10 reviews

1 / 31 77' Wrap around porch 20' x 40' In Ground Pool



Pets allowed:
Wi-Fi available:

Description from owner


Property was voted as Winner of Best of Citysearch!.

Shelter Island Hideaway is amongst the best summer getaway Vacation destination. The most confusing part is deciding whether you treat yourself to a relaxing for a Week, Month or the entire season!

We have thought of most everything to assure your stay will be beyond comfortable and enjoyable, luxuriate in One of The Hamptons highest ranked vacation homes located on Bucolic and Beautiful Shelter Island. Shelter Island is often called 'The Jewel of The Hampton's, drive your car on to the Ferry, just 8 minutes from The North Fork, or 3 minutes from Sag Harbor, on the South Fork of Long Island.

Our three story Beach Vacation Home Rental is located just across the street from a ½ mile stretch of a semi-private beach. Located in the exclusive Shelter Island Estate Section, privacy abounds.

Your private estate Vacation home has 3,000'+ square feet of indoor space. Light and bright with multiple Skylights and Walls of French Glass doors means you're bathed in open, bright indoor space. But, that's not all, open the French doors on either of the two levels and walk right to covered wrap around porch overlooking the huge pool. The center level has a wrap large wrap-around porch where you can dine read, relax on the oversized Papasan chairs, lounge on the new high-end outdoor sectional sofa.

The lower level has its outdoor sitting area; kids love the space as they have their own sectional and some privacy, right outside of the opening French doors. Direct access to the pool from either outdoor space via a couple of stairs.

The Upper floor has it;s own Juliet balcony right off the bedroom, just open the French doors and enjoy the fresh Shelter Island breezes and views of the water and treed areas. With a combined outdoor porch space exceeding 1,500 square feet, the days biggest decision may be where to relax.

Your beautiful vacation home was designed and built in 2007 by Editor of International travel publication, each of the four distinct oversized bedrooms can be considered "Masters." There are two very large bedrooms on the center level with vaulted 20'+ ceilings and designed in a European fashion and are En-suite, & the privacy of water closet. The upper level has another very large bedroom with an attached reading room/music room area with a sleeper couch as an optional sleeping area. The lower level has a new large bedroom as well.

There are four full fabulous baths, 2 of which include both a shower and amazing Oversize heated Jacuzzi soaking tubs, Tubs. The lower level bathroom is brand new, comprised of marble flooring, two windows, twin glass and wood vanities each with a vessel sink. The shower is an oversized shower with glass tile and glass doors. The upper bathroom has a single pedestal sink, commode and tiled shower with a skylight above. Just beyond the beach is a closed glass door laundry room with new high-end LG Oversized Washer, Dryer and sink.

Your vacation home is the perfect place for getting away from the city craziness, designed to allow for both profound relaxations as well as entertaining. Like to swim, just steps from the first two levels is a private, fenced in landscaped property with the 20x40 pool where there is a second dining table as well as multiple teak lounge chairs. Also and a short stroll across to the waterfront where you will find your semi-private beach, more than a ½ mile long. This semi-private beach is perfect for watersports of all kinds as well swimming and snorkeling, or just relax and work on your tan. The beach faces West, so every clear night you'll enjoy spectacular Shelter Island sunsets, be sure to bring your camera. Pack a picnic or bring any of your favorites Martini, Wine, Beer or Margaritas (plastics of every variety available at the house for your use). Prefer a "Town Beach"? 1 mile down the road is Sunset Beach, also know as Crescent Beach. There are lifeguards there, a restaurant and yachts up 300' Barry Diller's come from all around the Hamptons.

The new media room is quite large, measuring 28 feet by 15 feet. Two couches and lots of floor pillows for watching movies on the 70' High Definition LED flat screen TV, films and excellent with the hidden Kevlar end in-ceiling speakers, subwoofer, Blu-Ray and DVD Players are driven by a 1500 watt of 5.1 Sound system. From here, you again have access to the wonderful outdoors of Shelter Island, just open the 12' of French doors.

Just off the media room, even though this is your vacation. You'll find you may need to to do a little work; there is an office area with Wi-Fi as well as hard-wired Ethernet high-speed Internet access and a desk with a daylight lamp and comfortable rolling chair.

