Pet-friendly holiday rentals in Oak Brook

Apartment in Roscoe Village

4.9 out of 5 average rating, 386 reviews

Beautiful & Inspiring Three Bedroom Home in Roscoe Village

Dim the lights and kick back on the couch, in the evening after a day’s adventures, leaving all cares behind. The stunning apartment located in a historic 1895 Chicago building, has a modern, ultra-cool feel, with an inspiring vibe and sensational light fixtures. Roscoe Village is a charming “village within the city” filled with taverns, independen shops and cute cafes. Being only a short walk to the train and a 15-minute cab ride to Chicago's downtown landmarks, this home has the perfect combination of convenience, comfort, and cool. Free street parking easily accessible (no onsite parking). The home is designed with every type of traveler in mind. Whether you're in Chicago on business, having fun with friends, visiting family, and vacationing with your children, you'll find this universal home to have every desired amenity. Business travelers can enjoy awesome high speed internet and a creative office space with great natural light. For groups of friends, the bedrooms feature a ton of closet space, giant dining / living room for catching up over a drink, and a full brand new kitchen to cook in. For traveling families and little ones, the office transforms into a kids room with a travel crib and changing mat. I’m always available to make sure your stay is nothing less than 5-Stars! I can be reached by text or phone, and always around to answer a question or handle a concern. Just 5 miles from downtown, Roscoe Village is a charming, laidback “village within the city” filled with casual taverns, independent shops, and cute cafes that spill out onto the sidewalks during the warm weather months. This cozy little pocket is an eclectic mix of unique boutiques, classic frame and brick homes, and locally owned eateries. *Paulina-Lincoln/Roscoe Brown Line is only a 9 minute walk! *Armitage Avenue shopping: 6 stops @ Armitage stop *River North nightlife: 9 stops @ Merchandise Mart stop *Loop stuff: 10 stops @ Washington / Wells *State & Michigan Avenue shopping: 10 stops @ State / Lake *1 mile from Wrigley Field action *1 block from Roscoe Street’s fun bars and restaurants *0.6 miles from Chicago’s newest and largest Whole Foods *1.7 miles from Regal Cinemas theater No parties and no drugs of any kind. We appreciate you respecting our neighbors. Pets are subject to breed restrictions. Pet fees: 1st pet: $125 per reservation for up to 2 nights and $45 per night after. 2nd pet: $50 per reservation for up to 2 nights and $45 per night after.

4.95 out of 5 average rating, 200 reviews

Apartment in Joliet

*The Belltower Haven*Large*Family Friendly*Wi-Fi

Completely remodeled, spacious floor plan, in prime location. Everything is new. Free Wi-Fi (480Mbps) and private parking for 2 cars. Short walking distance to most anything! Near Chicago, The Rialto Theatre, Shopping Mall, Harrah's Casino, Hollywood Casino, Haley Mansion, Route 66 Raceway, Chicago Speedway, Autobahn Country Club. We have a large comfy King Size bed along with several Queen beds. Note: You must be 21 or older to book. Must provide a photo of your D.L. or State ID upon request.

4.85 out of 5 average rating, 166 reviews

Townhouse in Old Town

Downtown Elegance ✨ Private Yard Parking

This unique space features designer kitchen, art by a local artist throughout, marble master bath and most incredible location. Walk to everything Chicago has to offer- Downtown, Mag Mile; North ave beach, zoo and Lincoln park, restaurants, bars, boutiques of Gold Coast and Old Town from this spacious townhouse on a quiet neighborhood street in historic Old Town. 4 bedrooms, 4 baths, 2 outdoor spaces, kitchen plus a bar, 1 car parking, laundry. Pets are welcome! Message me if you have questions!

Guest suite in Saint Charles

4.85 out of 5 average rating, 135 reviews

Cozy, Comfy, Close to Downtown

Discover serenity in our centrally located guest apartment in our charming St. Charles cottage. The space is pet-friendly with a fenced yard, featuring a spacious kitchen, living room, bath, queen-sized bed, and in-unit laundry. The yard offers views of the Fox River, a peaceful patio, friendly ducks, with award-winning parks & biking trails at your doorstep. Note: The unit is studio style located in the lower level of a home. The space is completely private. Only outdoor spaces shared. 😊🦆🪻🏡

4.82 out of 5 average rating, 179 reviews

Apartment in Austin

Reno btrm; Big family escape, W/parking, love pets

This apartment is on the top floor of an owner occupied two flat. It's located in a very quiet, family friendly neighborhood. The skylights bring in a ton of natural light. There is a full kitchen available with pots, pans, flat ware and dishes. I'll supply coffee/tea and snacks! It's a great option for short and long term stays. Dog friendly with an additional fee per animal ($25/day). Laundry available for a small fee. Brand new renovated bathroom with awesome shower. Thanks! Hannah and Emma

4.99 out of 5 average rating, 104 reviews

Home in Forest Park

NEW Gather in spacious 3 bedroom 2 bath home

CA relief: if IL is an option for temporarary housing, please reach out! I have 4 properties I will do whatever I can. Introducing Mohr Cottage in the heart of Forest Park. Spacious & recently updated 3 bedroom 2 full bath 2 story home is perfect for families or large groups looking space & comfort. Quiet residential neighborhood, blocks from restaurants, shops, coffee. Dogs welcome. Near public transportation, easy access to expressway to downtown Chicago. STRICT Non-smoking property.

4.85 out of 5 average rating, 118 reviews

Home in Naperville

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

4.96 out of 5 average rating, 107 reviews

Home in Elmhurst

Elmhurst NEW - Super Clean Modern Farmhouse!

