Compare Shelter Island Condo Rentals

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Featured Condo Rentals in Shelter Island

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Shelter Island

    Gurney's Montauk Resort & Seawater Spa

    Gurney's Montauk Resort & Seawater Spa

    290 Old Montauk Highway Montauk NY
    $411 nightly
    The price is $469 total per night from Dec 1 to Dec 2
    $469 total
    Dec 1 - Dec 2
    Total with taxes and fees
    8.2/10 Very Good! (881 reviews)
    Pier Blue Inn Old Saybrook - Essex

    Pier Blue Inn Old Saybrook - Essex

    1430 Boston Post Rd Old Saybrook CT
    $83 nightly
    The price is $95 total per night from Nov 18 to Nov 19
    $95 total
    Nov 18 - Nov 19
    Total with taxes and fees
    Water's Edge Resort & Spa

    Water's Edge Resort & Spa

    1525 Boston Post Road Westbrook CT
    $205 nightly
    The price is $236 total per night from Nov 23 to Nov 24
    $236 total
    Nov 23 - Nov 24
    Total with taxes and fees

Luxury Condos

Find luxury condos in Shelter Island
Get your vacation off to a fabulous start by booking a luxury condo in Shelter Island. They’re a great option if you want to pamper yourself a little more than usual on your next getaway. Plus, they give you a unique opportunity to see the city the way a local would. You’re not in a hotel—you’re home. Condominiums come in all shapes and sizes, and with Orbitz on your side, you’ll find exactly the right one for your trip.

Stay in a Shelter Island condo
Vacation condo rentals are a nice alternative to hotels with perks such as multiple bedrooms, living rooms, balconies, laundry facilities, Wi-Fi access and espresso machines. And don’t underestimate the power of the full kitchen in your condo: whipping up midnight snacks is a breeze, and hey, making a meal on your own without worrying about ordering in or going out to eat is just plain convenient. You might also have a pool, a gym and a hot tub on the property or close by.  

Exploring Shelter Island will be a breeze with a downtown condo as your home base. You’ll be close to the top sights, and within walking distance of great restaurants, shopping, and bars. Got leftovers? Put them in your fridge. Remember, you’re living like a local now.

Shelter Island Condo Rentals essential information

Accommodation
24 Condo Rentals
Lowest Price
$95
Highest Price
$469
Popular accommodation
Driftwood Resort, Montauk Oceanfront Condo @ Atlantic Bluffs Club - walk to Beach, Fishing & Town!, Offshore Spa & Residences, PERFECT, BEAUTIFULLY NEWLY DESIGNED 1,000 FT. MONTAUK OCEANFRT 3-LEVEL TOWNHOUSE, Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views, Cozy 2-bedroom condo with AC, fitness room in charming Westbrook. Oceanfront,, Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound, Montauk Mansion INDOOR + OUTDOOR POOLS, Atlantic Bluffs Club