Entire home

Shelter Island Retreat w/ Outdoor Pool!

Photo gallery for Shelter Island Retreat w/ Outdoor Pool!

A spacious living room with a white sofa, a glass coffee table, and a fireplace.
A modern living room with a pool table, a sofa set, a fireplace, and a television.
An outdoor patio with a stone floor, a grill, and a brick wall.
A spacious living room with a white fireplace, a staircase, and a large globe on a coffee table.
A fireplace with burning logs and decorative metal stands.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • On the beach
    A rare beachfront property in the area - enjoy direct access to the beach and sea.
  • Unmatched views, unforgettable moments
    Guests like the location for the scenic views.

Popular amenities

  • On beach
  • Balcony
  • Private pool
  • Arcade/game room
  • On-site fitness centre
  • Gas barbecue

Explore the area

View map
Shelter Island, NY
  • Place, Menhadden Lane Beach
    ‪4 min drive‬
  • Place, Gardiner's Bay Country Club
    ‪7 min drive‬
  • Place, Shelter Island Historical Society
    ‪10 min drive‬
  • Airport, Montauk, NY (MTP)
    ‪74 min drive‬

Rooms & beds

5 bedrooms (sleeps 8)

Additional Sleeping (Bonus Room)

1 King Bed

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Single Beds

Bedroom 4

4 Single Beds

Bedroom 5

1 Queen Bed

6 bathrooms, 1 half bathroom

Full Bathroom

Full Bathroom

Full Bathroom

Full Bathroom

Full Bathroom

Full Bathroom

Half Bathroom

Spaces

Deck or patio
Kitchen
Office
Balcony
Outdoor play area

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About the area

Shelter Island

Located in Shelter Island, this holiday home is on the beach. The area's natural beauty can be seen at The Hamptons Beaches and Menhadden Lane Beach, while Havens House and East End Seaport Maritime Museum are cultural highlights. Shelter Island Whale's Tail and Greenport Carousel are also worth visiting. Kayaking and power boating offer great chances to get out on the surrounding water, or you can seek out an adventure with hunting nearby.
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Map
Shelter Island, NY

What's nearby

  • Menhadden Lane Beach - 4 min drive - 4.3 km
  • Gardiner's Bay Country Club - 7 min drive - 7.1 km
  • Shelter Island Whale's Tail - 8 min drive - 8.2 km
  • Shelter Island Historical Society - 10 min drive - 9.5 km
  • Havens House - 10 min drive - 9.5 km

Getting around

  • Greenport Station - 29 min drive
  • East Hampton, NY (HTO) - 56 min drive

Restaurants

  • ‪Claudio’s Waterfront - ‬30 min drive
  • ‪Lucharitos - ‬30 min drive
  • ‪Sunset Beach Restaurant - ‬11 min drive
  • ‪Sunset Shack - ‬44 min drive
  • ‪Léon 1909 - ‬10 min drive

Frequently asked questions

Does Shelter Island Retreat w/ Outdoor Pool! have a pool?

Yes, this property has a pool.

How much does it cost to stay at Shelter Island Retreat w/ Outdoor Pool!?

As of 1 November 2026, prices found for a 1-night stay for 2 adults at Shelter Island Retreat w/ Outdoor Pool! on 2 January 2027 start from NZ$4,939, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Shelter Island Retreat w/ Outdoor Pool! pet-friendly?

No, pets are not allowed at this property.

How much is parking at Shelter Island Retreat w/ Outdoor Pool!?

On-site parking is available at the property.

What time is check-in at Shelter Island Retreat w/ Outdoor Pool!?

Check-in begins at 3:00 PM.

What time is check-out at Shelter Island Retreat w/ Outdoor Pool!?

Checkout is at 10:00 AM.

Where is Shelter Island Retreat w/ Outdoor Pool! located?

This Shelter Island holiday home is on the beach, 2 mi (3.2 km) from Menhadden Lane Beach, and within 6 mi (10 km) of Sunset Beach and Crescent Beach. Gardiner's Bay Country Club and Shelter Island Country Club are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 9 out of 9 reviews
Rating 8 - Good. 0 out of 9 reviews
Rating 6 - Okay. 0 out of 9 reviews
Rating 4 - Poor. 0 out of 9 reviews
Rating 2 - Terrible. 0 out of 9 reviews

9.6/10

Cleanliness

9.2/10

Check-in

9.6/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Such a beautiful . We really enjoyed our small get together on Shelter Island. Love the pool. Love the space.
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home with ensuite bathroom for every bedroom, well stocked kitchen, gorgeous backyard and pool and very responsive host. The WiFi connection for the TV was spotty.
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, communication, location, listing accuracy
This House was amazing. We stayed in home with bride and family.Plenty of space to get ready, closet space and bathrooms.Wifi access was great even during a storm.Beautiful setting. Well equipped with any appliances you may need. Great fridge space. Amazing indoors and out. Owner very receptive with a little glitch at check in with keys and house keeping service. Would absolutely return.
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful home in a gorgeous location.
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely house with great accommodations. Any questions we had were quickly answered. Perfect location - beautiful views from the decks. Look forward to returning!
Dinner at the house. Local oysters!
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, location, listing accuracy

Beautiful House

My family and I had a wonderful stay at this gorgeous property. The pool is terrific, the view is amazing, and the layout was perfect for our large family so we could all have our own spaces and bathrooms. We loved it.
Stayed 4 nights in Aug 2024
From a partner site

10/10 Excellent

The perfect getaway

Though we loved our outings on and around Shelter Island, we would have been just as happy never leaving the property! Our group enjoyed lazy days by the pool and delicious meals cooked at home in the gorgeous kitchen. Ashley was super responsive throughout the weekend, ensuring we had everything we needed. We just checked out last week and are already looking for a week we can come back next year (and hopefully stay even longer).
From a partner site

10/10 Excellent

Just Perfect

8 of us old college friends stayed here for 3 nights for our annual reunion. This property on Shelter Island provided everything we might need, and exceeded our expectations. The beds were comfortable. The showers were hot. There were ensuite bathrooms for each bedroom. The kitchen was large and had every utensil needed to cook and serve a group. The dining table accommodated everyone. The living room had a large sectional for relaxing. But the best part was the view, the patio, and the proximity to a gorgeous rocky beach. We sat around and admired the view of the ocean, played bocce (provided with the property), and walked on the beach. It was perfect.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house was amazing. Exactly as pictured no surprises. Extremely clean inside. Very comfortable, beds were great. A lot of space. Host was very easy to contact, very responsive and friendly. Bright, a lot of natural light. Easy kitchen, a lot of refrigerator and freezer space. Pool and pool area was terrific. Excellent pool for swimming or lounging in the pool. Pool was cleaned during our stay. Definitely recommended for stay on Shelter Island. Gorgeous view of the water. Quiet area. You will not be disappointed. Two opportunities, sweep and clean pool deck and furniture before guest arrival, may suggest replacing some pots and pans.
Stayed 3 nights in Jun 2026
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