Home Vacation Home Rentals By Owner In Shelter Island, NY

Showing 20 Of 86 Vacation Rentals
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Exceptional(12)

$877.28

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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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Bath 4

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Sleep 6

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Exceptional(8)

$1356.72

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Private Vacation Home

Waterfront Property on Shelter Island

Shelter Island, New York, United States

Amazing Waterfront Views.brAwaken to bird songs and swans gliding across the water. Sip coffee on the deck while planning the days adventures. Paddle board or kayak across the creek and have a swim at Wade’s beach. Come back and shower in the glorious outdoor shower and grill dinner and dine on the deck. Just as you think the landscape and the light can’t possibly get any more beautiful the sun begins to set and the light becomes even more beautiful. You will remember this special place and you will be thankful for the memories.
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Bath 3

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Sleep 6

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Exceptional(39)

$1104.42

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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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Bath 3

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Exceptional(2)

$1347.6

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Private Vacation Home

Immaculate Shelter Island Farmhouse with Pool and Minutes to Beach

Shelter Island, New York, United States

Perfect for every season. Bring your family (and another) to this recently renovated, spacious turn-of-the-century farmhouse. brbrSet on 1.29 acres with magnificent trees, there is a large heated pool surrounded by gardens, a meditation area under the ancient Catalpa tree, and a separate carriage house with second floor office / bedroom. Large trampoline in the yard for the kids. br Bikes for all to use. There is plenty of room for those who want to have their own areas to work, study, meditate or create. Located 1 mile from Wades beach (perfect for families), and walking distance to fine dining, tennis courts, gym, library and farmstands.brbrFrom the entry foyer, there is a library that flows into the formal living and dining areas, then into the kitchen which has a breakfast seating area at the center island, marble counters and doors that lead to an outdoor entertainment deck. Adjacent is a great room with a fireplace, vaulted ceilings and windows on three sides. Along the hallway is a laundry center and a first floor guest bedroom, full bath and two additional entrances. The second floor has two guest bedrooms that share a hall bath, and a very spacious master suite with window seat, walk in closet-dressing room, and spa-like bath with ball and claw soaking tub and frameless glass shower. brbrWe are open to long term rentals and would love to share our home with families in all seasons.
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Bath 3

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Sleep 10

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$748.53

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Private Vacation Home

Silver Beach Hideaway: newly updated quiet cozy cottage - 4 min walk to beaches!

Shelter Island, New York, United States

Nestled across a nature preserve, this lovely newly updated cottage is a perfect quiet spot to recharge your mind body and soul. Experience quintessential Shelter Island living. A 4-5 min walk to the best SI beaches and water access.
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Bath 2

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Exceptional(4)

$1542.24

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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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Bath 3

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$428.44

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Apartment

Charming Studio on Shelter Island

Shelter Island, New York, United States

Adorable studio with private entrance located on a quiet road. Kitchenette and large open living area with great natural light. Access to inlet perfect for kayaking, paddle boarding or watching sunset. Centrally located so easy to get to all that Shelter Island offers.
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Exceptional(5)

$1131.87

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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- 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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Bath 6

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Sleep 8

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Exceptional(16)

$2611.42

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Private Vacation Home

Relax and Enjoy!

Shelter Island, New York, United States

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!
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Bath 4

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Sleep 10

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$2339.15

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Private Vacation Home

Chic Coastal Farmhouse with Private Pool, Steps from the Water Your...

