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Charming updated home with pool on quiet street. Near Silver Beach

Photo gallery for Charming updated home with pool on quiet street. Near Silver Beach

Sunny pool
Well lit and comfortable Living Room
Living Room and Kitchen flow together
Open Floor Plan
New Kitchen with all new appliances

Reviews

10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 81500 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space

Explore the area

View in a map
Shelter Island, NY
  • Place, Crescent Beach
    ‪2 min drive‬
  • Place, Sunset Beach
    ‪3 min drive‬
  • Place, The Hamptons Beaches
    ‪12 min drive‬
  • Airport, New Haven, CT (HVN-Tweed - New Haven Regional)

Rooms & beds

3 bedrooms (sleeps 8)

3rd Bedroom

1 Double Bed

Kids Bedroom

1 Single Bed and 1 Single Bunk Bed

Master Bedroom

1 King Bed

2 bathrooms

Bathroom 2

Bathtub or shower · Toilet

Master Bathroom

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Garden
Dining area

About this property

Charming updated home with pool on quiet street. Near Silver Beach

Great house in great location. 3 bedrooms (including one with bunk bed and additional bed) . Open floor plan with updated kitchen and bathrooms. In addition to large pool, great yard and outdoor shower. Short walk to nearby beach or bike to Sunset or Shell Beach. Very friendly quiet neighborhood. Ideal for families with 2-4 kids. We hope our house feels like your home for the time you are here!
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

No pets allowed
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Smoking

Smoking is not permitted
Utilities are paid by renters and will be deducted from the security deposit.

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher

About the area

Shelter Island Heights

Silver Beach, a neighbourhood in Shelter Island Heights, is home to this holiday home. 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. Railroad Museum of Long Island and Norman E. Klipp Marine Park are also worth visiting. Discover the area's water adventures with power boating, sailing and fishing nearby, or enjoy the great outdoors with hiking.
View more Holiday homes in Shelter Island HeightsOpens in a new window
Map
Shelter Island, NY

What's nearby

  • Crescent Beach - 2 min drive - 2.1 km
  • Sunset Beach - 3 min drive - 2.8 km
  • The Hamptons Beaches - 12 min drive - 6.9 km
  • Cooper's Beach - 42 min drive - 35.8 km
  • Montauk Point - 59 min drive - 64.0 km

Getting around

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

Restaurants

  • ‪Vine Street Cafe - ‬7 min drive
  • ‪Sunset Beach Restaurant - ‬3 min drive
  • ‪Waypoint - ‬31 min drive
  • ‪Opties & Dinghies - ‬5 min drive
  • ‪Pridwin Hotel - ‬3 min drive

Frequently asked questions

Does Charming updated home with pool on quiet street. Near Silver Beach have a pool?

Yes, this property has a pool.

How much does it cost to stay at Charming updated home with pool on quiet street. Near Silver Beach?

As of 12 Mar 2026, prices found for a 1-night stay for 2 adults at Charming updated home with pool on quiet street. Near Silver Beach on 10 May 2026 start from £310, 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 Charming updated home with pool on quiet street. Near Silver Beach pet-friendly?

No, pets are not allowed at this property.

How much is parking at Charming updated home with pool on quiet street. Near Silver Beach?

On-site parking is available at the property.

What time is check-in at Charming updated home with pool on quiet street. Near Silver Beach?

Check-in begins at 4:00 PM.

What time is check-out at Charming updated home with pool on quiet street. Near Silver Beach?

Checkout is at 11:00 AM.

Where is Charming updated home with pool on quiet street. Near Silver Beach located?

Located in Silver Beach, this holiday home is within 2 miles (3 km) of Crescent Beach, Shelter Island Country Club and Sunset Beach. Shell Beach and Sylvester Manor 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. 17 out of 17 reviews
Rating 8 - Good. 0 out of 17 reviews
Rating 6 - Okay. 0 out of 17 reviews
Rating 4 - Poor. 0 out of 17 reviews
Rating 2 - Terrible. 0 out of 17 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Ruben R.

