Family-Friendly Vacation Rentals in Kathy Osterman Beach, IL: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Family Vacation Rentals
  3.  USA

  4.  Illinois

  5.  Chicago
  6.  Kathy Osterman Beach

Refine your search

Price per night

Amenity Filter

Rating

418 Best Family Vacation Rentals in Kathy Osterman Beach (Starting from $58)

Stylish Chicago Retreat Walk to Loyola University
Stylish Chicago Retreat Walk to Loyola University
House
Chicago, IL, USA
1.1k from Kathy Osterman Beach center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$584
Average price / night
Check Availability
Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.
Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.
Apartment
Chicago, IL, 60660, United States
0.9k from Kathy Osterman Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom3 Guests
10.0

Exceptional

57 reviews

$192
Average price / night
Check Availability
Uptown Bright & Modern Apt - Steps to Lake, Train, Amazing Food & Free Parking
Uptown Bright & Modern Apt - Steps to Lake, Train, Amazing Food & Free Parking
Apartment
Chicago, IL, USA
1.2k from Kathy Osterman Beach center

Air Conditioner, Internet, Parking, Security/Safety, Child Friendly

2 Bedrooms6 Guests
New to Booking
$347
Average price / night
Check Availability
Comfortable & Furnished Studio Apt with Wi-Fi - Magnolia CH
Comfortable & Furnished Studio Apt with Wi-Fi - Magnolia CH
Apartment
Chicago, IL, USA
1.2k from Kathy Osterman Beach center

Internet, Fireplace/Heating, Security/Safety, Guest Services, Pet Friendly, Child Friendly

1 Bedroom2 Guests
9.7

Exceptional

3 reviews

$427
Average price / night
Check Availability
STYLISH-LOCAL-COMFY-SAFE  5 night min.
STYLISH-LOCAL-COMFY-SAFE 5 night min.
Condo
Chicago, IL, 60660, United States
1.6k from Kathy Osterman Beach center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

70 reviews

$396
Average price / night
Check Availability
Stylish Modern 1BR Suite Right by Loyola University - StayGia
Stylish Modern 1BR Suite Right by Loyola University - StayGia
Apartment
Kathy Osterman Beach, Chicago, Illinois, USA
1.4k from Kathy Osterman Beach center

Internet, Wheelchair Accessible, Air Conditioner, Child Friendly

1 Bedroom4 Guests
8.5

Very Good

10 reviews

$125
Average price / night
Check Availability
Retro Apartment in Andersonville
Retro Apartment in Andersonville
Apartment
Chicago, IL, 60640, United States
1.7k from Kathy Osterman Beach center

AC, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

67 reviews

$202
Average price / night
Check Availability
The Bright Retreat in Andersonville
The Bright Retreat in Andersonville
Apartment
Chicago, IL, USA
1.6k from Kathy Osterman Beach center

Apartments, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

1 Bedroom4 Guests
8.0

Good

1 reviews

$214
Average price / night
Check Availability
-Lovely 5BD/3BR/3Parking on premises/Sleeps 14 guests/Andersonville
-Lovely 5BD/3BR/3Parking on premises/Sleeps 14 guests/Andersonville
Apartment
Chicago, IL, 60640, United States
1.7k from Kathy Osterman Beach center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms14 Guests
10.0

Exceptional

4 reviews

$1130
Average price / night
Check Availability
Charming 3bd Bungalow in Vibrant Andersonville home
Charming 3bd Bungalow in Vibrant Andersonville home
House
Chicago, IL, USA
1.6k from Kathy Osterman Beach center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Bungalows

3 Bedrooms8 Guests
New to Booking
$752
Average price / night
Check Availability
Ramblers' Station – Sporty 3BR Apt Steps from Loyola & Lake w/ Free Parking
Ramblers' Station – Sporty 3BR Apt Steps from Loyola & Lake w/ Free Parking
Apartment
Chicago, IL, 60626, United States
1.8k from Kathy Osterman Beach center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
10.0

Exceptional

27 reviews

$496
Average price / night
Check Availability
Hollywood Rentals LLC
Hollywood Rentals LLC
House
Chicago, IL, USA
1.6k from Kathy Osterman Beach center

Accommodations, Homestays, Lodgings, Vacation rentals, Places to stay

11 Bedrooms21 Guests
5.6

Review score

420 reviews

$58
Average price / night
Check Availability
3 BR / 2 BTH unit steps to the beach and close to Loyola
3 BR / 2 BTH unit steps to the beach and close to Loyola
Apartment
Chicago, IL, 60626, United States
1.8k from Kathy Osterman Beach center

