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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 52 Villas in Shelter Island with updated reviews, rates, and availability.

1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Outdoor pool, a heated 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
New Construction Greenport Pool House - 3 Blocks from Town
Outdoor pool, a heated pool

New Construction Greenport Pool House - 3 Blocks from Town

New Construction Greenport Pool House - 3 Blocks from Town
Picturesque 5 Bedroom Hamptons Villa with pool 3 min from beach
Interior

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
Hampton Private Retreat - last minute offer June 23-
Exterior

Hampton Private Retreat - last minute offer June 23-

10.0 out of 10, Exceptional, (19)
"We enjoyed Connie’s beautiful home. The kitchen was fully stocked, the bedrooms were very comfortable and the location was perfect. My family would definitely stay here again!"
Hampton Private Retreat - last minute offer June 23-
Villa Flasses
Outdoor pool

Villa Flasses

3.0 star property
Villa Flasses
Villa Direen Modern East Hampton Villa
Front of property

Villa Direen Modern East Hampton Villa

3.5 star property
Villa Direen Modern East Hampton Villa
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
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 Isaiah
Luxury Villa (6 Bedrooms) | Private kitchen | Full-size fridge, microwave, oven, stovetop

Villa Isaiah

3.5 star property
Villa Isaiah
Villa Spectrum
Porch

Villa Spectrum

3.5 star property
Villa Spectrum
MODERN 5 BEDROOM MONTAUK BEACH HOME
Interior

MODERN 5 BEDROOM MONTAUK BEACH HOME

MODERN 5 BEDROOM MONTAUK BEACH HOME
Waterfront Villa with Private Beach in Montauk
4 bedrooms, desk, iron/ironing board, free WiFi

Waterfront Villa with Private Beach in Montauk

Waterfront Villa with Private Beach in Montauk
Villa Skylar
40-inch flat-screen TV with cable channels, Smart TV, fireplace

Villa Skylar

3.5 star property
Villa Skylar
Villa Vajra
Exterior

Villa Vajra

3.5 star property
Villa Vajra
Chic Modern Retreat In Wainscott
Terrace/patio

Chic Modern Retreat In Wainscott

Chic Modern Retreat In Wainscott
Villa Nostro Palazzo
Front of property

Villa Nostro Palazzo

4.0 star property
Villa Nostro Palazzo
TBD by Rove Travel 7BR Pool Hot Tub
Villa | 7 bedrooms, Internet

TBD by Rove Travel 7BR Pool Hot Tub

2.0 star property
TBD by Rove Travel 7BR Pool Hot Tub
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
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1170)
"excellent overall stay"
The price is AED 555
AED 706 total
includes taxes & fees
19 May - 20 May
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (374)
"Good for a short stay "
The price is AED 583
AED 706 total
includes taxes & fees
4 May - 5 May
Montauk Oceanside Suites
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (283)
"Love the ocean view from the balcony"
The price is AED 565
AED 725 total
includes taxes & fees
5 May - 6 May
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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