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

What a stay

It was simply amazing. The property was clean. The owner was very responsive we needed something. They left us all the necessary information to get around in shelter island.
Stayed 7 nights in Jul 2025

10/10 Excellent

Pamela P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a “home away from homes” as it was such a clean and family friendly home with such a good eye for beach-chic decor and colors and every amenity needed to have a solid family vacay week. The pool was perfection, the neighborhood was quiet with wide streets and little traffic… many runs from the house to Shell Beach and down to the beautiful views along Crescent Beach. Enjoyed the local farmers market at Sylvester Manor and many restaurants. Host, Paul, was easy to communicate and very accommodating. We will definitely return for another Shelter Island getaway. And if we could give ten stars, we certainly would.
Stayed 7 nights in Jul 2025

10/10 Excellent

Liz C.

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

Great Shelter Island House!

We loved our stay here! The house was wonderful and the pool was a real value-add!
Stayed 7 nights in Jul 2019

10/10 Excellent

Laura M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay on Shelter Island. Paul was a responsive host. The house was well equipped with everything we needed - from basic items like extra garbage bags etc to bikes and beach toys. It meant the week was hassle free and we could enjoy the house and Shelter Island. The pool was lovely and got sun all day. The property was equipped with alarms on the doors to the pool area which gave us peace of mind traveling with young children. We would stay again!
Stayed 7 nights in Jun 2025

10/10 Excellent

Tomer M.

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

Wonderful two weeks at shelter island

We had a great time staying at Paul’s house. The pool was great and the house had all that we needed for a fun two weeks vacation. Paul was generous, responsive and helpful. The house and that area of Shelter island is wonderful location. I would 100% recommend this property.
Stayed 16 nights in Aug 2024

10/10 Excellent

Erica C.

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

Relaxing home away from home

We stayed at Paul's place for 9 days with my husband, 6-year old son and my in-laws and had a wonderful time. I would absolutely recommend this home and Shelter Island. The house and property exceeded our expectations from the listing and pictures. The pool was gorgeous - lots of direct sun, surrounded by tall trees, great deck with loungers and a table with an umbrella and some floats and noodles and such. We were basically in the pool most of the day every day. The backyard also features a hammock and a swingset, which was a really nice surprise for my son. The house itself is really beautifully decorated but not at all fussy. It felt very comfortable and truly like a home away from home with everything we needed. The master bedroom and kids rooms were great. The additional room is small with a full-size bed, not a queen. There were two TVs (not in the bedrooms) one internet-enabled with all the streaming services, which was great. And Shelter Island is so beautiful. You're a short drive from water in just about any direction so it's very pretty to drive around the island. We'd recommend Isola, Stars Cafe, Ram's Head Inn, The Islander, and Salt for food (we did take out the whole time). Sunset beach and Wade's beach were both lovely - Sunset beach is a great place to bring an evening meal and, you guessed it, watch the sunset. Also, Paul was a great host. He talked me through some details about the house over the phone before we arrived and was very accessible via text for quick questions we had. He was also flexible on our check in and check out times, which we really appreciated. We would love to come back again. Would definitely recommend!
Stayed 9 nights in Jul 2020

10/10 Excellent

Lina T.

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

Fabulous stay

My family had a lovely stay at Paul’s house. The house has everything that is needed for a family stay. We enjoy cooking and there were many pots and pans. Our children enjoyed the pool which is very large. There are many nice family friendly beaches within a 5-10 min ride. Paul was a river full host, very responsive and helpful. We look forward to staying again next summer.
Stayed 14 nights in Jul 2022

10/10 Excellent

Elizabeth I.

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

Amazing stay on Shelter!

We had SUCH a lovely time at this pretty home in a beautiful place. The kids had a blast in the pool, and we walked down to watch the sunset on the beach many evenings. Great set-up for a family - comfy beds, super-functional kitchen, cozy family room for games and movies. Paul and his house manager were really responsive and thoughtful (e.g., helping us get ready for a storm that blew through the island). Highly, highly recommend!!
Stayed 14 nights in Jul 2021

10/10 Excellent

Michael R.

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

Wonderful property and Vacation Stay!!

We had a wonderful time staying here! The house is very clean and the decor is comforting. The property owner does a great job keeping you informed and willing to answer any questions. While we were there in early Spring, we look forward to returning in the Summer to get another experience on the island, including use of the pool and the beautiful local beaches!!
Stayed 8 nights in Mar 2021

10/10 Excellent

Lingling X.

