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Relax and Enjoy!

Photo gallery for Relax and Enjoy!

Dine al fresco while watching the boats and sea planes
Enjoy the view while you swim!
Enjoy a heated swim or have a drink and soak on the martini ledge
Lounge on the daybed to take a break from swimming or watch the stars at night
Comfortable living room with Smart TV, speakers, record player, books and games

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
4 bedrooms4 bathroomsSleeps 10

Popular amenities

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

Explore the area

View in a map
Shelter Island, NY
  • Place, Shelter Island Country Club
    ‪5 min walk‬
  • Place, Sunset Beach
    ‪1 min drive‬
  • Place, Crescent Beach
    ‪1 min drive‬
  • Airport, New Haven, CT (HVN-Tweed - New Haven Regional)

Rooms & beds

4 bedrooms (sleeps 10)

Downstairs kids room

2 Twin Beds

Downstairs Master

1 King Bed and 1 Double Sofa Bed

Office 1

1 Queen Bed

Upstairs Kids' Room

2 Double Beds

Upstairs master bedroom

1 King Bed

4 bathrooms

Downstairs Kids' Bathroom

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Downstairs Master Bath

Soap · Towels provided · Bathtub or shower · Toilet · Shower only · Shampoo

Upstairs kids bathroom

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shower only · Shampoo

Upstairs Master Bathroom

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Garden
Dining area

About this property

Relax and Enjoy!

Stretch out and relax in this well-designed home high on a hill with truly spectacular water views from every room. Enjoy watching yachts and sea planes pull up to Sunset Beach, or peek over the Long Island Sound to Connecticut from the highest deck on the island. Eat a meal in one of our two outdoor dining areas, or lounge by the pool and enjoy the one-of-a-kind sunset view, flowering gardens, outdoor kitchen and sunken dining area, large daybed and sectional sofa. The kids can play in the fenced-in yard that measures 100' by 50'. Dog friendly!
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Pet friendly
Free WiFi

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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 only
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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, a first aid kit, and a deadbolt lock

We should mention

This property does not have elevators
A car is not required for transportation to and from this property

About the neighborhood

Shelter Island Heights

Located on the beach, this vacation home is in The Heights, a neighborhood in Shelter Island Heights. East End Seaport Maritime Museum and Greenport Carousel are local attractions and those in the mood for shopping can visit Greenport Farmers' Market and Love Lane. Shelter Island Whale's Tail and Railroad Museum of Long Island are also worth visiting. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and cycling nearby.
View more Vacation Homes in Shelter Island HeightsOpens in a new window
Map
Shelter Island, NY

What's nearby

  • Shelter Island Country Club - 5 min walk - 0.4 km
  • Sunset Beach - 1 min drive - 1.1 km
  • Crescent Beach - 1 min drive - 1.1 km
  • Sylvester Manor - 3 min drive - 2.8 km
  • The Hamptons Beaches - 13 min drive - 7.6 km

Getting around

  • Greenport Station - 22 min drive
  • East Hampton, NY (HTO) - 47 min drive

Restaurants

  • ‪Claudios Clam Bar - ‬23 min drive
  • ‪Aldo's - ‬22 min drive
  • ‪Noah's - ‬22 min drive
  • ‪Sunset Beach Restaurant - ‬19 min walk
  • ‪Goldberg’s Famous Bagels - ‬22 min drive

Frequently asked questions

Does Relax and Enjoy! have a pool?

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

How much does it cost to stay at Relax and Enjoy!?

As of Mar 17, 2026, prices found for a 1-night stay for 2 adults at Relax and Enjoy! on Apr 27, 2026 start from $1,076, 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 Relax and Enjoy! pet-friendly?

Yes, pets are allowed at this property. Some restrictions may apply, so please contact the property for more details.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Relax and Enjoy!?

Check-in begins at 4:00 PM.

What time is check-out at Relax and Enjoy!?

Check-out is at 11:00 AM.

Where is Relax and Enjoy! located?

Nestled on the beach, this The Heights vacation home is within 1 mi (2 km) of Shelter Island Country Club, Sunset Beach, and Crescent Beach. Sylvester Manor and East End Seaport Maritime Museum are also within 2 mi (3 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. 16 out of 16 reviews
Rating 8 - Good. 0 out of 16 reviews
Rating 6 - Okay. 0 out of 16 reviews
Rating 4 - Poor. 0 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

John J P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Terrific property
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Adam K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely terrific property. Beautiful views, pool, outdoor kitchen etc. cannot say enough about what a lovely time we had. The owners are extremely responsive and friendly. All around wonderful experience!!
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

Ellen S.

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

Family Reunion

Amazing 🩹
Stayed 6 nights in Jun 2025
Verified

10/10 Excellent

Thomas H.

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

Lovely home perfect for grandparents, family and infant.

Very smooth and pleasant experience all around.
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

Corissa S.

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

Great Family Vacation!

Our hosts were great, They were quick to reply and the house itself was perfect. Very clean and in a great location. The fact that we could bring our dogs was a major bonus and the view is spectacular. I would very much recommend this location and would consider staying there again.
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Lucy H.

