Home Vacation Rentals By Owner In Shelter Island, NY

Showing 20 Of 97 Vacation Rentals
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Exceptional(35)

$957.79

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Private Vacation Home

Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!

Shelter Island, New York, United States

Shelter Island is a unique place with incredible natural landscapes and gorgeous sunsets!brbrOnce you get off the ferry, drive to the end of a private road to find your oasis on a full acre of land where you will relax and enjoy the sun drenched backyard and pool with friends and family. Our home is designed to encourage you to spend as much time outside and includes a screened in sun porch perfect for reading and entertaining during sunny or rainy summer days. We have an outdoor fire pit for cool summer evenings, patio area with outdoor seating and a solar powered heater for the gunite saline pool! Please note our pool is open between Memorial Day to Labor Day each season.brbrInside our home, we offer 3 bedrooms upstairs and 1 bedroom downstairs. All linens and towels are provided with the rental. The upstairs has a completely private master bedroom suite which is open, airy and features a king sized bed with spacious walk-in closet and large spa-like bathroom with a walk in shower. Or enjoy a soak in the claw foot tub and feel your troubles melt away. There is an outside deck off the master bedroom where you can enjoy coffee and watch the sunrise. Master bedroom includes a Smart TV with cable. The second bedroom upstairs also shares access to the master deck and includes a queen sized bed. The third bedroom offers two twin beds (perfect for kids or two adults) or the beds may be pushed together to create a larger bed for a couple. We can also provide a crib for this bedroom. There is one full bathroom with shower with tub for these two guest bedrooms. The downstairs bedroom has a queen sized bed and a full bathroom with shower and tub across the hallway. The bathroom is perfectly located by the backdoor and offers a quick place to change in and out of your bathing suit or take a quick shower before or after a swim! Our Smart TVs also access Netflix, Amazon, Hulu, HBO, etc.brbrWe have a fully equipped kitchen to prepare all of the veggies and goodies picked up from the numerous farms and specialty stores Shelter Island and the North Fork offers. There is a gas BBQ grill for outdoor cooking. The living room has a comfy couch, gas fireplace, and Smart TV.brbrAdditional amenities include, oversized garage with an extra refrigerator/freezer and direct access to the backyard, onsite washer and dryer, multiple charging stations for all your devices, puzzles and lots of books for summer reading! We have a covered front porch with a swing, backyard hammock, plenty of beach towels, beach chairs and other equipment to help you enjoy any one of the beautiful beaches Shelter Island offers. brbrOur home is centrally located and short walking distance to Commander Cody's (great BBQ, seafood and fried chicken!), playground, and Town Center. It's a short drive to Mashomack Preserve where you can enjoy miles and miles of hiking along the coast or do some bird watching. It is a short drive to several restaurants and shops on the Island. brbrIt is easy enough to park at the North Ferry and walk on as a passenger to explore Greenport, NY (great food and shopping). Take your car off-island for some wine tasting at vineyards along the North Fork. A short drive from Greenport takes you to Orient Point and the cross sound ferry to New London, Connecticut. Or drive to the South Ferry from Shelter Island and travel to Sag Harbor, visit the Hamptons or go to the end of LI and check out Montauk. Lots of fishing and water sports in the area. From Montauk you can catch a ferry to Block Island. Shelter Island also offers summer camps for children. Other things to do include music at the famous Itzhak Perlman Music Center, or Jazz at Ram's Head Inn or checking out events at Sylvestor Manor.brbrDuring peak summer months (July and August) our preferred minimum stay is 14 days. Please note that we require a security deposit at time of booking and will issue a separate rental agreement for use of our property. Please be aware there is a local tax imposed by Suffolk County (as of 2023) on short term rentals. Happy to answer questions anytime!
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Exceptional(2)

