Kenwood Rentals by Owner
1400 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $309/Night
For 7 Nights US $2,160
1453.13 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Apartment
- Balcony/Terrace
- Parking
- Air Conditioner
US $319/Night
For 7 Nights US $2,233
500 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $186/Night
For 7 Nights US $1,302
172.22 ft²
2 Guests
1 Bedroom
1 Bathroom
House
- View
- Parking
- Air Conditioner
US $52/Night
For 7 Nights US $364
1800 ft²
2 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $87/Night
For 7 Nights US $609
107.64 ft²
90 Guests
30 Bedrooms
33 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $150/Night
For 7 Nights US $1,048
2400 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $793/Night
For 7 Nights US $5,551
96.88 ft²
6 Guests
2 Bedrooms
1 Bathroom
Apartment
- Pet Friendly
- Parking
- Air Conditioner
US $691/Night
For 7 Nights US $4,839
2087 ft²
4 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
US $224/Night
For 7 Nights US $1,566
1001.04 ft²
4 Guests
2 Bedrooms
1 Bathroom
Apartment
- Ocean View
- View
- Air Conditioner
US $56/Night
For 7 Nights US $392
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $451/Night
For 7 Nights US $3,156
850.35 ft²
4 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Pet Friendly
- Air Conditioner
- Internet
US $798/Night
For 7 Nights US $5,584
Why Choose Rent By Owner for your Kenwood vacation rental?
What makes our Rentals by Owner special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Kenwood Rentals by Owner
Where are the best neighborhoods to stay in Kenwood?
When considering where to stay in Kenwood, Chicago, Illinois, you’ll find neighborhoods that offer a blend of historic charm and elegant residential streets. Booking a rental by owner in this area provides a comfortable and authentic experience, giving you close access to the vibrant city life while enjoying a peaceful retreat. With well-preserved architecture and tree-lined avenues, Kenwood is an ideal choice for those seeking a welcoming community with easy connections to Chicago’s cultural and recreational highlights. Trust Rent By Owner to help you find the perfect short-term or long-term rental in this distinguished neighborhood of Chicago, Illinois.
East Hyde Park
This part of the city offers a vibrant, diverse atmosphere with many rental options that provide easy access to local amenities and cultural experiences, making it an ideal choice for your stay in the region.
View 34+ Rentals in East Hyde ParkNorth Kenwood
Located within walking distance of prominent parks and community spaces, North Kenwood presents a peaceful environment perfect for travelers seeking comfort and convenience during their visit.
View 763+ Rentals in North KenwoodIndian Village
Known for its charming residential streets, Indian Village provides a cozy setting where you can enjoy a quiet, authentic neighborhood experience close to the city's main attractions.
View 681+ Rentals in Indian VillageBest Times to Visit Kenwood
When should you plan your Rentals by Owner stay?
Timing your visit to this vibrant area can greatly enhance your experience, so consider planning your vacation during the seasons when the region offers its most authentic and enjoyable atmosphere.
Peak Season Highlights
Summer (June to August)
During the warm summer months, this area experiences its busiest season, making it ideal for travelers seeking lively atmospheres and outdoor activities.
Average Temperature Daytime: around 85°F - Nighttime: mid 70s°F
Fall (September to November)
Autumn brings pleasant weather and vibrant foliage, attracting visitors looking for a picturesque and comfortable stay in the region.
Average Temperature Daytime: high 70s°F to low 80s°F - Nighttime: mid 50s°F to mid 60s°F
Off-Season Highlights
Winter (December to February)
The cold winter months see fewer visitors, offering a quieter experience for those who appreciate a peaceful visit and lower rates on vacation rentals.
Average Temperature Daytime: around 30°F to 40°F - Nighttime: below 30°F
Early Spring (March to May)
As the region transitions from winter, early spring provides milder weather and fewer crowds, making it a good time for flexible travelers seeking affordability.
Average Temperature Daytime: mid 50s°F to mid 60s°F - Nighttime: 40s°F to low 50s°F
Weekly Weather Forecast for Kenwood
How to Book Your Kenwood vacation rental
What's our booking process?
Our platform allows you to browse a curated selection of rentals by owner. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Kenwood
Common Rentals by Owner Amenities
What amenities can you expect?
Our Rentals by Owner are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor patio or deck for relaxing and entertaining in the fresh air.
- Look for spacious yards or gardens that provide a peaceful outdoor retreat.
- Take advantage of barbecue grills for outdoor dining experiences in the region’s pleasant climate.
- Find a swimming pool or hot tub to unwind after exploring local attractions nearby.
- Utilize outdoor seating areas designed for enjoying sunrise or sunset views of the surrounding scenery.
- Explore properties with bike-friendly amenities, such as bike racks or trails accessible from your rental.
- Seek out rentals with outdoor fire pits for cozy evenings under the stars in this destination’s serene environment.
Top Attractions Around Kenwood
What attractions are nearby?
Within this vibrant region, you can enjoy a variety of activities nearby, from exploring scenic parks to discovering local cultural spots that make your stay truly memorable.
Family Activities
- Chicago Botanical Garden Family Tours: Discover the beauty of this renowned garden through engaging family-friendly programs nestled just outside the heart of the city, offering an educational and relaxing experience for all ages.
