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Houses for Rent in Head of the Harbor, NY

Average rent

$4,500

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445 Route 25a - Photo 1 of 1

5d+ ago

House for rent in Head of the Harbor

SINGLE_FAMILY - Colonial - Saint James, NY

445 Route 25a, Head of the Harbor, NY 11780

4 beds

2 baths

$4,200

House for rent

Elegant Colonial Home with Sunlit Spaces

This mint-condition colonial home features 4 bedrooms and 2 full bathrooms, providing ample space for comfortable living. The large kitchen opens to a cozy family room through French doors, complemented by a formal dining room and a welcoming sunroom. Enjoy off-street parking in the serene Head of the Harbor neighborhood, attended by the highly-rated Smithtown schools. The property, spanning 3,000 square feet, balances classic charm with modern living.

2 Sunset Dr - Photo 1 of 1

5d+ ago

House for rent in Head of the Harbor

Single Family Residence, Colonial - Head Of The Harbor, NY

2 Sunset Dr, Head of the Harbor, NY 11780

In-unit laundry | Outdoor space | Storage

6 beds

9 baths

$20,000

House for rent

Luxurious Estate with Tennis Court & Water Views

This stunning 6-bedroom, 10-bath estate spans 6,500 sq ft and sits on 3.9 acres. Features include a grand foyer, expansive open kitchen with top-of-the-line Wolf appliances, and luxurious primary suite with spa-like bath. Enjoy leisure in the billiard room and the entertaining “Tennis Lounge” in the finished basement. The property boasts outdoor perfection with a private tennis court and beautifully landscaped gardens, all with 24-hour gated security.

47 University Heights Dr - Photo 1 of 1

9h ago

Stony Brook house for rent in Stony Brook University

47 University Heights Dr, Stony Brook University, NY 11790

In-unit laundry | Garage parking | Fireplace

4 beds

2 baths

$4,500

House for rent

7 Hoover Ave - Photo 1 of 1

23h ago

House for rent in Nesconset

SINGLE_FAMILY - Ranch - Nesconset, NY

7 Hoover Ave, Nesconset, NY 11767

In-unit laundry | Outdoor space | Dishwasher

2 beds

1 bath

$3,850

$3,500

Price drop

House for rent

117 Blydenburg Ave - Photo 1 of 1

5d+ ago

House for rent in Smithtown

SINGLE_FAMILY - Cape Cod - Smithtown, NY

117 Blydenburg Ave, Smithtown, NY 11787

In-unit laundry | Outdoor space | Hardwood floor

4 beds

3 baths

$4,400

House for rent

19 Hamlet Woods Dr - Photo 1 of 1

5d+ ago

House for rent in St. James

SINGLE_FAMILY - Colonial - Saint James, NY

19 Hamlet Woods Dr, St. James, NY 11780

Outdoor space | Garage parking | Swimming pool

5 beds

4 baths

$8,000

House for rent

Nearby rental good for eco-living

$4,200

445 Route 25a

Nearby rental good for pet owners

$6,200

Centereach

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

$5,000

House for rent

68 Sycamore Cir - Photo 1 of 1
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2h ago

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68 Sycamore Cir, Stony Brook University, NY 11790

Storage | Garage parking | Fireplace

3 beds

2 baths

$4,575

$4,350

Price drop

House for rent

Available Sep 18

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19 New Mill Rd - Photo 1 of 1

5d+ ago

House for rent in Smithtown

SINGLE_FAMILY - Ranch - Smithtown, NY

19 New Mill Rd, Smithtown, NY 11787

In-unit laundry | Outdoor space | Garage parking

3 beds

2 baths

$5,500

House for rent

21 Fairway Dr - Photo 1 of 1

5d+ ago

House for rent in Centereach

SINGLE_FAMILY - Colonial - South Setauket, NY

21 Fairway Dr, Centereach, NY 11720

In-unit laundry | Outdoor space | Garage parking

4 beds

2 baths

$5,000

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.

