Villas in Shelter Island

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Compare 27 Villas in Shelter Island with updated reviews, rates, and availability.

Pool | Outdoor pool, a heated pool
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Interior
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
Luxury Villa (6 Bedrooms) | Living area | TV
Villa Direen - Modern East Hampton Villa
4.0 star property
Villa Direen - Modern East Hampton Villa
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Property grounds
New Construction Greenport Pool House - 3 Blocks from Town
New Construction Greenport Pool House - 3 Blocks from Town
4 bedrooms, desk, iron/ironing board, cribs/infant beds
Waterfront Villa with Private Beach in Montauk
Waterfront Villa with Private Beach in Montauk
Property grounds
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
Pool
Beautiful Mediterranean villa
10.0 out of 10, Exceptional, (1)
"The home was clean pool was great And the owners wonderful"
Beautiful Mediterranean villa
Fridge, microwave, oven, stovetop
MODERN 5 BEDROOM MONTAUK BEACH HOME
MODERN 5 BEDROOM MONTAUK BEACH HOME
Outdoor pool
Villa Roman
3.5 star property
Villa Roman
Outdoor pool
Villa Machis
3.5 star property
Villa Machis
Pool
Hilltop Villa overlooking the Harbor with gorgeous sunsets
Hilltop Villa overlooking the Harbor with gorgeous sunsets
Living area
Villa Lavender
3.5 star property
Villa Lavender
View from property
Chic Modern Retreat In Wainscott
Chic Modern Retreat In Wainscott
Front of property
Villa Nostro Palazzo
4.0 star property
Villa Nostro Palazzo
Outdoor pool
Villa Vajra
3.5 star property
Villa Vajra
Luxury Villa (6 Bedrooms) | Private kitchen | Full-size fridge, microwave, oven, stovetop
Villa Isaiah
3.5 star property
Villa Isaiah
Front of property
Villa Spectrum
3.5 star property
Villa Spectrum
40-inch flat-screen TV with cable channels, Smart TV, fireplace
Villa Skylar
3.5 star property
Villa Skylar
Outdoor pool, a heated pool
Villa Sofia
3.5 star property
Villa Sofia
Outdoor pool
Villa Red Hut
3.5 star property
Villa Red Hut
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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

Shelter Island Villas information

Number of reviews
15
Accommodation
27 Villas
Lowest Price
Highest Price

Frequently asked questions

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Recent reviews of Shelter Island hotels
Expedia verified reviews

The Atlantic Hotel

The Atlantic Hotel

5/5 Excellent
Non Hampton prices.
"Great prices, huge room, convenient and super friendly staff. Have stayed the past 3 weeks for business, good location"
A verified traveler stayed at The Atlantic Hotel
Posted 1 day ago
The Atlantic Hotel