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Holiday Homes in Long Island

Find and book unique holiday homes on Airbnb

Top-rated Holiday Homes in Long Island

Guests agree: These holiday homes are highly rated for location, cleanliness and more.

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Top Guest favourite
Holiday home in Quogue
5 out of 5 average rating, 25 reviews

The Hideout, Westhampton Beach Coastal Getaway

Welcome to the Hideout! This beautiful Hamptons getaway is the perfect escape for a staycation or vacation. The Hideout is a calm coastal design that will bring peace and serenity to anyone. This property features a gym, pool, hot tub, laundry room, and tennis court. There is also a desk with a printer, in case you have some work to do. It is about a 10 minute drive to Westhampton Main St. with food and shopping spots. It is about 8 min driving to Quogue Village beach (2.6 miles from the house)

Top Guest favourite
Holiday home in Guilford
4.99 out of 5 average rating, 116 reviews

Spacious Oceanfront Getaway with Spectacular Views

Perfect vacation getaway! Awaken to the sun rising over Long Island Sound! Panoramic waterfront views from 70 ft of windows spanning NY to RI. Quiet, private, updated home, NOT a cottage: >2200 sq ft, single level 3B/3B, + bonus lower-level walk-out/office. Master bed double shower/jacuzzi overlooking the water! Multiple oceanfront decks. 100 ft granite shoreline, short stroll to nearby sand beaches. Swim, fish, read a book, or watch the sailboats go by! (Not suitable for children/pets/events.)

Top Guest favourite
Holiday home in Long Beach
5 out of 5 average rating, 56 reviews

Beautiful 2-Bedroom/2 bath apartment in Long Beach

Year round treasure - kick back/relax in this calm, stylish apartment located in an Historic Long Beach home just over the road to the fabulous Boardwalk and beach. Perfectly situated on a quiet residential block in a beautiful, safe neighborhood, walking distance to local shopping, restaurants & entertainment. Come for the sun/sand or escape to an ideal live/work environment. Enjoy free Beach Concerts, local Farmer's Market, surfing, kite boarding, golf, fishing, kayaking ice skating & more.

Superhost
Holiday home in Stonington

Location, Location, Location - steps to Mystic

Steps from the famous Mystic Draw Bridge. Enjoy a stylish stay in at this centrally-located apt, walk to town and stumble home! Freshly painted open layout apt with recess lighting, Pottery Barn lounge sofa, 2 bedrooms, 2 full bathrooms and AC!! Full kitchen with airfryer, microwave and cooking essentials. Flat screen tv, wifi and Netflix, HBO, Hulu and Disney+. Washer and dryer is included but shared with the downstairs tenant. No outside access. No parties and no parking in driveway.

Guest favourite
Holiday home in Montauk
4.91 out of 5 average rating, 56 reviews

Private Entrance to Duplex Apartment on Lush Acres

Private Exterior Entrance to QUEEN BED bedroom and private bath ONE FLIGHT OF STAIRS UP. 1 mile to Ditch, half mile to L.I. Sound. Quiet, Out-of-the-way 1900s house on Several Acres. 100% non-smoking both inside and out. Friendly DOGS WELCOME provided they do not chew, scratch, bark when left alone, are picked up after outside and are kept OFF furniture. NO UN-HOUSEBROKEN PUPPIES. WE ACCEPT DOGS ONLY. NO CATS OR OTHER PETS. NO EXCEPTIONS. Friendly Dogs & Chickens live on property. 2 NIGHT MIN

Superhost
Holiday home in Miller Place
4.84 out of 5 average rating, 31 reviews

THE MULBERRY OASIS

Bring your family to the custom luxurious mansion on Long Island carefully curated furnishings. No need to lift a finger - wonderfully comfortable and professionally decorated spaces are ready for you to enjoy. Many bespoke items such as a large crystal entry chandelier- custom living room furniture that add unique character and charm. Amazing entertainer's kitchen with gray cabinet. A premier basement with amazing entertainer's, pool table, game table, theater room, exercise /sauna room.

Superhost
Holiday home in Elmont
4.8 out of 5 average rating, 112 reviews

Lovely 2-Bedroom Elmont Apartment (Lower Level)

Enjoy this centrally-located lovely full 2-bedroom private lower level apartment. With 2 Queen sized beds, this space can host up to 4 people comfortably. Ideal for travelers or families visiting NY. Located in a quiet neighborhood. In the center of many shops, restaurants, highways. This apartment is located 7 minutes away from the USB Arena, 10-15 minutes away from JFK airport, and in close proximity to Roosevelt Field Mall and Green Acres Mall. The next adventure is never too far away!

Top Guest favourite
Holiday home in Montauk
4.99 out of 5 average rating, 108 reviews

2 BR apartment near ocean in Hither Hills

Relax and enjoy a peaceful stay that is a short , 3 block walk to one of the most beautiful ocean beaches in the Hampton's! This apartment is located in beautiful, wooded quiet neighborhood. It is a short drive into town where you will find restaurants and shops. This apartment has an open concept living space with a fully equipped kitchen with everything you need ,2 cozy bedrooms and one bath with a walk in shower. We supply beach towels, chairs, umbrella and beach wagon.

Top Guest favourite
Holiday home in Highlands
4.96 out of 5 average rating, 116 reviews

2BR Oceanview Shore House, walk to beach/nightlife

** Beautiful newly renovated 2 bedroom that is walking distance from the NYC ferry, numerous bars and restaurants with live music, and steps away from the beach. Come explore the Highlands, where small town charm meets the Jersey shore. Everything is walking distance in this 1 square mile town. Enjoy waterfront restaurants , night life, tiki bars, fishing, kayaking, biking on the Henry Hudson Trail, hiking in Hartshorne Woods Park, and of course Sandy Hook Beaches.

Guest favourite
Holiday home in Westerly
4.93 out of 5 average rating, 46 reviews

Comfy Spacious Home Close to Beach

Only 1 mile from the Water and Breachway. Just minutes from excellent ocean views, scenic RI Shoreline, and local wildlife. Plenty to do with beaches, kayaking, fishing, and Historic Watch Hill. Kick back and relax, chill on the deck, and have a great time! The home is very close to shopping and local restaurants, offers a full kitchen and bath, towels and beach chairs for your convenience. Several board games, and books are provided too. Comfy, open, space to Enjoy!

Guest favourite
Holiday home in Greenport
4.91 out of 5 average rating, 47 reviews

Walk to town, Marina Views, Greenport Village

Enjoy this beautifully renovated first floor “Captains House” apartment in the heart of Greenport Village. Harbor Views! Walk to town. This 2 bedroom, 2 full bathroom home is bright with sunshine, has soaring ceilings and hard wood floors, easy to maintain for beachside living. Gourmet kitchen - top of line appliances -wolf stove. Primary Bedroom - King Size bed, en-suite beautifully tiled full bathroom. 2nd bedroom has 2 Full size beds. Fenced in backyard.

Top Guest favourite
Holiday home in New London
4.99 out of 5 average rating, 205 reviews

Modern & Cozy Beach House - Walk to Ocean Beach

Welcome to our modern and cozy vacation apartment in a quiet community just a 5 minute walk to Ocean Beach! ~Special features~ • Dog-friendly! Fully fenced backyard • Central Air Conditioning • New in-unit washer/dryer • 2 BR w/Queen Tuft&Needle mattresses • Futon and couch both fold into add’l beds • Gourmet kitchen; fully equipped & open concept island seating • Coffee bar w/complimentary K-cups • Patio seating area w/firepit & charcoal grill

Popular amenities for Long Island holiday homes

Destinations to explore