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

Family friendly

We had a great time at Shelter island with two kids. The house is clean and has everything we need for family time! Host is easy to access for questions or suggestions.
Stayed 8 nights in Oct 2020

10/10 Excellent

Diane B.

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

Review of Stay at Shelter Island Island Heights

We easily registered for the property and the owner responded quickly and communicated necessary information clearly including answering our questions.
Stayed 4 nights in Sep 2020

10/10 Excellent

Crista T.

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

We loved our stay!

We had a great time - everything was perfect for us. Paul was really helpful and his home is very clean, beautifully decorated and updated. We will definitely be back!
Stayed 14 nights in Aug 2020

10/10 Excellent

Anna F.

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

Sweet Intro to Shelter Island

The house is really sweet, with thoughtful beach decor. We really enjoyed the deck and pool, with the backdrop of a large country backyard. The neighborhood is very quiet, and a short walk to Bootleggers beach, for great sunsets. The hosts are the nicest people. Great communication and super kind and responsive. This was greatly appreciated in the context of arriving as first-timers on the island, looking for a little reprieve from stressful months of covid lockdown. Our stay on Shelter was exactly what we needed. Many thanks
Stayed 20 nights in Jun 2020

10/10 Excellent

Michelle P.

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

Great house & easy booking process!

This house was perfect for our group, we were a few couples in town for a wedding. We enjoyed the pool and deck area as well as the open floor plan of the kitchen/living room area. The house was very clean and the booking / checkin process was very easy. We had a few questions about the house once we got there and Paul was readily available to help. He is very responsive. We would definitely stay here again!
Stayed 2 nights in Sep 2019

10/10 Excellent

Michael S.

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

5 Penny’s Path

Really enjoyed our stay. The house is well appointed, and very clean.
Stayed 3 nights in Jun 2019

10/10 Excellent

Georges F., New York, US

Great house and host

We loved our stay this house. Great place, with a great pool and great location. The host was very helpful in answering any questions we had.
Stayed 4 nights in Aug 2018

10/10 Excellent

James S.

Great house in quiet neighborhood

We really enjoyed our stay. Shelter Island has a lot to offer and this house provided the perfect base to explore. The owners were very helpful with local knowledge and easy to deal with.
Stayed 3 nights in Aug 2018

About the host

Hosted by Paul B

Host profile image
Our family has been coming to Shelter Island for 12 years. We used to rent every summer and decided to buy 3 years ago. We found house we loved on a quiet street that reminds us of our childhood. Our 3 kids love riding their bikes around the neighborhood and beyond. We often ride or walk to the beach in the morning and then sometimes fish or golf in the afternoon. Shelter Island is one of the few places in the area that makes you feel like you have transported into a different time. A quieter time. It is easy to reconnect and read a book or play a board game when all of your day-to-day worries were left behind as you boarded the ferry.

Why they chose this property

5 Pennys Path is special to us because it is a charming house with a pool in a neighborhood that is pretty much self contained. We had a vision for the home and opened up the living area when we redid the kitchen. We also redid the two bathrooms so it feels very new inside. The pool is a big attraction and, fortunately, there is nice flat yard also. We like our neighbors and everyone in the area is very friendly. The location is great. We sometimes don't use the car unless we are going grocery shopping or to play golf. The Silver Beach area is one of the nicest parts of Shelter Island and Shell Beach is probably the best kept secret (shh) on the Island. There is so much to do there including swim, fish, shell, play sports or just relax.

What makes this property unique

The new kitchen, bathrooms and central AC make our home a very easy place to be. The pool right off the back room allows for hours of fun for the family. The house has an open floor plan that allows families to stay connected to each other (instead of the their devices). The location is great for anyone who likes to walk or ride bikes. The neighborhood is unique in that there are 3 parallel roads connected at either end so there is no reason for anyone to enter unless they are a resident or visitor. The Silver Beach area has great quiet beaches and nice fishing. You can walk to Bootlegger's Alley and watch the sunset in less than 5 minutes which, by the way, is a really nice way to end the day. Town and Sunset Beach are short bike rides (and very short drives) away so most major attractions are right nearby. This is a special place to us and we hope it will be to you!

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