Short-Term Rentals in Head of the Harbor, NY: Compare 10+ Sites & Save

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38 Best Short-Term Rentals in Head of the Harbor (Starting from $97)

Duplex Studio Apartment
Duplex Studio Apartment
Apartment
Smithtown, NY, USA
4.5k from Head of the Harbor center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

1 Bedroom4 Guests
9.0

Fabulous

1 reviews

$97
Average price / night
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The Bella Vista St James! Waterfront house with a beach dock and so much more!
The Bella Vista St James! Waterfront house with a beach dock and so much more!
House
Saint James, NY, 11780, United States
0.9k from Head of the Harbor center

AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$1819
Average price / night
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Dreams of Paradise Luxury Home with Pool!
Dreams of Paradise Luxury Home with Pool!
House
NY, USA
5.2k from Head of the Harbor center

Luxury, Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings

4 Bedrooms10 Guests
New to Booking
$892
Average price / night
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Modern 1 bedroom apartment near Stony Brook university hospital walking distance
Modern 1 bedroom apartment near Stony Brook university hospital walking distance
House
Stony Brook, NY, 11790, United States
2.6k from Head of the Harbor center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$843
Average price / night
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Blue Cottage East Setauket
Blue Cottage East Setauket
House
Setauket, NY, USA
5.4k from Head of the Harbor center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs, Places to stay

5 Bedrooms10 Guests
New to Booking
$346
Average price / night
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WATERFRONT ESTATE... 60 Minutes from NYC and HAMPTONS
WATERFRONT ESTATE... 60 Minutes from NYC and HAMPTONS
House
St James, NY, 11780, United States
2.7k from Head of the Harbor center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

6 Bedrooms10 Guests
New to Booking
$11452
Average price / night
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Comfort Stay by Stony Brook University & Hospital
Comfort Stay by Stony Brook University & Hospital
Apartment
Centereach, NY, USA
8.5k from Head of the Harbor center

Air Conditioner, Parking, Barbecue/Outdoor Cooking, Transportation/Shuttle, Pet Friendly, Bar, Guest Services

2 Bedrooms5 Guests
New to Booking
$225
Average price / night
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Beautiful Private Room Near Stony Brook University
Beautiful Private Room Near Stony Brook University
Apartment
Stony Brook, NY, 11790, United States
2.8k from Head of the Harbor center

AC, Free Parking, Heater, Hot Tub, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$238
Average price / night
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Tranquil and Pet-Friendly Estate on Long Island!
Tranquil and Pet-Friendly Estate on Long Island!
House
Hauppauge, NY, USA
8.7k from Head of the Harbor center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms8 Guests
8.0

Good

1 reviews

$430
Average price / night
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3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches
House
Stony Brook, NY, 11790, United States
2.9k from Head of the Harbor center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
7.4

Good

3 reviews

$567
Average price / night
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Stylish 2BR House Near Stony Brook University and shopping, fully renovated
Stylish 2BR House Near Stony Brook University and shopping, fully renovated
House
Stony Brook, NY, 11790, United States
3.2k from Head of the Harbor center

AC, Dryer, Fireplace, Heater, Internet, Laundry, Microwave, No Smoking, TV

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$770
Average price / night
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Stylish 4BR house near Stony Brook University & Hospital
Stylish 4BR house near Stony Brook University & Hospital
House
Stony Brook, NY, 11790, United States
3.6k from Head of the Harbor center

AC, Barbecue, Heater, Internet, Microwave, No Smoking, Toys, TV

1 Bedroom2 Guests
New to Booking
$989
Average price / night
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Charming 1 bedroom Stony Brook cottage -walking distance to village & university
Charming 1 bedroom Stony Brook cottage -walking distance to village & university
Cottage
Stony Brook, NY, 11790, United States
4.2k from Head of the Harbor center

AC, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Patio

1 Bedroom4 Guests
10.0

Exceptional

7 reviews

$285
Average price / night
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Cozy Riverside Cottage
Cozy Riverside Cottage
Cottage
Kings Park, NY, 11754, United States
5.1k from Head of the Harbor center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

4 reviews

$342
Average price / night
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'Dreams of Paradise' Luxury Home w/ Pool!
'Dreams of Paradise' Luxury Home w/ Pool!
House
Lake Grove, NY, 11755-1901, United States
5.2k from Head of the Harbor center

