Pet-friendly holiday rentals in Homewood

4.88 out of 5 average rating, 127 reviews

The kitchen features contemporary blue cabinetry paired with light wood accents. A large stainless steel refrigerator stands beside a gas stove. A white farmhouse sink is centered beneath a window, while a modern light fixture illuminates the space.

Home in Miller

Updated House Close to Beach + National Park

Walk to the Beach & National Park This newly renovated home is just 2.5 blocks from the beach and a two-minute drive to the National Park at West Beach. The home’s main level features a large living room and dining area,full bathroom, 2 bedrooms, modern eat-in kitchen, large patio for outdoor entertaining, gas grill and propane fire pit and fenced yard. The fully finished basement has two bedrooms, a full bathroom, laundry room and rec room with a full-sized ping pong table and smart TV

4.96 out of 5 average rating, 108 reviews

Home in Miller

New sauna, steps from beach and National Park

Perfect for family or friends to relax and enjoy Indiana’s Dunes National Park! The Holliday House is a 2022 custom built home with lake views and a beach path just STEPS from the front door! This 2000 sq ft open concept design features 3 bedrooms and 3 bathrooms, 16’ ceilings, open great room with beautiful indoor/outdoor kitchen, custom dining seating for 8, and loft hammock. Hosts live next door and are easily available if needed! Everything is on the 1st floor except for the 3rd bedroom.

4.98 out of 5 average rating, 145 reviews

A natural pathway leads to a charming safari yurt, adorned with greenery and decorative elements. A wooden archway introduces the entrance, while a nearby barrel sauna complements the serene outdoor setting, surrounded by trees and mulch landscaping.

Yurt in Flossmoor

Glamping Yurt&RV Gaming Room Pool/Hotub/Court more

GLAMPING FUN mid April - Nov Sleeps up to 16 RV w/bathroom - 2 beds 20' Safari Yurt - 5 beds 30' Event yurt - 2 truffle beds Game Room - queen and full bed Gazebo 2 - beds Wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Mini golf; 3-n-1 bball/volley & pickleball court For an additional $225 extra guest not glamping over night is allowed. (Up to 25 guest but only up to 16 glamping overnight) Extra guest must leave by 8:30 p.m. on weekdays 9:30 p.m. on weekends

4.92 out of 5 average rating, 125 reviews

A vibrant garden area is filled with a variety of lush green plants and colorful flowers. Stone elements lead to a small water feature, surrounded by dense foliage. The peaceful setting offers a natural retreat, inviting exploration or relaxation.

Apartment in Homewood

Charming Garden Apartment

Make yourself at home in a charming apartment with all the amenities! Lose yourself birding or reading a book surrounded by lush gardens. Take a short walk to downtown Homewood to enjoy shopping & dining or catch the train to Chicago. 🏳️‍🌈 BLM Safe space! After a day of exploring, a king-sized sleep number bed & lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs welcome! This suite has a kitchenette with a convection toaster oven & induction cooktop.

4.86 out of 5 average rating, 102 reviews

A welcoming living area is highlighted by a navy blue sofa positioned beside a decorative plant. A round coffee table rests atop a patterned area rug featuring shades of blue and yellow. Light-colored walls and large windows enhance the brightness of the space.

Home in Homewood

Charming Homewood Away from Home

Keep it simple at this cozy, charming brick ranch tucked away on a quiet, friendly street. Just minutes from the Metra line for an easy ride into downtown Chicago, and close to all the great local shopping and dining in downtown Homewood. House Guidelines: • No smoking, no parties, no large gatherings • Be mindful of neighbors • Narrow driveway, limit 2 cars • No extra guests without notice • Pets are welcome, but must be added to your reservation • We have a moderate cancellation policy

4.91 out of 5 average rating, 133 reviews

A spacious living room features large windows allowing natural light. A modular sectional sofa is arranged invitingly in front of a sleek fireplace. A modern coffee table sits atop an area rug with geometric patterns, and an expansive wall-mounted TV awaits entertainment.

Home in Chicago

Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!

No cleaning fees! Gorgeous gem 10 miles from Downtown, Airport, Lake Michigan, and United Center! 15 miles from Wrigley Field and the Zoo. Next to CTA! 6 bedrooms 2 bathrooms, 10 beds. Sleeps 18 comfortably. Perfect for large groups! Modern smart home with air hockey, pool table, video games, 2 ping pong tables, foosball, 9 big screen TVs including 85" Samsung QLED with surround sound, outdoor dining, charcoal grill, cornhole, dining room, game room, 2 living rooms, and full kitchen.

4.97 out of 5 average rating, 333 reviews

The living room features a spacious brown sectional sofa facing a coffee table, with a wall-mounted artwork above. A ceiling fan and natural light enhance the open space, which transitions to a dining area visible in the background, creating a welcoming and cozy atmosphere.

