Apartment holiday rentals in Shelter Island Heights

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

Beautiful duplex corner townhouse unit completely renovated in 2021 & in the heart of Bridgehampton Village. 2 min walk to shops, restaurants, main street and a bicycle ride to the beach. Situated all the way at the end of the building it provides ample privacy with Pool open July 4 - Labor Day only. Free parking (2 spots) w/ extra guest parking. Central air conditioning, private patio, ring doorbell/cam, self check in, curated kitchen w/ all supplies. Linens, towels, soap & shamp included

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

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.

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

Freeboard at Soundview · Beach+Ocean+Sunrise

Welcome to Freeboard Studio at Soundview, Old Colony Beach in Old Lyme, Connecticut. Located just 1 block from Old Colony Beach! The ultimate getaway for a couple seeking relaxation and outdoor beach adventures. This 2nd floor location is ideally situated with a queen memory foam bed, kitchenette w/ 50" TV, reading lamp and AC. Walk 1 block south and you are at the beach!

1856 Trading House w/ walk to water

Located in quaint, quiet Historic Mount Sinai. 2mi to Cedar Beach, 2mi to Downtown Port Jefferson, and 2mi to Train Station. Converted convent built in 1856 w/winter water view, across the street from Mt. Sinai harbor, low tide clamming and high tide kayaking and fishing. Next to Episcopal Friary. Antique hardwood floors. Parking available on Premises. Yard Access.

One Bedroom Apartment Nestled in the Dunes

Beautiful First-Floor Unit This beautiful first-floor unit is just a 1-minute walk to the heated pool and features a kitchen, air conditioning, and comfortably accommodates up to 2 guests (including kids or infants). It’s the perfect space for a peaceful and relaxing stay. Minimum 5-night stay.

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.

Montauk Oceanfront Condo

Relax and Enjoy the sounds of the ocean! This 1 Bedroom 2 bathroom condo offers ocean front accommodations, Private Deck, Beach, Lounge Chairs & Umbrellas. Onsite heated pool, BBQS, Sun deck, Food truck for breakfast & Lunch! 1 King bed & 1 Queen bed.