$4,400

Smithtown

$3,400

Setauket-East Setauket

$3,200

Setauket-East Setauket

86 Krispin Ln - Photo 1 of 1

5d+ ago

House for rent in Setauket-East Setauket

SINGLE_FAMILY - East Setauket, NY

86 Krispin Ln, Setauket-East Setauket, NY 11733

In-unit laundry | Storage | High ceilings

2 beds

2 baths

$3,400

House for rent

305 Smithtown Boulevard #11 - Photo 1 of 1

5d+ ago

Lake Ronkonkoma house for rent in Ronkonkoma

305 Smithtown Boulevard #11, Ronkonkoma, NY 11767

Hardwood floor

1 bed

1 bath

$2,850

$2,650

Price drop

House for rent

Available Jan 5

132 Hallock Rd - Photo 1 of 1

5d+ ago

House for rent in Lake Grove

132 Hallock Rd, Lake Grove, NY 11755

In-unit laundry | Dishwasher | Microwave

5 beds

3 baths

$5,000

House for rent

62 Forest Ave - Photo 1 of 1

5d+ ago

House for rent in Lake Grove

SINGLE_FAMILY - Ranch - Lake Grove, NY

62 Forest Ave, Lake Grove, NY 11755

In-unit laundry | Outdoor space | Garage parking

4 beds

2 baths

$4,200

House for rent

12 N Ridge Rd - Photo 1 of 1

5d+ ago

House for rent in Old Field

House (Detached), Contemporary - Setauket, NY

12 N Ridge Rd, Old Field, NY 11733

In-unit laundry | Outdoor space | Garage parking

4 beds

3 baths

$6,675

House for rent

3 Artesian Way - Photo 1 of 1

5d+ ago

House for rent in Nissequogue

SINGLE_FAMILY - Contemporary - Saint James, NY

3 Artesian Way, Nissequogue, NY 11780

In-unit laundry | Carpet

3 beds

2 baths

$5,000

House for rent

340 Main St - Photo 1 of 1

5d+ ago

House for rent in Setauket-East Setauket

SINGLE_FAMILY - Cottage - East Setauket, NY

340 Main St, Setauket-East Setauket, NY 11733

In-unit laundry | Storage | High ceilings

2 beds

1 bath

$3,500

$3,200

Price drop

House for rent

338 Main St - Photo 1 of 1

5d+ ago

House for rent in Setauket-East Setauket

SINGLE_FAMILY - Cape Cod - East Setauket, NY

338 Main St, Setauket-East Setauket, NY 11733

In-unit laundry | Walk-in closets | Dishwasher

3 beds

2 baths

$4,500

$4,200

Price drop

House for rent

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41 Morning Dr - Photo 1 of 1

5d+ ago

House for rent in Centereach

SINGLE_FAMILY - Ranch - Centereach, NY

41 Morning Dr, Centereach, NY 11720

In-unit laundry | Outdoor space | Storage

3 beds

1 bath

$3,500

House for rent

44 Sycamore Cir - Photo 1 of 1

5d+ ago

Stony Brook house for rent in Stony Brook University

SINGLE_FAMILY - Ranch - Stony Brook, NY

44 Sycamore Cir, Stony Brook University, NY 11790

In-unit laundry | Outdoor space | Storage

3 beds

2 baths

$4,800

House for rent

15 Sherry Ln - Photo 1 of 1

5d+ ago

House for rent in Hauppauge

SINGLE_FAMILY - Colonial - Hauppauge, NY

15 Sherry Ln, Hauppauge, NY 11788

Outdoor space | Garage parking | Furnished

4 beds

2 baths

$5,300

$5,000

Price drop

House for rent

765 Meadow Rd - Photo 1 of 1

5d+ ago

House for rent in Smithtown

SINGLE_FAMILY - Ranch - Smithtown, NY

765 Meadow Rd, Smithtown, NY 11787

In-unit laundry | Outdoor space | Assigned parking

2 beds

1 bath

$2,900

House for rent

63 Hastings Dr - Photo 1 of 1

5d+ ago

Stony Brook house for rent in Stony Brook University

SINGLE_FAMILY - Cape Cod - Stony Brook, NY

63 Hastings Dr, Stony Brook University, NY 11790

In-unit laundry | Outdoor space | Storage

5 beds

2 baths

$4,200

House for rent

34 Huyler Rd - Photo 1 of 1

5d+ ago

House for rent in Setauket-East Setauket

Single Family Residence, Colonial - East Setauket, NY

34 Huyler Rd, Setauket-East Setauket, NY 11733

In-unit laundry | Garage parking | High ceilings

4 beds

2 baths

$6,900

House for rent

25 Jeremy Cir - Photo 1 of 1

5d+ ago

Lake Ronkonkoma townhouse for rent in Ronkonkoma

Condominium - Nesconset, NY

25 Jeremy Cir, Ronkonkoma, NY 11767

On-site laundry | Garage parking

2 beds

2 baths

$3,500

House for rent

Showing 1 - 25 of 25 results
Home > House Rentals in Head of the Harbor
Updated: January 21, 2026

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Discover houses for rent in Head of the Harbor, NY

🌇Available house rentals25 houses
💰Best rent deal305 Smithtown Boulevard #11
🍃With outdoor space
⭐Popular amenities, ,
👚With laundry facilities
🍽With dishwasher
🚗With garage parking
🏠With photos