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House vacation rentals in Oak Park

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Popular amenities for Oak Park house rentals

House rentals with a pool

Guest favorite
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 favorite
A spacious living room is featured with a cream-colored sectional couch facing a mounted flat-screen TV. Natural light pours in through large windows adorned with blinds. A stone accent wall adds texture, complemented by two decorative pieces and a ceiling fan.
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
A sunny backyard features a round in-ground pool surrounded by lush green grass and vibrant flower pots. The house showcases a two-story design with a balcony and large windows, providing views of the serene outdoor space and nearby landscaping.
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 favorite
A spacious basement game area features a classic pool table with a vibrant green felt surface, complemented by cues and an arranged set of colored balls. Nearby, a seating area with leather couches and an arcade machine is visible along the wooden-paneled wall.
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
A cozy loft area features exposed brick walls and wooden beams. A compact sleeping space includes a spacious bed covered in neutral bedding. Two white chairs and a small side table are positioned for seating, with a window allowing natural light to enter.
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 favorite
A spacious backyard is illuminated by soft evening light, showcasing a lush green lawn framed by well-maintained gardens. Multiple seating areas are visible, including a hammock, lounge chairs, and patio furniture. A large tree offers shade, while a pool is partially seen beyond the greenery.
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
The exterior of a mid-century modern ranch home is displayed, featuring a flat roof and a large, contemporary garage door. Lush greenery surrounds the entrance, complemented by a well-maintained lawn. The driveway provides ample space for parking, enhancing accessibility.
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 favorite
A spacious living area is featured, highlighted by a neutral palette and large windows with blinds allowing natural light. A stone fireplace serves as a focal point, complemented by white sofas and an ornate coffee table. A television is mounted above the fireplace for entertainment.
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
The exterior of a multi-story brick home is presented, featuring a distinctive rounded entrance. The facade showcases elegant architectural details and decorative trim, while landscaped greenery surrounds the property. A pathway leads to the front door, flanked by well-maintained shrubs and seasonal foliage.
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 favorite
The exterior of the home is showcased, featuring a light-colored facade complemented by neatly trimmed shrubs. Stairs lead up to a welcoming entrance, while a well-kept lawn and mature trees provide shade. The roofline is distinctive, adding character to the overall appearance.
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 favorite
A comfortable living room showcases a blue sectional sofa, accompanied by wooden side tables. Natural light filters through the window treatments, highlighting the classic fireplace, which features a mirror above it. A small ottoman is placed near a wicker chair, adding to the cozy atmosphere.
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 favorite
A modern kitchen is viewed from a doorway, featuring white cabinetry and a spacious island with seating. Natural light filters through the windows, highlighting the sleek countertops and decor. A warm area rug adds texture to the hardwood floor, creating a welcoming atmosphere.
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 favorite
A single-story brick home with a well-maintained front yard features green shrubs and a neat pathway leading to the entrance. Large windows allow natural light to illuminate the interior, while a tree provides shade near the entrance.
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 favorite
A spacious sleeping area features a queen-size bed with layered white bedding and decorative pillows. Light fills the room from a nearby window, while a wooden dresser and nightstand provide storage. A textured stone wall adds visual interest to the overall decor.
Home in Humboldt Park
4.95 out of 5 average rating, 63 reviews

Private Logan Square Garden Apt

Ana ClaudiaRating, 5 stars1 week ago
O espaço da Janice é extremamente aconchegante. A cozinha é super equipada (geladeira, fogao, cafeteira, panelas e demais utensílios... alem de manteiga e temperos básicos). O quarto é lindo e a cama super confortável. O banheiro estava limpo e havia itens de higiene de ótima qualidade, além de um excelente secador de cabelo. A televisão era grande e a sala super confortável. Amamos tudo. Quando voltar à Chicago, será a minha escolha!!
Guest favorite
A two-story brick home features a welcoming front porch with a stoop and entrance framed by tall windows. Lush greenery and vibrant flower beds add color to the exterior, enhancing the inviting presence of the residence.
Home in Chicago
4.95 out of 5 average rating, 21 reviews

Big house in the BEST Location!

Mary Anne KarungariRating, 5 stars1 week ago
We had a wonderful stay. The house was clean, we had all we needed to make meals and the beds were comfortable. We would have appreciated blinds in the two smaller bedrooms but enjoyed the rooms nonetheless. My friends say Thank you for your hosting.
Superhost
A modern living area is highlighted by a sectional sofa adorned with decorative cushions. Natural light enters through multiple windows, complementing the sleek design. A flat-screen television is mounted on the patterned wall, and a soft rug covers the polished hardwood floor.
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 favorite
A bright living room features a mix of comfortable seating with a tan leather sofa and two light-colored armchairs. A wooden coffee table sits center stage, complemented by decorative items. Large windows allow natural light to flow in, enhancing the cozy atmosphere.
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 favorite
A comfortable living area is highlighted by a blue sofa, accompanied by a decorative throw pillow featuring the Chicago flag. A coffee table with books and magazines sits in front of the sofa. An array of city-themed artwork adorns the wall, while a television is mounted nearby.
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 favorite
A bright living area features a cozy sofa adorned with decorative pillows. Two wooden coffee tables are positioned on a neutral area rug, while an accent chair complements the space. Large windows are dressed with light curtains, allowing natural light to fill the room.
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
A cozy living room features four plush purple chairs arranged around a circular table. A modern television is mounted above a white brick fireplace, complemented by bookshelves filled with various items. A large potted plant adds a touch of greenery, enhancing the warm atmosphere.
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 favorite
A spacious living room features a large sectional sofa adorned with various cushions, complemented by a cozy throw. A sleek flat-screen television is mounted above a natural stone fireplace. Large windows allow natural light to fill the room, enhancing the inviting atmosphere.
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 favorite
A modern dining area features a large marble table set with plates and utensils, surrounded by upholstered chairs. Pendant lights illuminate the space, highlighting the sleek kitchen in the background, equipped with stainless steel appliances and white cabinetry.
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
A spacious living room is presented, featuring a large, comfortable couch and a small armchair. A glass coffee table sits in the center, while natural light enters through two windows dressed with light curtains. The room includes a view of the adjacent kitchen area.
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
The charming blue house, framed by lush greenery, showcases a spacious front porch and multiple gabled roofs. A pathway leads to the entrance, surrounded by well-maintained shrubs and flowers, reflecting the property’s inviting character in a tranquil setting.
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

  • Wifi availability

    130 properties include access to wifi

Destinations to explore

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  5. Oak Park
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