House vacation rentals in Homewood

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Popular amenities for Homewood house rentals

House rentals with a pool

Superhost
Home in Michigan City
4.85 out of 5 average rating, 52 reviews

Vip! 4BD 5 min to Lake, W pool heater.

LeslyRating, 5 stars5 months ago
Stayed there for almost a month never had a problem really clean and a quiet neighborhood I’ll definitely stay there again and the host responds very quickly 100% recommend this house !
Guest favourite
Home in Highland Park
4.92 out of 5 average rating, 142 reviews

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

JeffRating, 5 stars4 months ago
We were in town for Thanksgiving visiting family with our dogs for 4 nights. Communication with host was great. The house was very clean, well furnished (we cooked the Thanksgiving meal there), recently renovated kitchen (huge kitchen island) with high end appliances, and yes there are 6 bedrooms (some small but nice). Rooms are split between three floors so everyone had room/privacy. Backyard with pool was great, lots of space for dogs, everything is fenced in but the front which was not a problem as the house is on a dead-end street with very little traffic. This is definitely a superhost home, all your condiments, lots of nice touches and snacks/gifts. We will definitely stay there again on our next visit to family in Chicago. House is locate between 41 and 94 making travel around Chicago easy.
Top guest favourite
Home in Michiana Shores
4.94 out of 5 average rating, 94 reviews

Splash (Pool! Hot Tub!) at Aqua House by the Lake

ElizabethRating, 5 stars1 month ago
Everything was great. Anytime I had a question Greg was right there to answer it. I recommend booking with Greg anytime. Me and my family had a great weekend. Thank you
Guest favourite
Home in Chesterton
4.98 out of 5 average rating, 40 reviews

Pool House near the Indiana Dunes

KrishnaRating, 5 stars6 months ago
We had a great stay!! The house was perfect for the five of us and our dog, with enough space for all of us to feel comfortable. The bathrooms were clean and the kitchen was well stocked. The pool was the best part! Melissa was super prompt when it seemed like the heat to the pool wasn’t running and we were back in there in no time - the heated water was perfect for this fall weather! We also tried some of the recommended spots and overall, this was exactly the quick getaway we needed!
Top guest favourite
Home in Bloomingdale
4.93 out of 5 average rating, 46 reviews

Whole House With Hot Tub And Spacious Bedrooms

NafisahRating, 5 stars1 week ago
Moiz and his team were extremely responsive and helpful throughout the booking process. The home was clean and spacious enough for our family of 6.
Superhost
Home in Michiana Shores
4.77 out of 5 average rating, 13 reviews

(2025 Open!) Private Heated Pool and Pet Friendly!

RichardRating, 5 stars19 months ago
We enjoyed our stay with our son and his family. The house, yard and pool were perfect for our grandson and their two dogs. The neighborhood was very quiet and walkable. Our only possible concern was the lack of communication about the lawn being mowed and the pool being serviced on the Friday of our stay. It would have been nice to know so we could have had the dogs inside before people came into the yard.
Guest favourite
Home in Michigan City
4.95 out of 5 average rating, 63 reviews

Home near the lake with an inground pool

FreddieRating, 5 stars1 month ago
Clean house and will definitely book again for our needs. Very comfortable with everything.
Superhost
Home in Miller
4.83 out of 5 average rating, 35 reviews

Entire House With Pool - Backyard Beach Getaway

CrystalRating, 5 stars4 months ago
This home was super cozy for my big family. Everything was clean, comfortable, and the way it is set up makes you feel right at home. This home had everything we needed. TV’s, kitchen items, recommendations, and even fun family games and activities to do. Every time I visit the area I’ll be checking to see if it’s available. 10/10

Weekly house rentals

Guest favourite
Home in Valparaiso
4.95 out of 5 average rating, 125 reviews

Lakefront House, Pontoon, Deck, Fire Pit & More!

RubyRating, 5 stars4 months ago
Very pleasant stay over Thanksgiving while visiting family. Quiet, peaceful lake setting (even though it was very cold out and no swimming in the lake at 20 degrees!).. It was a good place to rest after the noise and activity of our large family 3 day gathering!
Guest favourite
Home in Roscoe Village
4.92 out of 5 average rating, 277 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

KateRating, 5 starstoday
We loved Sharlene’s place! It was so clean and spacious. The neighborhood was great, easy parking, and she was a great communicator. Highly recommend!
Top guest favourite
Home in Lake View
4.93 out of 5 average rating, 153 reviews

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

JulietRating, 5 stars5 months ago
Lovely place in a good location.
Superhost
Home in Glendale Heights
4.8 out of 5 average rating, 44 reviews

Spacious 4 Bed Room suburban home

BrandeeRating, 5 stars19 months ago
Uthuman’s was a great place to stay! It was cozy! There were plenty of towels available. The beds were comfy and everything was clean. I had quick responses to any questions I had. I would recommend staying here!
Superhost
Home in Miller
4.81 out of 5 average rating, 58 reviews

Indiana Dunes Park Getaway w/Firepit, Near Beach

NicholasRating, 5 stars7 months ago
Kelly’s place was wonderful. There’s a lot to enjoy here from a wonderful backyard with a fire pit, a lovely front porch, a chill side porch with a grill, a second floor balcony, and a sun room. The place was perfectly clean when I got there and they so nicely left out plenty of clean towels and sweatshirts for myself and my friends. I would definitely stay again if I came back to the area!
Top guest favourite
Home in Wicker Park
4.97 out of 5 average rating, 32 reviews