Shelter Island, New York, United States

Ram Island BeautybrbrChic Coastal Farmhouse with Private Pool, Steps from the Water Your Stylish Shelter Island Escape Awaitsbrbr3BR/3BA: Heated pool, fenced-in yard, outdoor dining, gas BBQ, Sonos system and light-filled interiors designed for relaxed luxurybrbrTucked away on a peaceful, tree-lined street in the heart of Shelter Island, this newly renovated beach-cottage-style farmhouse blends timeless coastal charm with modern comfort. Located just moments from Coecles Harbor, the home offers partial water views and easy access to the islands beaches, restaurants, shops, and scenic bike routesmaking it the perfect setting for a relaxing getaway with family or friends.brbrSet on a spacious, fully fenced property surrounded by lush greenery, the outdoor spaces are designed for effortless summer living. Enjoy long afternoons by the private heated pool, unwind in the lounge seating, gather around the firepit at night, or dine outdoors with the gas grill and alfresco dining area. A detached pool house cabana adds a flexible fourth sleeping space with a sleeper sofa and full bathroomideal for guests seeking additional privacy or a separate retreat by the pool.brbrInside, the home is bright, stylish, and thoughtfully designed for comfort. Large windows fill the interiors with natural light, while a double-sided fireplace anchors two separate living rooms perfect for relaxing or entertaining. The updated kitchen features high-end appliances and a spacious island, complemented by a formal dining room and wet bar for easy hosting. Additional amenities include central air conditioning, high-speed WiFi, Sonos speakers, washer/dryer, and dedicated work-from-home spaces.brbrThe home comfortably accommodates guests across three bedrooms in the main house plus the detached cabana suite. The primary suite features a king bed and spa-like ensuite bath with a soaking tub and walk-in shower. Two guest bedrooms each offer queen beds and access to full bathrooms, while the detached cabana provides additional sleeping accommodations with a sleeper sofa and private bath.brbrSpend your days exploring nearby Crescent Beach and Wades Beach, dining at local favorites like Vine Street Caf, or enjoying the laid-back charm that makes Shelter Island such a special destination. At days end, return home to your own private retreat and settle into the slower pace of island living.brbrThis property has a max occupancy of 8brbrBedroomsbrbrBedroom 1 - Primary: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard ClosetbrbrBedroom 2 - Guest: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Standard ClosetbrbrBedroom 3 - Guest: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Jack & Jill Ensuite Bathroom, Standard ClosetbrbrBedroom 4 Cabana: One Sleep Sofa, Pool House First Floor/Main Floor, Air Conditioning, Ensuite Bathroom, TV, Balcony/DeckbrbrBathroomsbrbrBathroom 1 - Primary Ensuite: Full Bath, First Floor/Main Floor, Ensuite, Shower, TubbrbrBathroom 2 - Guest: Full Bath, First Floor/Main Floor, Ensuite, ShowerbrbrBathroom 3 - Guest: Full Bath, First Floor/Main Floor, Ensuite, ShowerbrbrBathroom 4 Cabana: Full Bath, Pool House First Floor/Main Floor, ShowerbrbrTVsbrbrBedroom 1 - Primary: StreamingbrbrBedroom 4 CabanabrbrOutdoors & Pool/SpasbrDeck/Patio, Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Fire Pit (Wood-Burning), Bicycle, Beach Chairs, Beach Umbrella, Cooler, Fence Around The Yard, Fence Around The Pool, Private Pool (Outdoor, Heated, Saltwater)brbrAmenitiesbrBed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Air Conditioning, Heating, Hot Water, Usable Fireplace (Wood-Burning), Kitchen, Stove, Oven, Refrigerator, Wine Fridge, Ice Maker, Dishwasher, Microwave, Coffee (Pot, Nespresso), Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television (Kitchen, Den, Additional Structure (Pool House, guest house, detached garage)), Cable TV, Smart TV, Speaker System (Sonos), Steam Room, Ping Pong Table, Private Entrance, Parking, Garage (Detached), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Laptop-Friendly Workspace, Essentials, Privacy (Completely Private)brbrSpecial FeaturesbrPartial water views of Coecles Harbor. Easy walk (1/2 mile) to Rams Head Inn hotel/restaurant/bar with stunning sunset views.brbrLocationbrbrNearby Beaches:brReel Point (a beautiful peninsula beach 1/2-mile from the house, the point of which marks the entrance to Coecles Harbor). 10-min walk or 3-min bike ride.brbrNearby Grocery Stores:brIGA, Marie Eiffel MarketbrbrNearby Restaurants and Bars:brSunset Beach, Lon 1909, Vine Street, Chez Marie, Rams Head Inn, Chequit Hotel & Restaurant, Opties & Dinghies, Commander Cody's Fish Shoppe, etc.brbrOther Location Information:brTuthill Dr. is a private road on Big Ram Island, one of the most coveted and quiet areas on Shelter Island. Car presence de minimus. Extremely safe and quiet for kids and families to walk and ride bikes on the local roads.brbrOther FAQ'sbrbrPool Fenced In: YesbrbrBackyard Fenced In: YesbrbrEstimated Square Footage: 2,160brbrSuitability: Not handicap accessible.brPrimary renter must be at least 25 years old.brbrPet Policy: One hypoallergenic, non-shedding dog of 20 lbs or less is permitted. Non hypoallergenic/shedding dogs or any dogs over 20 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire).brbrUtility Disclaimer: Utility fees are included in the total rental amount. Guest shall be responsible for the costs associated with excessive usage of utilities during the term of the Reservation.brbrCleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest's expense.brbrAdditional Guests: No additional guests beyond the max occupancy of this listing are permitted.brbrEvents Policy: Events are prohibitedbrbrSpecial Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed.brbrPool Disclaimer: Pool generally open from mid-May through mid-October.brFor energy conservation purposes, the pool heater may only be operational from 8am to 6pm.brbrOff-Season Disclaimer: Landscaping and outdoor furniture available from April through October.brbrPayment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Marquis will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners'). Should Marquis be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Marquis is notified in writing 72 hours or more prior to the start of the reservation.brbrNote: All payments must be made prior to check-in.brbrVRBO charges the guest directly for their service fee and applicable taxes, while StayMarquis charges separately for the rental rate. As a result, you will see two separate charges at the time of booking-one from VRBO and one from StayMarquis.brbrIf there is a second installment, it will be collected directly by StayMarquis shortly after the first installment.brbrPayment Method: Balance payments made with credit card are capped at $3,500. Payments over $3,500 shall be made by check, ACH or wire.brbrSecurity Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement.brbrWhile StayMarquis manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, StayMarquis will provide you with a Guest Experience Manager who can help facilitate any request, from grocery shopping to organizing a private chef.brbrGuest Experience: This property is part of our 'Elite' program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed.brbrShowings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.
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Exceptional(6)

