Luxury furnished rentals in Shelter Island, NY
Shelter Island sits in the bays between Long Island's North and South Forks and can be reached only by ferry. We place clients in furnished Shelter Island homes for summers and longer stays when they want water and quiet.
Living in Shelter Island
The island feels rural and unhurried, with winding roads, small harbors and a handful of restaurants. Mashomack Preserve, protected by The Nature Conservancy, covers about a third of the island with trails, woods and shoreline.
Furnished luxury homes in Shelter Island
Furnished options include waterfront homes with docks, historic Victorian houses in the Heights and the village of Dering Harbor, and newer homes on wooded lots with water views. Island summer leases typically start around Memorial Day and end after Labor Day.
Getting around
The South Ferry connects to North Haven near Sag Harbor, and the North Ferry connects to Greenport on the North Fork, each a crossing of only a few minutes. Greenport has an LIRR station and Hampton Jitney service, and the drive from Manhattan takes about 2.5 to 3 hours plus the ferry.
Who we place here
Families who want a quieter summer, boaters and sailors, and clients who want to be near the Hamptons without being in them.
Shelter Island at a glance
- Reached only by ferry
- Mashomack Preserve covers about a third of the island
- Between the North and South Forks
- Short drive from Sag Harbor and Greenport
Questions
How much does a luxury furnished rental in Shelter Island, NY 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 Shelter Island
Send the dates, household size and any must-haves. We reply with what is genuinely available, not a list.