AC, Arcade, Crib, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry

4 Bedrooms10 Guests
9.6

Exceptional

5 reviews

$1291
Average price / night
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Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Apartment
Kings Park, NY, 11754, United States
5.4k from Head of the Harbor center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

19 reviews

$178
Average price / night
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The Suite at North Shore Long Island, Prime Location, Unique and sophisticated
The Suite at North Shore Long Island, Prime Location, Unique and sophisticated
Apartment
Smithtown, NY, 11787, United States
5.6k from Head of the Harbor center

AC, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
9.8

Exceptional

8 reviews

$185
Average price / night
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Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
Apartment
Smithtown, NY, 11787, United States
5.8k from Head of the Harbor center

AC, Heater, Internet, Living Area, No Smoking, TV

2 Bedrooms4 Guests
6.8

Good

3 reviews

$229
Average price / night
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Spacious Modern Style Complex
Spacious Modern Style Complex
Apartment
Centereach, NY, 11720, United States
5.8k from Head of the Harbor center

AC, Free Parking, Heater, Internet, Living Area, Microwave, No Smoking, Patio, TV

1 Bedroom2 Guests
9.0

Fabulous

45 reviews

$108
Average price / night
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Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
House
Centereach, NY, 11720, United States
6.4k from Head of the Harbor center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
10.0

Exceptional

46 reviews

$548
Average price / night
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Spacious Home Located Close to Stony Brook!
Spacious Home Located Close to Stony Brook!
House
Lake Grove, NY, 11755, United States
6.4k from Head of the Harbor center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
7.8

Good

27 reviews

$403
Average price / night
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Updated top level apartment - modern design with open floor plan
Updated top level apartment - modern design with open floor plan
Apartment
Kings Park, NY, 11754, United States
6.8k from Head of the Harbor center

AC, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio

2 Bedrooms4 Guests
10.0

Exceptional

8 reviews

$334
Average price / night
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Private 1 bedroom apt in a quiet neighborhood, close to all!
Private 1 bedroom apt in a quiet neighborhood, close to all!
Apartment
Centereach, NY, 11720, United States
7.0k from Head of the Harbor center

AC, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom4 Guests
9.6

Exceptional

26 reviews

$246
Average price / night
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Charming 1-bedroom house in Ronkonkoma with AC, WiFi, Washer & Dryer
Charming 1-bedroom house in Ronkonkoma with AC, WiFi, Washer & Dryer
House
Ronkonkoma, NY, 11779, United States
8.1k from Head of the Harbor center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom4 Guests
9.0

Fabulous

6 reviews

$322
Average price / night
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Spacious one Bedroom Apt with  private entrance
Spacious one Bedroom Apt with private entrance
Apartment
Centereach, NY, 11720, United States
8.4k from Head of the Harbor center

AC, Barbecue, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, TV

1 Bedroom4 Guests
7.8

Good

10 reviews

$343
Average price / night
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Charming 3-bedroom house with WiFi and AC in Ronkonkoma, Lake views.
Charming 3-bedroom house with WiFi and AC in Ronkonkoma, Lake views.
House
Ronkonkoma, NY, 11779, United States
8.4k from Head of the Harbor center

AC, Free Parking, Heater, Internet, Kitchen, No Smoking, Patio, TV

3 Bedrooms8 Guests
10.0

Exceptional

25 reviews

$485
Average price / night
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Cozy studio in enjoyable Lake Ronkonkoma area with AC and parking provided.
Cozy studio in enjoyable Lake Ronkonkoma area with AC and parking provided.
Apartment
Lake Ronkonkoma, NY, 11779, United States
8.4k from Head of the Harbor center

AC, Heater, Internet, No Smoking

New to Booking
$461
Average price / night
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Other accommodation types in Head of the Harbor:

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Head of the Harbor.

Head of the Harbor Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 38 verified short-term rentals in Head of the Harbor, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Head of the Harbor vary depending on location, property size, and travel dates. Rates typically start from around $97 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Head of the Harbor include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Head of the Harbor, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Head of the Harbor often include amenities such as Fireplace/Heating, Wellness Facilities, and Bedding/Linens, providing a comfortable and convenient stay.

Short-term rentals in Head of the Harbor are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.