Head of the Harbor holiday rentals, St. James: holiday houses & more

Discover a selection of holiday rentals in Head of the Harbor that are perfect for your trip. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as parking and a fireplace. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

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Find the best place to stay - Head of the Harbor

Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters

Sleeps 12 · 5 bedrooms · 3+ bathrooms

Designer beach cottage & studio with bikes, outdoor shower, deck - walk to beach

Sleeps 12 · 5 bedrooms · 1+ bathroom

Top rated rentals - Head of the Harbor

Lovely property

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Book a holiday rental for your Head of the Harbor getaway

Enjoy the wineries and other features of Head of the Harbor. One of the city's many top draws is its parks. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Head of the Harbor

Are you hoping to find things to do in the city? Venture out of your cosy holiday rental and experience everything that makes Head of the Harbor a fun place to get away to. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

Stonebridge Golf Links and Country Club (6 mi / 9.7 km)
Town of Brookhaven Wildlife and Ecology Center (9.6 mi / 15.5 km)
Cold Spring Harbor Laboratory (16.5 mi / 26.6 km)
Adventureland (17.2 mi / 27.7 km)
Boomers! Medford (11 mi / 17.7 km)
Bowl Long Island at Patchogue (12.3 mi / 19.8 km)

Exploring the natural landscape of Head of the Harbor

Whether you're an outdoor enthusiast or just want to take in the scenery, Head of the Harbor is a great spot to appreciate mother nature. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

Avalon Park and Preserve (0.5 mi / 0.8 km)
Sunken Meadow State Park (5.3 mi / 8.5 km)
Private (5.5 mi / 8.8 km)
Lake Ronkonkoma (5.8 mi / 9.3 km)
Bayard Cutting Arboretum State Park (10.9 mi / 17.5 km)
Fire Island National Seashore (12.6 mi / 20.3 km)

Transport options to and around Head of the Harbor

The nearest airport is in Islip, NY (ISP-MacArthur), located 8.5 mi (13.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Shirley, NY (WSH-Brookhaven Calabro), which is 15.9 mi (25.5 km) away.

Frequently asked questions

How much does it cost to rent a holiday rental in Head of the Harbour?

Length of stay, season and property type are some things that can determine the price of a holiday home. Simply enter your travel dates to find your ideal fit. From comfy cottages to sprawling villas, all Vrbo holiday rentals provide unbeatable value.

How much does it cost to rent a beach house in Head of the Harbour?

Prices for beach houses in Head of the Harbour vary depending on the size and style of the property and when you plan to travel. All you need to do is enter your travel dates into Vrbo and how many guests to see your options and prices. From there you can use our filters to refine your search results by ratings, amenities, nearby activities and more.

What are the top attractions for families in Head of the Harbour?

There's no time to get bored during your Head of the Harbour holiday with these family-friendly attractions:

Short Beach
Avalon Park and Preserve

How old do you have to be to rent a holiday rental in Head of the Harbour?

The minimum age requirements can differ between properties on Vrbo, so be sure to look at the rules of the holiday home in Head of the Harbour you want to book. But usually, it's 16, 18 or 21.

How long can I rent a holiday rental in Head of the Harbour for?

It's down to the Head of the Harbour property. To browse a list of options offering extended stays, simply enter your dates and number of people into Vrbo's search page. You can enjoy having the whole place to yourself, along with amenities such as air conditioning, a fully-equipped kitchen and a yard where the kids can run and play. Keep your eyes peeled for any long-term stays that offer weekly or monthly discounts.