- South Shore Cultural Center: Explore arts, music, and community events designed for families, with scenic lakeside views that make every visit memorable in this cultural hub nearby.
- Lake Michigan Beaches: Spend a sunny day enjoying swimming, picnicking, and building sandcastles along the pristine shores, perfect for family outings in this scenic region.
- Kenwood Park: Take advantage of open green spaces, playgrounds, and walking trails that provide fun and relaxation for children and adults alike in this peaceful neighborhood setting.
Adult Activities
- Visit the Museum of Science and Industry Chicago: Explore engaging exhibits that showcase innovation and science, offering a fascinating experience for adults seeking educational adventure in this area.
- Enjoy a golf day at Harborside International Golf Center: Play a round on well-maintained courses that provide stunning views of the surrounding region, perfect for relaxation and recreation.
- Experience local cuisine at nearby fine dining restaurants: Indulge in a variety of culinary delights that highlight the area's diverse food scene, ideal for discerning travelers looking to savor authentic flavors.
- Explore the scenic lakefront parks: Take a leisurely walk or bike ride along the paths overlooking Lake Michigan, offering tranquil outdoor activities just moments from your rental here.
Other Places to Stay in Kenwood, IL
Muddy Waters’ House
North Kenwood
Indian Village
Obama's House
Kam Isaiah Israel Congregation
KAM Synagogue
4944 S Woodlawn Ave
Elijah Muhammad House
Hyde Park Art Center
49th Street Beach
Kenwood Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of nearby restaurants to enjoy authentic regional cuisine and get a true taste of the area's culinary scene.
- Utilize Public Transportation: Make your stay more convenient by using local transit options to easily access popular attractions around here without parking concerns.
- Visit Neighborhood Parks: Spend relaxing moments at nearby parks and outdoor spaces to unwind and experience the natural beauty of this destination.
- Plan Your Sightseeing Early: Organize visits to local landmarks and hotspots in advance to maximize your time and ensure you don’t miss must-see locations in this region.
Transportation Options
- Chicago Transit Authority (CTA) trains and buses: You can easily access the broader Chicago area through the reliable CTA network that connects this neighborhood to downtown and beyond.
- Divvy Bike Sharing: For an eco-friendly and flexible way to explore, you might consider using the city's bike-sharing system, which is conveniently available nearby.
- Rental Car Services: Several rental agencies operate within the region, offering convenient options if you prefer driving yourself during your stay.
- Taxis and Rideshare Services: Popular ride-hailing apps provide quick transportation options for navigating the local streets with ease.
Local Customs Options
- Respect for Local Heritage: You’ll find that honoring the area's cultural history is an important custom, especially when visiting historic sites and participating in community events here.
- Dining Etiquette: When enjoying meals in this region, it’s customary to engage in friendly conversation and appreciate the local culinary traditions with politeness and openness.
- Community Participation: Engaging in neighborhood activities or local festivals reflects a welcoming spirit and helps you connect with residents here in the area.
- Environmental Awareness: Visitors are encouraged to practice eco-friendly habits, such as recycling and conserving resources, to support the region’s commitment to sustainability.
Kenwood Rentals by Owner Frequently Asked Questions
1. What are the top Vacation Rentals in Kenwood?
There are a lot of options in Kenwood. If you plan on staying in the Kenwood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Kenwood:
- FRONTDESK Open 1 BR Apt 6 miles to Downtown
- Warm & Elegant Studio Apt in Chicago - Algonquin 02-009A
- Gorgeous North Kenwood Hyde Park Unit
- FRONTDESK Modern Studio Apt in East Hyde Park
- FRONTDESK First-Class Studio Apt in Hyde Park
- UChicago, Lake, Sci Museum with Gym + W&D | Zencity
- UChicago, Lake, Sci Museum | Gym + W&D | Zencity
- Classic HP 1BR with Fast Transit to UChicago & DT by Zen Rentals
- UChicago, Shops + Eats, Lake | Gym + W&D | Zencity
- Frontdesk | Modern Studio Apt in East Hyde Park
2. How many Vacation Rentals are available in Kenwood?
Currently, the total number of properties listed by RBO in 2026 is over 42 in the Kenwood area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Vacation Rentals in Kenwood.
3. What is the cancellation policy for rental properties in this area?
Cancellation policies vary by listing. You should review the specific rental's cancellation terms on the listing page or contact the owner directly to understand any potential fees or restrictions.
4. How do I communicate with the property owner before booking?
You can reach out to the owner through the messaging platform provided on Rent By Owner. It's recommended to ask any questions regarding the rental and confirm details before completing your reservation.
5. Are there any additional fees I should be aware of when booking a rental here?
Additional fees such as cleaning, service charges, or local taxes may apply. These details are typically outlined in the listing or disclosed during the booking process, so review them carefully.
6. What amenities are usually included in rentals by owner in this region?
Most rentals offer essential amenities like Wi-Fi, kitchen facilities, and linens. Specific amenities vary per property, so check the individual listing for a complete list to ensure it meets your needs.
7. Is there a minimum stay requirement for renting here?
Minimum stay requirements differ among listings. This information is displayed on each property’s page, or you can confirm with the owner directly to plan your visit accordingly.
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