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Villas in Shelter Island

Our top choices for Shelter Island villas

Hampton Private Retreat - last minute offer June 23-
Exterior

Hampton Private Retreat - last minute offer June 23-

10.0 out of 10, Exceptional, (19)
"We enjoyed Connie’s beautiful home. The kitchen was fully stocked, the bedrooms were very comfortable and the location was perfect. My family would definitely stay here again!"
Hampton Private Retreat - last minute offer June 23-
New Construction Greenport Pool House - 3 Blocks from Town
Outdoor pool, a heated pool

New Construction Greenport Pool House - 3 Blocks from Town

10.0 out of 10, Exceptional, (1)
"This was a great house for a large group! It was clean, and the backyard was perfect for our group to enjoy. The host was quick to respond to any questions we had. "
New Construction Greenport Pool House - 3 Blocks from Town
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
Interior

Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach

10.0 out of 10, Exceptional, (17)
"House was amazing and owner was fantastic! Highly recommend!!!"
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
Iconic Charles Moore Springs home with dock and our home is pet-friendly
Interior

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

2.0 star property
10.0 out of 10, Exceptional, (2)
"Lovely place! We hope to stay there again sometime soon!"
Iconic Charles Moore Springs home with dock and our home is pet-friendly
Villa Direen Modern East Hampton Villa
Villa, Garden View | Living area

Villa Direen Modern East Hampton Villa

3.5 star property
Villa Direen Modern East Hampton Villa
Villa Flasses
Outdoor pool

Villa Flasses

3.0 star property
Villa Flasses
Southampton Paradise with Saltwater Pool & Spa & 3 minutes to Best Beach in USA
TV, fireplace

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

Southampton Paradise with Saltwater Pool & Spa & 3 minutes to Best Beach in USA
TBD by Rove Travel 7BR Pool Hot Tub
Villa | 7 bedrooms, Internet

TBD by Rove Travel 7BR Pool Hot Tub

2.0 star property
TBD by Rove Travel 7BR Pool Hot Tub
Villa Sofia
Outdoor pool, a heated pool

Villa Sofia

3.5 star property
Villa Sofia
Live on the Water: Dock, Beach, Boat, Kayak & Fish
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (1)
"I have rented many houses in the Hamptons and this was the best by far! Family friendly, great hosts and magical spot!"
Live on the Water: Dock, Beach, Boat, Kayak & Fish
Luxurious beach house on the Long Island sound
Living area

Luxurious beach house on the Long Island sound

Luxurious beach house on the Long Island sound
Villa Nostro Palazzo
Front of property

Villa Nostro Palazzo

4.0 star property
Villa Nostro Palazzo
Waterfront Villa with Private Beach in Montauk
Dining

Waterfront Villa with Private Beach in Montauk

Waterfront Villa with Private Beach in Montauk
Villa Isaiah
Luxury Villa (6 Bedrooms) | Private kitchen | Full-size fridge, microwave, oven, stovetop

Villa Isaiah

3.5 star property
Villa Isaiah
Villa Skylar
40-inch flat-screen TV with cable channels, Smart TV, fireplace

Villa Skylar

3.5 star property
Villa Skylar
Villa Perlman
Luxury Villa (5 Bedrooms) | Bathroom | Free toiletries, bathrobes, slippers, towels

Villa Perlman

3.5 star property
Villa Perlman
Villa Red Hut
Outdoor pool

Villa Red Hut

3.5 star property
Villa Red Hut
Villa Charlotte
Front of property

Villa Charlotte

3.0 star property
Villa Charlotte
Fabulous familly villa in East hampton village fringe
Fridge, microwave, oven, stovetop

Fabulous familly villa in East hampton village fringe

Fabulous familly villa in East hampton village fringe
MODERN 5 BEDROOM MONTAUK BEACH HOME
Interior

MODERN 5 BEDROOM MONTAUK BEACH HOME

MODERN 5 BEDROOM MONTAUK BEACH HOME
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.
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Top Shelter Island Hotel Reviews

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