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House vacation rentals in Oak Park

Find and book unique houses on Airbnb

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Popular amenities for Oak Park house rentals

House rentals with a pool

A spacious living area is characterized by a plush gray sofa and a round coffee table. Decorative wall elements and a vibrant red holiday tree enhance the modern decor. Soft lighting is provided by a statement chandelier hanging from the ceiling.
Home in Glen Ellyn
4.83 out of 5 average rating, 12 reviews

Pardizes Suites

CrystalRating, 5 stars1 week ago
I was speechless when I walked in her house it was beyond beautiful nothing was out of place at all when I say she had everything you can think of to accommodate us all she had all the toiletries you could think of the kitchen was stocked with all kind of seasonings dishes she even stocked breakfast sausages she put balloons out she really out done herself she went above and beyond it was plenty of games there the rooms were beautiful the beds were so comfortable I didn’t want to get up it was the best airbnb I ever stayed in we were all blown away by how beautiful and clean and neat it was Lisa is a very great hostess you all make sure to book with her she is great
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 stars4 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 stars4 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 stars3 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!
A spacious living area features a large projector screen displaying a vibrant image. Comfortable seating surrounds a modern electric fireplace, while a potted plant and decorative artwork add subtle touches to the space. Natural light is invited through nearby sliding glass doors.
Home in Logan Square
New place to stay

LUXURY - Movie Theater + Spa House

JuanRating, 5 stars1 week ago
Great getaway place to stay at. Beautiful patio area as well!
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.
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.
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!
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 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

TiffanyRating, 5 stars6 days 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 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.
Top guest favorite
An outdoor seating area features a wooden deck surrounded by green plants. Comfortable gray sofas are arranged around a central fire table, offering a cozy gathering space. A pergola provides partial shade, and hanging flower baskets add a splash of color to the environment.
Home in Chicago
5 out of 5 average rating, 10 reviews

Exquisite Chicago Modern Rooftop, Sleeps 9

MuhammadRating, 5 stars1 week ago
The whole process was very easy

Private house rentals

Guest favorite
A charming raised brick ranch home with a welcoming front porch is displayed. The exterior features large windows, a wooden front door, and a neat landscaping area with greenery, enhancing the curb appeal along a tree-lined street.
Home in Logan Square
4.96 out of 5 average rating, 91 reviews

City Cottage in Logan Square-Avondale

AshleyRating, 5 stars1 month ago
We loved this cute little house! Super walkable and close to lots of stuff in Logan Square; although we thoroughly enjoyed the peacefulness of hanging out in the private backyard. Would definitely stay again!
Guest favorite
A shaded outdoor deck features comfortable seating arrangements with deep blue cushions. A wooden coffee table occupies the center, while a grill is positioned at one side. Soft lighting enhances the cozy atmosphere as the sun sets in the background.
Home in Skokie
4.97 out of 5 average rating, 76 reviews

Luxe Limewash Getaway w/Sun Deck

LindaRating, 5 stars1 week ago
We were a group of four teachers planning a girls get away. Elijah’s place was very nice. We asked if we could get in early and he sent us the code right away.He had put a case of water in the refrigerator which we really appreciated. The sectional in the living room was very comfortable and a great place for conversation. The patio in the back was great to sit outside. Overall, it was a very nice place to relax after busy days of sightseeing!
Guest favorite
A modern dining area is presented with a dark wooden table set for meals, featuring plates and wine glasses. A large TV mounted on the wall displays streaming options. A stylish kitchen in the background includes stainless steel appliances and bright cabinetry.
Home in Villa Park
4.92 out of 5 average rating, 49 reviews

New!Fully renovated/King bed/Free Wi-Fi

TrayanaRating, 5 stars4 days ago
We really enjoyed ourselves at this Chicago gem. The mattress was wonderful and the entire space was very clean.
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, 7 reviews

Stylish Convenient House Peaceful Retreat 4BR 2BTH

RheaRating, 5 stars1 week ago
This place is spacious, clean and looks exactly like the listing. We have family in the area so will definitely be staying here again!
Guest favorite
A modern, renovated home is showcased with bright white brick and large windows. A neatly maintained lawn and driveway lead to the home, complemented by soft outdoor lighting. A garage with a wooden door is visible in the background, enhancing the home's curb appeal.
Home in Skokie
4.96 out of 5 average rating, 56 reviews

Culinary DREAM - Pizza Oven/BBQ/Smoker

PritpalRating, 5 stars2 weeks ago
Great house. Very clean and spacious.
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.
Guest favorite
The image features a brick house with a garage, set amidst a well-kept front lawn adorned with fallen leaves. A large tree provides shade to the front yard, while light filters through its branches, creating a serene outdoor environment.
Home in Chicago
5 out of 5 average rating, 37 reviews

Family Home in Chicago-O'Hare

KathyRating, 5 stars2 months ago
We love staying in this little house that’s actually quite big, wonderful outdoor area. Unfortunately it was too cold for us to enjoy it, but looked really amazing. Kitchen had everything we needed to enjoy our stay. Beds were extremely comfortable and hot water was fantastic. Close to the airport and convenient to lots of nice restaurants.
Superhost
An open-concept living area showcases modern decor with plush seating arranged around a coffee table. A large smart TV is mounted on the wall, complemented by artwork above the fireplace. Light hardwood flooring and a staircase lead to the upper level, creating a bright and inviting space.
Home in Chicago
5 out of 5 average rating, 4 reviews

Luxury-Near Downtown & United Center-Sleeps 14

AlexisRating, 5 stars1 week ago
Dan is a gracious host! He takes great pride in his property and making sure guests are comfortable and satisfied with their stay. I recommend this property to anyone who truly wants a home away from home stay! My family and I will book again next year!

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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  2. United States
  3. Illinois
  4. Cook County
  5. Oak Park
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