Not your average Air BNB!!! 🏡 Newly renovated - CLEAN modern farmhouse in a great location! ✨ ✅Pet Friendly! 🐕 ✅15 min from O'hare. ✈ ✅25 min to Downtown Chicago 🏦 ✅Close to Grocery, restaurants, coffee, shopping, golf, expressways, down town Elmhurst ,Train and Oakbrook and Fashion Outlet Mall. ✅3 great sized bedrooms, 2 living area sofas converts into sleepers ✅Smart TV in family room and Master. ✅ Back patio with dining and seating ✅Large fenced in yard.

4.88 out of 5 average rating, 284 reviews

Apartment in River North

River North's Rock N Roll

Decorated with rock n' roll memorabilia located above a trendy restaurant. This cozy apartment also features high ceilings and a carved canopy bed. Minutes to Mag Mile and the Loop! Free parking available. Only blocks from Michigan Avenue shopping district and blocks from downtown loop. CTA Brown line station across the street. River North Art Galleries, Great Dining, Millennium Park and all that Chicago has to offer only minutes away. Wrigley Field in 15 minutes.

4.96 out of 5 average rating, 351 reviews

Guest suite in Miller

Miller Mermaid Suite-100 yds from the beach!

100 yds from the beach, the cozy MERMAID SWEET awaits you and is well suited for a young family or 2-3 adult friends. This artsy basement open studio space includes a private entrance, kitchenette, unique art & a cozy reading/sleeping nook! Enjoy beautiful sunsets from the upstairs deck. BBQ on the grill. Visit local restaurants, shops & galleries. Hike wooded trails & swim by sandy, dune-grass beaches. . House-trained dogs welcome! Sorry no cats (allergies)

4.91 out of 5 average rating, 334 reviews

Condo in Logan Square

Susie's Space. 2BR easy parking & pet friendly

Sunny and spacious, 2 bedroom apartment in Avondale near the Green Exchange/ Greenhouse Loft Flexible, self check-in Easy street parking (with provided permits) Pet fee $80 per pet Bedroom 1 with a king sized bed Bedroom 2 with a full bed Air conditioning and ceiling fans Soft linens and towels Separate dining room Fully equipped kitchen Free WIFI Smart TV for streaming Garden in back with a fire pit and charcoal grill Laundry room in basement

4.76 out of 5 average rating, 149 reviews

Apartment in Oak Park

1BR Apartment - Walk to Shops - Downtown OAK PARK

Your family will be close to everything when you stay at this centrally-located place. - 4 min drive to the train - 2 min drive to grocery stores & shopping - 20 min drive to Downtown Chicago Enjoy the historic neighborhood and see Frank Lloyd architecture nearby. ➢ Everything is sanitized/washed/cleaned after every guest ➢ Fast, Dedicated Wifi ➢ 2 Smart TVs (Living Room, Bedroom) ➢ Fully equipped + stocked kitchen / bathroom ➢ Pack 'n Play

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Popular amenities for Oak Brook pet-friendly home rentals

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Pet-friendly house rentals

4.87 out of 5 average rating, 130 reviews

Home in Naperville

Home away from home

5 out of 5 average rating, 22 reviews

Home in Elgin

Little Blue House

4.81 out of 5 average rating, 191 reviews

Home in Blue Island

Warm and comfortable inviting Suburban home !

5 out of 5 average rating, 17 reviews

Home in Aurora

Evergreen Retreat

4.93 out of 5 average rating, 59 reviews

Home in Riverdale

Beautiful , fully renovated

4.94 out of 5 average rating, 124 reviews

Home in Chicago Ridge

Quiet cul-de-sac with huge fenced in backyard

4.98 out of 5 average rating, 49 reviews

Home in Geneva

Spacious 2082 sq ft Home & 1 Mile Walk 2Town/River

4.91 out of 5 average rating, 106 reviews

Home in Forest Park

Adorable house Madison Street w/ 2 car garage!

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Pet-friendly home rentals with a pool

4.92 out of 5 average rating, 142 reviews

Home in Highland Park

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

4.77 out of 5 average rating, 73 reviews

Apartment in River North

Level ◆ Brand New Luxe One Bedroom

4.85 out of 5 average rating, 86 reviews

Apartment in West Loop

Quiet but in the Heart of City walk Everywhere

4.83 out of 5 average rating, 35 reviews

Home in Miller

Entire House With Pool - Backyard Beach Getaway

4.9 out of 5 average rating, 69 reviews

Apartment in The Loop

DTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool

4.79 out of 5 average rating, 19 reviews

Apartment in Bridgeport

Modern unit in Bridgeport-Chicago

Apartment in Logan Square

4.92 out of 5 average rating, 12 reviews

2-level PH w/ 2 Luxe Suites Combined; Spa Access

4.86 out of 5 average rating, 146 reviews

Apartment in Old Town

Level ◆ Two Bedroom Deluxe Corner Suite + Balcony

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Private, pet-friendly home rentals

Guest suite in Portage Park

4.94 out of 5 average rating, 156 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

4.96 out of 5 average rating, 28 reviews

Apartment in Westchester

Short Drive to Hospitals/Airports/Downtown Chicago

4.91 out of 5 average rating, 359 reviews

Tiny home in Burr Ridge

Less is more! Pet friendly Tiny Home near Chicago!

4.86 out of 5 average rating, 7 reviews

Tiny home in Morris

Cozy Tiny Home, LG Fenced yard add RV Brisbon/ 80

4.73 out of 5 average rating, 124 reviews

Home in Markham

The Country Life! Entire House.

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 334 reviews

a SIMPLE place

5 out of 5 average rating, 4 reviews

Townhouse in Munster

Townhome Near Munster/Hospital/BP Refinery