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Search Villas in Shelter Island

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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 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
A heated pool

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)
"My family and I could not have picked a more beautiful home to celebrate my mom’s 80th birthday! We had a few rainy days and two 18 year olds, who were more than happy to stay at home and take advantage of the pool table, ping pong table, full gym…everything! Conny was so warm and welcoming in all of her communications. Her home is absolutely stunning! It was beautifully decorated and had many spaces to gather as a family. We spent every morning having coffee on the front porch and afternoons in...
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
Exterior

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
Smart TV, fireplace, DVD player, table tennis

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
Front of property

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
Front of property

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
Villa (Multiple Bedrooms) | Terrace/patio

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

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!

10.0 out of 10, Exceptional, (41)
"This is the most magical property with a gorgeous pool, beautiful large trees, a pond and a badmitten court. My two children loved it. The property was a 3-4 minute drive from everything and yet felt totally isolated and removed from everything. I will say that the house was more cozy than we expected as the bedrooms upstairs were a steep walk and there was only one bathroom for the entire house. But we made do and had a lovely time."
The price is AED 2,938
AED 5,267 total
includes taxes & fees
30 Apr - 1 May
Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!
Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1155)
"Beautiful hotel."
The price is AED 545
AED 695 total
includes taxes & fees
29 Apr - 30 Apr
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (369)
"We stayed for a night and it was great. It was great location and setting. Overall stay was fantastic. Bathtub was a bit old, could not hold the water and if you are more than 1 person, you have to space your baths so you can all enjoy warm water. "
The price is AED 500
AED 611 total
includes taxes & fees
17 Apr - 18 Apr
Montauk Oceanside Suites
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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