Home in Manteno

Two king beds with 3 bedroom 2 bath

4 minutes from I-57 expressway. This is a three bedroom two full bath townhome with a 2 car attached garage. King bed & 55' smart tv in the master bedroom. The Master bedroom also has a full bathroom with complimentary body wash, shampoo & conditioner. 2nd bedroom has a king size bed with king size hotel pillows. 3rd bedroom has queen bed with 55" smart tv. In closet you will find a deluxe queen size air bed with extra pillows & linens. Patio has table & chairs & charcoal grill.

4.89 out of 5 average rating, 131 reviews

A round dining table is set with blue dishware and a floral centerpiece. Four light-colored chairs surround the table, placed on a patterned area rug. Natural light is visible through two softly shaded windows, and a tall green plant adds a touch of greenery to the room.

Apartment in Beverly

Beverly Cottage Loft

Whether you're looking to stay near family or be close to downtown, our place has it all. This tranquil cottage is located in Beverly which is one of the safest neighborhoods in the city of Chicago. Downtown is a quick 20 minute drive and there are also many restaurants and bars in this area. This cottage has been renovated and have all the essentials you need. All you need to do is unpack your bags and enjoy your vacation. The space is modern, clean, and cozy.

4.81 out of 5 average rating, 235 reviews

A cozy living area is displayed with a pair of beige sofas, accented by decorative pillows. Framed wall art complements the decor. A soft rug is positioned on the wooden floor, while a lampshade on a side table adds subtle illumination.

Home in Blue Island

Warm and comfortable inviting Suburban home !

160 year old land mark community, Framed cedar bevel siding 2 story home, front porch , 10 ft high ceilings, kitchen canned lighting home. 6 feet fence In closed yard, whole house water filtration system , Quite neighborhood with sidewalks . 19 miles to downtown Chicago , Metra train station and bus route, in walking distance . driving to the city of Chicago 5 minutes to major expressways . Host is willing to be available for any and all information 24/7.

4.96 out of 5 average rating, 142 reviews

A charming single-story home is surrounded by lush greenery and colorful landscaping. The house features a light exterior with dark shutters and a welcoming front porch. A small tree adds a splash of color to the neatly manicured lawn.

Home in Munster

Cozy three bedroom home in Munster , Indiana.

Plan your next escape to Indiana or Illinois and stay in this beautifully renovated and thoughtfully appointed 3 bedroom and 1 bath home. Located in the quiet and safe suburb of Munster, Indiana, the property is just a 3 minute, easy access to the I-94 Highway. Exciting Downtown Chicago is just 30 minutes away! Walk to Riverside Park and take in the scenic view while enjoying a morning croissant and coffee from one of the quaint neighbourhood cafés.

4.99 out of 5 average rating, 107 reviews

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

Cozy Home in Brookfield

Discover tranquility just minutes from the busy city life! Nestled in the heart of Brookfield, IL, our charming home offers the perfect blend of suburban serenity and urban convenience. Just an 8-minute walk from the train station, you'll find easy access to downtown Chicago while enjoying the peaceful atmosphere of our neighborhood. Max 4 overnight guests. No parties or events. Pets allowed (no exotic pets or animals with a bite history).

4.89 out of 5 average rating, 209 reviews

A corner jacuzzi whirlpool tub is positioned against a wall, featuring multiple jets for relaxation. A white toilet and a small wooden stool are visible nearby. Light gray walls are complemented by a window covered with a light-colored curtain, allowing natural light to filter in.

Home in Chicago Ridge

Quiet cul-de-sac with huge fenced in backyard

3 bedroom, 2 bath ranch home on a quiet cul-de-sac. Big fenced in backyard for the kids, dog, & adults to play during the day, then relax by the fire at night. Walking distance (50 ft.) to the bar/restaurant with private entrance. 15 miles (25 mins) from downtown Chicago. And for you couples, come back home from your busy day, sit back and relax in the 8 jet jacuzzi whirlpool tub that will comfortably fit both of you.

Popular amenities for Homewood pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.96 out of 5 average rating, 124 reviews

A modern living area features a contemporary design with a stylish gray sofa and brown leather chairs. A sleek, geometric area rug sits beneath a coffee table, while framed black-and-white photographs line the walls. Large windows allow natural light to illuminate the space.

Home in Humboldt Park

Rooftop Skyline | 5 Ensuites | Games | DT 14 mins

4.85 out of 5 average rating, 191 reviews

Home in Worth

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

4.93 out of 5 average rating, 112 reviews

Home in Brookfield

Remodeled | Game room | Fire Pit | 5 Min to Zoo

4.97 out of 5 average rating, 239 reviews

A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.

Home in Berwyn

RetroModern Bungalow | free parking | pet friendly

4.96 out of 5 average rating, 132 reviews

The collage showcases various areas of the property, including a modern living space with a wall-mounted TV, a two-story exterior featuring stone details, an outdoor patio area with seating under a pergola, a game room equipped with a ping pong table, and a bathroom with a jacuzzi tub and neatly arranged towels.

Home in Westchester

Jacuzzi, King Beds, Easy Access to DT Chicago!

