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Houses for Rent in Head of the Harbor, NY

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2 Sunset Dr - Photo 1 of 1

5d+ ago

House for rent in Head of the Harbor

SINGLE_FAMILY - Colonial - Head Of The Harbor, NY

2 Sunset Dr, Head of the Harbor, NY 11780

In-unit laundry | Outdoor space | Storage

6 beds

9.5 baths

$20,000

House for rent

6-bed colonial estate with tennis court & harbor views

6-bed house in Head of the Harbor, this colonial estate spans 6,500 sqft across 3.9 landscaped acres with gated security. The 9.5-bath layout features a Wolf kitchen, billiard room, observation tower with harbor views, and fully finished basement with tennis lounge. Multiple fireplaces, balconies, and a private tennis court complete this luxury retreat.

7 Chestnut St - Photo 1 of 1

3d ago

Stony Brook house for rent in Stony Brook University

SINGLE_FAMILY - Cape Cod - Stony Brook, NY

7 Chestnut St, Stony Brook University, NY 11790

In-unit laundry | Outdoor space | Storage

3 beds

1 bath

$3,800

House for rent

8 College Dr - Photo 1 of 1

3d ago

Stony Brook house for rent in Stony Brook University

SINGLE_FAMILY - Colonial - Stony Brook, NY

8 College Dr, Stony Brook University, NY 11790

In-unit laundry | Dishwasher

4 beds

2 baths

$5,300

House for rent

116 Cambon Ave - Photo 1 of 1

5d+ ago

House for rent in St. James

SINGLE_FAMILY - Cape Cod - Saint James, NY

116 Cambon Ave, St. James, NY 11780

In-unit laundry | Garage parking | Air conditioning

4 beds

2 baths

$4,600

House for rent

496 Route 25a - Photo 1 of 1

5d+ ago

House for rent in St. James

SINGLE_FAMILY - Victorian - Saint James, NY

496 Route 25a, St. James, NY 11780

In-unit laundry | Outdoor space | Storage

5 beds

3 baths

$4,500

House for rent

93 Maple Rd - Photo 1 of 1

5d+ ago

House for rent in Kings Park

SINGLE_FAMILY - Cape Cod - Kings Park, NY

93 Maple Rd, Kings Park, NY 11754

Hardwood floor | Dishwasher

2 beds

1 bath

$2,800

House for rent

Nearby rental good for eco-living

$4,400

Kings Park

Nearby rental good for pet owners

$5,100

Westport

40 Seabrook Ln - Photo 1 of 1

5d+ ago

Stony Brook house for rent in Stony Brook University

SINGLE_FAMILY - Colonial - Stony Brook, NY

40 Seabrook Ln, Stony Brook University, NY 11790

In-unit laundry | Garage parking | Carpet

3 beds

2.5 baths

$4,700

House for rent

219 Lower Sheep Pasture Rd - Photo 1 of 1

5d+ ago

House for rent in Setauket-East Setauket

SINGLE_FAMILY - Ranch - East Setauket, NY

219 Lower Sheep Pasture Rd, Setauket-East Setauket, NY 11733

In-unit laundry | Garage parking | Fireplace

3 beds

2 baths

$4,200

House for rent

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57 Penn St - Photo 1 of 1

5d+ ago

House for rent in Lake Grove

57 Penn St, Lake Grove, NY 11755

In-unit laundry | Outdoor space | Air conditioning

2 beds

1 bath

$3,450

House for rent

214 Old Town Rd - Photo 1 of 1

5d+ ago

House for rent in Setauket-East Setauket

SINGLE_FAMILY - Cape Cod - East Setauket, NY

214 Old Town Rd, Setauket-East Setauket, NY 11733

In-unit laundry | Outdoor space | Garage parking

4 beds

3 baths

$4,950

House for rent

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Find sweet deals near Head of the Harbor

These rentals are 10%-30% cheaper than the local average price for similar rentals.

