House holiday rentals in Homewood

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Popular amenities for house rentals in Homewood

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 stars6 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 stars5 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.
Guest favourite
Home in Michiana Shores
4.94 out of 5 average rating, 96 reviews

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

KatrineRating, 5 stars2 weeks ago
We had such a wonderful weekend getaway at this property. Very close to the beach along with the hot tub and fire pit it made for the perfect vacation. Inside was cosy and welcoming. There is a little pizza place down the road. Lots of beautiful nature preserves to go hiking and we stopped off at 3 Oaks for a fantastic lunch. Thank you for helping us have the perfect Easter and for all your great communication and flexibility.
Guest favourite
Home in Chesterton
4.98 out of 5 average rating, 40 reviews

Pool House near the Indiana Dunes

KrishnaRating, 5 stars7 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
4.94 out of 5 average rating, 48 reviews

Whole House With Hot Tub And Spacious Bedrooms

KarinaRating, 5 stars3 weeks ago
Amazing stay! This place has everything you need for both short and long visits. The location is extremely safe and convenient with shops within walking distance. My family and I thoroughly enjoyed the entire property, especially the game room and TV room which were perfect for entertainment. Moiz, the host, was very kind and quick to respond to any needs we had. Thank you for everything! We would definitely stay here again
Superhost
Home in Michiana Shores
4.77 out of 5 average rating, 13 reviews

Private Heated Pool and Pet Friendly!

RichardRating, 5 stars20 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
4.92 out of 5 average rating, 64 reviews

Home near the lake with an inground pool

FreddieRating, 5 stars2 months 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, 36 reviews

Entire House With Pool - Backyard Beach Getaway

CrystalRating, 5 stars5 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
4.94 out of 5 average rating, 127 reviews

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

JamesRating, 5 stars2 weeks ago
Leah was a phenomenal host, very responsive and fast with her replies to my questions. The place was super comfortable and welcoming. It was peaceful and quiet just as advertised. Had a wonderful stay!
Guest favourite
Home in Roscoe Village
4.92 out of 5 average rating, 282 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

MontiraRating, 5 stars1 week ago
2nd time staying at Sharleen’s place—wonderful experience! We like location, friendly and quiet neighborhood, walkable to restaurants. We would recommend to guests looking for a space in Roscoe. 🙂
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 stars6 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 stars20 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 stars8 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, 33 reviews

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

LaureenRating, 5 stars1 month 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, 26 reviews

Serene Settings

JoeRating, 5 stars3 weeks ago
A hidden gem! Perfect hideaway for city and country folks alike.
Top guest favourite
Home in Itasca
5 out of 5 average rating, 52 reviews

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

JanetRating, 5 stars1 week ago
This was our second time staying at Jehu's home in Itasca, IL. We have family and friends nearby so the location is perfect. The beds are comfortable, and the house is very clean. Having bottled water, coffee, a variety of beverages and snacks at our disposal was a plus. Jehu was very responsive to any questions we had. We would definitely book this property again for our next visit to the Chicagoland area.

Private house rentals

Top guest favourite
Home in Oak Park
5 out of 5 average rating, 5 reviews

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

VinceRating, 5 stars4 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 Elmhurst
5 out of 5 average rating, 48 reviews

Big Family Home with 4 King Beds

GabrielRating, 5 stars1 week ago
I will be recommending this place to everyone for a nice get together. The neighborhood was nice and quiet and it is a beautiful place to relax or to have as an activity weekend. Plenty of stuff to do
Guest favourite
Home in Naperville
4.89 out of 5 average rating, 126 reviews

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

NathanRating, 5 stars3 weeks ago
It was a comfortable stay. Tons to do in the area. Can’t go wrong!
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 stars10 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 stars1 month 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.
Guest favourite
Home in Michigan City
4.94 out of 5 average rating, 445 reviews

Small Clean Home Near Beach, Casino, Outlet Mall

EricaRating, 5 stars6 days ago
Rina & John’s place really felt like home. The neighborhood is peaceful & the home is walking distance to the park and basically within a 5 minute drive to the restaurants, mall’s & attractions. I will definitely choose to stay with Aruba and John again in the future.
Superhost
Home in Homer Glen
5 out of 5 average rating, 3 reviews

4 bedroom home rental in quiet neighborhood

LoriRating, 5 stars71 months ago
Quiet neighborhood, spacious and comfortable home. The yard is inviting and a great entertaining space! Very kind hosts.
Guest favourite
Home in Prospect Heights
4.96 out of 5 average rating, 24 reviews

Upscale-5 Bed 4.5 Bath-3/4 Acre- 5400 sq ft

StevenRating, 5 stars3 weeks ago
What a find. Easily the nicest Airbnb I've stayed in lately. Upper class residence for an affordable price. Plenty of space for activities. Would absolutely stay again.

Quick stats about house rentals in Homewood

  • Total rentals

    30 properties

  • Nightly prices starting at

    £38 before taxes and fees

  • Total number of reviews

    790 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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  2. United States
  3. Illinois
  4. Cook County
  5. Homewood
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