Shelter Island Villas

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Villas in Shelter Island

New Construction Greenport Pool House - 3 Blocks from Town

Greenport NY

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

Hampton Private Retreat - last minute offer June 23-

Southampton NY

When you stay at this villa in Southampton, you'll be on the waterfront, within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.

Pool

Hot Tub

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

Southampton NY

Located in Southampton, this villa is within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.

Pool

Hot Tub

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

Southampton NY

With a stay at this villa in Southampton, you'll be on the waterfront, within a 10-minute drive of The Hamptons Beaches and North Main Street Historic District.

Hot Tub

Kitchen

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

East Hampton NY

With a stay at this villa in East Hampton, you'll be on the waterfront, within a 5-minute drive of The Hamptons Beaches and Three Mile Harbor.

Washer

Dryer

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 Clubhouse Hamptons.

Pool

Washer

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 Sebonack Golf Course.

Pool

Parking included

Villa Lavender

1854 Noyac Path Sag Harbor NY

With a stay at this villa in Sag Harbor, you'll be within a 5-minute drive of The Hamptons Beaches and Elizabeth A. Morton National Wildlife Refuge.

Pool

Kitchen

Villa Skylar

Montauk Highway Southampton NY

With a stay at this villa in Southampton, you'll be within a 10-minute drive of The Hamptons Beaches and Cooper's Beach.

Pool

Kitchen

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

Villa Red Hut

832 Millstone Road Water Mill NY

With a stay at this villa in Water Mill, you'll be in a provincial park, within a 10-minute drive of The Hamptons Beaches and Elizabeth A. Morton National Wildlife Refuge.

Pool

Kitchen

Glass House by Rove Travel Heated Pool & Hot Tub

145 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

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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.