Vacation rentals in Kathy Osterman Beach

4.96 out of 5 average rating, 338 reviews

A lush garden pathway winds through vibrant flower beds and greenery, leading to a cozy seating area nestled under a tree. The stone path is framed by various plants, showcasing a tranquil outdoor setting perfect for relaxation.

Guest suite in Chicago

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

5 out of 5 average rating, 11 reviews

The exterior of a historic brownstone building is showcased, featuring a beautifully detailed entrance surrounded by brick and stone. A set of steps leads up to the front door, flanked by decorative wrought iron railings and lush greenery, creating a welcoming atmosphere.

Home in Chicago

Top Floor in Historic Old Town!

Unbeatable Location in Historic Old Town Triangle! This charming top-floor apartment is on a quiet cul-de-sac in the heart of Old Town Triangle, steps from St. Michael’s Church, North Ave Beach, Lincoln Park Zoo, and Wells Street’s entertainment district. The sun-filled space features an oversized private patio, and 3 bedrooms with queen beds, closets, and dressers. The spacious kitchen and dining areas are perfect for gatherings. The “L” stop is just two blocks away for easy access to the city.

5 out of 5 average rating, 28 reviews

Home in Highland Park

Sanctuary on the Ravine

Take it easy at this unique and tranquil get away, walking distance to Ravinia and Beaches 3 Blocks.This historic, beautifully decorated and well maintained home has a lovely, peaceful & serene setting. Multiple indoor and outdoor seating arrangements. Fully stocked kitchen that opens to family room looking out onto several multilevel brick patios and a quiet, private ravine. The extra large living room has a down feathered sectional couch that seats up to 10 people. No parties or gatherings

Top guest favorite

A quaint street scene features a coffee shop sign labeled 'Honey Hill Coffee' hanging above, with paved walkways lined by small businesses. Decorative plants are seen in hanging pots, and trees provide shade along the sidewalk, enhancing the inviting atmosphere.

Home in Wauconda

4.95 out of 5 average rating, 65 reviews

The Adorable "Blue Breeze"!

Enjoy time at our centrally-located, family-friendly home. Close by, you'll find a public fishing dock and the popular Phil's Beach. A peaceful space with an outside patio and grill, perfect for relaxing at end of day. We also have a large driveway that can accommodate your boat making it easy to enjoy a day on Bangs Lake or a short 15 min trip to Fox Lake. Nearby attractions include the Volo Museum, Jurassic Gardens, and Lake County Discovery Museum. Please note the backyard is not fenced in.

A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.

4.94 out of 5 average rating, 176 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Top guest favorite

A modern kitchen featuring a large island with seating for six, complemented by sleek cabinetry and stainless steel appliances. Natural light fills the space through a nearby window, and an adjacent dining area is visible, offering a blend of functionality and style.

Home in Chicago

5 out of 5 average rating, 11 reviews

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

4.85 out of 5 average rating, 68 reviews

Home in Oak Park

A Comfortable Stay While You are Away in Oak Park

Welcome to this Oak Park home, conveniently minutes from the main expressway, train station, downtown Chicago, and the Medical Center. This entire Oak Park house is ideal for travelers seeking a tranquil and welcoming space to unwind in after a long day, medical professionals, visiting patients at the Medical Center, and families needing long-term housing. The residence is minutes from downtown Oak Park and the historical landmarks of Frank Lloyd Wright's home and studio.

A bright living space features a sectional couch positioned around a glass coffee table. Large skylights and windows allow natural light to fill the room, which is accented by a decorative rug and a modern electric fireplace. A television hangs on one wall, displaying a scenic landscape.

4.92 out of 5 average rating, 12 reviews

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: - Uber-fast Wifi streaming, - Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches - European decor - 2 kitchens - The popular 606 Trail access is 100 ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

4.85 out of 5 average rating, 34 reviews

The exterior of the tiny house is shown, featuring a light grey façade with two symmetrical windows on the upper level and a white door at the bottom. A wooden staircase leads to the entrance, surrounded by minimal landscaping and a clear blue sky above.

Guesthouse in Evanston

Tiny house in West Village Arts District

This tiny house (750 sq ft) invites you to explore Evanston's West Village Arts District and shop creative businesses. Just down the block is the newly renovated Robert Crown Recreation Center, where you can check out library books and movies, play soccer, tennis, ice hockey and go ice skating year round. This Tiny House is located in our backyard, so please be respectful of noise and the amount of guests you book on the reservation!

A bright entryway features a wooden floor and white walls, leading to an open living space. A glass-front cabinet showcases various dishware, while a dark wooden door provides access to another room. Natural light fills the area, enhancing the vintage charm.

4.89 out of 5 average rating, 73 reviews

Spacious 2 Bed Apartment, Perfect Location

Located just blocks away from the Brown Line CTA stop, This massive 2 bedroom apartment will add some vintage charm to your vacation in a safe, low key neighborhood while never taking you far from the action. This unit is ideal for travelers looking for a comfortable home base while exploring everything downtown and the north side of Chicago have to offer.

4.95 out of 5 average rating, 104 reviews

A modern kitchen features sleek dark cabinetry and stainless steel appliances. Natural light enters through skylights, highlighting a small dining table with two chairs. The warm wood flooring complements the design, while a light fixture hangs gently from the exposed beam ceiling.

Guesthouse in Oak Park

O'Malley Oasis!

Your home away from home at this centrally-located coachhouse apartment.Queen sized bed, fully equipped eat-in kitchen, relaxing living area with recliner, leather couch and big screen tv. Walk to downtown or explore Chicago via public transportation just a few blocks away. Adorable porch and your own entry. Parking spot included!

Top guest favorite

The exterior of a three-story residential building is depicted, featuring a wooden porch with steps leading to the front door. Large windows allow natural light to enter, and greenery surrounds the entrance, complementing the light-colored siding and red brick foundation.