84+ Private Villas and Holiday Rentals in Head of the Harbor |
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Head of the Harbor Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Head of the Harbor

Discover more than 84 vacation rentals available in Head of the Harbor. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Head of the Harbor.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Head of the Harbor, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Head of the Harbor. On average, places to stay near Head of the Harbor offer 655.94 ft², with nightly prices averaging US $668.

With Casai, finding and comparing holiday rentals in Head of the Harbor is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Head of the Harbor

Type Count
Vacation Homes 41
Holiday Apartments 21
Cottages 3
Villas 2

Use these Quick Filters to Find a Holiday Rental in Head of the Harbor

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Head of the Harbor.

Weather in Head of the Harbor, NY

View the weather forecast for Head of the Harbor before booking your Head of the Harbor Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Head of the Harbor, NY

Casai offers a large selection of top attractions around Head of the Harbor . Research things to do on your vacation before you visit Head of the Harbor.


Avalon Park and Preserve
Harmony Vineyards
Stony Brook Grist Mill
Stony Brook University
Port Jefferson
Paramount Theater
Fairfield University
Lake Ronkonkoma
Norwalk Maritime Aquarium
Baseball Heaven
Oheka Castle
Tanger Outlets
Farmingdale State College
Webster Bank Arena
Sunken Meadow State Park
Historic South Norwalk
Robert Moses Beach
Adventureland
Ocean Beach
Sagamore Hill National Historic Site

Other Places to Stay in Head of the Harbor, NY


St. James 76 Properties
Avalon Park and Preserve 74 Properties
Stony Brook Grist Mill 74 Properties
Harmony Vineyards 73 Properties

Frequently Asked Questions About Head of the Harbor?

What are the top holiday rentals in Head of the Harbor?

With numerous options available in Head of the Harbor, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Head of the Harbor:

Which holiday homes in Head of the Harbor are best for families?

If you're searching for a family-friendly holiday home in Head of the Harbor, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Head of the Harbor:

How many Casai.nz holiday rentals are available in Head of the Harbor?

As of 2025, Casai boasts over 84 properties listed in the Head of the Harbor area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Head of the Harbor.


People Also Ask

There are 84 Head of the Harbor, NY Holiday Rentals

Recently Booked Holiday Rentals in Head of the Harbor