Condo holiday rentals in Shelter Island Heights

Montauk Retreat - Steps from Beach and Town

This 2nd floor 2-room suite across the street from the beach is steps to shops, restaurants & more! The bedroom & living room are separated by a galley kitchen. Heated pool is open through Columbus Day, allowing you to take advantage of those last warm days. Includes toiletries, beach towels & chairs, a fully stocked kitchen with a Keurig and tea kettle, & board games! Features a queen-sized bed and pull-out sofabed, a large smart TV, fast WiFi, dining table and terrace overlooking the pool.

Harper House Heart of DT Mystic Luxury Getaway

Historic Downtown Mystic. This immaculate designed winter retreat is professionally managed and offers an enjoyable winter stay. Just steps to Deep Water Marinas, Fine Restaurants including Captain Daniel Packer Inn, SIFT Bakery, Train Station, and Unique Shops. This modern apartment features a fully equipped high-end kitchen with a microwave, blender, toaster, cooking essentials, and a Keurig machine. 1 on-site parking space and a shared common backyard space if available for your enjoyment.

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)

Coastline View Studio

This sun drenched studio apartment is perfect for families, couples or friends looking to get away and discover Montauk! Located in Montauk's harbor district. This unit is perfectly located to experience all that Montauk has to offer... Sit back on the balcony and enjoy a glass of wine as the sun sets perfectly over Culloden Point. A short walk to the Harbor, the Dock, Gosmans, TTs, Salivars, Sunday Funday, La Fin, Viking Fleet (fishing, Whale watching & Ferry).

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 Apartment in Downtown Mystic

Newly renovated apartment in an old house built in 1845. The property is right in the center of Mystic on the Groton side of the draw bridge. Walking distance to restaurants and area attractions including Mystic Seaport Museum. Off-street parking. Short drive to Stonington Borough and Watch Hill RI. Maximum of 2 people allowed. All guests must be at least 27 years of age. No parties allowed on premises. Pets not allowed. No smoking on premises.

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.

The Anchor at Soundview · Beach+Ocean+Sunrise

Welcome to The Anchor private room 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, w/ 50" TV, and AC. Walk 1 block south and you are at the beach!

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.