Long Island, New York, stretches east of New York City and offers a diverse coastal experience that blends beach life, cultural richness, and suburban comfort. Whether you're headed for the Hamptons, North Fork wine country, or historic seaside towns, there’s a perfect vacation rental waiting. Guests can choose from oceanfront homes, charming cottages, modern apartments, or family-friendly Airbnbs nestled in quiet neighborhoods. Long Island offers a refined yet relaxed getaway, with something for every traveler.
Good to know: Visit and neighborhood recommendations in Long Island
From the glitz of the Hamptons to the rustic farms of the North Fork, Long Island caters to a wide range of tastes and adventures. Visitors can surf Atlantic waves, tour lighthouses, sip local wines, or indulge in fresh seafood by the marina. Museums, historic mansions, and lively downtowns enrich the inland areas, while the coastlines provide peace and recreation. Long Island feels like a true escape while staying close to the buzz of the city.
Top areas to stay at in Long Island
The Hamptons
Synonymous with luxury and beach culture, the Hamptons include villages like East Hampton, Southampton, and Montauk. Visitors can rent upscale Airbnbs ranging from chic beach houses to country estates with pools. The area offers high-end dining, art galleries, and some of the most beautiful beaches in New York.
North Fork
North Fork is Long Island’s wine region, dotted with family-run vineyards, quaint farms, and harbor towns. Vacation rentals include farmhouse stays, cozy cottages, and waterfront homes with serene views. It's a more laid-back alternative to the Hamptons, ideal for wine tastings, farm-to-table dining, and biking through the countryside. North Fork is perfect for romantic getaways and scenic retreats.
Fire Island
Accessible by ferry, Fire Island is a car-free barrier island with stunning beaches and iconic boardwalks. Rentals here often include beach cottages and bungalows within steps of the ocean. The island has a welcoming, inclusive vibe with lively communities like Ocean Beach and Cherry Grove.
Port Jefferson
Located on Long Island’s north shore, Port Jefferson is a walkable harbor town filled with boutiques, cafes, and ferry views. Vacation rentals include waterfront apartments and charming historic homes. The town also offers kayaking, music festivals, and cozy coastal vibes year-round.
Long Beach
Closer to New York City, Long Beach offers a wide sandy shoreline, a bustling boardwalk, and a laid-back surf culture. Airbnbs include condos with ocean views, beach houses, and modern studios. The area is perfect for quick getaways, especially for NYC residents craving sea and sun.
Must-visit places and attractions in Long Island
Montauk Point Lighthouse
At the eastern tip of Long Island, this historic lighthouse offers sweeping ocean views and a glimpse into maritime history. Visitors can tour the museum, climb to the top, and explore surrounding beaches and trails. It’s one of the island’s most iconic landmarks.
Old Westbury Gardens
This magnificent estate features a historic mansion, formal gardens, and fountains set on 200 acres. Guided tours reveal the Gilded Age lifestyle, while seasonal events bring in art, music, and nature. It’s a peaceful and elegant destination in western Long Island. Visitors of all ages will enjoy the serene beauty.
Long Island Aquarium
Located in Riverhead, this attraction features marine life exhibits, shark dives, and a butterfly garden. Families can explore touch tanks, interactive experiences, and educational shows. It’s a fun and educational stop for kids and adults alike. The aquarium anchors Riverhead’s growing downtown scene.
Robert Moses State Park
This beachfront park offers soft sand, fishing piers, nature trails, and lighthouse tours. With fewer crowds than other beaches, it's a favorite among locals. Visitors can surf, sunbathe, or walk along the shoreline dunes.
Long Island Wine Country
Stretching across the North Fork, wine country features dozens of vineyards offering tastings, live music, and farm-fresh food pairings. Guests can tour wineries like Bedell Cellars or Sparkling Pointe and enjoy laid-back afternoons in scenic settings.