$1480.14

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Private Vacation Home

Beautiful Spacious Traditional Home w/Pool, 2 minutes from Beaches, Golf, Tennis

Shelter Island, New York, United States

Traditional Hamptons style Home on a blissfully quiet cul-de-sac, with beautiful details, all impeccably renovated. Wrap around porch with three seating areas overlooks the expansive front yard. Roomy bedrooms, jetted tubs with separate showers in each full bathroom. The Primary Bedroom Suite has a Balcony that overlooks the large in-ground Saltwater Pool, generous Deck, Lounging and Dining Furniture, the large Propane Grill, and 6+ acres of natural preserved land. Formal Living Room with Baby Grand Piano; bright private Office/Library with large window seat; breezy screened in Sun Room; large well-equipped Chef’s Stainless Kitchen with marble counter tops, and a Dining Table that seats 8 comfortably. Basement/Game room with 10 foot ceilings, separate entrance leading to the Back Yard and Pool, two reclining couches, full wet bar, Pool Table with Ping Pong topper. Adjoining spa-like Bathroom with double sinks, jetted tub for two, WC, and a very generously sized walk-in Shower. There are 4 Large TVs with Cable and Premium Services in the Home. Shelter Island is a paradise all its own. Sunset Beach is 2 minutes down the road, and all other spectacular Shelter Beaches are under 5 minutes away. The Island has 2 Golf Courses, Hiking/Biking trails, Tennis, Restaurants, Bars, Boutique Shopping, and IGA, and million dollar views. Drive-on Ferry access is simple from the North or South Fork of Long Island. In just a few minutes you’re in Paradise!
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Exceptional(3)

$1189.12

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Private Vacation Home

Shelter Island Retreat w/ Outdoor Pool!

Shelter Island, New York, United States

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!brbr-- THE PROPERTY --brbrSeasonal Outdoor Pool | Fully Equipped Home Gym | Free WiFi (High Speed) | 110 Mi to NYC | 5,000 Sq FtbrbrBedroom 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 brbrOUTDOOR 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, trampolinebrINDOOR 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, booksbrKITCHEN: Refrigerator, stove/oven, blender, toaster, cooking basicsbrGENERAL: Central A/C + heating, complimentary toiletries, linens/towels, washers/dryers, hair dryer, hangers, beach towels, trash bags/paper towelsbrFAQ: Steps required for entry, bedroom + bathroom on 1st floor, zero-entrance shower brPARKING: Driveway (7 vehicles)brbr-- THE LOCATION --brbrTHINGS 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)brGET 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)brWINE & 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)brAIRPORTS: Long Island MacArthur Airport (58 miles), Laguardia Airport (101 miles)brbr-- REST EASY WITH US --brbrEvolve 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.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: There are a few steps required for entry, but there is a bedroom and bathroom with a zero-entrance shower on the main floorbr- NOTE: The outdoor pool is open seasonally from May-September and the kayaks are only available in the spring and summer months
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Private Vacation Home

50's Shelter Island Home w new pool, 3 bed 3 bath

Shelter Island, New York, United States

This bright, cheery 3 bedroom / 3 bathroom Shelter Island cottage located in Montclair Colony is the perfect peaceful escape. Situated on a quiet corner with a new (2020), salt water, gunite, heated pool with automatic cover and large fenced in yard with outdoor shower.brbrThe mid-century beach bungalow was built in 1951 and offers great natural light and a beautiful cross breeze in every room.brbrThe main house is stylishly decorated and features an open layout with kitchen, dining room, living room, sun room, 2 bedrooms and 2 bathrooms. Central A/C throughout house (with exception of sunroom.)brbrCorner master bedroom has king size bed, ceiling fan, desk and large walk-in closet plus newly renovated (2021) en-suite bathroom with large shower and radiant heated floors. Second bedroom has full bed with convertible queen size day bed, ceiling fan and closet. Guest bathroom also newly renovated and includes shower/tub. brbrThe private guest house located above the 2-car garage has a separate entrance, queen size bed, kitchenette, 2 closets and window AC unit. brbrEntertain outdoors on the private deck with large table, ceiling fan, Adirondack rocking chairs & ottomans, chaise lounges and BBQ. Enjoy the expansive yard with outdoor shower, fire pit and fenced in vegetable garden. Includes beach chairs, beach umbrella, kayaks, ping pong table, cable, wifi and Sonos stereo system.brbrClose to the beaches, boat launch, restaurants and ferries. Walking distance to 3x town boat launches + Salt and Shipwreck.
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Exceptional(1)

