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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
Pool

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
Exterior

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
Pool

New Construction Greenport Pool House - 3 Blocks from Town

New Construction Greenport Pool House - 3 Blocks from Town
Villa Direen Modern East Hampton Villa
Exterior

Villa Direen Modern East Hampton Villa

3.5 star property
Villa Direen Modern East Hampton Villa
Villa Flasses
Pool

Villa Flasses

3.0 star property
Villa Flasses
Iconic Charles Moore Springs home with dock and our home is pet-friendly
Miscellaneous

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
Exterior

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
Miscellaneous

Waterfront Villa with Private Beach in Montauk

Waterfront Villa with Private Beach in Montauk
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
Live on the Water: Dock, Beach, Boat, Kayak & Fish
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
MODERN 5 BEDROOM MONTAUK BEACH HOME
Living area

MODERN 5 BEDROOM MONTAUK BEACH HOME

MODERN 5 BEDROOM MONTAUK BEACH HOME
Chic Modern Retreat In Wainscott
Exterior

Chic Modern Retreat In Wainscott

Chic Modern Retreat In Wainscott
Villa Lavender
Pool

Villa Lavender

3.5 star property
Villa Lavender
Hilltop Villa overlooking the Harbor with gorgeous sunsets
Exterior

Hilltop Villa overlooking the Harbor with gorgeous sunsets

Hilltop Villa overlooking the Harbor with gorgeous sunsets
Villa Nostro Palazzo
Terrace/patio

Villa Nostro Palazzo

4.0 star property
Villa Nostro Palazzo
Villa Vajra
Exterior

Villa Vajra

3.5 star property
Villa Vajra
Villa Sofia
Outdoor pool

Villa Sofia

3.5 star property
Villa Sofia
Villa Isaiah
Front of property

Villa Isaiah

3.5 star property
Villa Isaiah
Villa Skylar
Front of property

Villa Skylar

3.5 star property
Villa Skylar
Villa Spectrum
Porch

Villa Spectrum

3.5 star property
The price is SAR 7,889
SAR 11,820 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
Exterior

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 SAR 648
SAR 813 total
includes taxes & fees
24 Dec - 25 Dec
Montauk Manor
Montauk Oceanside Suites
Front of property

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 SAR 483
SAR 588 total
includes taxes & fees
30 Dec - 31 Dec
Montauk Oceanside Suites
Windward Shores Ocean Resort
Property grounds

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 SAR 474
SAR 623 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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