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Holiday home rentals in Long Island Sound

Find and book unique holiday home rentals on Airbnb

Top-rated holiday home rentals in Long Island Sound

Guests agree: these holiday home rentals are highly rated for location, cleanliness and more.

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Guest favourite
A serene beachfront landscape is captured during sunset, showcasing two adjacent houses with wooden exteriors. Soft sand and natural grasses lead to the water's edge, where the gentle waves reflect the warm colors of the sky, enhancing the tranquil atmosphere.
Holiday home in Fire Island
4.74 out of 5 average rating, 46 reviews

Bay Front Beach House 49E

Our beach front house located directly on the Great South Bay has its own private beach, swim area, outdoor shower, barbeque & boat mooring. The house is close to the ferry and easily accessible to restaurants and everything Fire Island has to offer. The house boasts 1 water front bedroom, 1/2 bath & washer/dryer on the main level upstairs; dining/living area(XL twin bed) full gourmet kitchen, 2nd WF oversized bedroom & full bath. Our guests can enjoy sweeping views of the bay, beach, and sunset

Top guest favourite
A spacious deck features multiple blue Adirondack chairs, all facing the tranquil waters of Long Island Sound. The horizon showcases a gentle gradient of pastel colors, signaling the transition from day to evening, while the calm water reflects the serene atmosphere.
Holiday home in Guilford
4.99 out of 5 average rating, 126 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 Warren
4.98 out of 5 average rating, 205 reviews

Private new house on 10 acres of pristine nature

Brand new home! Bring friends and family to this private and stylish place. House provides everything you need for a comfortable and peaceful stay. Fully equipped kitchen, inviting living spaces, large front and back yards with many exploring trails and a pond a few steps away from the house. Close to many 5 star restaurants, wineries, galleries and shops. Hiking, swimming, boating, skiing just to mention a few outdoor activities Close by: Kent School Mohawk Ski Area Lake Waramug High Watch

Guest favourite
A bright living area features high ceilings and large windows that provide views of the outdoors. A comfortable white sofa faces an outdoor deck, while a round dining table with upholstered chairs is positioned nearby. Natural light floods the space, enhancing its airy feel.
Holiday home in Amagansett
4.78 out of 5 average rating, 41 reviews

White Beach House- summer 2026 open!

This clean, bright, and airy cottage offers a serene escape with stunning views of Napeague Harbor. Just a short walk away lies one of the most beautiful ocean beaches The home feature- 3 comfortable bedrooms & 3 full bathrooms and an outdoor shower Inside, The cottage is well-appointed and designed. While the train from Amagansett to Montauk does pass behind the house, it does not obstruct the tranquil bay views. Please note: Due to health concerns, we are unable to accommodate animals.

Guest favourite
Holiday home in Elmont
4.83 out of 5 average rating, 129 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!

Superhost
Holiday home in East Hampton
4.71 out of 5 average rating, 114 reviews

17- Newly Built Gorgeous Private Apt-East Hampton

Our newly built, chic units are located in the beautiful iconic Village of East Hampton. We have 4 units available, please check other ones if this one is sold out. Very spacious studio unit with a queen bed. All units have been curated as a boutique hotel room, modern, beautiful and with everything you need for a great stay! Close to shops, beach, &short drive to Montauk. All units have memory foam mattress, wifi, smart TV(no cable just streaming aps) & a new kitchen with essentials!

Top guest favourite
Holiday home in New London
4.99 out of 5 average rating, 218 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

Top guest favourite
An inviting living area is presented, featuring a white brick fireplace as a focal point. Comfortable seating includes light-colored sofas adorned with varying throw pillows. Large windows allow natural light to fill the space, and double doors lead to the outdoor area.
Holiday home in Montauk
4.97 out of 5 average rating, 113 reviews

2 BR apartment near ocean in Hither Hills

Relax and enjoy a peaceful stay that is a 3 block walk to one of the most beautiful ocean beaches in the Hamptons! This apartment is located in a beautiful, wooded, quiet neighborhood. Town is 1.5 miles away. This apartment has an open concept living space with a fully equipped kitchen. There are 2 cozy bedrooms and one bath with a walk in shower. We prefer families and mature adults. We supply beach towels, chairs, umbrella and beach wagon.

Guest favourite
The spacious great room features a large stone fireplace, complemented by cathedral ceilings and wooden beams. Natural light enters through multiple windows, illuminating various seating areas. A cozy arrangement of chairs and a coffee table invites relaxation.
Holiday home in Salt Point
4.92 out of 5 average rating, 88 reviews

Riverfront rustic farmhouse near Rhinebeck

This historic Clinton Hollow house was built by Isaac Fraleigh in the late 1700's and overlooks the waterfalls of Wappingers Creek. The house has the architectural details of an antique colonial and the open, spacious feel of a modern contemporary. The great room with its big fireplace has different vibes and seating areas and is just perfect for family and friends gathering. The Petanque field in the garden add a fun convivial activity.

Guest favourite
A spacious living area is highlighted by vaulted wood ceilings and large windows, offering expansive views. A comfortable sectional sofa sits on a patterned area rug, with a wooden coffee table in the center. A brick fireplace adds warmth and charm to the room.
Holiday home in Napanoch
4.89 out of 5 average rating, 45 reviews

Cozy Catskills retreat w/views & fireplace

Gorgeous rustic retreat with a large indoor fireplace, mountain and pond views, just 1.5 hours from NYC. On almost 5 private acres with flowers and trees, you will feel like you are in your own sanctuary. Enjoy the large view-facing living room with working fireplace, vaulted and wood ceilings. An ample screened porch, expansive decking and outdoor firepit surrounded by Adirondack chairs. This home is the perfect reset!

Top guest favourite
A small enclosed garden area features a wooden table and chairs surrounded by greenery. A barbecue grill is positioned on one side, while sliding glass doors provide access to the interior. The space is enclosed by wooden privacy fencing, enhancing the tranquil atmosphere.
Holiday home in Beacon
4.99 out of 5 average rating, 97 reviews

Private, modern carriage house. Great for couples.

Newly built in 2022, our charming, modern carriage house is tucked away within a small courtyard garden on a quiet residential street in the heart of Beacon NY. Guests will enjoy an efficient, elegantly designed and furnished interior with views of the Mount Beacon ridgeline from this comfy and private abode. The owners are long-time Airbnb hosts who work hard to ensure their guests have a peaceful, relaxing stay.

Superhost
Holiday home in Asbury Park
4.88 out of 5 average rating, 113 reviews

1 Bedroom Apt with Private Roof Deck Near Beach

This newly renovated 1 bedroom apartment has everything needed for your beach getaway. The property is located a 5 minute walk from the boardwalk and beach and includes 2 adult beach badges with beach blanket and 2 beach towels. Downtown with plenty of restaurants and bars is only about a 10 minute walk. Feel like staying in? Our private roof deck is the perfect place to relax for a quiet dinner in.

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