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Holiday rentals with beach access in Woodlawn

Find and book unique rentals with beach access on Airbnb

Top-rated rentals with beach access in Woodlawn

Guests agree: these rentals with beach access are highly rated for location, cleanliness and more.

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Top guest favourite
A modern living area features a spacious orange sofa and a wooden coffee table positioned on a light rug. A large flat-screen television is mounted on the wall, with a stylish lamp and potted plant nearby. An open kitchen with white cabinetry and stainless-steel appliances is visible in the background.
Flat in Edgewater
4.98 out of 5 average rating, 130 reviews

Bright & Modern Apt | Steps to Lake, Train, Food

This is the ideal location for your trip to Chicago! Steps from the Red Line Train, Foster Beach, Lake Shore Drive, Lake Front Trail, amazing Restaurants & a quality grocery store. You'll enjoy a clean & spacious 2 bedrooms apartment w/ friendly neighbors, flawless check-in & reserved parking. This place is safe & provides a beautiful & stocked apartment to relax after a busy day in the city. Short walk to Andersonville & Asia on Argyle for wonderful food options. The Riv &Aragon for concerts

Top guest favourite
A well-lit bedroom features a spacious bed with a soft, green blanket and burgundy pillows. A wooden desk and chair sit near a closet with sliding doors. Two vibrant artworks adorn the wall, and a cozy area rug adds comfort to the floor.
Guest suite in South Side
4.93 out of 5 average rating, 109 reviews

Cozy 2BD Lake Apt Near Downtown, McCormick & More

Enjoy your getaway in this cozy solar powered and eco-sustainable garden apartment 5 minutes walking to Lake Michigan where you can access beaches, bike paths, prairies, parks & more! We are less that 8 min away from downtown, the University of Chicago, Soldier Field, the Field Museum and more. Our home is located in the historic Oakland neighborhood, central to so much of what Chicago has to offer. We love welcoming guests to our garden apartment where making your stay relaxing is our pleasure

Guest favourite
A vibrant living area showcases eclectic décor, featuring a colorful mural with artistic motifs on one wall. A round coffee table sits in the center, surrounded by cream-colored sofas adorned with green cushions. A wet bar with wooden stools is visible in the background.
Flat in South Side
4.91 out of 5 average rating, 163 reviews

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TVs, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

Top guest favourite
A modern kitchen is depicted with a stainless-steel refrigerator and oven, complemented by a tiled backsplash. Light cabinetry provides ample storage, while a cozy couch with a blue accent pillow offers a welcoming touch. Natural light brightens the space, enhancing the functionality.
Flat in Bronzeville
4.94 out of 5 average rating, 175 reviews

Cozy 2 bdrm near McCormick Place & Wintrust Arena

Come enjoy Chicago via our cozy apartment in the quiet yet friendly Historical Bronzeville community. We are nestled between Hyde Park and South Loop, where you will find plenty of restaurants, theaters, and nightlife. Only minutes away from McCormick Place, 10-15 min drive from downtown and 3-12 miles from all the sports arenas and airports. You can bike or walk to the nearest grocery store, park, gym, and beach. The nearest bus and/or train is 2-3 blocks away for your convenience as well.

Guest favourite
A lush garden area is visible, featuring a green lawn surrounded by various plants and trees. A hammock hangs between two supports, providing a comfortable resting spot. Sunlight filters through the foliage, illuminating the outdoor furniture and creating a peaceful atmosphere.
Flat in West Town
4.85 out of 5 average rating, 311 reviews

Wicker Park Historic, Art-Filled, Urban Oasis #1

Entire 2 bedroom apartment in art-filled, Wicker Park building 5 min. Uber to downtown Chicago. Public transportation 3 blocks away. Restaurants, shops, parks, and nightlife within walking distance. Space includes -Brand new bathroom, walk in shower -1 bdrm w/ queen size bed - large closet -1 bdrm w/ single size bed, desk, shelf space -Pull out queen size couch bed -Fully equipped kitchen -AC -Personal back porch -Beautiful garden w/ outdoor furniture -1 parking space included + parking passes

Top guest favourite
An outdoor terrace features comfortable lounge seating and a grill. A panoramic view of the Chicago skyline is visible, showcasing various architectural styles and buildings under a clear blue sky.
Townhouse in West Loop
4.99 out of 5 average rating, 278 reviews

Spacious 4-Level/4-Bedroom Townhouse in West Loop

Spacious Townhouse in Chicago's Hip Foodie Neighborhood: West Loop/Fulton Market. This is a Private, 4-Story Townhouse on a Tree-Lined Street just Steps from the Action...while still quiet enough for a good night's sleep. Walk to some of the Nation's Top Restaurants (near Restaurant Row), Clubs, Pubs, Groceries, Parks, Coffee Shops. Easy Train Transit to O'Hare, Navy Pier, Mag Mile, McCormick Place, etc...Terrace w/Skyline Views & Attached Garage Parking for 1 Regular-Sized Vehicle Included!

