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Stunning Shelter Island Estate

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Exterior
Outdoor pool, a heated pool
8 bedrooms, desk, iron/ironing board, travel crib
Outdoor dining
Fridge, microwave, oven, stovetop

Reviews

10 out of 10

Exceptional

Entire home

8 bedrooms7 bathroomsSleeps 14650 sq m

Popular amenities

  • Pool
    Pool
  • Barbecue grill
    Barbecue grill
  • Washer
    Washer
  • Pet friendly
    Pet friendly
  • Kitchen
    Kitchen
  • Air conditioning
    Air conditioning

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Stunning Shelter Island Estate

Stunning Shelter Island traditional over 3 floors with pool and separate contemporary guest house in luxury settings. Short walk to Sunset Beach, restaurants, tennis and golf. Entertaining space galore, movie screen, wrap around decks, fully private garden. 4 King size en-suite bedrooms, 3 queen size bedrooms, and a kids bedroom.
Main House: 3 King size en-suite bedrooms, 1 King size bedroom, and a kids bedroom with double bunk beds.
The First Floor has a kids bedroom with double bunk beds adjoining a King size bedroom that opens onto the pool patio, A Media Room with a pull out double sofa bed, A Playroom, Summer Kitchen and Laundry Room.
The second floor has a king size master suite. Cathedral ceilings open plan spacious living room, dinning room, chef's kitchen and breakfast area. Top of the line appliances. A full wrap around deck including multiple dining and lounging areas, fire-pit and BBQ. The third floor has two King Size en-suite guest master suites and a drop down movie screen theater lounge. The Garden is fully enclosed and private, there is a 50 foot pool, patio and lounging area and also a secluded playground.
The Guest House has a King Size Master Suite and and 2 queen size bedrooms with a second bathroom. A large dining/kitchen area with fully retractable wall of windows onto the pool patio. Additional built in BBQ area and lounge seating, and outdoor shower.
The pool is typically open from Memorial Day to mid Sept, weather dependent. The pool season can be extended by request though.

Property manager

Rory

Languages

English

Property amenities

Beach

  • Near the beach
  • Beach sun loungers
  • Beach towels

Pool/Spa

  • Private pool
  • Outdoor pool
  • Heated pool
  • Fence around the pool

Internet

  • Free WiFi

Parking and transportation

  • Electric car charging station on site
  • Onsite parking
  • Car recommended

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Toaster
  • Coffee/tea maker
  • Electric kettle
  • Lobster/crab pot

Dining

  • Dining table

Bedrooms

  • 8 bedrooms
  • Bed sheets provided
  • Sofa bed

Bathrooms

  • 6.5 bathrooms
  • Bathtub or shower
  • Jetted bathtub
  • Bidet
  • Toilet paper
  • Hair dryer
  • Shampoo
  • Outdoor shower
  • Towels provided
  • Soap

Living spaces

  • Fireplace
  • Living room
  • Dining room
  • Wood stove

Entertainment

  • Smart TV with cable/satellite service
  • Foosball table
  • Arcade/game room
  • Stereo
  • Music library
  • Video library
  • Books
  • Games

Outdoor areas

  • Balcony
  • Fenced yard
  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Firepit

Laundry

  • Washing machine and dryer

Work spaces

  • Printer
  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • 2 total (up to 50 lbs per pet)
  • Welcoming dogs only

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health or beauty spa
  • Near a hospital
  • Near outlet shopping

Things to do

  • Water park
  • Fitness facilities nearby
  • Golf privileges
  • Golfing on site
  • Tennis on site
  • Kayak on site
  • Bicycle on site
  • Power boating nearby
  • Horse riding nearby
  • Sailing nearby
  • Wildlife and game walks nearby
  • Winery tours nearby
  • Fishing nearby
  • Kayaking nearby
  • Water skiing nearby
  • Cycling nearby

Safety features

  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 7000 sq ft (650 sq m)

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 28

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total (up to 50 lbs per pet)
Restrictions apply; for more information contact the property at the number on the booking confirmation
Note from host: Small dogs allowed, extra deposit required