The new first-floor level also includes 12' of French glass doors that lead out to the second covered outside area with slate floors and finished walls and lighting, comfortably furnished for your to lounge, grab a bike or a pool toy.

We are constantly upgrading the Shelter Island Hideaway Vacation Home! Last year we bought a new Media room TV, going from 55' to 70'. We recently installed Martha Stewart wall-to-wall carpeting on the entire upper level. The kitchen though just ten years old was completely remodeled and updated, with all professional stainless steel side by side refrigerator, a five burner Professional convection gas range with warming drawer, new Professional Series Microwave Convection and a super quite Kitchen Aide stainless inside and out the dishwasher. For easy cleanup and beauty, you're sure to enjoy the solid surface high-end Silestone countertops and the glass tile backsplash.

Shelter Island Hideaway will provide you with that much-needed vacation to remember. Spend your time relaxed, enjoying the company of friends and family, watching and listening to the dozens of species of birds, smiling as the the bunnies hop by, the sunset views of passing deer and take in the natural professionally landscaped and maintained property and grounds. No need to do anything, allow Mariano, our Grounds person, to take care of the property on the weekend, the pool company to come in and professionally service and clean the pool every week. We have set up a system so if you require an additional cleaning while at home, you can easily arrange one (payment is your responsibility).

Everything you need is here at Shelter Island Hideaway Your vacation home is equipped with 2, BBQ's, if you prefer charcoal, there is a Weber grill for your use, or if you prefer gas, just fire up the Gas Weber grill. Weprovidehave a few loaner bicycles on the premise, there are pool floats and more, remember, this is your time to relax, so just do it!

New Feature: Dreaming of getting out on the water? Our 30' Cruiser may be available for fishing, sightseeing, cruising around the Island or Hamptons or even Charter Gourmet Cruise. Just ask, and we will do our best to accommodate your needs.

The Hampton's Shelter Island Description: 'Un-Hampton' Hampton's are what you will experience while staying our Shelter Island Hideaway Vacation House Rental on Shelter Island. Just 100 miles from Manhattan you can vacation as if you were in the French Riviera. Travel just a mile to the cosmopolitan Sunset Beach and Hotel. Sunset Beach's hipster credentials come courtesy of its owner, André Balazs, of Chateau Marmont and Standard Hotel fame. You can yacht and celebrity gaze here if you so desire or simply enjoy this Hamptons area NY area protected Island peaceful nature, surrounded by dozens of Coves and Bays, The Long Island Sound, and preserves.

The Hamptons are the Hampton 's, today's playground of wealthy New Yorkers, a more retail oriented version of what the North Fork used to be in the days of Gatsby and before. Shelter Island is located between the forks of Long Island, is a different story, quaint, relatively uncharted territory.

From Shelter Island Hamptons Home you can walk to the Perlman Music Camp.

