A rare beachfront property in the area - enjoy direct access to the sand and sea.
Unmatched views, unforgettable moments
Guests like the location for the scenic views.
5 bedrooms6+ bathroomsSleeps 8
Popular amenities
On beach
Private pool
Onsite parking available
Kitchen
Washer
Air conditioning
Explore the area
Shelter Island, NY
Menhadden Lane Beach
Place, Menhadden Lane Beach
4 min drive
Gardiner's Bay Country Club
Place, Gardiner's Bay Country Club
7 min drive
Shelter Island Whale's Tail
Place, Shelter Island Whale's Tail
8 min drive
Montauk, NY (MTP)
Airport, Montauk, NY (MTP)
74 min drive
Rooms & beds
5 bedrooms (sleeps 8)
Additional Sleeping (Bonus Room)
1 King Bed
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
2 Twin Beds
Bedroom 4
4 Twin Beds
Bedroom 5
1 Queen Bed
6 bathrooms, 1 half bathroom
Full Bathroom
Full Bathroom
Full Bathroom
Full Bathroom
Full Bathroom
Full Bathroom
Half Bathroom
Spaces
Deck or patio
Kitchen
Office
Balcony
Outdoor play area
About this property
Shelter Island Retreat w/ Outdoor Pool!
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 the Hamptons!
-- 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
Our prices include all fees. No hidden fees.
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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 and a first aid kit
About the neighborhood
Shelter Island
Located in Shelter Island, this vacation home is on the beach. The area's natural beauty can be seen at The Hamptons Beaches and East Hampton Main Beach. Shelter Island Whale's Tail and East End Seaport Maritime Museum are also worth visiting. Discover the area's water adventures with kayaking and motor boating nearby, or enjoy the great outdoors with hunting.
Gardiner's Bay Country Club - 7 min drive - 7.1 km
Shelter Island Whale's Tail - 8 min drive - 8.2 km
Shelter Island Historical Society - 10 min drive - 9.5 km
Mashomack Preserve - 11 min drive - 10.9 km
Getting around
Greenport Station - 29 min drive
East Hampton, NY (HTO) - 56 min drive
Restaurants
Claudio’s Waterfront - 30 min drive
Lucharitos - 30 min drive
Aldo's - 30 min drive
Noah's - 30 min drive
La Capricciosa - 29 min drive
Frequently asked questions
Does Shelter Island Retreat w/ Outdoor Pool! have a pool?
Yes, this property has a pool.
How much does it cost to stay at Shelter Island Retreat w/ Outdoor Pool!?
As of Aug 20, 2026, prices found for a 1-night stay for 2 adults at Shelter Island Retreat w/ Outdoor Pool! on Oct 8, 2026 start from $1,387, 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 Shelter Island Retreat w/ Outdoor Pool! pet-friendly?
No, pets are not allowed at this property.
How much is parking?
Onsite parking is available at the property.
What time is check-in at Shelter Island Retreat w/ Outdoor Pool!?
Check-in begins at 3:00 PM.
What time is check-out at Shelter Island Retreat w/ Outdoor Pool!?
Check-out is at 10:00 AM.
Where is Shelter Island Retreat w/ Outdoor Pool! located?
This Shelter Island vacation home is on the beach, 2 mi (3.2 km) from Menhadden Lane Beach, and within 6 mi (10 km) of Sunset Beach and Crescent Beach. Gardiner's Bay Country Club and Shelter Island Country Club are also within 6 mi (10 km).