Jones Beach State Park
One of the most popular beaches in the state, Jones Beach features miles of sandy coastline, boardwalks, and summer concerts at the amphitheater. Facilities include snack bars, playgrounds, and outdoor showers. It’s a classic beach day destination close to the city.
Sagamore Hill National Historic Site
The former home of Theodore Roosevelt, this historic estate in Oyster Bay offers guided tours, museum exhibits, and walking trails. Visitors can learn about Roosevelt’s life and presidency in the home he called his “Summer White House.” The grounds are great for a picnic or leisurely stroll.
Planting Fields Arboretum
This public garden in Oyster Bay boasts greenhouses, woodland trails, and beautifully maintained lawns. The Coe Hall historic mansion is also open for tours. Planting Fields is perfect for nature walks, seasonal blooms, and quiet afternoons.
Where to Find a Vacation Rental Near Long Island
New York City, New York
Just west of Long Island, New York City needs no introduction. Visitors can explore Central Park, Times Square, and world-class museums before escaping to the island’s peaceful shores. It’s an ideal urban counterpoint to Long Island’s coastal calm. Stay in an apartment in New York City to enjoy iconic energy before retreating to the coast.
Stamford, Connecticut
Located across the Long Island Sound, Stamford offers a mix of beaches, corporate centers, and a growing arts and dining scene. Ferries connect to Long Island, and the city has easy train access to New York City. It’s a great jumping-off point for regional exploration. Travelers often relax in a vacation rental in Stamford that balances shoreline calm with city access.
Bridgeport, Connecticut
Just north by ferry, Bridgeport offers attractions like the Beardsley Zoo and waterfront Seaside Park. It’s a historic industrial town with cultural institutions and growing redevelopment. It provides an alternative gateway to Long Island’s eastern shores. Enjoy an affordable getaway in a house in Bridgeport close to ferries and parks.
Shelter Island, New York
Located between the North and South Forks, Shelter Island is accessible by ferry and offers a peaceful, nature-rich setting. Visitors can stay in beach houses, cottages, and tucked-away Airbnbs with island charm. It’s perfect for kayaking, biking, or simply disconnecting. Discover calm mornings and sea breezes from a vacation rental in Shelter Island surrounded by trails and coastal inlets.
New Haven, Connecticut
About two hours north via ferry and road, New Haven is known for Yale University, art museums, and historic New England ambiance. Travelers can enjoy pizza tours, theater, and architectural walks. It’s a cultural detour that pairs well with a coastal escape. Settle into an airbnb in New Haven within reach of ivy-covered halls and lively eateries.
Embark on an exploration of vibrant island activities and ecosystems
The pristine beaches invite water enthusiasts to dive into myriad exciting aquatic experiences. In the pleasing surf of Playa Pelada, surfers can embrace the symphony of waves with a comfortable Playa Pelada airbnb. Equally captivating is the sheltered cove of Playa Potrero, offering serene sailing adventures with its enticing Playa Potrero vacation rentals.
Contemplating the ocean's depth, this destination is a splendid gateway to diving and snorkeling. Immerse yourself in the crystalline waters by exploring the diverse marine ecosystems found via accommodations like Bayahibe airbnb, swim alongside the vibrant marine life at the French territory with vacation rentals in Guadeloupe, or discover the coral gardens with Cayman Brac airbnb. Enhance your underwater escapades with fascinating dives close to holiday homes Bimini.
Its Caribbean location connects you to lush island getaways. Consider settling into the tranquil hideaways found through Cayman Islands airbnb, where the shores invite solitude and reflection. For a lively cultural flavor, take to the sun-drenched beaches available among places to stay in Martinique or venture into mystic retreats with vacation rentals Montserrat.
Apart from the azure waters, this location opens a realm of natural splendor rich in wildlife. Discover flourishing fauna with vacation rentals in Salem as your sanctuary in Jamaica's lush settings. Observe diverse species basking in their natural habitat while staying at Playa Avellanas airbnb, or explore the historic essence amid quiet landscapes through vacation rentals in Sint Eustatius, where nature thrives uninterrupted.