TripAdvisor Property ID: 4900154

About the area

'Un-Hampton' Hampton's is what you will experience while staying our Shelter Island Hideaway Vacation House rental on Shelter Island. Just 100 miles from Manhattan you can vacation as if you were in the French Riviera. Travel just a mile to the cosmopolitan Sunset Beach and Hotel. Sunset Beach 's hipster credentials come courtesy of its owner, André Balazs, of Chateau Marmont and Standard Hotel fame. You can yacht and celebrity gaze here if you so desire or simply enjoy this Hamptons area NY area protected Island peaceful nature, surrounded by dozens of Coves and Bays, The Long Island Sound and preserves. The Hamptons are the Hampton's, today's playground of wealthy New Yorkers, a more retail oriented version of what the North Fork used to be in the days of Gatsby and before. Shelter Island is located between the forks of Long Island, is a different story, quaint, relatively uncharted territory. From both Shelter Island NY Vacation homes you can walk to the Perlman Music Camp or to the gorgeous and famous Sunset Beach for the beat of today's Music, Celebrity watching, Yacht gazing and of course swimming, skiing, boating and picnicking. For Independence Day, July 4th Sunset Beach features a fabulous Fireworks display. Shelter Island allows for you to enjoy the quiet streets for biking, rollerblading and the dozens of gentle coves for kayaking and canoeing, fishing and boating... It really doesn't get any better than this! Shelter Island is just a few minute ferry ride to both the exciting Hampton's, and Greenport. The South Fork has the Hamptons nightlife, while the North Fork has a bountiful selection of top Wineries, Orient Point and Water front bars, Pubs and Eateries; including fantastic Restaurants like the Zagats rated and Conde Naste Hot List restaurants, the Frisky Oyster. Shelter Island is considered the jewel of the Hampton's. Lulled by the tides of its Peconic, Gardener's and Shelter Island Bays, this NY Vacation Island is an 8,000-acre paradise; Shelter Island offers pristine beaches, breathtaking water views, historic homes and gourmet eateries in a truly unique pristine upscale setting. Our Vacation home allows you to enjoy the peaceful and quiet streets, Creeks and Bays for kayaking, canoeing, fishing and the Mashomack Park with its multitude trails and nature programs for both children and adults. More than one-third of the island has been set aside as the Nature Conservancy's Mashomack Nature Preserve, a great destination for hiking and witnessing the island, it 's many species of wildlife and birds, just a as it originally was nearly 400 years ago. From our Hamptons area Shelter Island Vacation Home rental it is just a short ferry ride to the south's Sag Harbor and East Hampton with its restaurants, Movie Theater and famous shops. The North ferry takes you to The North Fork and Greenport with its Tall Ships, famous Merry-Go-Round, boutique shops, and dozens of Wineries, restaurants and surrounding vineyards. McArthur airport is just 50 miles west, and just bit further to Kennedy Airport, LaGuardia Airport, and Newark NJ airport. From most areas you can take the Hampton Jitney, or the Long Island railroad directly to Greenport and a $2 ferry ride across to Shelter Island.

Getting around

Walking, biking and driving. There is also a cab company on the Island

Getting here

Directions from LI/Queens/Brooklyn: Route 495 to Exit 71. Bottom of hill at stop sign make a left Follow road around past gas station Go straight to a stop light (past FEDEX) Continue on to next stop sign and make a right on Sound Avenue Take Sound Ave approximately 22 miles till you will pass a stretch where you can see water on left and a beach (across is CT). Continue on Sound Ave till you see a large campground on right. Go about ¾ mile further, there will be a sign for Greenport, followed by  a small green sign on right saying Shelter Island - turn right Take that road till end (about 1 mile), make left Go a couple of blocks, you will see another Shelter Island Ferry sign, turn right  and then first left This will take you t

Interaction with guest

We are not on-site. Occasionally we will meet you at check in. We have a cleaning company that also helps, manage the property nd are available quickly. I am 2 hours away, but can be available if need be.

Owner profile

David J



  • Bedroom 1: Queen Bed
    Bedroom 2: Queen Bed
    Bedroom 3: Queen Bed
    Bedroom 4: Queen Bed
    Beds in other rooms: Twin bed


  • Air conditioning
  • Balcony/Terrace
  • Grill
  • Heating
  • Balcony/Terrace
  • Fireplace
  • High Speed Internet
  • Hot tub/Jacuzzi
  • Linen provided
  • Private outdoor pool (unheated)
  • Parking Included
  • Secure parking
  • Balcony/Terrace
  • Pet Friendly
  • Waterfront
  • Wi-Fi available


  • Clothes dryer
  • Dishwasher
  • DVD player
  • Hair dryer
  • Iron
  • CD player
  • Refrigerator
  • Satellite TV
  • Microwave
  • Stove
  • Toaster
  • Video player
  • Washing machine


  • Cycling Trips
  • Fishing
  • Water sports
  • Horse riding

Reviews (10)

Excellent – based on 10 reviews Excellent
10 reviews


Reviewed 9 Jun 2015

This home was absolutely stunning. Photos don't do it any justice. It's grand in person. My girlfriends and I decided to take a mini getaway and we could not have chosen a better home. Super spacious, more than enough room for 8-10 people. Pool area was definitely our favorite place. We lounged out everyday, catching some great sun! The Sonos system Henry has in his home is out of this world ! We had music on all around the clock, it played outdoors by the pool and the patio which was a plus since it's so spacious, the sound was everywhere you wanted it to be. There's a speaker in every room and you can adjust it as needed. Truly a fantastic add to the home. Henry is great as well! He's connected remotely to everything in case something goes wrong. Definitely looking to come back int the fall for a family trip ! :)