4.96 out of 5 average rating, 125 reviews

The open living area showcases a cozy seating arrangement with a brown sofa and modern chairs. A ceiling fan hangs above, and the space is illuminated by warm light from the nearby kitchen. A large TV is mounted on the wall opposite the seating area.

Home in Porter

Dunes Homestead - Near Dunes + Lake + Dog Friendly

4.89 out of 5 average rating, 222 reviews

A cozy living room features a brick fireplace as a focal point, surrounded by comfortable leather seating arranged for relaxation. Light-colored curtains frame large windows, while a plush area rug adds warmth to the wooden floor. A wooden door and wall decor complement the inviting space.

Home in Glen Ellyn

4.78 out of 5 average rating, 157 reviews

A spacious living area features an array of seating options, including a light gray sofa and colorful accent chairs. Natural light floods in through multiple windows, highlighting the wood flooring and inviting decor. A dining table is situated nearby, along with a small coffee station.

Home in Elmhurst

Cozy Ranch w/ King Bed & 3 Baths – Great Location!

Pet-friendly home rentals with a pool

4.77 out of 5 average rating, 230 reviews

A modern living area features a dark gray sofa, complemented by decorative pillows and a coffee table. Large windows provide ample natural light and city views, while plants add a touch of greenery. The space is designed with clean lines and a neutral palette.

Apartment in The Loop

Beautiful Corner 2 Bedroom in the Loop | Roof Deck

4.93 out of 5 average rating, 128 reviews

The modern kitchen features white cabinetry and a spacious island with four bar stools. A stainless steel refrigerator stands next to a gas stove and microwave. Natural light filters through large windows, illuminating the elegant countertops and sleek finishes.

Apartment in West Town

Cozy Duplex Down in Wicker Park East w/ Parking

Apartment in Downtown Chicago

A modern kitchen area features a large island with seating for four, complemented by sleek cabinetry. Floor-to-ceiling windows provide expansive views of the city skyline, allowing natural light to fill the space.

Level ◆ Two Bedroom Deluxe Corner Suite + Balcony

4.87 out of 5 average rating, 168 reviews

4.96 out of 5 average rating, 24 reviews

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

Munster hide away

4.91 out of 5 average rating, 23 reviews

Cabin in Custer Park

Cabin Getaway

4.63 out of 5 average rating, 38 reviews

A large swimming pool is surrounded by a concrete deck and a wooden fence. Lush greenery is present in the background, adding to the serene atmosphere. A few lounge chairs are placed nearby, creating a space for relaxation.

Home in Miller

Cheerful 4 bedroom 2 king size beds, 2 queen size

4.86 out of 5 average rating, 43 reviews

A modern kitchen with an expansive island features sleek countertops and stainless steel appliances. Large windows fill the open living area with natural light, showcasing city views. A comfortable seating area and dining table create an inviting space for relaxation and meals.

Apartment in West Loop

Level Two Bedroom Suite | Fulton Market

4.76 out of 5 average rating, 66 reviews

Townhouse in Chesterton

South Shore Escape

Private, pet-friendly home rentals

4.93 out of 5 average rating, 354 reviews

A bedroom features a spacious bed dressed in deep blue linens, complemented by decorative pillows. The walls are painted in a rich blue, accented by round mirrors. Two bedside lamps illuminate the space, while a patterned area rug lies on the hardwood floor.

Condo in Oak Park

Picture Perfect 3Bed Steps from Train and FLW

4.84 out of 5 average rating, 19 reviews

Apartment in Homewood

Two Bedroom Apartment Walk to Metra

4.9 out of 5 average rating, 39 reviews

An open living area features a light grey sectional sofa complemented by a wooden accent table. Natural light fills the space through large windows, illuminating a neutral area rug on the wooden floor. A dining table with chairs occupies the background, along with a wall-mounted television.

Home in Homewood

4BR/2BA Family Home + Fenced Backyard

4.95 out of 5 average rating, 44 reviews

A light-filled living area showcases a comfortable sectional sofa arranged around a circular coffee table. A soft area rug anchors the space, while a dining table with black chairs is visible in the background. Wall art depicting an urban skyline adds a modern touch.

Home in Homewood

Charming & Cozy Getaway - A Heroic Stay Awaits!

4.89 out of 5 average rating, 35 reviews

Apartment in Homewood

Basement Apartment

4.95 out of 5 average rating, 44 reviews

A spacious farmhouse is depicted, surrounded by lush green grass and trimmed bushes. The structure features a large deck, inviting guests to enjoy the outdoors. Sunlight filters through the trees, casting gentle shadows on the ground, creating a serene atmosphere.

Farm stay in Crete

Escape to relax in peace

5.0 out of 5 average rating, 50 reviews

A spacious wooden deck descends to a fenced backyard featuring a well-maintained lawn. The outdoor seating area includes a large table set for meals, with views of the lake and surrounding greenery visible beyond the yard.

Home in Cedar Lake

Lakeside Loft