Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly

Photo gallery for Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly

A rectangular swimming pool with a tiled deck, surrounded by a wooden fence and lush greenery.
A living room with a fireplace, a sofa, two armchairs, a coffee table, and a lamp.
A spacious living room with a fireplace, a sofa, a coffee table, and a bookshelf.
A spacious living room with a sofa, armchair, and coffee table, wooden flooring, and a large window.
A spacious living area with a wooden dining table and chairs, a blue armchair, a fireplace, and a bookshelf.

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.
  • Arcade/game room
    A rare find - fun for all ages with on-site arcade/game room.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Patio
  • Private pool
  • Dog-friendly
  • Toys
  • On-site fitness centre
  • Barbecue

Explore the area

View map
Shelter Island, NY
  • Place, Crescent Beach
    ‪3 min drive‬
  • Place, Sunset Beach
    ‪3 min drive‬
  • Place, Shell Beach
    ‪4 min drive‬
  • Airport, Montauk, NY (MTP)
    ‪70 min drive‬

Rooms & beds

3 bedrooms (sleeps 7)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Single Bunk Bed and 1 Single Bed

Living Room 1

1 Queen Bed

2 bathrooms

Bathroom 1

Towels provided · Toilet · Shower only · Hair dryer

Bathroom 2

Towels provided · Bathtub or shower · Bathtub · Toilet · Hair dryer

Out Door Shower

Towels provided · Shower only · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Number of living rooms
Outdoor play area
Garden
Dining area

Add dates for prices

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About the area

Shelter Island Heights

Located near the beach, this holiday home is in Silver Beach, a neighbourhood in Shelter Island Heights. Havens House and East End Seaport Maritime Museum are cultural highlights, and some of the area's attractions include Shelter Island Whale's Tail and Greenport Carousel. Travelling with kids? Consider Railroad Museum of Long Island and Norman E. Klipp Marine Park. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with horse riding and hiking/biking trails.
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Map
Shelter Island, NY

What's nearby

  • Crescent Beach - 3 min drive - 2.9 km
  • Shelter Island Country Club - 3 min drive - 2.8 km
  • Sunset Beach - 3 min drive - 3.2 km
  • Shell Beach - 4 min drive - 3.9 km
  • Shelter Island Historical Society - 6 min drive - 5.7 km

Getting around

  • Greenport Station - 25 min drive
  • East Hampton, NY (HTO) - 44 min drive

Restaurants

  • ‪Pridwin Hotel - ‬3 min drive
  • ‪Sunset Beach Restaurant - ‬3 min drive
  • ‪Port Bar & Grill - ‬25 min drive
  • ‪Eddie’s - ‬28 min drive
  • ‪Waypoint - ‬31 min drive

Frequently asked questions

Does Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly have a pool?

Yes, this property has an outdoor pool.

Is Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 453 kg per pet.

How much is parking at Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly ?

On-site parking is available at the property.

What time is check-in at Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly ?

Check-in begins at 4:00 PM.

What time is check-out at Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly ?

Checkout is at 11:00 AM.

Where is Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly located?

This family-friendly Shelter Island Heights holiday home is located near the beach, within 2 mi (3 km) of Crescent Beach and Sunset Beach. Shelter Island Whale's Tail and Shell Beach are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 21 out of 23 reviews
Rating 8 - Good. 2 out of 23 reviews
Rating 6 - Okay. 0 out of 23 reviews
Rating 4 - Poor. 0 out of 23 reviews
Rating 2 - Terrible. 0 out of 23 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Enjoyed our family vacation on Shelter Island. Great house, pool, accessories, and neighborhood (walk to beach).
Stayed 8 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a very comfortable, well appointed and well equipped house. It is perfect for a family or group of friends to enjoy recreation and creature comforts. We fully enjoyed the pool and pool house as we luckily had perfect days and nights to enjoy it all. Tara could not have been more helpful and accommodating host!
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house, yard and neighborhood and very accommodating and helpful host! Great weekend.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, we walked to the beach every day! Tara was a very warm and communicative host.
Stayed 14 nights in Aug 2025
Verified review

10/10 Excellent

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

Perfect Stay

Amazing from check in to check out. Highly recommend.
Stayed 32 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
My wife and I just finished spending the month of August at this beautiful home on Shelter Island. Amazing gunite pool which is surrounded by an awesome landscaped property. The property is in a quiet neighborhood mid island . Two miles from shell beach and a 5 minute drive into town. Three bedrooms, one with bunkbeds for grandkids. A well appointed kitchen with all the cooking necessities is one of the highlights. Can’t say enough about the just Tara.. extremely communicative and responsive to all requests. Highly recommend this property if you are planning a trip to Shelter Island.
Stayed 31 nights in Jul 2026
Verified review

10/10 Excellent

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

Perfect Stay

Lovely getaway in a very sweet house. Property manager very responsive. Perfect location.
Stayed 3 nights in Sep 2024
Verified review

10/10 Excellent

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

Perfect Shelter Island Oasis

The home was clean and well appointed. The pool and pool house were fantastic. The grounds were well manicured. Communication was excellent.
Stayed 3 nights in Jun 2023
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy

Shelter Island Family Vacation.

