Fairfield County · Westchester & Connecticut

    Luxury furnished rentals in Westport, CT

    Westport is a shoreline town with a long creative and artistic history, a busy downtown on the Saugatuck River and some of the most popular beaches in Fairfield County. We find furnished Westport homes for summer seasons and longer stays alike.

    Living in Westport

    Downtown sits on the river with shops and restaurants along Main Street, and the Saugatuck neighborhood near the train station has its own dining scene. Compo Beach draws crowds in summer, Sherwood Island State Park, the first state park in Connecticut, sits on the eastern shore, and a long-running summer theater keeps the arts at the center of town life.

    Furnished luxury homes in Westport

    Furnished options include beach cottages and larger shingle-style homes near Compo, riverfront properties along the Saugatuck, and estates on wooded land north of the Merritt Parkway. Summer rentals near the beach are the most competitive.

    Getting around

    New Haven Line trains from Westport (Saugatuck) and Greens Farms stations reach Grand Central in about 70 to 85 minutes. Interstate 95 and the Merritt Parkway serve the town, and Westchester County Airport is about 35 to 40 minutes away.

    Who we place here

    Families spending a summer at the beach, executives at investment firms and corporate offices in Westport and Stamford, and creative professionals who want a town with an artistic identity.

    Westport at a glance

    • Compo Beach on Long Island Sound
    • Sherwood Island, Connecticut's first state park
    • Downtown on the Saugatuck River
    • Two New Haven Line stations

    Questions

    How much does a luxury furnished rental in Westport, CT cost?

    Most placements we arrange at this level run from about $15,000 to $80,000 or more a month, depending on size, term, season and services. We quote privately against your exact dates.

    What is the minimum stay?

    Thirty days. Seasonal and annual terms are common, and extensions are handled early and quietly.

    Are these homes listed publicly?

    Usually not. Most come through direct owner relationships and are shown privately, with an NDA when requested.

    Can a family office or business manager handle everything?

    Yes. We regularly work entirely through a family office, business manager, relocation team, counsel or a private-client insurance adjuster.

    Request private options in Westport

    Send the dates, household size and any must-haves. We reply with what is genuinely available, not a list.

    Response within one business day, usually within hours. Your info is confidential.