Children and extra beds

Children are welcome

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Note from host: No outdoor music. Must be considerate of neighbors
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

A car is recommended for transportation to and from this property

Property is also known as

Stunning Shelter Island Estate Private vacation home
Stunning Shelter Island Estate Shelter Island Heights

About the neighborhood

Map
Shelter Island Heights, NY

What's nearby

  • Crescent Beach - 4 min walk
  • Sunset Beach - 7 min walk
  • Railroad Museum of Long Island - 25 min drive
  • Kontokosta Winery - 25 min drive
  • 67 Steps Beach - 27 min drive

Getting around

  • Greenport Station - 24 min drive
  • East Hampton, NY (HTO) - 43 min drive

Restaurants

  • ‪Sterlington Deli - ‬24 min drive
  • ‪Stars Cafe - ‬4 min drive
  • ‪Sunset Beach Restaurant - ‬8 min walk
  • ‪Aldo's - ‬24 min drive
  • ‪Southold Fish Market - ‬28 min drive

Frequently asked questions

Does Stunning Shelter Island Estate have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Stunning Shelter Island Estate pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 50 lbs per pet.

What time is check-in at Stunning Shelter Island Estate?

Check-in begins at 4:00 PM.

What time is check-out at Stunning Shelter Island Estate?

Check-out is at 11:00 AM.

Where is Stunning Shelter Island Estate located?

This family-friendly Shelter Island Heights vacation home is located near the beach, within a 10-minute walk of Crescent Beach and Sunset Beach. Shelter Island Country Club and Sylvester Manor are also within 2 mi (3 km).

Stunning Shelter Island Estate Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 29 out of 29 reviews" "
Rating 8 - Good. 0 out of 29 reviews" "
Rating 6 - Okay. 0 out of 29 reviews" "
Rating 4 - Poor. 0 out of 29 reviews" "
Rating 2 - Terrible. 0 out of 29 reviews" "

10/10

Cleanliness

Reviews

10/10 Excellent

Lily H.

Liked: Cleanliness
Girls trip
Gorgeous property minutes from North Ferry. Hosts were incredibly responsive throughout entire process. The pool and grounds were gorgeous and kitchen well-stocked with all kinds of food-prep accoutrements for cooking big meals— the perfect venue for our girl’s trip of 12. We didn’t have children with us though the space appeared to be well-equipped to host families with young children, too.
Stayed 3 nights in Sep 2024

10/10 Excellent

Sabrina D., Brooklyn

Liked: Cleanliness
Stunning Shelter Island Estate
Wonderful stay at this place. We celebrated with friends for 2 weeks and the owners were very kind and responsive. The pool is a plus and the poorhouse is not a poolhouse but almost a house by itself. Highly recommended!
Stayed 3 nights in May 2024

10/10 Excellent

Sabrina D., Brooklyn

Liked: Cleanliness
Great house with amazing host
Our weekend stay was fabulous. We had a low-key relaxing weekend with our friends to celebrate our 50th birthday. Communication with the owner was very good and the house was beyond expectations. The garden and the pool were a plus. highly recommended!
Stayed 3 nights in May 2024

10/10 Excellent

Michael E.

Liked: Cleanliness
Great stay!
Highly recommend this spot. Great location, walk to beach, easy drive to town and restaurants. Has all the toys and cooking tools you need for a great stay.
Stayed 15 nights in Aug 2023

10/10 Excellent

Anne G.

Liked: Cleanliness
Wonderful family time
This house is amazing. The design is excellent for families. All four bedrooms in the main house have king beds and private baths. The guest house has 3 bedrooms, one with a king and private baths. The kitchen has everything for great cooking. The pool is so well designed. There’s a large area for kids and toddlers and then plenty of space for adults to swim, and a secure cover. Great balcony, outside play gym, walk to the beach. We loved Shelter Island. Loved the farm produce, the fish market, biking around, the IGA is surprisingly well stocked. We loved kayaking and the beaches. It was our first vacation on Long Island and we would definitely come back and try to rent this home again. The owners were exceptional—great communicators, quick to answer questions and respond to any issues that came up. Highly recommend.
Stayed 9 nights in Aug 2023

10/10 Excellent

Paul S.