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl

LaureenRating, 5 stars2 weeks ago
The location alone makes this home worth booking. Add that there’s ample room for family/friends and it’s a gem in the middle of a great Chicago neighborhood. We were a group of six and loved every minute.
Guest favourite
Home in Valparaiso
4.96 out of 5 average rating, 23 reviews

Serene Settings

FranciscoRating, 5 stars2 weeks ago
Absolutely the hardest place to say bye to after being there awhile. A perfect piece of home without missing any if the necessaries/luxuries.
Top guest favourite
Home in Itasca
5 out of 5 average rating, 50 reviews

RANCH, House-tel: updated full kitchen, comfy beds

KellyRating, 5 stars2 weeks ago
We absolutely loved our stay with Jehu in Itasca! I grew up there in my childhood and her home made us feel so cared for and comforted. It is beautifully laid out, well appointed and so convenient for travelers that want to stay in the suburbs but have easy access to the city and airport. I plan to stay often when I return!

Private house rentals

Guest favourite
Home in Algonquin
4.85 out of 5 average rating, 61 reviews

The River House Sauna/Kayaks/Hot Tub/Fire Pit

TracyRating, 5 stars4 days ago
Beautiful home on the river. Comfortable, relaxing atmosphere with high quality furnishings and a well stocked kitchen. We used the hot tub to unwind at night after a full day of activity. The patio space and grill were fantastic to use on the sunny afternoon we had off from activity. The town is within walking distance and has really good local restaurants. Close to a big shopping complex.
Superhost
Home in Oak Park
5 out of 5 average rating, 5 reviews

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

VinceRating, 5 stars3 months ago
This is the 2nd time this year we rented from Michael. He continued to impress with the responsiveness. This time we filled the whole house, all bedrooms and both floors, 12 in total, mix of kids and adults. We decorated for Christmas, made it feel like we were home for the holidays. We walked all around the neighborhood, got coffee in the morning, fresh bread from a fabulous bakery in Downtown Oak Park and always felt safe and enjoyed the friendly neighborhood. The home and bedrooms were warm when you wanted them warm during the day and cool at night to sleep in. Kitchens were well equipped and all the appliances worked perfectly. The tankless water heater was a blessing when we were all trying to get out for a family event. At one point we realized that we were out of trash bags on Christmas morning. Michael had them there in less than 30 minutes. Over the top responsiveness. Being 10 minutes from the Eisenhower makes this convenient to either Downtown or Oak Brook.
Top guest favourite
Home in Batavia
5 out of 5 average rating, 62 reviews

Bliss in Batavia near the Fox River

LindaRating, 5 stars1 month ago
We had a family gathering there so we could just hang out together. Perfect place for that! It was comfortable for everyone, ages 8 months to 93 years old! Thanks for your help with everything, Mark!
Guest favourite
Home in Naperville
4.89 out of 5 average rating, 121 reviews

California King Bed | Fast Wi-Fi | 75" Smart TV

AllisonRating, 5 stars3 weeks ago
Vic’s place was just what we needed
Guest favourite
Home in Miller
4.9 out of 5 average rating, 29 reviews

Rivera House-fun and comfort steps from the beach

EmilyRating, 5 stars9 months ago
We had an absolutely lovely time! We took a family trip and the house was perfect for 6 adults and 5 kids. The beach was super close to walk to. The large house was perfect for everyone to have their own space. The spacious living room/kitchen was a great place to spend family time cooking, playing games, eating, etc where we could all be together but doing separate things. There were plenty of towels for everyone for that many days which surprised me! Inga had thought of everything! There was all the extras you might need too like cooking basics, sunscreen, flashlight, bug spray, beach chairs, toys, umbrellas! And the espresso machine was also a hit with our family! Thank you so much Inga for having us!! We made memories that will last a lifetime in your beautiful home!
Superhost
Home in Markham
4.73 out of 5 average rating, 124 reviews

The Country Life! Entire House.

DeniseRating, 5 stars2 weeks ago
Cathy was a great host, very responsive! House was great, it accommodated our family size perfect. The only thing in my opinion that was missing was washer and dryer access in the home. We were traveling with toddlers and couldn’t wash a load of clothes. But aside from that everything else was great.
Superhost
Home in Michigan City
5 out of 5 average rating, 3 reviews

Sleep 18, Chef Experience! 12 min walk to beach

KellyRating, 5 stars7 months ago
I stayed at Jacki’s home with my friends and sisters for my bachelorette weekend. We are all in our 30s and loved the ample space, with plenty of bathrooms and sleeping options. And we were all so impressed with the decor and design! We had lots of memorable convos gathered in the beautiful kitchens and living rooms. The hot tub was such a nice amenity and when we had an issue, Jacki had a worker come out right away. She is very responsive and helpful, and provides great recommendations for the local area. We also walked to the beach, which was lovely. There are loads of restaurants nearby and in new Buffalo. We also went to the casino and that was really fun. This house is great for all kinds of large gatherings. I wish we had longer to enjoy it!
Guest favourite
Home in Michigan City
4.94 out of 5 average rating, 438 reviews

Small Clean Home Near Beach, Casino, Outlet Mall

ClaireRating, 5 stars3 weeks ago
Had a great stay here with some friends! It was a clean and cozy space in a really nice area. It was a very inviting space with lots of little things that made us feel right at home :)

Quick stats about house rentals in Homewood

  • Total rentals

    30 properties

  • Nightly prices starting at

    $71 CAD before taxes and fees

  • Total number of reviews

    750 reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

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  3. Illinois
  4. Cook County
  5. Homewood
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