Apartment holiday rentals in Shelter Island Heights

Waterfront Summer Escape in Wine Country: 2BR

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on your private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

Endless Summer Studio Condo w Balcony Bayview

Look no further for your perfect holiday in Montauk! This stylishly renovated large waterfront studio condo has everything you need for a truly amazing stay because there’s no place like home, except for the beach. This gated waterfront complex includes tennis courts, a heated swimming pool, hot tub, fishing pier with a gazebo, BBQ by the beach waiting for you to have a lobster bake, walking trails, an on-site laundry room and parking. Get sand on your toes and let the Mtk sun kiss your nose!

Greenport Getaway at Cliffside Condos

Welcome to our Cliffside condo in Greenport, a comfortable 2-bedroom retreat perfect for families and friends. The home features a queen bed in the primary bedroom, two twin beds in the second bedroom, and a pullout sofa in the living area. Enjoy easy access to the private beach, seasonal pool, BBQ on the great lawn and the most beautiful sunsets over the Long Island Sound. You’re just minutes from Greenport’s shops, restaurants, and vineyards, an ideal North Fork getaway to relax and unwind.

Montauk Waterfront Condo w/ Sunset Views

Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool / sauna / jacuzzi only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

Beautiful Waterview Condo on the North Fork of LI

Waterview luxury suite accommodates up to 6 guests with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. This location is minutes from town as well as wineries and centrally located to the ferry which can take you to Shelter Island and the South Fork. The resort is well maintained with a pool , BBQ grills and private beach access as well as ample parking for guests.

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

This is our 5th season as the owners of Unit #126, which is of the nicest units at Montauk Manor. We are hosting our 925 sq. ft. one BR loft corner unit with a cathedral high ceiling, brand new kitchen and bathrooms plus with a sleeper sofa and TVs on both floors. Montauk Manor is an amazing property that features 3 tennis courts, indoor & outdoor pools, a nice sized fitness center, an on-site restaurant/bar and much more!

Beautiful condo on Long Islands Northfork

This condo is beautifully decorated and has a wonderful stone fire place. Gorgeous shiplap walls with Navy accents. There is also a new deck and wonderful dinning set outside. This unit has capabilities to be handicap accessible. Both bedroom have private bathrooms. The living room sectional opens up to a full sleeper making this condo able to sleep six people. All rooms have flat screen smart tv's.

Beautiful Condo on the Ocean Bluffs

Located just outside of town on Old Montauk Highway that runs along the ocean. Just a 10 minute walk to town, enjoy a private beach, beautiful grounds and stunning pool. Located at the Atlantic Bluffs Club, one of the nicest private condo facilities in Montauk, you get to enjoy the peace and tranquility of Montauk yet you’re just a short walk to the village with its restaurants, shops and nightlife.

Newly Renovated Modern Townhouse w/Pool & Tennis

Newly renovated townhouse minutes from main street & the beach. 2 bedroom, brand new kitchen & appliances, living room w/fireplace in beachy grey & cream tones will make you feel right at home. Includes a pool & tennis court steps out the front door. Less than a 10 min drive to Shinnecock Hills Golf Club, you can easily enjoy the upcoming US Open Championship. July:$23,000 August: $25,000

Waterfront Elevated Bungalow - Spectacular Views

Bright, skylit, sunny, and clean bay-front apartment with gorgeous water and sunset views. Large private wraparound deck, spacious living room, kitchenette, two full bathrooms, and a California-king size bed. Less than 250 feet from bay and 3.5 miles from ocean beaches! Two week minimum. Large discount for full summer stay.

Deluxe Studio Apt@The Montauk Manor

Beautiful, deluxe studio apartment with every amenity. Registered historical landmark. Magnificent lobby with fireplace, restaurant. Cable TV with HBO, DVD and WI FI. Great news the in-door pool, jacuzzi and sauna are now open! The restaurant is now open! Don’t miss out on the fabulous beaches.

Waterfront Condo C-204 at The Cliffside Resort

Water's Edge luxury suite with amazing waterfront views, Suite C-204, accommodates up to 6 guests (See The Space below) with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York.