeth always responded quickly and it was a seamless check in and check out process.
Guest favourite
Home in Berwyn
4.91 out of 5 average rating, 43 reviews

Berwyn Bungalow

ChinouRating, 5 stars1 week ago
We really enjoyed staying at this amazing place. Neighborhood was quiet and safe and parking was not so hard to find. Also, really glad we had such a helpful host as well. Communication was always there along with a friendly vibe. Definitely a 10 out of 10 in our books.
Top Guest favourite
Home in Oak Lawn
5 out of 5 average rating, 8 reviews

Stylish Convenient House Peaceful Retreat 4BR 2BTH

JulieRating, 5 stars6 days ago
We had a great stay at this Airbnb! The neighborhood felt nice and safe, and it was conveniently close to the store. The home was clean, newly remodeled, and had a modern, stylish feel. The appliances were all high-quality, and the kitchen was well-stocked, which made it easy and enjoyable to cook meals during our trip. The shared living areas were spacious and comfortable, though the bedroom was a bit on the smaller side. We did encounter a couple of minor issues: the glass door on the downstairs shower leaked slightly, causing puddles on the floor. As Texans, we’re accustomed to stronger air conditioners, so we had to lower the thermostat quite a bit to keep the upstairs cool. That said, it worked out fine. It would have been helpful to have the check-out instructions posted in the home, though they were available online. Son was an excellent host—very communicative and accommodating throughout our stay. We appreciated his attentiveness and would stay here again!
Superhost
Home in Austin
4.85 out of 5 average rating, 68 reviews

A Comfortable Stay While You are Away in Oak Park

KarenRating, 5 stars2 months ago
The house looked just like the beautiful photos & Jay was incredibly responsive throughout the visit. This home is located close to 290 to go downtown or further out to the 'burbs quickly. We needed a home to stay last minute, and Jay was accommodating to that as well - we were happy to find this spot with all the space we needed inside and out. As a bonus, we met neighbors who were very friendly.
Top Guest favourite
Home in Lombard
5 out of 5 average rating, 29 reviews

Spacious Home in Chicago Suburbs

NatoshaRating, 5 stars1 week ago
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! 🤩
Guest favourite
Home in Burbank
4.83 out of 5 average rating, 23 reviews

Cozy getaway in the city.

CynthiaRating, 5 stars1 week ago
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.
Superhost
Home in Cicero
4.71 out of 5 average rating, 277 reviews

Close2city 3 bedroom with private parking (MDW)

RubinaRating, 5 stars2 weeks ago
Daniel was very responsive and accommodating. The private parking was great and the neighborhood was close enough to get into the city with ease.
Superhost
Home in Oak Park
5 out of 5 average rating, 16 reviews

Beautiful Large Home in Oak Park

KarenRating, 5 stars36 months ago
This home is convenient to groceries and takeout, has a lovely neighborhood for biking or strolling, and so comfortable for hanging out on the porch or having a bbq in the private back yard. Diverse urban setting gives your stay a real feel for Oak Park vibe. The downtown is close, historic, and interesting. Frank Lloyd Wright homes and Unity Temple are very convenient for touring easily. Blake and Lindy are generous and gracious hosts who welcomed our crew for a family reunion and wedding gathering...a perfect stay!

Quick stats about house rentals in Oak Park

  • Total rentals

    130 properties

  • Total number of reviews

    3.9K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    130 properties include access to Wi-Fi

Destinations to explore

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  5. Oak Park
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