Shelter Island Villas

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Villas in Shelter Island

Hampton Private Retreat - last minute offer June 23-

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.

Pool

Hot Tub

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

Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach

Hampton Bays NY

With a stay at this villa in Hampton Bays, you'll be a 4-minute drive from The Hamptons Beaches and 8 minutes from Good Ground Park.

Pool

Hot Tub

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.

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

Southampton NY

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

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.

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.

TBD by Rove Travel 7BR Pool Hot Tub

Amagansett NY

With a stay at TBD by Rove Travel 7BR Pool Hot Tub in Amagansett (Napeague), you'll be steps from The Hamptons Beaches and 6 minutes by foot from Amagansett Beach.

Free WiFi

Outdoor Space

Villa Sofia

133 Stephen Hands Path East Hampton NY

Located in East Hampton (East Hampton North), this villa is within a 5-minute drive of The Jewish Center of the Hamptons and The Hamptons Beaches.

Waterfront Villa with Private Beach in Montauk

Montauk NY

Located in Montauk, this villa is on the waterfront, within a 5-minute drive of Shadmoor State Park and Montauk Marine Basin.

Villa Perlman

25 Aqua Dr Southampton NY

With a stay at this villa in Southampton, you'll be on the beach, within a 5-minute drive of The Hamptons Beaches and Meschutt Beach.

Pool

Kitchen

MODERN 5 BEDROOM MONTAUK BEACH HOME

Montauk NY

With a stay at this villa in Montauk, you'll be a 2-minute drive from The Hamptons Beaches and 5 minutes from Hither Woods Preserve.

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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.