
Ahoy There
8 guests
4 bedrooms
Shelter Island, The Hamptons
This Hamptons home does island life the modern way. In the mornings, hit up the local farmers’ markets and seafood shops.
Ahoy There
8 guests
4 bedrooms
Shelter Island, The Hamptons
This Hamptons home does island life the modern way. In the mornings, hit up the local farmers’ markets and seafood shops.
Villa Menantic
8 guests
4 bedrooms
Shelter Island Heights, Shelter Island
Set across seven private acres on Shelter Island’s Menantic Peninsula, this waterside property epitomises tranquillity. Wake up to views on one of the home's two private balconies, before whipping up breakfast in the state-of-the-art kitchen and sipping your morning coffee as you paddle in the sea.
Sea Aster
6 guests
3 bedrooms
Sag Harbor, Southampton
Sea Aster sits in an ideal spot for exploring beach and town life. Sag Harbor Main Street, with its restaurants, boutiques and artisan bakeries, is less than fifteen minutes’ walk away, and you can get to Haven’s Beach – a perfect spot to watch the sun set – in ten.
Explore the 798 most perfect homes in our collection
Explore our family friendly hotel alternatives in Shelter Island. We’ve cherry-picked a collection of spacious homes in safe, residential neighbourhoods popular with local parents. Find a fully furnished home with fun kids' bedrooms, well-equipped kitchens, multiple bathrooms and often outdoor space too. Our friendly team of Plum Experts are on-hand 24/7 to help you book your dream family friendly hotel alternative in Shelter Island.