Kenwood Pet Friendly Vacation Rentals
Condo
10.0Exceptional
(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
Fireplace/Heating
Pet Friendly
Kitchen
Parking
US $381/Night
7 Nights - US $2,669
Apartment
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
2497.23 ft²
Hot Tub- Pet Friendly
- Parking
Air Conditioner
US $405/Night
7 Nights - US $2,835
House
- Chicago
- ·
- Bronzeville
- 0.16 mi to center
8.6Fabulous
(89 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
Balcony/Terrace- Kitchen
- Parking
US $190/Night
7 Nights - US $1,331
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $271/Night
7 Nights - US $1,900
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
559.72 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
Internet
US $491/Night
7 Nights - US $3,437
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
US $329/Night
7 Nights - US $2,300
Apartment
- Chicago
- ·
- Bronzeville
- 0.39 mi to center
9.8Exceptional
(23 Reviews)
1 Bedroom
1 Bath
4 Guests
750 ft²
Oceanfront- Fireplace/Heating
Ocean View- Balcony/Terrace
US $217/Night
7 Nights - US $1,517
Apartment
- Chicago
- ·
- Bridgeport
- 0.29 mi to center
8.6Fabulous
(16 Reviews)
1 Bedroom
1 Bath
4 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $176/Night
7 Nights - US $1,235
Apartment
8.0Excellent
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
Child Friendly
US $215/Night
7 Nights - US $1,507
Pet-Friendly Vacation Rentals in Kenwood
Over 220+ Pet-Friendly Vacation Rentals in or Near Kenwood
Apartment
7.8Very Good
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $247/Night
7 Nights - US $1,731
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- Fireplace/Heating
View- Pet Friendly
- Air Conditioner
US $441/Night
7 Nights - US $3,089
Condo
- Chicago
- ·
- Grand Boulevard
- 0.49 mi to center
1 Bedroom
1 Bath
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $180/Night
7 Nights - US $1,259
Condo
- Chicago
- ·
- Grand Boulevard
- 0.71 mi to center
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $252/Night
7 Nights - US $1,765
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
333.68 ft²
- Pet Friendly
- Air Conditioner
- Internet
- Child Friendly
US $380/Night
7 Nights - US $2,657
Apartment
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $215/Night
7 Nights - US $1,507
Apartment
- Chicago
- ·
- East Hyde Park
- 0.13 mi to center
2 Bedrooms
2 Baths
4 Guests
1157 ft²
- Fireplace/Heating
Pool- Pet Friendly
- Kitchen
US $215/Night
7 Nights - US $1,505
Apartment
- Chicago
- ·
- Washington Park
- 0.45 mi to center
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $131/Night
7 Nights - US $919
Apartment
2 Bedrooms
2 Baths
6 Guests
1074 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $124/Night
7 Nights - US $868
Luxury Places to Stay in Kenwood
Over 211+ Luxury Places to Stay in or Near Kenwood
Hotel
9.1Exceptional
(220 Reviews)
4 Baths
349.83 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $2,333/Night
7 Nights - US $16,331
Apartment
8.8Fabulous
(3 Reviews)
5 Bedrooms
3 Baths
12 Guests
2400 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $876/Night
7 Nights - US $6,129
Apartment
7.7Very Good
(3 Reviews)
3 Bedrooms
1 Bath
6 Guests
1001.04 ft²
- Pet Friendly
- Air Conditioner
- Internet
- Child Friendly
US $847/Night
7 Nights - US $5,932
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $845/Night
7 Nights - US $5,917
Apartment
- Chicago
- ·
- South Shore
- 0.66 mi to center
3 Bedrooms
2 Baths
8 Guests
3500 ft²
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $828/Night
7 Nights - US $5,794
Apartment
5.0Average
(1 Review)
2 Bedrooms
1 Bath
4 Guests
904.17 ft²
- Pet Friendly
- Air Conditioner
- Internet
- Child Friendly
US $801/Night
7 Nights - US $5,605
House
- Chicago
- ·
- Washington Park
- 0.75 mi to center
10.0Exceptional
(21 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $703/Night
7 Nights - US $4,923
House
10.0Exceptional
(12 Reviews)
5 Bedrooms
3 Baths
8 Guests
4000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $692/Night
7 Nights - US $4,841
Apartment
7.8Very Good
(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
1001.04 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $691/Night
7 Nights - US $4,839
Top-Rated Vacation Rentals with a Pool in Kenwood
Over 8+ Top-Rated Vacation Rentals with a Pool in or Near Kenwood
House
- Chicago
- ·
- Grand Boulevard
- 0.32 mi to center
8.3Excellent
(12 Reviews)
6 Bedrooms
5 Baths
15 Guests
3196.88 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
US $657/Night
7 Nights - US $4,597
Apartment
- Chicago
- ·
- East Hyde Park
- 0.13 mi to center
1 Bedroom
1 Bath
2 Guests
685 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $98/Night
7 Nights - US $686
Apartment
- Chicago
- ·
- East Hyde Park
- 0.13 mi to center