Top guest favourite
A modern kitchen features sleek gray cabinetry and stainless steel appliances, including a refrigerator and oven. A neutral area rug complements the wood flooring. Natural light is provided by large windows, and stylish wall decor adds a contemporary touch to the space.
Apartment in Lake View
4.98 out of 5 average rating, 248 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

Guest favourite
Flat in Wrigleyville
4.78 out of 5 average rating, 256 reviews

Cozy Bedroom in Wrigleyville (Entire Apt)

You can’t beat this location! Right in the middle of Boystown and steps from Wrigley Field, you’ll be surrounded by some of the city’s best bars, restaurants, and nightlife. Cubs Stadium is just one block away, and the Addison Red Line station is a quick 5-minute walk, making it easy to explore all of Chicago. No shared space: Due to updated COVID-19 policies, this unit is now 100% private. Once you book, the entire place is yours and the additional listing will be blocked immediately.

Top guest favourite
A private patio provides a cozy seating area featuring a 3-seater sofa and two accent chairs. A round coffee table sits in the center, with the urban street view visible beyond the wrought iron railing.
Flat in Downtown Chicago
4.94 out of 5 average rating, 107 reviews

Gold Coast Pristine 3BD|2BR| Patio |Parking| Beach

FREE GARAGE PARKING! Garage Clearance 6ft. Step into luxury in this modern loft with 3 bedrooms, 2 bathrooms and a private patio with breathtaking views. Experience the feeling of being at home in a bright and spacious haven amidst Chicago's most sought-after neighborhood "Gold Coast" This centrally located gem is situated within walking distance of much of Chicago Downtown's exquisite dining, upscale boutiques, popular tourist destinations, and just a stone throw away from Oak Beach.

Top guest favourite
A row of historic brick homes is set along a tree-lined street. Each home features ornate details on the facade, with stairs leading to the entryways. Greenery and flowers enhance the surrounding gardens, adding to the neighborhood's vibrant character.
Flat in Lincoln Park
5 out of 5 average rating, 108 reviews

Lincoln Park DePaul Rowhouse Historic Bissell St

Exclusive Lincoln Park location. Beautiful historic landmarked block. Perfect for a weekend getaway or longer stay. You will have your own apartment with a private entry and brick patio to relax and enjoy coffee in this vibrant and historic neighborhood. Just a couple minute walk to exclusive Armitage Shopping District and DePaul University. Short walk to the lakefront, free Lincoln Park Zoo, Peggy Notebaert Nature Museum and Organic Farmer's Market during summer months.

Top guest favourite
A spacious living area is furnished with two leather sofas, a coffee table, and a decorative rug. A television is mounted above a tiled fireplace, and large windows allow natural light to fill the room. A comfortable armchair is positioned near the window.
Flat in Lake View
4.99 out of 5 average rating, 150 reviews

Spacious 2 Bedroom in the heart of Lakeview!

Come enjoy this warm and spacious 2br/1ba vintage apartment in the heart of Lakeview! 10 Minute walk to Wrigley Field and steps away from many dining and shopping options. Fully stocked kitchen, dining room (seats six), decorative fireplace, TV w/ Fire Stick, two bedrooms with queen beds, office space for working remote, and large private deck with gas grill. Very close to Lake Shore Drive, short walk to the Belmont L, and easy access to many buses. Two night minimum stay.

Top guest favourite
A bright living area features large windows allowing natural light to fill the space. A mix of seating options includes a red sofa and a dark chair, complemented by plants and a piano. Bookshelves line the walls, offering a cozy and inviting atmosphere.
Flat in Downtown Chicago
4.93 out of 5 average rating, 114 reviews

2br/2ba, A+ location by Mag mile, views & spacious

Unbeatable location next to Water Tower Place, with lots of natural light and partial lake view in a quiet vintage building with lots of character. Walk to nearly any attraction in central Chicago. I'm happy to help with sightseeing advice and discounts on popular tourist attractions. (Guests love: Location, View, Comfortable room and bed, Friendly/helpful host, Flexible luggage policy) Please see Airbnb listing 12323073 for additional reviews of this apartment.

Popular amenities for rentals with beach access in Woodlawn

When is the best time to visit Woodlawn?

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Avg. price$91 SGD$116 SGD$140 SGD$129 SGD$152 SGD$183 SGD$174 SGD$169 SGD$162 SGD$142 SGD$117 SGD$116 SGD
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Quick stats about holiday rentals with beach access in Woodlawn

  • Total holiday rentals

    Explore 30 holiday rentals in Woodlawn

  • Nightly prices starting at

    Woodlawn holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,190 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Woodlawn holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Woodlawn rentals

  • 4.5 Average rating

    Woodlawn stays receive an average rating of 4.5 out of 5 from guests

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