AC, Balcony, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
10.0

Exceptional

44 reviews

$391
Average price / night
Check Availability
Lovely Near Loyola - Enjoy the Wonderful Outdoor Space and Sun Room - Room for the Whole Crew apts
Lovely Near Loyola - Enjoy the Wonderful Outdoor Space and Sun Room - Room for the Whole Crew apts
Apartment
Kathy Osterman Beach, Chicago, Illinois, USA
1.6k from Kathy Osterman Beach center

Apartments, Accommodations, Parking, Lodgings, Places to stay

3 Bedrooms7 Guests
New to Booking
$544
Average price / night
Check Availability
Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
Apartment
Chicago, IL, 60626, United States
2.0k from Kathy Osterman Beach center

AC, Balcony, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

244 reviews

$428
Average price / night
Check Availability
Uptown Gem
Uptown Gem
Apartment
Chicago, IL, USA
2.0k from Kathy Osterman Beach center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom4 Guests
10.0

Exceptional

12 reviews

$117
Average price / night
Check Availability
Great Location-Beautiful Friendly Andersonville Neighborhood
Great Location-Beautiful Friendly Andersonville Neighborhood
Apartment
Chicago, IL, 60640, United States
2.0k from Kathy Osterman Beach center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms4 Guests
10.0

Exceptional

199 reviews

$289
Average price / night
Check Availability
Chicago North Shore Hideaway
Chicago North Shore Hideaway
Apartment
Chicago, IL, USA
2.3k from Kathy Osterman Beach center

Pet Friendly, Air Conditioner, View, Security/Safety, Internet, Child Friendly

1 Bedroom3 Guests
6.0

Review score

2 reviews

$113
Average price / night
Check Availability
100 Yr. Old Chicago Brick Craftsman with yard, Near Beach and Loyola!
100 Yr. Old Chicago Brick Craftsman with yard, Near Beach and Loyola!
House
Chicago, IL, 60626, United States
2.0k from Kathy Osterman Beach center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

31 reviews

$431
Average price / night
Check Availability
Cozy 1BR Retreat Near Transit, Dining And Parking
Cozy 1BR Retreat Near Transit, Dining And Parking
Apartment
Chicago, IL, USA
2.5k from Kathy Osterman Beach center

Air Conditioner, Parking, Security/Safety, Internet, Child Friendly

1 Bedroom4 Guests
New to Booking
$133
Average price / night
Check Availability
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
Apartment
Chicago, IL, 60626, United States
2.1k from Kathy Osterman Beach center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms5 Guests
10.0

Exceptional

56 reviews

$354
Average price / night
Check Availability
Family Friendly 2BD/2BA Near Wrigley, Lincoln Square
Family Friendly 2BD/2BA Near Wrigley, Lincoln Square
Condo
Chicago, IL, 60640, United States
2.2k from Kathy Osterman Beach center

AC, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Elevator, Fireplace, Fitness Equipment

2 Bedrooms4 Guests
10.0

Exceptional

59 reviews

$539
Average price / night
Check Availability
3 Bedroom/ 2 Bathroom Luxury Suite in Vibrant Andersonville
3 Bedroom/ 2 Bathroom Luxury Suite in Vibrant Andersonville
Apartment
Chicago, IL, 60640, United States
2.2k from Kathy Osterman Beach center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking

3 Bedrooms6 Guests
10.0

Exceptional

24 reviews

$819
Average price / night
Check Availability
First Floor Brownstone Newly Renovated
First Floor Brownstone Newly Renovated
Condo
Chicago, IL, 60626, United States
2.2k from Kathy Osterman Beach center

AC, Dryer, Fireplace, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
New to Booking
$75
Average price / night
Check Availability
Only Urban Beach House in Chicago
Only Urban Beach House in Chicago
House
Chicago, IL, 60626, United States
2.4k from Kathy Osterman Beach center

AC, Arcade, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet

4 Bedrooms8 Guests
9.4

Superb

60 reviews

$1043
Average price / night
Check Availability
Chicago charm! Quiet and inviting !
Chicago charm! Quiet and inviting !
Apartment
Chicago, IL, 60659, United States
2.7k from Kathy Osterman Beach center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

28 reviews

$380
Average price / night
Check Availability
Spacious home w Chef’s Kitchen, Natural Light, Open Floor Plan, Ideal for Groups
Spacious home w Chef’s Kitchen, Natural Light, Open Floor Plan, Ideal for Groups
House
Chicago, IL, 60626, United States
3.0k from Kathy Osterman Beach center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

10 reviews

$841
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in Kathy Osterman Beach.

Where to stay in Kathy Osterman Beach? Best neighborhoods & areas

Kathy Osterman Beach Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 418 verified family-friendly vacation rentals in Kathy Osterman Beach. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Kathy Osterman Beach vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $58 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Kathy Osterman Beach offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Kathy Osterman Beach are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Kathy Osterman Beach often include amenities such as Child Friendly, Internet, and Fireplace/Heating. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.