1 Bedroom
1 Bath
2 Guests
685 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $79/Night
7 Nights - US $553
Apartment
- Chicago
- ·
- Indian Village
- 0.10 mi to center
2.5Average
(2 Reviews)
1 Bedroom
1 Bath
3 Guests
500 ft²
- Pool
- Pet Friendly
- Kitchen
- Air Conditioner
US $152/Night
7 Nights - US $1,064
Condo
- Chicago
- ·
- Bridgeport
- 0.89 mi to center
5 Bedrooms
4 Baths
11 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $847/Night
7 Nights - US $5,929
Apartment
- Chicago
- ·
- East Hyde Park
- 0.13 mi to center
1 Bedroom
1 Bath
2 Guests
703 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $139/Night
7 Nights - US $973
Apartment
- Chicago
- ·
- Indian Village
- 0.10 mi to center
2 Bedrooms
2 Baths
4 Guests
1087 ft²
- Pool
- Pet Friendly
- Kitchen
- Air Conditioner
US $137/Night
7 Nights - US $959
Apartment
- Chicago
- ·
- Indian Village
- 0.10 mi to center
2 Bedrooms
2 Baths
4 Guests
1097 ft²
- Pool
- Pet Friendly
- Kitchen
- Air Conditioner
US $125/Night
7 Nights - US $875
Large Vacation Homes & Villas in Kenwood
Over 5+ Large Vacation Homes & Villas in or Near Kenwood
House
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $243/Night
7 Nights - US $1,704
House
- Chicago
- ·
- Back of the Yards
- 0.65 mi to center
5 Bedrooms
1 Bath
9 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $182/Night
7 Nights - US $1,277
House
- Chicago
- ·
- Back of the Yards
- 0.85 mi to center
5 Bedrooms
1 Bath
9 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $107/Night
7 Nights - US $746
Apartment
- Chicago
- ·
- Grand Boulevard
- 0.66 mi to center
8.8Fabulous
(5 Reviews)
4 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $409/Night
7 Nights - US $2,861
Condo
- Chicago
- ·
- Washington Park
- 0.36 mi to center
4 Bedrooms
2 Baths
31 Guests
1800 ft²
- Hot Tub
Spa- Fireplace/Heating
- Ocean View
US $349/Night
7 Nights - US $2,443
Wheelchair Accessible Vacation Homes in Kenwood
Over 64+ Wheelchair Accessible Vacation Homes in or Near Kenwood
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
8 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $582/Night
7 Nights - US $4,075
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $351/Night
7 Nights - US $2,454
Hotel
- Chicago
- ·
- Indian Village
- 0.09 mi to center
8.0Excellent
(1000 Reviews)
1 Bath
Breakfast- Pet Friendly
- Kitchen
- Parking
US $140/Night
7 Nights - US $979
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
9.4Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $522/Night
7 Nights - US $3,651
Apartment
7.5Very Good
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
322.92 ft²
- Pet Friendly
- Air Conditioner
- Internet
Wheelchair Accessible
US $108/Night
7 Nights - US $756
Apartment
- Chicago
- ·
- East Hyde Park
- 0.30 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $255/Night
7 Nights - US $1,786
Apartment
9.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $219/Night
7 Nights - US $1,534
Apartment
8.4Excellent
(6 Reviews)
3 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $306/Night
7 Nights - US $2,142
Apartment
6.0Good
(1 Review)
2 Bedrooms
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $240/Night
7 Nights - US $1,678
Kenwood Petfriendly and Airbnb Homes Under $200
Over 95+ Kenwood Petfriendly and Airbnb Homes Under $200
Condo
2 Bedrooms
2 Baths
3 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $119/Night
7 Nights - US $835
Apartment
9.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
796.53 ft²
- View
- Pet Friendly
- Parking
- Air Conditioner
US $183/Night
7 Nights - US $1,281
Apartment
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $105/Night
7 Nights - US $735
Apartment
- Chicago
- ·
- Greater Grand Crossing
- 0.74 mi to center
7.4Very Good
(23 Reviews)
2 Bedrooms
1 Bath
4 Guests
129.17 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $131/Night
7 Nights - US $920
Apartment
8.4Excellent
(5 Reviews)
3 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $160/Night
7 Nights - US $1,123
Apartment
- Chicago
- ·
- Washington Park
- 0.19 mi to center
3 Bedrooms
2 Baths
5 Guests
1800 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $199/Night
7 Nights - US $1,390
Apartment
- Chicago
- ·
- Washington Park
- 0.59 mi to center
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $163/Night
7 Nights - US $1,139
New
Apartment
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $131/Night
7 Nights - US $915
Apartment
2 Bedrooms
2 Baths
8 Guests
- Pet Friendly
- Air Conditioner
- Child Friendly
Laundry
US $150/Night
7 Nights - US $1,050
Instantly Bookable Vacation Homes in Kenwood
Over 52+ Instantly Bookable Vacation Homes in or Near Kenwood
Apartment
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
7 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $233/Night
