Condo vacation rentals in Shelter Island Heights

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!

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)

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

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 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!

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.

Stunning, Spacious, Spotless. Close to Yale.

This is a gorgeous two bedroom apartment. The main bedroom has two twin beds, a walk-in closet, and its own private bathroom. The second bedroom has a queen size bed and its own private bathroom and closet. Fully equipped open kitchen. Living dining space. In unit washer/dryer.

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.