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

Wonderful house, fantastic view.

We loved this house: coffee on the terrace overlooking the Sound, mornings at nearby beaches, afternoons of badminton and hanging out by the pool, big family dinners at the large outdoor table, and jigsaw puzzles while watching soccer tournaments at night. We are a family of cooks and the kitchen is very well-equipped with a spacious counter layout. The house was breezy and comfortable. Great stay.
Stayed 14 nights in Jun 2024
Verified

10/10 Excellent

Janet R.

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

Wonderful vacation experience!

Peaceful, private, and relaxing, with a knock-out view from almost every room. (We even enjoyed the flashing skies from the bedroom balconies during an evening lightening storm.) We loved our stay. The house had a variety of bedroom options for every member of the family, and the kitchen was roomy and well stocked, making it a fun experience preparing dinner every night! Virginia was immediately responsive and helpful, and the short walk to town was lovely. If you are looking for a tranquil family retreat, I would not hesitate to recommend this home.
Stayed 5 nights in Jun 2023
Verified

10/10 Excellent

Thomas H.

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

Wonderful!

Had never been to Shelter Island before and this property was recommended to us by a friend. It was perfect for a group of adult friends to celebrate and relax for a long weekend. Manager/owner couldn't be nicer and more helpful. The house is excellent with everything we needed, amazing views, and super convenient location to walk to many things, didn't even need the car on this trip at all. We hope to be back!
Stayed 3 nights in Oct 2020
Verified

10/10 Excellent

Sheila G.

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

Wonderful Sunset

Beautiful, well appointed home, multiple family ready dining areas all with views, all bedrooms have stunning views and their own bathrooms. Fantastic pool with single access heavy door to prevent small children from entering without oversight. Sunsets every night. It was perfect in every way. We plan to return soon. Hosts were welcoming to our grandchildren and grandpuppy, and were available/responsive to our questions.
Stayed 6 nights in Sep 2024
Verified

10/10 Excellent

Susan M.

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

Shelter Island Sunsets

We were in town for a family wedding week. The house was perfect for 8 adults, as everyone had a comfortable room with their own en suite. There is also a loft space with access to a half bath. The house was beautifully furnished and the beds were very comfortable. Virginia was an incredible host! She thought of everything and is very responsive. The views from every floor were spectacular and we loved the gorgeous pool! You can walk to town, the beaches, dining and shopping. Great location. We highly recommend this home! You won’t be disappointed.
Stayed 6 nights in Jul 2024
Verified

10/10 Excellent

David A.

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

Amazing Birthday Weekend

It was a very special birthday. Both my adult boys were in town and we wanted to spend the weekend together. The house was far beyond our expectations. It was spacious. a bedroom for my wife and I and two more, one for each boy with more in addition had we had needed them. It was furnished beautifully and even more there was nothing that we needed that it didn’t have. I cooked the second night and I especially was impressed at having the nicest and sharpest knife I had ever had in similar situations. A small thing but representative of everything else. It had an amazing view from all 4 floors of the bay, which was such a plus as on the night of my birthday there was a terrific display of fireworks right below us. And then there was the pool with its motorised retractable cover which my younger so declared was the most wonderful he had ever been in. And he has been in many. The water was soft and refreshing and the perfect temperature. The stay was wonderful and our family will always remember its graciousness.
Fireworks the night of my birthday.
The pool
The livingroom
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

Talia

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a fabulous house with the most beautiful view! We had the best time - it was easy, clean, wonderful place to spend the weekend. Will be back!
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

David M.

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

Lovely, comfortable house. Spectacular views

We had a great time and the owner was terrific.
Stayed 12 nights in Nov 2020
Verified

10/10 Excellent

Rob M.

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

Wonderful house, pool, view

We had a great experience at the house. The pool was amazing and the view of the bay was spectacular. The owners are very responsive and addressed every question very quickly. Highly recommended!
Stayed 7 nights in Jul 2020
Verified

10/10 Excellent

Marco S.

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

Lovely getaway

The house is very comfortable, with plenty of well-appointed bedrooms and bathrooms, a very well equipped kitchen, and a fantastic pool area. Virginia and Greg are attentive owners and were eager to ensure our stay was as enjoyable as possible
Verified

10/10 Excellent

Michelle Q.

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

YOU'LL NEVER WANT TO LEAVE THIS PROPERTY!

This home is even BETTER than the pictures! We had the absolute pleasure of a full month of family time in June. We all wish it could have been longer. The huge heated pool with those views made it hard to pull ourselves away, and THOSE SUNSETS!!! The location is perfect. You can walk into town or to the beach (about a mile away), yet is is so peaceful and private, you barely know you have neighbors. The house was impeccably clean, and stocked with everything you could possibly imagine. The beds were so comfortable, and it was so dark and quiet for sleeping. Friendly owners, Virginia and Greg, were very welcoming and responsive to any questions we had. Thank you so much for sharing your slice of heaven with us, Virginia and Greg! We plan to return!
Stayed 28 nights in Jun 2020

About the host

Hosted by Virginia Anderson

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Premier Host

They consistently provide great experiences for their guests
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