7 Nights - US $1,634
Condo
- Chicago
- ·
- North Kenwood
- 0.17 mi to center
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $311/Night
7 Nights - US $2,180
Apartment
- Chicago
- ·
- East Hyde Park
- 0.31 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $224/Night
7 Nights - US $1,566
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $237/Night
7 Nights - US $1,660
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $210/Night
7 Nights - US $1,467
Apartment
9.8Exceptional
(9 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $258/Night
7 Nights - US $1,809
Apartment
9.6Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $234/Night
7 Nights - US $1,641
Apartment
9.6Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $213/Night
7 Nights - US $1,491
Apartment
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $188/Night
7 Nights - US $1,314
Book a Last Minute Place to Stay in Kenwood
About Kenwood Vacation Rentals
There are more than 699 places to stay in Kenwood and many that are available that welcome pets. These options include dog-friendly hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many pet-friendly places to stay in Kenwood.
Are you seeking a last-minute pets-allowed hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With PetFriendly Kenwood, you can quickly compare different options to find the hottest deals with a single click. Looking for pet travel at a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Kenwood. Places to stay near Kenwood are 640.07 ft² on average, with prices averaging US $370 a night.
PetFriendly makes it easy to find and compare hotels, resorts, and holiday rentals in Kenwood with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your pet-friendly place to stay today.
Show more
Show less
Top Dog Hotels, Pet-Friendly Vacation Rentals, and Places to Stay in Kenwood
| Type | Count |
|---|---|
| Holiday Apartments | 441 |
| Vacation Homes | 124 |
| Villas | 2 |
| Cottages | 1 |
Use these Quick Filters to Find a Vacation Rental in Kenwood
★ Pro Tip: PetFriendly™ has the best results when it comes to finding places to stay that accept pets anywhere around the world. Travelers can find and compare over 10 million listings from all over the world. Use the intelligent Filter feature to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, inns, resorts, and more. Enjoy Pet Travel without Hassle in Kenwood.
Weather in Kenwood, IL
View the weather forecast for Kenwood before booking your hotel or rental.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Other Places to Stay in Kenwood, IL
Frequently Asked Questions About Kenwood?
What are the top vacation rentals in Kenwood?
Find the best options in or near Kenwood for pet-friendly travel. If you are planning a trip or vacation in Kenwood, consider a week or two at exciting pets-allowed hotels, resorts, or other suggested properties best known as Top Vacation Rentals and Places to Stay in Kenwood:
- Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
- Large historic home minutes from downtown Chicago and the lakefront.
- Modern Apt Near U of Chicago!
- Modern & Spacious Stay in Historic Bronzeville
- Spacious 3BR · Bronzeville/South Loop · Sleeps 8
- Luxe Loft vibe with King Suite - 4BR 3Ba
- NEW Eco Stay by UChicago, Lakefront & Hyde Park!
- South Loop · 3 Kings · Steps from McCormick Place
- Lively & Fully Furnished 1BR Apartment - Kenwood 408
- Stylish 3BR Gem in Prime Location
Which vacation homes in Kenwood are best for families?
Are you looking for a family-friendly and pet-friendly hotel, resort, or vacation home in Kenwood? Check these highly-rated pet accommodations and places to stay with excellent reviews for families or groups staying in Kenwood:
- Modern & Spacious Stay in Historic Bronzeville
- Luxurious Stay at Modern Apartment with Self Check-in Mins Frm Downtown
- Family-friendly, spacious, next to Jackson Park. Free parking.
How many PetFriendly vacation rentals are available in Kenwood?
PetFriendly™ updates its properties regularly to bring you a great selection of places to stay with their pet policies clearly spelled out. At present, the total number of active properties listed by PetFriendly in 2026 is over 699 in the Kenwood area, and still growing every day. When we combine listings from multiple websites and travel providers, PetFriendly can provide you with a huge selection of the best places to stay that welcome pets in Kenwood.
Nearby Neighborhood (3)
| Neighborhood | Property Count |
|---|---|
| East Hyde Park Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 32 |
| North Kenwood Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 772 |
| Indian Village Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 681 |
People Also Ask
Finding the best prices in Kenwood
Map
