Shelter Island Retreat w/ Outdoor Pool!

Shelter Island, New York
$1132 avg/night Minimum Stay 2 Nights
Bed 5

Bed

Bath 6

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

Night 2 nights

Min Stay

If you’re looking to escape bustling city life, book this 5-bedroom, 6.5-bath home in the Hamptons area! This Shelter Island vacation rental features an office and free WiFi, as well as amenities like a game room and pool to ensure a productive and restorative stay. With fun activities year-round, you can kayak on the nearby ocean, sip on some wine at the Wölffer Estate Vineyard, witness stunning views from Montauk Point, catch a Polo match, or get your holiday shopping done in theHamptons!

-- THE PROPERTY --

Seasonal Outdoor Pool | Fully Equipped Home Gym | Free WiFi (High Speed) | 110 Mi to NYC | 5,000 Sq Ft

Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Twin Beds | Bedroom 4: 2 Twin Bunk Beds | Bedroom 5: Queen Bed | Bonus Room: King Bed

OUTDOOR LIVING: Private beach w/ wood-burning fire pit & beach chairs, kayaks (available spring/summer months), near ocean, walk to beaches, deck, gas grill + outdoor kitchen area, outdoor fireplace, fire pit, bicycles, boating, beach chairs, beach umbrella, trampoline
INDOOR LIVING: 3 Smart TVs w/ cable, en-suite bathrooms, walk-in closet, laptop-friendly workspace, game room w/ pool table, gas fireplaces, dining areas, jetted bathtub, shower, books
KITCHEN: Refrigerator, stove/oven, blender, toaster, cooking basics
GENERAL: Central A/C + heating, complimentary toiletries, linens/towels, washers/dryers, hair dryer, hangers, beach towels, trash bags/paper towels
FAQ: Steps required for entry, bedroom + bathroom on 1st floor, zero-entrance shower
PARKING: Driveway (7 vehicles)

-- THE LOCATION --

THINGS TO SEE + DO: Sylvester Manor Educational Farm - farm stand + theatre + live music in summer months (4 miles), Shelter Island Historical Society (5 miles), Horton Point Lighthouse Nautical Museum (12 miles), The Hamptons (16 miles), Parrish Art Museum (18 miles), Long Island Aquarium (29 miles), Montauk Point Lighthouse Museum (37 miles)
GET OUTSIDE: Lower Beach (1 mile), Upper Beach (3 miles), Coecles Harbor Marina & Boatyard (4 miles), Mashomack Preserve Entrance - walking trails (5 miles), 67 Steps Beach (8 miles), Sagg Main Beach - surfing, deep sea fishing, water sports (17 miles)
WINE & DINE: Ram's Head Inn (0.9 miles), Marie Eiffel Market (5 miles), Vine Street Cafe (5 miles), Greenport Harbor Brewing Company (7 miles), Kontokosta Winery (8 miles), One Woman Winery Greenport (10 miles), The Old Field Vineyards (10 miles), Sparkling Pointe Vineyards & Winery (12 miles), Channing Daughters Winery (13 miles), Wölffer Estate Vineyard (14 miles)
AIRPORTS: Long Island MacArthur Airport (58 miles), Laguardia Airport (101 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: There are a few steps required for entry, but there is a bedroom and bathroom with a zero-entrance shower on the main floor
- NOTE: The outdoor pool is open seasonally from May-September and the kayaks are only available in the spring and summer months

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    On The Beach
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 5000 Sq Ft (465 Sq M)
  • KITCHEN

    Blender Cookware/dishes/utensils Paper Towels Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony Firepit Gas Grill
  • POOL/SPA

    Private Pool
  • BATHROOMS

    6.5 Bathrooms Hair Dryer Towels Provided
  • WORKSPACES

    Desk Office
  • LANGS SPOKEN

    English French German Spanish
  • THINGS TO DO

    Bicycle On Site Fitness Center Fitness Facilities Nearby Hunting Nearby Kayak On Site Kayaking Nearby Marina Nearby Power Boating Nearby
  • ENTERTAINMENT

    Arcade/game Room Books Pool Or Billiards Table TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Playground
  • LOCATION HIGHLIGHTS

    Near A Health Or Beauty Spa Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Availability

Review Review

  • craig h.

    Submitted Sep 9, 2025

    Stayed Sep 5, 2025

    Wonderful home in a gorgeous location.

  • Elizabeth P.

    Submitted Jun 6, 2025

    Stayed May 22, 2025

    Lovely house with great accommodations. Any questions we had were quickly answered. Perfect location - beautiful views from the decks. Look forward to returning!

  • Sara

    Submitted Oct 7, 2024

    Stayed Dec 31, 1969

    8 of us old college friends stayed here for 3 nights for our annual reunion. This property on Shelter Island provided everything we might need, and exceeded our expectations. The beds were comfortable. The showers were hot. There were ensuite bathrooms for each bedroom. The kitchen was large and had every utensil needed to cook and serve a group. The dining table accommodated everyone. The living room had a large sectional for relaxing. But the best part was the view, the patio, and the proximity to a gorgeous rocky beach. We sat around and admired the view of the ocean, played bocce (provided with the property), and walked on the beach. It was perfect.

  • Lauren R.

    Submitted Sep 9, 2024

    Stayed Aug 29, 2024

    My family and I had a wonderful stay at this gorgeous property. The pool is terrific, the view is amazing, and the layout was perfect for our large family so we could all have our own spaces and bathrooms. We loved it.

  • kerry

    Submitted Jul 6, 2023

    Stayed Dec 31, 1969

    Though we loved our outings on and around Shelter Island, we would have been just as happy never leaving the property! Our group enjoyed lazy days by the pool and delicious meals cooked at home in the gorgeous kitchen. Ashley was super responsive throughout the weekend, ensuring we had everything we needed. We just checked out last week and are already looking for a week we can come back next year (and hopefully stay even longer).

Your dates are Available!

Total

Includes taxes and fees
$1,132+
View details