Entire home

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

Family-friendly stay with outdoor pool in Shelter Island Heights

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

A pool with two lounge chairs, a house with a porch, and a wooden fence.
A pool table in a room with a view of a backyard.
A spacious living area with a wooden dining table and chairs, a blue armchair, a fireplace, and a bookshelf.
A backyard patio with outdoor furniture, a wooden fence, and a variety of plants.
A house with a covered porch, surrounded by a garden with purple flowers and a stone wall.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 7

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

Explore the area

View in a 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

Room options

About the area

Shelter Island Heights

Silver Beach stay.Your stay at this Silver Beach vacation home places you within 2 miles (3 km) of Crescent Beach and Sunset Beach. Shell Beach and Shelter Island Whale's Tail are also within 3 miles (5 km).

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
  • ‪Nookies - ‬27 min drive

About this property

Entire place

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

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

* Please Read House Rules And Policy's Before Booking*
*Check In And Check Out Times Are Firm*

PERFECT FOR FAMILIES — DOGS WELCOME!

Enjoy summer on Shelter Island in this beautifully maintained and private home, tucked behind mature evergreens and conveniently located near Sunset Beach, Crescent Beach, Crab Creek, and the resort areas. Shelter Island Heights is also just a short bike ride away.

The house is spacious, bright, well equipped, and set up for easy summer living, with a private pool, great outdoor spaces, and plenty of amenities for families and children.

THE HOME

The bright, sun-filled interior has an open layout with plenty of room to relax.

Just off the foyer, the living room features:

• Extra-large queen-size sleeper sofa
• Large windows overlooking the veranda
• Fireplace
• Easy access to the fully equipped kitchen

The kitchen opens to the dining area, with French doors leading directly to the outdoor deck.

Down the hall you'll find:

• Full guest bathroom
• Guest bedroom with bunk bed and trundle
• Second guest bedroom with Queen-Size bed
• Home office area with direct access to the pool deck
• Spacious primary en-suite King Sized bedroom

The lower level has a media room with a projection screen and reclining chairs, Popcorn machine as well as a laundry area.

OUTDOOR LIVING & POOL

The private, fully fenced grounds are designed for spending as much time outdoors as possible.

• In-ground Gunite swimming pool (open through Columbus day)
• Outdoor shower
• Outdoor dining area with pizza oven
• Gas grill
• Sun Day bed lounger
• Fire pit with Adirondack chairs
• S’mores station
• Vegetable and herb cutting garden
• Pool cabana with pool/ping-pong table, Dart Board
• Smart TV (all premium channels)
• Bluetooth indoor/outdoor speakers
• Extra refrigerator
• Food and beverage area
• Poolside lounge chairs
• Fully fenced-in yard

INCLUDED AMENITIES

The home comes fully equipped for your stay, including:

• Cable with all premium channels
• Nest-controlled central A/C
• ADT alarm system
• Ring front doorbell
• Pool maintenance
• Lawn maintenance
• Garbage pickup

FAMILY & BEACH GEAR

A variety of family, beach, and outdoor items are available for guests to use:

• Board Games
• Kayak
• Baby stroller(s)
• Jogging stroller
• Pack & Play
• Child safety gate
• Pool/door alarm
• Pool floats
• Clamming nets
• Skateboards
• Scooters
• 3 adult bicycles
• 1 teen bicycle
• 2 children’s bicycles
• Bike pump
• Beach Chairs
• Beach Towels
• Beach Umbrella

DOG FRIENDLY

Dogs are welcome with a $200 pet fee.

Guests are asked to please clean up after their dogs throughout the yard and grounds.

HOUSE RULES

This is a quiet, family-oriented neighborhood. We ask that guests be considerate of the neighbors and take good care of the property during their stay.

Maximum Occupancy: 4 Adults (unless other wise approved)

NO PARTIES
NO SMOKING
NO CANDLES OR INCENSE
NO exceptions.

For everyone's comfort and safety:

• Bunk beds are for children ages 13 and under only.
• Children must be supervised at all times around the pool deck and fire pit.
• Guests and visitors must park in the driveway only. No parking on the main road.
• Please lock all doors when leaving the property, including the pool house French doors and garage doors.
• Before checkout, please place all garbage in the outdoor trash bins.
• Please report any damage or breakage promptly.
• Guests are responsible for any damage they cause to the property or household items, as reported by the house manager.
• Please clean up after your dog throughout the property.

The perfect Shelter Island home with everything you need to spend the summer/fall swimming, biking, grilling, relaxing, and enjoying the island.

Similar properties

Property amenities

Beach

  • Beach nearby
  • Beach loungers
  • Beach towels

Pool/Spa

  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Wheelchair-accessible parking available

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Separate dining area

Entertainment

  • Books
  • Games
  • Smart TV
  • Stereo
  • Video games

Outdoor areas

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

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair
  • Printer

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total (up to 999 lbs per pet)

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 3 on-site accessible parking spaces
  • No elevator (single-level property)
  • Wheelchair-accessible parking
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board
  • Limited housekeeping
  • Phone
  • Safe

Location highlights

  • In a village
  • Near the bay
  • Near the marina

Things to do

  • Arcade/game room
  • Bicycles
  • Billiards/pool table
  • Gym
  • Kayak
  • Table tennis
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby
  • Winery tours nearby

Safety features

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

General

  • Bicycles
  • Garden

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 30

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
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Start the dishwasher
Strip any used beds and gather used towels
Remove leftover food and drinks and take out the trash
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.

Rules

Check In And Check Out Times Are Firm Please be respectful of the Neighbors Absolutely no parties, No Loud music. 3 Cars Max No Parking on the Street
$200 Pet Fee Pets Not Allowed On Beds / Furniture Beds Must Be Stripped At The End Of The Stay No Loud Music 3 Cars Max No Street Parking
Bunk Beds Are For Ages 13 And Under.

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 2 (weight limit: 999 lbs per pet)
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

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
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
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.

Frequently asked questions

How close is Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly to the airport?

This vacation home is 13.5 mi (44-min drive) away from the East Hampton, NY (HTO) airport, the closest popular airport to the property.

Does Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly to the beach?

This vacation home is 5.7 mi (29-min drive) from The Hamptons Beaches and 1.4 mi (3-min drive) from Crescent Beach. Don't forget your sunscreen!

Does Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly ?

No, there is no casino at this vacation home.

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.

Is there free parking at Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly ?

Free parking is not available at this vacation home.

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

This vacation home features an outdoor pool.

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

There are no spa services available at this vacation home.

How close is Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly to downtown Shelter Island Heights?

This vacation home is 1.8 mi away from Shelter Island Heights.

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

Reviews

10

Exceptional

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

Reviews

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

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 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

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

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

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

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