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

4 bedrooms4 bathroomsSleeps 10

Popular amenities

Pool

Kitchen

Washer

Dryer

Pet-friendly

Free WiFi

Check out the area

Shelter Island, NY

Sunset Beach15 min walk
Kontokosta Winery23 min drive
67 Steps Beach25 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

Amenities

Pool

Kitchen

Washer

Dryer

Pet-friendly

Free WiFi

Kitchen

Washer

Dryer

Air conditioning

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

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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 vacation home is in The Heights, a neighborhood in Shelter Island Heights. The Hamptons Beaches and Sunset Beach reflect the area's natural beauty and area attractions include East End Seaport Maritime Museum and Shelter Island Whale's Tail. Railroad Museum of Long Island and Norman E. Klipp Marine Park 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
Greenport Carousel - 22 min drive
Railroad Museum of Long Island - 22 min drive
Kontokosta Winery - 23 min drive
67 Steps Beach - 25 min drive

Getting around

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

Restaurants

Lucharitos - 22 min drive
Sunset Beach Restaurant - 19 min walk
Aldo's - 22 min drive
Claudio's Main Restaurant - 22 min drive
Port 104 - 21 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.

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

Corissa S.

24 July 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 July 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.

22 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