Book Villas in Shelter Island, NY

Top Villas in Shelter Island

Hampton Private Retreat - last minute offer June 23-

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This villa features a gym and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.

New Construction Greenport Pool House - 3 Blocks from Town

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This villa features an outdoor pool and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.

Southampton Paradise with Saltwater Pool & Spa & 3 minutes to Best Beach in USA

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This villa features an outdoor pool and a gym. There's a hot tub on site, and laundry facilities and barbecue grills are also offered.

Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach

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A hot tub is featured at this villa, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

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

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This villa featured laundry facilities and barbecue grills.

Villa Direen Modern East Hampton Villa

137 Stephen Hands Path, East Hampton, NY

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An outdoor pool, free self parking, and barbecue grills are featured at this villa. A garden and a picnic area are also provided.

Villa Flasses

94 Spring Pond Ln, Southampton, NY

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An outdoor pool, free self parking, and barbecue grills are featured at this villa. A garden, a picnic area, and a virtual front desk are also on offer.

TBD by Rove Travel 7BR Pool Hot Tub

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Free WiFi in public areas and a garden are available at this villa.

Villa Sofia

133 Stephen Hands Path, East Hampton, NY

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An outdoor pool, free self parking, and concierge services are featured at this villa. A terrace, a garden, and barbecue grills are also on offer.

Fabulous familly villa in East hampton village fringe

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An outdoor pool is featured at this villa, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

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

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This villa features a gym and a hot tub. Families will appreciate the playground and onsite laundry facilities. A garden, concierge services, and barbecue grills are also on offer.

Luxurious beach house on the Long Island sound

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A gym is featured at this villa, along with laundry facilities.

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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

Montauk Blue Hotel

108 South Emerson Avenue, Montauk, NY

$146 nightly

$167 total

Oct 26 - Oct 27

Total with taxes and fees

9/10 Wonderful! (142 reviews)

Shelter Island Villas essential information

Accommodation	40 Villas
Lowest Price	$90
Highest Price	$603
Popular accommodation	Hampton Private Retreat - last minute offer June 23-, New Construction Greenport Pool House - 3 Blocks from Town, Southampton Paradise with Saltwater Pool & Spa & 3 minutes to Best Beach in USA, Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach, Iconic Charles Moore Springs home with dock and our home is pet-friendly, Villa Direen Modern East Hampton Villa, Villa Flasses, TBD by Rove Travel 7BR Pool Hot Tub, Villa Sofia, Fabulous familly villa in East hampton village fringe, Live on the Water: Dock, Beach, Boat, Kayak & Fish, Luxurious beach house on the Long Island sound