Wonderful opportunity to spend time in the wonderful Southold community of Bay Haven. Choose to spend the sunny days by your own pool, or head down the block to the comm...

Beautifully reworked classic Victorian in the heart of historic Southold Hamlet. Fresh paint in all the rooms, hardwood floors, new refrigerator, dishwasher and range. Cl...

Available 2026: September $12,500; October $12,500 - Available 2027: May $12,500; July $22,500; Aug-LD $28,000; September $12,500; October $12,500; November $8,500 Experi...

Step into a special piece of North Fork history. Originally the Main Bayview Schoolhouse, this distinctive, furnished, Southold property has been thoughtfully converted i...

Tucked away among the trees, this charming home offers the perfect blend of privacy and natural light. Thoughtfully furnished and move-in ready, it features inviting livi...

A quintessential North Fork retreat in Beixedon Estates in an extraordinary waterfront setting. Tucked beside the winding Hippodome Creek and surrounded by lush coastal l...

Clean and Tidy 2 Bedroom/1.5 Bath Cottage with North Fork Character and Charm, Located Near Bay Beach and Farmstand. Nice Yard and Deck for Enjoyable Outdoor Living. Ju...

Two week minimum rental. Available in July and August, $4,500 / week. August 16 through Labor Day, $5,500/week. 3% discount for rentals longer than 3 weeks. Perfectly...

YEAR ROUND - Monthly Rate $3,700 STARTING OCTOBER 1 - ALSO AVAILABLE AS SEASONAL RENTAL. The Yellow House sits on five secluded acres in Southold on the North Fork of Lo...

Available: August $15.5K, Oct 1, 2026 to Sept 30, 2027 - Monthly Rate $3,700. The Yellow House sits on five secluded acres in Southold on the North Fork of Long Island, o...

Summer is here, and this home has vacation written all over it. Enjoy spectacular sunset water views of the Long Island Sound from the spacious wrap-around deck or from t...

2026 Availability: July $12,000; August $14,000. Newly renovated Southold home offering 3 bedrooms and 2 full baths, ideally located just 0.2 miles from South Harbor be...

Offered June $10,000 ($2,500/wk); July $20,000 ($5,000/wk); Aug $25,000 ($6,250/wk); Sept $12,000 ($3,000/wk); Oct $10,000 ($2,500/wk). Two-week minimum. This contempora...

Newly renovated and pristine year-round rental in the heart of Southold's beautiful Colonial Village, an exclusive 55 an over adult community. This fantastic home has hea...

Experience effortless one-level living in this immaculate Southold retreat. Set in the coveted Terry Waters community with its own sandy beach just down the road, this cl...

Seasonal Rental. Set directly across from Town Beach in Southold, this beautifully maintained seasonal rental captures the best of North Fork coastal living with unobstr...

August Rental $14,500: This elegant mid-century coastal charming North Fork rental is nestled in Southold Shore Community with a bayfront beach, marina and water access f...

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 dr...

Waterfront Studio Condo in Southold property features living room / kitchen combo with 1 Queen Size bed and 2 pull out trundle beds which can become 1 full size bed. outd...

North Fork summers are defined by sun-soaked beach days, vineyard hopping, and slow evenings spent cooking under the open sky—and this charming 3-bedroom, 2-bath cottage ...

Mint mid-century modern cottage offering 3 bedrooms and 2 baths, ideally located just 100 yards from sandy Founders Landing beach. The interior features clean, modern lin...

Enjoy this spacious vacation rental located just a short distance from Southold Town Beach. With room for the whole family, this home features three en-suite bedrooms plu...

Step inside this charming 2 bedroom, 1 bath bungalow nestled on the serene shores of Great Pond in Southold. This cozy waterfront retreat offers tranquil water views and ...

Tucked away on the peaceful edge of freshwater Great Pond in Southold, this delightful 2-bedroom, 1-bath cottage offers the perfect blend of comfort and charm. Enjoy quie...

A relaxed North Fork summer retreat with a private beaches, a pool for long afternoons, and easy access to vineyards, farmstands, and waterfront dining. Summer on the No...

This Spacious Open Floor Plan Home Features Two Separate Living Areas, a Treetop Waterview Deck, A Chef's Kitchen with Pantry and a Large Stylish Dining Table. This Invit...

2026 Availability: June $30,000. July RENTED. Perfect summer getaway with 5 bed, 4.5 bath in the heart of the North Fork. The home sits on 1.24 acres and features an op...

Experience the ultimate North Fork summer in this stunning new construction home, designed for effortless entertaining and elevated coastal living. Professionally decorat...

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 ...

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 ...