Charming house, nice location. Everyone enjoyed the pool and playing pool! Would benefit from a deep clean.
Stayed 7 nights in Jun 2023
Verified review

10/10 Excellent

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

Summer Vacation

Nice property set up nicely for a family with children.
Stayed 10 nights in Jul 2024
Verified review

10/10 Excellent

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

Great Beach Week

We had a wonderful stay at this property! Tara was extremely communicative and absolutely everything we needed was available at the house. The pool and the attached pool house with tons of fun games and activities was such a fun addition and we were super comfortable all week. The fenced in yard was perfect for our adventurous dog. Would highly recommend for families!
Stayed 8 nights in Jun 2025
Verified review

10/10 Excellent

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

Great house in beautiful area!

Great house in a quiet neighborhood with a lot to do! Pool area was great, the pool house had pool and other fun games, there was a fire pit area with wood for use, and house was close to numerous beaches. Host/house manager were very responsive and pleasant to deal with. Would highly recommend this house for a Shelter Island stay!
Stayed 2 nights in Jun 2023
Verified review

10/10 Excellent

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

Shelter Island in the off-season is the best season.

We loved staying in the house. The island was blissfully quiet on our late September weekend. We even made great use of the basement theater to watch college football when some inclement weather kept us indoors. I would certainly rent the house again.
Stayed 2 nights in Sep 2023
Verified review

10/10 Excellent

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

Amazing Family Stay

We had the most amazing time at this awesome property. The owners and property managers were on top of everything and the communication was A++. The home was updated and comfortable although we pretty much lived in the pool through our stay. The location was great .. Quiet yet close to the most beautiful beaches and great restaurants. We had a blast ferry hopping to the hustle and bustle of North/South Forks but we all loved coming back to this quiet retreat. Cannot wait to come back!!
Stayed 11 nights in Jul 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Tara is the best as is this beautiful property with excellent pool, bbq grill, plenty of outside activities, fire pit, bikes and so much more. Extremely responsive to questions. A!
Stayed 14 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
I cannot emphasize enough what a fantastic property this is--the location, the layout, the grounds (much bigger in person than in photos) and super speedy communication with Tara, the host. She was immensely helpful and positive with a variety of small problems (example-coffee maker didn't work and less than 24 hours later a new one was on the doorstep). And it's such a plus that she accepts pets (who had a ball btw, lots of gardens to sniff around). We made a lot of use of the lovely pool (which had a great assortment of pool inflatables and toys) and the movie room. If our grandson had been older I'm sure he would have loved the pool house pool table (the pool house is also much larger than in photos). We had a great time on SI, due, in no small way, to this lovely housel
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

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

Wonderful vacation experience!

We had an absolutely amazing time at Tara’s house on Shelter Island. From start to finish, everything was seamless and hassle-free. Her property exceeded all of my expectations - it was clean, well-maintained, and beautifully decorated. She was also very responsive and accommodating, ensuring that our stay was comfortable and enjoyable. I cannot recommend it enough for anyone looking for a fantastic vacation rental experience.
Stayed 7 nights in Aug 2023
Verified review

10/10 Excellent

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

Fabulous

The pictures don't do it justice. Lots of love and care put into this place. Quiet neighborhood. Cycled everywhere. A great kitchen if you you're into cooking.
Stayed 5 nights in Aug 2023
Verified review

10/10 Excellent

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

Special Place on the Island!

Tara made the entire experience super easy! Check in was clearly communicated as well as the different items around the house. My wife, son, and I truly enjoyed our stay at the house and would recommend it highly to any other family looking to create wonderful summer memories on Shelter. A+++
Stayed 16 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our family agreed that this was probably the best rental home experience we've ever had. Home was exactly as described, extremely clean, with basically every possible amenity and a few that were completely unexpected. For example, there were pre-made smores ready for use on the outdoor fire pit, and even the exact same slushy machine we have at home and meant to bring but forgot! The pool was clean and beautiful, and the garage-turned-teen-gaming-hangout was a fantastic match for our situation, which was that we had our 2 teen children as well as two other teens with us for the week. All 4 of them said it was their best "chill" vacation week ever and were very sad to leave. This is a fantastic house in particular for people planning to do a lot of "pool-party"-like hosting, and/or with teens/kids who like gaming and movie watching. We even were able to use the downstairs exercise room with weights (again, we debated bringing our dumbbell weights but didn't), which isn't even advertised. Finally, the host Tara was very responsive - and even reimbursed me the same day after I had to go to the hardware store and buy a couple of tools that they didn't have onsite in order to fix the brakes on one of their bikes. All in all, thanks to Tara for one of the best vacations our family has ever taken.
Stayed 6 nights in Jun 2026
Verified review

10/10 Excellent

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

Excellent vacation house

Girls weekend on Shelter Island. This house was perfect for us ! The hosts were faboulous and the location was perfect.
Stayed 2 nights in Oct 2022
Verified review

10/10 Excellent

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

It was wonderful!!!

If you are ever going to shelter island look no further! I’m sure there is nothing to compare, it was fabulous all the way we were there for a wedding . My daughter traveled from London to be there, everyone woke up in the morning with such happiness! Thank you Tara, and PAula , it was Perfect ❤️
Stayed 3 nights in Sep 2022
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 8 nights in Jun 2026
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