Owner's reply: Thank you, we are so glad you enjoyed your vacation and look forward to having you back soon! David

“Wonderful Family Vacation”

Reviewed 2 Oct 2011

We stayed at this amazing house from Sep 10-17 and had the best time (we = two couples and two toddlers). The house was perfect. Great location with all the amenities you can imagine inside and outside the house (pool, large back yard, outdoors storage for bikes, grills, 4 bedrooms (one of them a loft), the best kitchen, nice entertainment room, etc. The house was also just 2 minutes away from a very nice beach, totally quiet, literally across the street. The owner was very easy to deal with and everything was done very professionally. We had a small issue with the fridge and called and he responded right away. Problem solved in 5 minutes. There were really no cons. Maybe the fact that you have to bring your own garbage to the local recycling dump but that was not a big deal because we knew about it from all the information that the owner gave us. We would love to come back next year.

“shelter island home”

Reviewed 6 Oct 2010

The house was a lovely surprise. It was a classic beachhouse, incredibly equipted and clean,and no musty smell that is typical. The "compound" has 3 houses, each with it's own personality. (We rented the red house.) It is a great place for a family reunion. We had 12 people eating dinner in the dining room and it was a delight! We would definately recommend this rental to anyone.


Reviewed 19 Jul 2010

My family and I could not ask for a better family vacation at this beautiful and inviting Shelter Island retreat. House is charming, warm and conveniently located to beach. Sunsets were amazing!!! If your looking for a beautiful, private quiet getaway can't go wrong here.

“Perfect Getaway”

Reviewed 29 Sep 2008

The perfect antidote to city living. Whether it's beautiful weather so you can enjoy the pool or raining and you have the porch as well as fireplaces, this place is truly magical. The house is very comfortable and the cottage is so special. Each has its own special features. The house's kitchen is big enough for a big family to cook together-the hammock is crying "Nap!" and being a block and half away from the water to see the sunset makes it even more inviting. I would definitely recommend this to anyone who wants a beautiful, well-appointed, extremely clean and very private space. I work at Dwell and feel that design is very important. This fits the bill.

“The Perfect Beach House Experience”

Reviewed 27 Sep 2008

This is a special place. The main house is lovely -- open, airy, beautifully furnished, comfortable with one of those wide wrap-around porches that beckon you to sit, read, relax, chat. I ended up spending almost a whole day in this incredible spot. The grounds are also lovely -- the pool, the lawn and being one block from a quiet, almost private-feeling beach was incredible. The "cottage" is also an incredible place-a jewel in the crown. It's also an open, airy space with it's own entrance, pool(s) and rock stream. The property is truly a paradise and Shelter Island is really magical. Once you get on the ferry, you really feel that you're "away." I had a wonderful time here.

“Lovely Paradise”

Reviewed 19 Sep 2008

We had such a great time here, and love, love, love this house. Shelter island is a great low-key vacation spot, and this house offers the perfect opportunity to take advantage of it. The pool is great, the hammock is true paradise, and the open nature of the house is great for groups. We had a blast and will recommend it to all of our friends.


Reviewed 19 Aug 2008

every minute of my time at this beautiful home was enjoyable. the pool is heavenly, as are the grounds. cooking in the kitchen was a dream - everything you could possibly need for a gourmet meal or simple island brunch. Shelter Island is in my heart forever!

“Pure Bliss”

Reviewed 13 Aug 2008

My first visit to Shelter Island was absolutely perfect. The home was spectacular- open, airy with a "wrap around" terrace that we practically lived on all week. Jumping in the refreshing pool between long bike rides, runs to Sunset beach, and shopping in Sag Harbor made the experience that much more enjoyable. If you have not been to Shelter Island before I highly recommend that you do so and this home was a great base for one of the most relaxing vacations I have taken in my life.

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Owner Supplied Testimonials

Had a fabulous time, the home is beautiful, the Island is wonderful, already booked for next year.

JK Solomon Brothers VP

The house is beautiful, the pool is great. Love the huge outdoor covered porch and the fact that the waterfront was across the street. Took kids back to the home for lunch everyday, or if they were in the sun too much.

Very close to everything on the Island, really enjoyed Shelter Island more that the Hamptons.

CR NYC Attorney