Relax and Enjoy!

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Entire home

Dine al fresco while watching the boats and sea planes

Lounge on the daybed to take a break from swimming or watch the stars at night

Enjoy a heated swim or have a drink and soak on the martini ledge

Overview
Amenities
Policies
Location
Host

Exceptional

4 bedrooms4 bathroomsSleeps 10

Popular amenities

Parking available
Pet-friendly
Pool
Gym
Beach view
Dryer

Explore the area

Shelter Island, NY

Greenport Carousel
‪22 min drive‬
Kontokosta Winery
‪23 min drive‬
67 Steps Beach
‪25 min drive‬
East Hampton, NY (HTO)
‪47 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

Downstairs kids room

2 Single Beds

Downstairs Master

1 King Bed and 1 Double Sofa Bed

Kids' Room

2 Double Beds

Office 1

1 Queen Bed

Upstairs Master

1 King Bed

4 bathrooms

Downstairs Kids Room

Bathtub or shower · Toilet

Downstairs Master

Toilet · Shower only

Upstairs kids

Bathtub or shower · Toilet

Upstairs Master

Bathtub · Toilet · Shower only

Spaces

Deck or patio

Porch or lanai

Kitchen

Balcony

Outdoor play area

Garden

Dining area

About this property

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. 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. Dog friendly!

Property manager

Virginia Anderson

Add dates for prices

Amenities

Pool

Kitchen

Washer

Dryer

Pet-friendly

Free WiFi

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Pool
Kitchen
Washer
Dryer

House Rules

Check in after 4:00 PM

Minimum age to rent: 30

Check out before 11:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed

Dogs only

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

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, a first aid kit and a deadlock

We should mention

A car is not required for transport to and from this property

About the area

Shelter Island Heights

Located on the beach, this holiday home is in The Heights, a neighbourhood in Shelter Island Heights. The Hamptons Beaches and Orient Beach State Park reflect the area's natural beauty and area attractions include East End Seaport Maritime Museum and Greenport Carousel. 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.

Shelter Island, NY

What's nearby

Sunset Beach - 15 min walk - 1.3 km
Greenport Carousel - 22 min drive - 3.4 km
Railroad Museum of Long Island - 22 min drive - 3.6 km
Kontokosta Winery - 23 min drive - 5.2 km
67 Steps Beach - 25 min drive - 5.6 km

Getting around

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

Restaurants

‪Sterlington Deli - ‬22 min drive
‪Stars Cafe - ‬9 min walk
‪Lucharitos - ‬22 min drive
‪Sunset Beach Restaurant - ‬19 min walk
‪Aldo's - ‬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.

Is Relax and Enjoy! pet-friendly?

Yes, pets are allowed at this 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!?

Checkout is at 11:00 AM.

Where is Relax and Enjoy! located?

Nestled on the beach, this The Heights holiday 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 miles (3 km).

Exceptional

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

Learn more

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Sheila G.

8 Sept, 2024

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

10/10 Excellent

Susan M.

19 Jul, 2024

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

10/10 Excellent

Lucy H.

6 Jul, 2024

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

10/10 Excellent

Corissa S.

24 Jul, 2023

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

10/10 Excellent

Janet R.

1 Jul, 2023

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

10/10 Excellent

Thomas H.

7 Aug, 2021

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

10/10 Excellent

David M.

2 Dec, 2020

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

10/10 Excellent

Thomas H., Bronxville, NY USA

20 Oct, 2020

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

10/10 Excellent

Rob M.

22 Aug, 2020

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

10/10 Excellent

Marco S.

17 Aug, 2020

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

10/10 Excellent

Michelle Q.

14 Jul, 2020

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