Liked: Cleanliness
Great Stay!
My family and I had a great time staying here. The property was beautiful and had everything we needed. The hosts were very communicative and helpful.
Stayed 6 nights in Jun 2023

10/10 Excellent

Sharon B., Bala Cynwyd, PA

Liked: Cleanliness
Fantastic stay on beautiful property
This was our second summer vacationing with our adult children and young grandchildren in this beautiful home. We were all excited to return to this peaceful, very comfortable, and well-maintained property and highly recommend it to others! Great pool, easy walk down a wooded path to the beach, helpful hosts….a five star experience.
Stayed 10 nights in Jun 2023

10/10 Excellent

Toby B.

Liked: Cleanliness
So Nice
Everything about this 15 day stay was excellent. The property/house is so accommodating and comfortable. The hosts are the nicest people I’ve ever rented from. Available for help anytime. Highly recommended.
Stayed 17 nights in Aug 2022

10/10 Excellent

Robert F.

Liked: Cleanliness
Shelter Island Bliss
We rented this property for 2-weeks for multiple generations of family and friends to enjoy and it fully delivered. House is amazing and backyard is a peaceful oasis. The 4-BDR pool house is a huge plus! Loved everything about our experience there, including close location to Crescent Beach!
Stayed 14 nights in Jul 2022

10/10 Excellent

Bruce F.

Liked: Cleanliness
great 2 weeks.
very nice house. second time using it . Hosts were very communicative and great. no problems at all. Highly recommend
Stayed 14 nights in Jul 2022

10/10 Excellent

Sharon B., Bala Cynwyd, PA

Liked: Cleanliness
Fantastic stay on Shelter Island
Our experience staying at Rory and Grainne’s property was fabulous from start to finish. Lots of pre-trip communication made the decision to rent the property easy, and check-in was a breeze. The home itself is beautiful, comfortable and spacious, with plenty of room and privacy for a multi-generation family (our case) or two families vacationing together. It also was spotless on arrival with lots of nice welcoming touches including wine, cookies, and plenty of high end shampoos, conditioners, and soaps. Our young grandchildren loved the well-stocked playroom, and the kitchen is a cook’s dream. The heated pool was a big hit with all ages, and the beach is a short walk down a private road. The hosts’ info guide came with great suggestions for local attractions and markets that helped us get oriented to the island right away. In short, we loved this special home and hope to return sometime.
Stayed 9 nights in Jun 2022

10/10 Excellent

Kristi B.

Liked: Cleanliness
Beautiful family getaway
Our family attended a wedding in Greenport and we needed a large house for us, our adult children, spouses and grandchildren. This home was perfect for us! Plenty of room, well cared for, wonderful amenities, great internet connection and easy, efficient communication with the hosts. We would love to rent again in the future!
Stayed 4 nights in Apr 2022

10/10 Excellent

Angela S.

Liked: Cleanliness
Outstanding Property and Outstanding Time!
We celebrated a wonderful Thanksgiving at the home of Grainne and Rory. Our family was able to shelter away from the rat race and enjoy each other's company. The home is beautiful and feels like a real home filled with love and warmth. Very nice amenities, the kitchen is stocked with best-in-class appliances, cookware, and utensils. The Guest House exceeded my expectations. Very comfortable, spacious, and nice. Lots of space to spread out for private time and wonderful space for gathering together. We look forward to visiting again when it’s warmer.
Stayed 5 nights in Nov 2021

10/10 Excellent

Carol T.

Liked: Cleanliness
Private hideaway in perfect location
This house was really fun for a family vacation. We had an infant toddler’s and adult children and grandparents. Everyone was happy with the property and the house and we all had an amazing time together.
Stayed 14 nights in Aug 2021

10/10 Excellent

Matthew S.

Liked: Cleanliness
Amazing Stay with Great Hosts
My family had an amazing stay on Shelter Island. This is a beautiful home with plenty of room and a great layout. Everything is very well kept and clean. The location can't be beat, with close and easy access to Sunset Beach and other parts of the island. Grainne and Rory were amazing hosts...very attentive and accessible. They genuinely cared about their guests' experience. This one is an easy five stars!
Stayed 14 nights in Aug 2021

10/10 Excellent

Keivn P.