$3,900

Kings Park

$4,100

Port Jefferson Station

$4,250

Centereach

19 Sunflower Ridge Rd - Photo 1 of 1

5d+ ago

Townhouse for rent in Centereach

19 Sunflower Ridge Rd, Centereach, NY 11720

In-unit laundry | Outdoor space | Storage

4 beds

2.5 baths

$4,800

House for rent

47 Madison St - Photo 1 of 1

5d+ ago

Townhouse for rent in Smithtown

47 Madison St, Smithtown, NY 11787

Swimming pool | Fireplace | Residents lounge

3 beds

2.5 baths

$10,000

House for rent

81 Bellwood Ave - Photo 1 of 1

2h ago

House for rent in Centereach

81 Bellwood Ave, Centereach, NY 11720

In-unit laundry | Outdoor space | Fitness center

4 beds

2 baths

$4,000

House for rent

Listings within 10 miles
175 Richmond Blvd - Photo 1 of 1

5d+ ago

House for rent in Ronkonkoma

SINGLE_FAMILY - Other - Ronkonkoma, NY

175 Richmond Blvd, Ronkonkoma, NY 11779

Dishwasher

2 beds

2 baths

$3,295

House for rent

Lincoln Blvd & Motor Pkwy #1 - Photo 1 of 1

5d+ ago

House for rent in Central Islip

Lincoln Blvd & Motor Pkwy #1, Central Islip, NY 11788

In-unit laundry | Garden | Storage

3 beds

1 bath

$3,750

House for rent

Available Aug 1

153 W Main St - Photo 1 of 1

3d ago

House for rent in Kings Park

SINGLE_FAMILY - Cape Cod - Kings Park, NY

153 W Main St, Kings Park, NY 11754

Outdoor space | Garage parking | Air conditioning

3 beds

1.5 baths

$3,900

House for rent

196 Sterling St - Photo 1 of 1

5d+ ago

House for rent in Port Jefferson Station

SINGLE_FAMILY - Cape Cod - Port Jefferson Station, NY

196 Sterling St, Port Jefferson Station, NY 11776

In-unit laundry | Air conditioning | Hardwood floor

4 beds

2 baths

$4,100

House for rent

1334 Connetquot Ave - Photo 1 of 1

5d+ ago

House for rent in Central Islip

SINGLE_FAMILY - Ranch, Split Level - Central Islip, NY

1334 Connetquot Ave, Central Islip, NY 11722

Hardwood floor

3 beds

1 bath

$3,600

House for rent

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802 Sara Cir - Photo 1 of 1

5d+ ago

Townhouse for rent in Terryville

SINGLE_FAMILY - Port Jefferson Station, NY

802 Sara Cir, Terryville, NY 11776

In-unit laundry | Outdoor space | Storage

2 beds

2.5 baths

$3,500

House for rent

Listings within 20 miles
35 Sloop Walk - Photo 1 of 1

5d+ ago

House for rent in Bay Shore

SINGLE_FAMILY - Ranch - Summer Club, NY

35 Sloop Walk, Bay Shore, NY 11706

In-unit laundry | Outdoor space | Air conditioning

5 beds

3 baths

$12,000

House for rent

7 E End Walk - Photo 1 of 1

5d+ ago

House for rent in Bay Shore

SINGLE_FAMILY - Cottage - Atlantique, NY

7 E End Walk, Bay Shore, NY 11706

In-unit laundry

3 beds

1.5 baths

$5,000

House for rent

39 39 Midway Walk - Photo 1 of 1

5d+ ago

House for rent in Bay Shore

SINGLE_FAMILY - Atlantique, NY

39 39 Midway Walk, Bay Shore, NY 11706

In-unit laundry | Deck | Hardwood floor

4 beds

2 baths

$5,000

House for rent

91 S Penataquit Ave - Photo 1 of 1

15h ago

House for rent in Bay Shore

SINGLE_FAMILY - Ranch - Bay Shore, NY

91 S Penataquit Ave, Bay Shore, NY 11706

In-unit laundry | Swimming pool | Hardwood floor

4 beds

2.5 baths

$5,750

House for rent

848 Udall Rd - Photo 1 of 1

1d ago

House for rent in West Islip

848 Udall Rd, West Islip, NY 11795

Furnished

Studio

0 baths

$3,600

House for rent

Available Jul 20

4 Rose St - Photo 1 of 1

2d ago

House for rent in Sayville

SINGLE_FAMILY - Ranch - Sayville, NY

4 Rose St, Sayville, NY 11782

Garage parking | Dishwasher

3 beds

2 baths

$4,300

House for rent

Average rent

The average rent for houses in Head of the Harbor, as of July 2026, is flat compared to last month and unchanged year-over-year.
$4,700

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Showing 1 - 25 of 25 results
Home > House Rentals in Head of the Harbor
Updated: July 22, 2026

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Discover houses for rent in Head of the Harbor, NY

🌇Available house rentals25 houses
💰Best rent deal93 Maple Rd
🍃With outdoor space
⭐Popular amenities, ,
👚With laundry facilities
🍽With dishwasher
🚗With garage parking
❄️With air conditioning
🏠With photos