Book Villas in Shelter Island, NY

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Top Villas in Shelter Island

1.5 Acre Luxury Escape - Saltwater Pool with Water Views

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This villa features an outdoor pool and a spa tub. A garden and barbecue grills are also provided.

Hot Tub

Pet friendly

Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach

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A spa tub is featured at this villa, along with a garden and barbecue grills.

Hot Tub

Fireplace

Villa Direen - Modern East Hampton Villa

137 Stephen Hands Path, East Hampton, NY

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An outdoor pool, free parking, and laundry facilities are featured at this villa. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, a picnic area, and dry cleaning are also on offer.

Pool

Parking included

Iconic Charles Moore Springs home with dock and our home is pet-friendly

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A spa tub is featured at this vacation home, along with barbecue grills.

Hot Tub

Fireplace

New Construction Greenport Pool House - 3 Blocks from Town

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This villa features an outdoor pool and a spa tub. A garden and barbecue grills are also provided.

Hot Tub

Pool

Waterfront Villa with Private Beach in Montauk

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An outdoor pool is featured at this villa, along with a garden and barbecue grills.

Fireplace

Pool

Luxurious beach house on the Long Island sound

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A gym is available at this villa.

Washer

Dryer

Live on the Water: Dock, Beach, Boat, Kayak & Fish

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A spa tub is featured at this villa, along with a garden and barbecue grills.

Hot Tub

Fireplace

Beautiful Mediterranean villa

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Stay at this villa in East Marion. Popular attractions Truman's Beach and Island's End Golf and Country Club are located nearby.

MODERN 5 BEDROOM MONTAUK BEACH HOME

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An outdoor pool is featured at this villa, along with a garden and barbecue grills.

Pool

Outdoor Space

Villa Roman

155 Chardonnay Dr, East Quogue, NY

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An outdoor pool, free parking, and laundry facilities are featured at this villa. A terrace, a garden, and a free grocery shopping service are also on offer.

Pool

Parking included

Villa Machis

2765 Deerfield Rd, Sag Harbor, NY

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This villa features an outdoor pool and a gym. Free self parking, a terrace, and a garden are also offered.

Pool

Parking included

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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.

Top hotels in Shelter Island

Quality Inn Old Saybrook - Westbrook

100 Essex Rd, Old Saybrook, CT

$98

per night

May 27 - May 28

7.4/10 Good! (961 reviews)

Shelter Island Villas essential information

Accommodation	27 Villas
Lowest Price	$98
Highest Price	$526
Popular accommodation	1.5 Acre Luxury Escape - Saltwater Pool with Water Views, Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach, Villa Direen - Modern East Hampton Villa, Iconic Charles Moore Springs home with dock and our home is pet-friendly, New Construction Greenport Pool House - 3 Blocks from Town, Waterfront Villa with Private Beach in Montauk, Luxurious beach house on the Long Island sound, Live on the Water: Dock, Beach, Boat, Kayak & Fish, Beautiful Mediterranean villa, MODERN 5 BEDROOM MONTAUK BEACH HOME, Villa Roman, Villa Machis