$1311.83

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Private Vacation Home

Waterfront Charmer with boat slip on idyllic Shelter Island for summer rental

Shelter Island, New York, United States

This home is a water lover’s paradise on sheltered water with easy access to surrounding east end towns. “2 East” features over 1500 square feet of decks & porch on three levels overlooking West Neck Harbor, with an opportunity to be in sun or shade and still enjoy spectacular water views. There are two deep water slips at our private dock for boats and ample room for swimming.brThe house is available summer season Memorial Day- Labor Day, or monthly July - Labor Day. Please contact owner for seasonal or monthly rates.brbr“2 East” has an open floor plan allowing guests to enjoy the outdoor view from within. The gourmet kitchen includes a Viking stove and two prep areas. Enjoy the water views from the dining room, or on the deck at the teak table under the market umbrella. The first floor includes a sun room, small media room, and a guest bedroom and bath. Upstairs there are two master suites with generous size bedrooms and baths. brbrSuite one has a king bed, spacious classic bath, and a sun deck overlooking the water accessible by French doors. It is perfect for waterside breakfast, afternoon cocktails, or just leisurely reading. In summer, the Big Dipper is directly over head for nighttime stargazing. brbrSuite two has a large bedroom with king size bed and an adjoining office (or child's room with foldout couch). High speed Internet access with wonderful water views makes any office work a pleasure. This suite also has a Jacuzzi bath and a large shower. High ceilings and ceiling fans give each suite a “country feel”, and the central a/c is rarely needed. brbrA deck surrounds the house in addition to the front porch. One portion of the property has a sandy beach perfect for swimming and kayaking that is adjacent to the bulk heading and dock. There is an outdoor food prep area, an outdoor grille and of course an outdoor shower. This house is the perfect setting for the ultimate summer living experience. brbrShelter Island has many fine restaurants and free concerts at the world renowned Perlman Music Center which is a few blocks away. There are many beaches and so many summer activities happening on the island. You will be able to have the beauty and serenity of the island and the house, and the stimulation of everything going on outside if you choose to participate. It is just a three minute ferry ride to Sag Harbor and the South Fork and all if its offerings and a ten minute ferry ride to Greenport and the North Fork with its farms and vineyards. brCome to “2 East” and relax, unwind and be surrounded by nature with its osprey, deer, red tail hawks and blue herons right out the window. br
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Exceptional(12)

$378.54

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Private Vacation Home

Shelter Island Sun Filled Modern Waterfront Home with Dock

Shelter Island, New York, United States

Summer 2023 calendar has been updated ! The month of July is now available and can be rented for the entire period or in 2 week blocks- August 1-18 is also available Please note 2 week minimum rental period brbrThis serene, modern sun drenched spacious home is located on one of Shelter Island's scenic bays with full water access at the edge of the property. There is a dock which can accommodate small motor craft. There are also two kayaks- a single and a double -along with a canoe and 2 SUP‘s -all for renter use complete with paddles and lifejacketsbrbrThe spacious deck offers offers dining for up to 10 along with a large Weber grill area There is a separate seating area for loungingbrbrThis home was recently completely renovated by award winning Studio DuBois Architecture. The waterfront ground floor offers a high ceilinged open floor plan with kitchen, living and dining areas brbrThere cooks kitchen is fully equipped- Warm textured modern finishes make for inviting and relaxing living spaces throughout . The large Rumford fireplace provides extra coziness in the winter months. The TV room, with its large sectional sofa is perfect for movies, sports and binge watching. brbrThere are 3 beautifully appointed and generous en-suite bedrooms-2 of which are upstairs with waterfront views. The upstairs suites both have king beds and the downstairs suite has a queen bed. All bedrooms have ample closets, black out window coverings and are fully carpeted. There is a superb property manager on call.brbrThe house is centrally located and just minutes to the town center, Heights district and several of the town's main beaches. Wades Beach is down the road. brPlease note br- no children under 6( babies allowed )br- no pets br- one month rental preferredbr- 2 week minimum rental period during the summer seasonbrbrYour Shelter Island waterfront getaway awaits !
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Exceptional(7)

