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Entire home

Relax and Enjoy!

Photo gallery for Relax and Enjoy!

Outdoor dining
Outdoor pool, a heated pool
4 bedrooms, iron/ironing board, free WiFi, bed sheets
Outdoor dining
Combined shower/bathtub, hair dryer, towels, soap

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms4 bathroomsSleeps 10

Popular amenities

  • Beach view
  • Gym
  • Parking available
  • Pool
  • Dryer
  • Washer

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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!

Property manager

Virginia Anderson

Property amenities

Beach

  • On the beach
  • Beach loungers
  • Beach towels

Pool/Spa

  • Heated pool
  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Car not required
  • Parking on site

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 4 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Wood stove

Entertainment

  • Books
  • Games
  • Music library
  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Printer

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a hospital
  • Near the bay

Things to do

  • Golf
  • Gym
  • Heated pool
  • Tennis
  • Birdwatching nearby
  • Cycling nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Sailing nearby
  • Water skiing nearby
  • Water tubing nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 30

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Restrictions apply; for more information contact the property on the number on the booking confirmation
Note from host: dogs only

Children and extra beds

Children are welcome

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

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

Property is also known as

Vrbo Property
Spacious Beach House With Stunning Water Views
The Pool is Open for the Season! Private vacation home
The Pool is Open for the Season! Shelter Island Heights

About the area

Located on the beach, this holiday home is in The Heights, a neighbourhood 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 cycling and hiking/biking trails nearby.
Visit our Shelter Island Heights travel guideOpens in a new window
View more Holiday homes in Shelter Island HeightsOpens in a new window
Map
Shelter Island, NY

What's nearby

  • Sunset Beach - 2 min drive - 1.1 km
  • Railroad Museum of Long Island - 21 min drive - 3.1 km
  • Greenport Carousel - 22 min drive - 3.4 km
  • Kontokosta Winery - 24 min drive - 4.8 km
  • 67 Steps Beach - 25 min drive - 5.5 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).

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Relax and Enjoy! Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 14 out of 14 reviews
Rating 8 - Good. 0 out of 14 reviews
Rating 6 - Okay. 0 out of 14 reviews
Rating 4 - Poor. 0 out of 14 reviews
Rating 2 - Terrible. 0 out of 14 reviews

10/10

Cleanliness

Reviews

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

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

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

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

10/10 Excellent

Thomas H., Bronxville, NY USA

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

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

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

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

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

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

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