Shelter Island Villas
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Villas in Shelter Island

New Construction Greenport Pool House - 3 Blocks from Town
With a stay at this villa, you'll be centrally located in Greenport, just a 4-minute walk from Greenport Farmers' Market and 5 minutes by foot from Railroad Museum of Long Island.
Pool
Hot Tub

1.5 Acre Luxury Escape - Saltwater Pool with Water Views
With a stay at this villa in Orient Point, you'll be within a 10-minute walk of Orient By The Sea Marina and Orient Point County Park.
Pool
Kitchen

Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
With a stay at this villa in Hampton Bays, you'll be within a 15-minute drive of The Hamptons Beaches and All Star Bowling.
Pool
Hot Tub

Villa Flasses
94 Spring Pond Ln, Southampton, NY
With a stay at this villa in Southampton, you'll be within a 5-minute drive of The Hamptons Beaches and Shinnecock Hills Golf Course.
Pool
Parking included

Villa Direen Modern East Hampton Villa
137 Stephen Hands Path, East Hampton, NY
With a stay at this villa in East Hampton (East Hampton North), you'll be within a 10-minute drive of The Hamptons Beaches and The Jewish Center of the Hamptons.
Pool
Washer

Villa Spectrum
37 Neck Path, East Hampton, NY
With a stay at this villa in East Hampton, you'll be within a 5-minute drive of The Hamptons Beaches and Leiber Collection.
Pool
Kitchen

Amagansett Dunes Luxury w/ Pool + Elevator + 2 Min walk to private beach
With a stay at this villa in Amagansett (Beach Hampton), you'll be within a 5-minute walk of The Hamptons Beaches and Amagansett Beach.
Pool
Kitchen

Villa Edwards Hole
18 Edwards Hole Rd, East Hampton, NY
With a stay at this villa in East Hampton, you'll be within a 10-minute drive of The Hamptons Beaches and Eastville Heritage House.
Pool
Kitchen

Luxurious beach house on the Long Island sound
Located in Riverhead, this villa is within a 5-minute drive of Hallockville Museum Farm and Martha Clara Vineyards.
Washer
Dryer

Villa Keylime
With a stay at this villa in Sag Harbor, you'll be a 3-minute walk from The Hamptons Beaches and within a 5-minute drive of Eastville Heritage House.
Pool
Kitchen
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.
Shelter Island Villas essential information
Accommodation | 44 Villas |
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Lowest Price | |
Highest Price | |
Popular accommodation | New Construction Greenport Pool House - 3 Blocks from Town, 1.5 Acre Luxury Escape - Saltwater Pool with Water Views, Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach, Villa Flasses, Villa Direen Modern East Hampton Villa, Villa Spectrum, Amagansett Dunes Luxury w/ Pool + Elevator + 2 Min walk to private beach, Villa Edwards Hole, Luxurious beach house on the Long Island sound, Villa Keylime, Villa Coastal Bliss, Villa Victoria: Your Exquisite Luxury Retreat in Bridgehampton |
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