FOR RENT
Renters: Call Us to Find your Perfect Summer Rental!
Homeowners: Call to Find out How Shutters & Sails Can Help!
*As a reminder: Renters (on the East or West Ends) are not eligible for guest passes and
must purchase a Residential Vehicle sticker in order to obtain access to the East End of the Island.*
(860) 331-1510
Do Not Fear, We’re Still Here!
Southold, NY has just passed a new rental permit law going into effect! Click Here to Read The Full Rental Permit Law!
As a reminder: Renters (on the East or West Ends) are not eligible for guest passes and must purchase a Residential Vehicle sticker in order to obtain access to the East End of the Island.
Prospective Renters: Please feel free to call us to assist in finding you a rental for this upcoming summer
Home Owners: Please contact us to find out how we can help you navigate and complete the new requirements for this law!
Please call us for assistance with your rental booking at (860) 331-1510. Click Here to Read The Full Rental Permit Law
Renting on Fishers Island
We are as excited to introduce new people to Fishers Island as we are to welcome back old friends. We find great joy to hear how within hours of arriving, the stresses of mainland life drain away.
Please visit our Island Resources page for a quick reference to many of the services and amenities that are available on Fishers Island.
Most rental houses include an additional utility and cleaning charge.
For additional listings that may not
be featured on this website,
please contact us:
(631) 788-7921
e-mail info@shuttersandsails.com
We are happy to answer any questions,
and help you arrange your stay.
(Search by rental NAME, DATE, ROOM #, etc.)
| Rental Name |
Sleeps | BR | Area | Description | Weekly Rental |
Avail Cal |
|
|---|---|---|---|---|---|---|---|
 |
Hill Cottage | 9 | 5 | West End | tucked into North Hill | $2,800/week | |
 |
Treetops | 5 | 3 | West End | comfortable cottage near village |
$3,000/week | |
 |
Braemar | 10 | 5 | West End | water view | $3,400/week | |
 |
The Cabin | 6 | 3 | East End | Large front porchnear Isabella Beach | $3,500/week | |
 |
Isabella Cottage | 6 | 3 | East End | Water View | $3,500/week | |
 |
KinderHaus | 8 | 3 | East End | contemporary near the Big Club, water views |
$3,850/week | |
 |
Houghton House | 11 | 5 | East End | breathtaking views, private beach |
$6,000/week | |
 |
Robert’s Folly | 8 | 4 | West End | large back yard fenced koi pond |
$6,000/week (3 week minimum) | |
 |
The Pond House | 13 | 8 | East End | water views | $6,250/week | |
 |
Osprey Hill Cottage | 6 | 3 | East End | secluded house, water view |
$6,600/week (minimum 3 weeks) | |
 |
Brooks Point House | 12 | 6 | East End | secluded house near club water views |
$7,900/week Utilities Included! | |
 |
West Harbor House | 12 | 5 | West End | large house, sunset and water views |
Booked 2019! | |
 |
Walker House | 6 | 3 | West End | private enclosed porch |
Booked Summer 2019 | |
 |
Zinnia Hill | 9 | 5 | West End | on a hill overlooking the Villageacross from the library | Booked Summer 2019 | |
 |
White House | 6 | 3 | West End | screened porch and fenced yard in village | Booked Summer 2019 | |
 |
Lake House | 16 | 8 | East End | spacious, private, lakefront |
Booked Summer 2019 | |
 |
Osprey Hill | 10 | 5 | East End | secluded house, water view |
Booked Summer 2019! | |
 |
Skimmer’s Rest | 5 | 3 | East End | waterfront with beach | Call for Pricing | |
 |
The Laughing Place | 10 | 7 | West End | large house in the Village |
Call for Pricing |