Best Vacation Rental Manager Companies in Chicago, Illinois, 2025

FreeStand Home Solutions is a corporate housing rental management company that specializes in providing short-term, flexible furnished home rentals for business travelers in the Chicago, Illinois area. They offer premium amenities and designs that exceed typical hotel accommodations.

Coast to Cactus is a vacation rental management company that specializes in providing high-quality vacation homes in popular destinations across Arizona and San Diego, California. They offer a wide range of amenities and services to ensure a comfortable and memorable stay for their guests.

Tripalink is a property management company that specializes in modern apartment and home rentals in major cities across the United States, including Los Angeles, Seattle, Philadelphia, and more. They offer a range of services such as property management, vacation rentals, and student housing, catering to both residential and student housing sectors.

Domain is a premier short-term rental management company that specializes in providing luxury vacation rentals in the heart of Chicago. They offer tailored experiences and unparalleled service to ensure an unforgettable stay for their guests.

David Rigney Real Estate Solutions is an experienced real estate consulting group and broker serving the Illinois market. They specialize in managing short and long-term rentals, assisting homeowners facing pre-foreclosure challenges, and providing real estate education through their blog and podcast.

AllSet Turnover is a full-service vacation rental management company that specializes in managing Airbnb and VRBO properties in the Chicago area. They handle all aspects of property management, including listing optimization, pricing, guest communication, cleaning, and concierge services, allowing property owners to have a hands-off experience.

Hosty Co is a seasoned short-term rental management company that helps Chicago-area clients generate passive income through its expertise in interior design, investment property ownership, and industry connections to maximize the earning potential of vacation rental properties.

Homie Bees is a full-service vacation rental management company that specializes in managing Airbnb, VRBO, Expedia, and Booking.com listings. They offer comprehensive services including professional photography, dynamic pricing, 24/7 guest support, and dedicated local teams to ensure maximum profitability and a seamless experience for property owners.

BNB Rental Group is a vacation rental management company that specializes in short-term rental properties across the United States, including major cities like New York, Los Angeles, Chicago, Dallas, and Atlanta. They provide full-service management solutions for Airbnb and VRBO properties, handling everything from marketing and guest relations to cleaning and maintenance.

HouseStay is a vacation rental manager offering fully furnished turnkey homes and apartments for extended stays of 30 nights or more in the Los Angeles area. They provide a curated selection of entire residential accommodations, complete with utilities included, for individuals and businesses seeking a homelike alternative to hotels. With thorough background checks on both hosts and guests, HouseStay aims to create a trusted community for temporary housing needs across prime Los Angeles neighborhoods like Santa Monica, Hollywood, and Beverly Hills.

ENVITAE provides beautifully crafted, luxury vacation rental spaces in the heart of Chicago, offering guests a high-end residential experience with premium amenities and 24/7 concierge services.

Rentberry is a comprehensive real estate platform that provides property management and vacation rental services. They operate in over 60 countries worldwide, with a focus on major cities in the United States, Europe, and Asia Pacific regions. Rentberry caters to both tenants and landlords, offering features like online rental applications, virtual property tours, digital lease signing, and seamless rent collection.

PMI Chicago is a full-service real estate asset management company that provides professional Residential, Commercial, Association, Short-Term, and Realty services to property owners and investors in the Chicago area.

PRIDE Properties is a full-service vacation rental management company that specializes in acquiring, transforming, and operating high-return vacation rental properties. They offer expertise in local regulations, interior design, and property management to maximize profits for their investor clients.

Rental Relocation Inc. is a leading provider of corporate housing solutions, specializing in delivering exceptional furnished housing and meaningful savings to clients across a wide range of industries. With a focus on relocation, temporary living, business travel, intern housing, and military/government housing, the company leverages its extensive experience and best-in-class technology to source the right short-term housing solution for each client's unique needs.