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Search Villas in Shelter Island

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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 44 Villas in Shelter Island with updated reviews, rates, and availability.

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
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
Villa Flasses
Pool

Villa Flasses

3.0 star property
Villa Flasses
Villa Direen Modern East Hampton Villa
Exterior

Villa Direen Modern East Hampton Villa

3.5 star property
Villa Direen Modern East Hampton Villa
Villa Spectrum
Porch

Villa Spectrum

3.5 star property
Villa Spectrum
Villa Edwards Hole
Outdoor pool

Villa Edwards Hole

3.0 star property
Villa Edwards Hole
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
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 Keylime
Front view of the property

Villa Keylime

2.0 star property
Villa Keylime
Villa Victoria: Your Exquisite Luxury Retreat in Bridgehampton
Pool

Villa Victoria: Your Exquisite Luxury Retreat in Bridgehampton

2.0 star property
Villa Victoria: Your Exquisite Luxury Retreat in Bridgehampton
MODERN 5 BEDROOM MONTAUK BEACH HOME
Living area

MODERN 5 BEDROOM MONTAUK BEACH HOME

MODERN 5 BEDROOM MONTAUK BEACH HOME
Waterfront Villa with Private Beach in Montauk
Miscellaneous

Waterfront Villa with Private Beach in Montauk

Waterfront Villa with Private Beach in Montauk
Villa Coastal Bliss
Bathroom

Villa Coastal Bliss

Villa Coastal Bliss
Villa Gally
Outdoor pool

Villa Gally

2.0 star property
Villa Gally
YOU CAN WATCH THE SUNRISE FROM YOUR BALCONY
Exterior

YOU CAN WATCH THE SUNRISE FROM YOUR BALCONY

YOU CAN WATCH THE SUNRISE FROM YOUR BALCONY
Villa Emery
Front view of the property Outdoor pool

Villa Emery

2.0 star property
Villa Emery
Chic Modern Retreat In Wainscott
Exterior

Chic Modern Retreat In Wainscott

Chic Modern Retreat In Wainscott
Experience Serene Luxury: Villa Direen, Your East Hampton Escape
Pool view Garden Property Building Swimming Pool Sun lounger

Experience Serene Luxury: Villa Direen, Your East Hampton Escape

2.0 star property
Experience Serene Luxury: Villa Direen, Your East Hampton Escape
Discover Luxury and Serenity at Villa Edwards Hole in East Hampton
Pool

Discover Luxury and Serenity at Villa Edwards Hole in East Hampton

2.0 star property
Discover Luxury and Serenity at Villa Edwards Hole in East Hampton
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, (1116)
"We loved the manor, it had great amenities and an excellent experience. highly recommend! "
The price is SAR 491
SAR 634 total
includes taxes & fees
24 Feb - 25 Feb
Montauk Manor
Montauk Oceanside Suites
Front of property

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very Good, (362)
"I didn’t realize the property was mobile check-in and that all communication would be automated in the winter season. if you guys had that more clear on the Expedia it would be awesome. Otherwise the stay was great, clean room, no hassle to get in, right by the beach. "
The price is SAR 421
SAR 518 total
includes taxes & fees
27 Feb - 28 Feb
Montauk Oceanside Suites
Windward Shores Ocean Resort
Property grounds

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (272)
"Everything Was Great The Only Issues Were The Fridge Was Not Getting Cold And The Bed Was Not Comfortable But Property was Great "
The price is SAR 494
SAR 645 total
includes taxes & fees
20 Mar - 21 Mar
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.

Frequently asked questions

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