Search Villas in Shelter Island

Compare 29 Villas in Shelter Island with updated reviews, rates, and availability.

Iconic Charles Moore Springs home with dock and our home is pet-friendly
2.0 star property
Iconic Charles Moore Springs home with dock and our home is pet-friendly
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
10.0 out of 10, Exceptional, (13)
"Rented this place out for my partner’s 25th birthday. Tony was amazing, went out of his way to allow us to come early to check it out and get the floor plan - very communicative, the place was absolutely gorgeous. The weekend went off without a hitch and I gotta hand it to Tony for making it all happen."
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
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Villa Direen - Modern East Hampton Villa
4.0 star property
Villa Direen - Modern East Hampton Villa
New Construction Greenport Pool House - 3 Blocks from Town
New Construction Greenport Pool House - 3 Blocks from Town
Waterfront Villa with Private Beach in Montauk
Waterfront Villa with Private Beach in Montauk
Luxurious beach house on the Long Island sound
Luxurious beach house on the Long Island sound
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
Beautiful Mediterranean villa
10.0 out of 10, Exceptional, (1)
"The home was clean pool was great And the owners wonderful"
Beautiful Mediterranean villa
MODERN 5 BEDROOM MONTAUK BEACH HOME
MODERN 5 BEDROOM MONTAUK BEACH HOME
Villa Roman
3.5 star property
Villa Roman
Villa Machis
3.5 star property
Villa Machis
Hilltop Villa overlooking the Harbor with gorgeous sunsets
Hilltop Villa overlooking the Harbor with gorgeous sunsets
Villa Lavender
3.5 star property
Villa Lavender
Chic Modern Retreat In Wainscott
Chic Modern Retreat In Wainscott
Villa Nostro Palazzo
4.0 star property
Villa Nostro Palazzo
Villa Vajra
3.5 star property
Villa Vajra
Fabulous familly villa in East hampton village fringe
Fabulous familly villa in East hampton village fringe
Villa Isaiah
3.5 star property
Villa Isaiah
Villa Spectrum
3.5 star property
Villa Spectrum
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See all available properties in Shelter Island
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.

Other property types in Shelter Island

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1023)
"Best affordable hotel in Montauk"
The price is AED 1,098
AED 1,325 total
includes taxes & fees
6 Jun - 7 Jun
Montauk Manor
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (238)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is AED 887
AED 1,092 total
includes taxes & fees
9 Jun - 10 Jun
Windward Shores Ocean Resort
The Surf Club
3.5 star property
8.4 out of 10, Very Good, (222)
"Very nice location and nice condo"
The price is AED 914
AED 1,242 total
includes taxes & fees
13 Jun - 14 Jun
The Surf Club
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.

Recent reviews of Shelter Island hotels
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