Liked: Cleanliness
Vacation
It was a great peaceful spot. The kids loved the pool. Thank you
Stayed 7 nights in Jul 2021

10/10 Excellent

melinda H.

Liked: Cleanliness
Amazing Island Getaway
We had the most amazing week in this wonderful home. The house is beautiful and comfortable, fabulous location, convenient to the beach, 9 hole golf course, close to town and other parts of the island. The kitchen was well stocked, the grills and smoker great, plenty of pool lounge and beach chairs, beach towels, refrigerators anything and everything that you could possibly need was available and the dining room table had a seat for everyone! The pool was delicious and our Grandchildren would give it a big 👍up (the added benefit was it has a locking pool cover)! There are multiple sitting areas so you felt part of the group but not on top of each other. Our host, Grainne, was very helpful, organized and responsive to my every question no matter what. She went above and beyond in every way to ensure that our stay was special. Perfect for family gatherings with plenty of room for everyone!
Stayed 7 nights in Jul 2021

10/10 Excellent

Sonia A., Greenwich, CT

Liked: Cleanliness
Amazing house and host
Beautiful main and guest houses, very well equipped. We spent a lot of time inside as the weather was not so nice and everyone was very comfortable with a lot of space. Swimming pool is also gorgeous. Hosts are 5 stars. They reply super quick and care about their house and us having a great time there. We hope to be back at some point.
Stayed 4 nights in May 2021

10/10 Excellent

Fredrick B.

Liked: Cleanliness
Family Reunion
Family reunion for 9 siblings and a few spouses, this was a great place for us to get together. A beautiful place, with all the perks
Stayed 7 nights in May 2021

10/10 Excellent

Eli K., San Diego, CA

Liked: Cleanliness
Fabulous Home Close to Beach With GreatAmenitues
This was a family vacation to celebrate 2 graduations, 2 birthdays and an anniversary. The hosts were very responsive throughout our stay guiding us when we asked anything. Very nice accommodating couple- thank you Rory and Grainne. The house has everything you need for a comfortable enjoyable stay. Loved the decor, beds,cook- in kitchen, bbq, kayaks, bikes, outdoor shower and of course the pool! The appliances abound- coffee maker, express machine, mixer, blender and ice maker in pool house. Games too! Easy to is Apple TV’s were a plus late night. Never been to Shelter Island-before and we ALL had a terrific stay!

10/10 Excellent

Brian K.

Liked: Cleanliness
Beautiful home in Shelter Island
Everything was great and the owners were extremely helpful before and during the stay. The house is beautiful and a great place for our families to connect.
Stayed 3 nights in Jan 2020

10/10 Excellent

Daniel L.

Liked: Cleanliness
Perfect wedding weekend
We LOVED this place. Amazing location, amazing house, amazing hosts! Can’t wait to come back and stay again!
Stayed 3 nights in Oct 2019

10/10 Excellent

Elaine G.

Liked: Cleanliness
Wonderful home!
One of our best experiences ever renting a property. Owners were most responsive. Family loved the spacious home and pool. Lots of happy memories made there.
Stayed 7 nights in Jul 2019

10/10 Excellent

steven r.

Liked: Cleanliness
Gorgeous Compound -Gracious Host
Just returned from a wonderful weeks stay at this spacious home with the plus of a 3 bedroom pool house . More than enough room for all seven adults and five children. Everything one could need was supplied and in abundance. T
Stayed 7 nights in Jun 2019

10/10 Excellent

Verified traveler

Liked: Cleanliness
Anniversary getaway
This was an amazing week for my family to always remember! All the kids and grandkids surprised my parents for their 40th anniversary with some time away for us to all spend together at shelter island. The house couldn’t have been a better backdrop. The bedrooms, ample sitting space, playroom, pool and so much more were led way to a fantastic week. Rory and Grainne couldn’t have been more accommodating and gracious from start to finish! Hope to come back!!!