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Search Villas in Shelter Island

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Compare 45 Villas in Shelter Island with updated reviews, rates, and availability.

1.5 Acre Luxury Escape - Saltwater Pool with Water Views

10.0 out of 10, Exceptional, (1)
"Very nice house In great shape and outstanding pool area."
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, (17)
"This is a large and extremely comfortable house. The owner is attentive to any questions you might have. LOVED spending time there. "
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach

New Construction Greenport Pool House - 3 Blocks from Town

New Construction Greenport Pool House - 3 Blocks from Town

Villa Direen Modern East Hampton Villa

3.5 star property
Villa Direen Modern East Hampton Villa

Villa Flasses

3.0 star property
Villa Flasses

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"My family really enjoyed staying at this special property, and the direct access to the water was icing on the cake! Britta was a fantastic, responsive host."
Iconic Charles Moore Springs home with dock and our home is pet-friendly

Amagansett Dunes Luxury w/ Pool + Elevator + 2 Min walk to private beach

Amagansett Dunes Luxury w/ Pool + Elevator + 2 Min walk to private beach

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

MODERN 5 BEDROOM MONTAUK BEACH HOME

MODERN 5 BEDROOM MONTAUK BEACH HOME

Chic Modern Retreat In Wainscott

Chic Modern Retreat In Wainscott

Villa Lavender

3.5 star property
Villa Lavender

Hilltop Villa overlooking the Harbor with gorgeous sunsets

Hilltop Villa overlooking the Harbor with gorgeous sunsets

Villa Nostro Palazzo

4.0 star property
Villa Nostro Palazzo

Villa Vajra

3.5 star property
Villa Vajra

Villa Sofia

3.5 star property
Villa Sofia

Villa Isaiah

3.5 star property
Villa Isaiah

Villa Skylar

3.5 star property
Villa Skylar

Villa Spectrum

3.5 star property
The price is AED 7,713
AED 11,557 total
includes taxes & fees
24 Dec - 25 Dec
Villa Spectrum
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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Other property types in Shelter Island

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1084)
"Clean, spacious and very comfy with beautiful views! Can’t wait to stay again in the future "
The price is AED 634
AED 795 total
includes taxes & fees
24 Dec - 25 Dec
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very Good, (347)
"Needs to have someone man the phones…"
The price is AED 472
AED 575 total
includes taxes & fees
30 Dec - 31 Dec
Montauk Oceanside Suites

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (264)
"Stayed for the second time at Windward and have no complaints. will book again next time I'm in Montauk!"
The price is AED 464
AED 609 total
includes taxes & fees
5 Jan - 6 January 2025
Windward Shores Ocean Resort
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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