Oak Street Beach Villa Rentals

Compare Villas, Resorts, & Rentals in Oak Street Beach, Chicago, Illinois, USA

New Top-Tier Stay: 49th Fl, Lakefront & City Views
10.0 (1 Review)
2 Bedrooms 5 Guests
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10.0 (4 Reviews)
5 Bedrooms 10 Guests
New
1 Bedroom 2 Guests
New Panoramic Lake Views: Premier Amenities for Groups
New
9 Bedrooms 22 Guests
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10.0 (3 Reviews)
6 Bedrooms 20 Guests
From GB £140 per night
New
2 Bedrooms 2 Guests
New 43 Fl World-Class Escape w/Breathtaking Lake Views
New
3 Bedrooms 2 Guests
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10.0 (3 Reviews)
2 Bedrooms 6 Guests
From GB £197 per night
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10.0 (465 Reviews)
1 Bedroom 2 Guests
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10.0 (2 Reviews)
3 Bedrooms 8 Guests
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10.0 (2 Reviews)
4 Bedrooms 10 Guests
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10.0 (1 Review)
4 Bedrooms 10 Guests
From GB £437 per night
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10.0 (1 Review)
2 Bedrooms 4 Guests
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10.0 (1 Review)
2 Bedrooms 4 Guests
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10.0 (1 Review)
2 Bedrooms 3 Guests
From GB £1,122 per night
10.0 (1 Review)
3 Bedrooms 6 Guests
10.0 (1 Review)
2 Bedrooms 4 Guests
10.0 (1 Review)
3 Bedrooms 8 Guests
|
9.9 (74 Reviews)
3 Bedrooms 6 Guests
10.0 (397 Reviews)
1 Bedroom 4 Guests
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9.8 (6 Reviews)
10 Bedrooms 24 Guests
10.0 (236 Reviews)
2 Bedrooms 6 Guests
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9.7 (12 Reviews)
6 Bedrooms 15 Guests
10.0 (224 Reviews)
1 Bedroom 4 Guests
From GB £190 per night
9.7 (9 Reviews)
1 Bedroom 4 Guests
10.0 (203 Reviews)
2 Bedrooms 8 Guests
10.0 (187 Reviews)
2 Bedrooms 7 Guests
10.0 (64 Reviews)
2 Bedrooms 5 Guests
10.0 (61 Reviews)
1 Bedroom 4 Guests
10.0 (56 Reviews)
2 Bedrooms 6 Guests
10.0 (41 Reviews)
2 Bedrooms 5 Guests
10.0 (4 Reviews)
2 Bedrooms 6 Guests
From GB £275 per night
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9.5 (288 Reviews)
3 Bedrooms 7 Guests
From GB £177 per night
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9.8 (181 Reviews)
1 Bedroom 2 Guests
10.0 (4 Reviews)
1 Bedroom 2 Guests
From GB £112 per night
9.5 (23 Reviews)
2 Bedrooms 4 Guests
From GB £249 per night
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9.4 (103 Reviews)
1 Bedroom 2 Guests
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9.5 (2 Reviews)
4 Bedrooms 20 Guests
From GB £228 per night
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9.0 (249 Reviews)
1 Bedroom 2 Guests
From GB £200 per night
10.0 (4 Reviews)
1 Bedroom 2 Guests
|
9.4 (11 Reviews)
4 Bedrooms 8 Guests
10.0 (3 Reviews)
2 Bedrooms 4 Guests
From GB £215 per night
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9.4 (5 Reviews)
4 Bedrooms 10 Guests
10.0 (3 Reviews)
2 Bedrooms 5 Guests
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9.3 (29 Reviews)
4 Bedrooms 14 Guests
10.0 (3 Reviews)
2 Bedrooms 7 Guests
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9.3 (3 Reviews)
4 Bedrooms 20 Guests
10.0 (3 Reviews)
2 Bedrooms 7 Guests
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9.2 (19 Reviews)
9 Bedrooms 24 Guests
10.0 (3 Reviews)
2 Bedrooms 5 Guests
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9.2 (17 Reviews)
17 Bedrooms 43 Guests
From GB £324 per night
10.0 (3 Reviews)
1 Bedroom 3 Guests
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9.2 (17 Reviews)
13 Bedrooms 27 Guests
10.0 (3 Reviews)
1 Bedroom 2 Guests
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9.2 (17 Reviews)
3 Bedrooms 6 Guests
10.0 (3 Reviews)
1 Bedroom 4 Guests
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9.2 (15 Reviews)
24 Bedrooms 48 Guests

About Oak Street Beach Vacation Rentals

There are more than 3359 incredible getaway rentals that are available in Oak Street Beach. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Oak Street Beach.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Oak Street Beach, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Oak Street Beach. Places to stay near Oak Street Beach are 739.24 ft² on average, with prices averaging GB £337 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Oak Street Beach. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

Frequently Asked Questions About Oak Street Beach?

What are the top hotels or resorts in Oak Street Beach?

How many hotels, resorts, or rentals are available in Oak Street Beach?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2025 is over 3359 in the Oak Street Beach area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Oak Street Beach. 

Nearby Neighborhood (12)

Neighborhood Property Count
Downtown Chicago Rental Villas and Private Getaways in Chicago, Illinois 1769
Near North Side Rental Villas and Private Getaways in Chicago, Illinois 795
The Loop Rental Villas and Private Getaways in Chicago, Illinois 776
River North Rental Villas and Private Getaways in Chicago, Illinois 462
South Loop Rental Villas and Private Getaways in Chicago, Illinois 372
Lakeview Rental Villas and Private Getaways in Chicago, Illinois 235
West Loop Rental Villas and Private Getaways in Chicago, Illinois 198
Lincoln Park Rental Villas and Private Getaways in Chicago, Illinois 143
Hyde Park Rental Villas and Private Getaways in Chicago, Illinois 84
O'Hare Rental Villas and Private Getaways in Chicago, Illinois 66
Gold Coast Rental Villas and Private Getaways in Chicago, Illinois 39
Magnificent Mile Rental Villas and Private Getaways in Chicago, Illinois 4128