West Side Oceanfront Vacation Rentals
House
10.0(71 Reviews)
2 Bedrooms
1 Bath
5 Guests
880 ft²
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
US $432/Night
7 Nights - US $3,021
Hotel
9.3(360 Reviews)
1 Bath
338.47 ft²
Private Pool- Oceanfront
- Fireplace/Heating
Pool
US $619/Night
7 Nights - US $4,336
Apartment
9.8(10 Reviews)
1 Bedroom
1 Bath
5 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
View
US $213/Night
7 Nights - US $1,489
Hotel
9.0(375 Reviews)
5 Baths
676.59 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $440/Night
7 Nights - US $3,080
Condo
9.6(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
1500 ft²
- Fireplace/Heating
- Ocean View
- View
Pet Friendly
US $406/Night
7 Nights - US $2,842
US $235/Night
7 Nights - US $1,644
Apartment
8.8(3 Reviews)
1 Bedroom
1 Bath
12 Guests
1023 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $374/Night
7 Nights - US $2,621
Hotel
8.8(249 Reviews)
14 Baths
377.5 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $423/Night
7 Nights - US $2,963
Apartment
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $272/Night
7 Nights - US $1,903
Hotel
8.3(247 Reviews)
4 Baths
234.12 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $339/Night
7 Nights - US $2,376
Apartment
2 Bedrooms
1 Bath
5 Guests
1300 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $253/Night
7 Nights - US $1,769
Why Choose Rent By Owner for your West Side Oceanfront Vacation Rentals?
What makes our Oceanfront Vacation Rentals 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.
Weekly Weather Forecast for West Side
How to Book Your West Side Oceanfront Vacation Rentals
What's our booking process?
Our platform allows you to browse a curated selection of oceanfront vacation rentals. 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 West Side
Common Oceanfront Vacation Rentals Amenities
What amenities can you expect?
Our Oceanfront Vacation Rentals 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
Other Places to Stay in West Side, IL
Near West Side
West Town
West Loop
East Village
University Village / Little Italy
Lower West Side
Pulaski Park
Noble Square
River West
West Loop Gate
Heart of Chicago
Wicker Park
Frequently Asked Questions About West Side Oceanfront Rentals
1. What are the top Oceanfront Rentals in West Side?
There are a lot of options in West Side. If you plan on staying in the West Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Oceanfront Rentals in West Side:
- Holiday Inn & Suites Chicago-Downtown by IHG
- Level Chicago - Fulton Market
- 1F Chicago's Little italy Graystone nearDowntown
- Designer 5+ Bedroom Indoor Outdoor Living Central Wicker Park! Family Discounts!
- Dublex 3 bedroom unit with FREE Garage Parking in Wicker Park
- Stunning City Views & Private Rooftop Deck Oasis
- Newly Renovated Apartment! 10 Minutes From Dowtown And The Beach!
- 2BR 2 BATH MINUTES FROM DOWNTOWN
2. How many Oceanfront Rentals are available in West Side?
Currently, the total number of properties listed by RBO in 2026 is over 32 in the West Side area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Oceanfront Rentals in West Side.
More Rentals You May Like Near West Side
Hotel
8.2(656 Reviews)
7 Baths
335.64 ft²
Private Beach- Oceanfront
- Fireplace/Heating
- Ocean View
US $299/Night
7 Nights - US $2,095
House
10.0(63 Reviews)
4 Bedrooms
3 Baths
15 Guests
3000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,217/Night
7 Nights - US $8,521
Condo
10.0(51 Reviews)
3 Bedrooms
2 Baths
7 Guests
2400 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $667/Night
7 Nights - US $4,670
House
10.0(17 Reviews)
4 Bedrooms
3 Baths
7 Guests
2500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $432/Night
7 Nights - US $3,023
House
10.0(1 Review)
7 Bedrooms
3 Baths
20 Guests
3600 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $999/Night
7 Nights - US $6,996
House
9.8(30 Reviews)
5 Bedrooms
3 Baths
20 Guests
4000 ft²
- Oceanfront
Hot Tub- Fireplace/Heating
- Ocean View
US $1,551/Night
7 Nights - US $10,855
House
9.2(26 Reviews)
4 Bedrooms
4 Baths
10 Guests
2400 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,588/Night
7 Nights - US $11,114
Apartment
8.8(19 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Ocean View
- View
Kitchen
US $424/Night
7 Nights - US $2,970
House
1 Bedroom
1 Bath
4 Guests
301 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $279/Night
7 Nights - US $1,953
Apartment
2 Bedrooms
1 Bath
8 Guests
807 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $252/Night
7 Nights - US $1,761
House
1 Bedroom
1 Bath
4 Guests
344 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $243/Night
7 Nights - US $1,699
Apartment
10.0(290 Reviews)
4 Bedrooms
2 Baths
8 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $330/Night
7 Nights - US $2,310
