Luxury Properties for rent in Southold, New York

Start your summer in pure luxury by securing this brand-new, beautifully decorated, modern farmhouse rental in Southold for the month of June, perfectly situated on the desirable...

Presented by Mackenzie Needham | Daniel Gale Sotheby's International Realty

Offered June $15,000; July $25,000; August $30,000; September $20,000; October $15,000. This contemporary waterfront home on Great Pond enjoys sunrise over the water and...

Presented by Janet Markarian | Daniel Gale Sotheby's International Realty

2026 Rates: no availability New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool...

Presented by William Walters | Daniel Gale Sotheby's International Realty

2026 Rates: mdw- June 30 $12,000; September $12,000; October $10,000: Discover your perfect getaway in this expansive and meticulously updated ranch home, designed for relaxation...

Presented by William Walters | Daniel Gale Sotheby's International Realty

Impressive Goose Creek home with water views and large heated in-ground pool! This four bedroom, three bath house features a first floor primary bedroom with en-suite, a gourmet...

Presented by Mackenzie Needham | Daniel Gale Sotheby's International Realty

Your quintessential North Fork summer starts here. Tucked away in the quiet beach community of Paradise Shores, this Bayfront cottage is the summer retreat you’ve been dreaming...

Presented by JoAnn Wind | Daniel Gale Sotheby's International Realty

Settle into summer on the North Fork in this beautifully maintained and updated 4 bedroom, 3 full bath home located in the Angel Shores community of Southold. The layout is ideal...

Presented by Natalie Hough | Daniel Gale Sotheby's International Realty

Escape to the heart of the North Fork with this beautifully appointed 3-bedroom, 3-bath seasonal rental in picturesque Southold, ny. Nestled among the region's famed vineyards,...

Presented by Mary Terry | Sotheby's International Realty - Southampton Brokerage