$828.81

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Private Vacation Home

Elegant Treetop Modern with Heated Gunite Pool Steps from Hay Beach

Shelter Island, New York, United States

A 3 minute walk to wide sandy beach (Hay Beach/Menhaden Lane), this pristine 4 bedroom, 4 bath cedar clad three-level modern offers the essence of living in a treetop. With an entire wall of sliding doors in the living room overlooking cherry trees and wrap around deck, bay breezes waft throughout gently. The kitchen is a chef's delight, with granite counters, maple cabinets, Viking stove, Monogram refrigerator, Miele dishwasher, and sliding doors to an outdoor BBQ. STRONG WIFI /ORBI system throughout house.brbrThe first floor has two bedrooms with exotic sea grass floor coverings and skylights with shades and shared full bath. The second floor has a TV room/library with two balconies with scenic views, a spacious master suite with spa like bath and full bath in hall. The lower level is above grade, featuring a media room which is also convertible to a full bedroom with adjacent full bath. The grounds are sequestered and lovely, with a far-eastern influence. brbrThe heated Gunite pool has mahogany decking, lush bamboo gardens, sound system controlled through remote to the home, established red maples and river stone paths. The golf course is immediately adjacent. With a popular rental history, this home has all the ingredients for a fabulous vacation or work retreat! brbrHouse is about 2.0 miles from Island's main supermarket/IGA and 1.5 miles from Island's popular ice cream store/kids' mini golf course, Whales Tale.brbrNOTE 1: Child protected stairs, kitchen access, pool access, and optional door knob protector for stair access to lower floor.brNOTE 2: Extra cost associated with any utilities expenses above and beyond covered amounts.
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Exceptional(41)

$1433.85

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Private Vacation Home

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!

Shelter Island, New York, United States

Score Big at our fabulous Hamptons Cottage where work meets play in style! Settle into this charming 1700’s cottage nestled on 7 private acres of lush greenery adorned with majestic trees-your very own oasis! There are steep steps up to the second floor. br* Excellent Wifi: Say goodbye to buffering and hello to productivity with top-notch Wifi, ensuring seamless work-from-home sessions! br*Poolside Paradise: Dive into relaxation mode with a heated saltwater gunite pool-the ultimate spot to soak up the sun and splash around. Plus, keep an eye out for our resident turtles and frogs in the pond! Propane usage will be charged after stay.br*Cozy pool house: Need extra space Our pool house offers an additional bedroom, kitchenette and a half bathroom-perfect for guests or a private retreat!br* Outdoor Delights: Rinse out in style with an invigorating outdoor shower, then unwind on the screened-in-porch-an ideal spot for sipping your morning coffee or enjoying evening cocktails.br*Modern Comforts: This cottage is equipped with all the bells and whistles, including a recently installed chef's kitchen, A/C, heating, and a Sonos sound system-ensuring your stay is as luxurious as it is comfortable.br*Beach Bonanza:brJust a ten minute stroll lies Wades Beach, beckoning you with its sandy shores and sparkling waters-paradise found!br With room to accommodate up to 10 guests, this dreamy cottage is your ticket to an unforgettable Hamptons getaway. So grab your bags, grab your laptop, and get ready to blend work with pleasure like never before! Ahhhh Shelter Island!!
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$1250.76

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Private Vacation Home

AIA AWARD WINNING COUNTRY ESTATE IN TRANQUIL SHELTER ISLAND

Shelter Island, New York, United States

Discover the beauty of Shelter Island from this Award winning, Architect owned and designed, 4-bedroom estate. brbrWhether you're lounging by the fireplace in the cozy clearstory living room or enjoying the fresh air on the spacious iconic wrap around porch, this property is perfect for a relaxing carefree summer getaway. The First floor encompasses an open floor plan seamlessly connecting kitchen, dining, living room and cozy den spaces as well as a private master suite. Second floor has 3 additional bedrooms and bathroom with access to an exterior observation deck perfect for bird watching with an early morning coffee. Guests will also have access and use of the first floor to the accessory 2 car garage structure on the property. brbrThis Property is located within a prominent Hamptons style estate area of the Island and within walking distance to multiple beaches. Bicycles, kayaks and paddle boards can be rented on island if so desired. And don't forget to take a hike at the Mashomack Preserve, with over 2000 acres of interlacing tidal creeks, woodlands and freshwater marshes, it is not to be missed. brbrWe hope you'll enjoy your stay at our estate.brbrNearby Beaches:brShell Beach, Crescent Beach (Sunset Beach), Crab Creek Beach, Bootleggers Alley Beach.brbrNearby Grocery Stores:brIGA brbrNearby Restaurants and Bars:brDan Brock's Barbecue at Ellie's country store excellent sides and puddings in mason jars.brbrMarie Eiffel- in the Heights a wonderful great take-out food.brbrRam's Head Inn- always special even just for cocktails on the beautiful lawn in Adirondack chairs.brbrKyles- fantastic homemade jelly and cinnamon doughnuts croissants and cakes.brbrCommander Cody's- great fish store, and fabulous barbecue- pan fried chicken, and take out fish.brbrVine Street Cafe- excellent food, five stars.brbrMaria's kitchen- great take out Mexican- great homemade chips and guac.brbrShelter island slice for pizza.brbrChequit- in town.brbrSaltbrbrLeon 1909
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