Entire home

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 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 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.
A spacious living area with a wooden dining table and chairs, a blue armchair, a fireplace, and a bookshelf.

Reviews

10 out of 10
Exceptional

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.
3 bedrooms2 bathroomsSleeps 7

Popular amenities

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

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

Where you'll sleep

3 bedrooms (sleeps 7)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Twin Bunk Bed and 1 Twin 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

About this property

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.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 30
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

Pets allowed: dogs less than 999 lbs per pet (limit 2 pets total)
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Smoking

Smoking is not permitted

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.
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.

Important information

You need to know

Property # 2708504
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

About the neighborhood

Shelter Island Heights

Located near the beach, this vacation home is in Silver Beach, a neighborhood 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. Traveling with kids? Consider Railroad Museum of Long Island and Bay Street Theatre. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with horse riding and hiking.
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
  • ‪Nookies - ‬27 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.

How much does it cost to stay at Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly ?

As of Sep 23, 2026, prices found for a 1-night stay for 2 adults at Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly on Dec 1, 2026 start from $697, 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 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 999 lbs per pet.

How much is parking?

Onsite 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 ?

Check-out 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 vacation 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 mi (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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
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
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

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

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
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

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
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

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

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

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

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
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

About the host

Hosted by TARA MICHELLE

Host profile image

Why they chose this property

The location is ideal for those who enjoy walking or biking. The neighborhood’s unique layout—three parallel streets connected only at the ends—means minimal traffic, ensuring a peaceful environment for residents and visitors.

Located in the serene Silver Beach area, you’ll find quiet beaches and excellent fishing and clamming spots. A short five-minute walk brings you to Bootlegger’s Alley, a perfect place to watch stunning sunsets and end your day on a relaxing note. Nearby, Sunset Beach and the town center are easily accessible by bike or car, making major attractions just a short trip away.

This home has been a special place for our family, and we’re excited to share it with you!

What makes this property unique

Looking For A Perfect Island Getaway? Look No Further!! Minutes to the Beach for Relaxing... Fishing and Clamming. Don't miss the Beautiful Sunset Dinners at 1901 Grill, ice cream and mini golf at Whales Tale...Want to stay home?...NO Problem! This Vacation home has all you need ...Crystal Clear refreshing Gunite Pool, Outdoor Shower and super comfy lounge chairs!! Hungry? BBQ on the Gas Grill or Make Your Own Pizza / Flat breads with the Gas/Wood Pizza Oven.. Pool House with Outdoor surround sound speakers. Pool Table, Smart TV with all premium channels and food and beverage area. Projector Screening room with popcorn machine and candy...Fire Pit with Adirondack chairs and s'mores bar...Vegetable / Herb cutting Garden, Baby Stroller(s), Jogging Stroller, Pack and Play, Child Gate, Pool Alarm, Adult, Teen and Child Bicycle's
Covered front porch with rocking Adirondack chairs is great for relaxing.

Languages:

English, Spanish

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