
Holiday home rentals in Long Island Sound
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Top-rated holiday home rentals in Long Island Sound
Guests agree: these holiday home rentals are highly rated for location, cleanliness and more.

Bay Breeze-Mins from Beach, Towns and Activities
Hot tub all year! Close to Shinnecock Hills (US Open '26). Message about full season rentals at an amazing price. This 4 br/2 bth home boasts a new kitchen, garage, indoor fireplace, beach chairs (6), beach umbrellas (3), and fenced backyard. Wifi, soaps, linens, and coffee provided. Bedrooms have BeautyRest mattresses and blackout curtains. Short walk to East Landing Beach and drive to all towns. Red Creek Park, wineries, golf, outlets, and farms are all nearby. NO SMOKING/PARTIES/LOUD MUSIC

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.)

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

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.

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.

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!

The Dahlia Villa within Westerhall Gardens
Reconnect with nature at this unforgettable escape. A gorgeous mature garden in a park like setting. Two queen bedrooms, great room, 75 inch TV. Radiant bathroom floor. Outdoor 45,000 gallon salt pool…that’s shared with other property (summer months - POOL IS FOR REGISTERED GUESTS ONLY - NO EXCEPTIONS) Decompress in our sauna. This a no smoking/vaping property. A sprawling 17plus acre estate. Dahlia Villa is a beautiful two bedroom completely independent unit on the estate.

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

Newport Condo with Harbor View and Rooftop Deck!
A beautiful, bright and sunny space with 2 bedrooms and 2 full baths. This 3rd floor condo has sweeping views of Newport's bustling harbor and vibrant downtown areas. With vaulted ceilings and many windows, this condo offers a rare birds eye view of the city. The open layout is filled with light pouring in everywhere. The beautiful rooftop deck offers spectacular views of Newport harbor! Great option for couples. Parking for one car is included!

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.

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.

UNIQUE and GORGEOUS historic loft style rental
Beautifully bright third floor loft style space with private entry available for your enjoyment. Basic kitchen, laundry, and bath are located on the second floor. Due to the stairs in this unique space, it would be ideal for a single traveler or couple looking for a getaway. Walkable to historic Woodbury, minutes to amazing land trust hiking trails in Roxbury, and only 1.5 hours from NY City.
Popular amenities for holiday home rentals in Long Island Sound
Family-friendly holiday home rentals

Seaside Getaway! 3 Blocks to Beach +Washer/Dryer

Dreamy Catskills mountain getaway w/ yoga studio

1/2 Block From the Beach, Pool, Game Room, Parking

2 Bed Apt * Walk to Rides, Waterpark, Golf, Beach

Beach Getaway | The Escape @ Ocean Gate

Berkshire Getaway Vacation rental

John Clarke House -1870- 2nd Floor 2 Bedroom 3 Bed

Dupont Beach House C
Holiday home rentals with a patio

Ocean Cove

Large Private Hidden Estate! 30+ ppl, HotTub, Pool

Gorgeous renovated 4 bedroom house in Ocean Grove

The Hideout, Westhampton Beach Coastal Getaway

Cozy Catskills retreat w/views & fireplace

Kingston/Woodstock Oasis: Pool, Hot Tub, Game Room

Serene 4-bdrm lake house

Lakefront Vacation 4-bedroom home w/boat house
Holiday home rentals with a washing machine and dryer

Renovated Victorian Home 5 mins walk to the beach!

The Perfect Shelter Island Getaway! With Pool

Bay Front Beach House 49E

Renovated North Fork Retreat-Rental Permit #0781

Vacation home steps from the beach

Dreamy 1-Bedroom Bradley Beach Hideaway

Oceanview Townhouse, steps away from the beach

Cute 3 bedroom house with screen porch
Destinations to explore
- Boutique hotels Long Island Sound
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- Rentals with lake access Long Island Sound
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- Rentals with an accessible-height bed Long Island Sound
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