$1180.58

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Private Vacation Home

WATERFRONT with Private Beach Boat Dock and Launch Ramp

Shelter Island, New York, United States

Lovely two bedroom sleeps 5 with huge deck and endless waterfront views. Fresh paint all new linens choice of two private community beaches one within a one min walk. Dock, boat and trailer parking at the house, cement boat ramp walking distance. Lots of great fishing fluke, flounder, striped bass weakfish, bluefish, snapper etc. nearby or fish from the park at the canal or from the dock at the house.
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Exceptional(53)

$501

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Private Vacation Home

Relaxing Private Retreat Near Preserve. Pets Welcome!

Shelter Island, New York, United States

Welcome to your private retreat in the perfect blend of comfort, space, and relaxation. With 9 years of hosting experience at this property, we’ve thoughtfully created a stay that feels welcoming, easy, and memorable from the moment you arrive.brSituated on a spacious .8-acre lot, this 3-bedroom, 2-bath home offers an exceptional sense of privacy and tranquility. The property sits directly across from a preserve and beside an unbuilt plot, giving you peaceful natural surroundings and extra privacy.brInside, we have an open floor kitchen/dining/den area with plenty of space. Also, the bedroom floor is recently renovated. Pets welcome!
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Exceptional(1)

$1481.17

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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 of 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.
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Bath 3

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$1356.15

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Private Vacation Home

Year round family home on Shelter Island with indoor heated pool and dock.

Shelter Island, New York, United States

Perfect winter weekend getaway or spring / summer/ fall retreat. With a stone fireplace and indoor heated pool. Consider this family home your home away from home while you visit Shelter Island. With four bedrooms, including two king bed rooms, two queen bed rooms, and a 2 twin bed loft above one queen room, Three full bathrooms. Located on West Neck lagoon with dock. Canoe and kayaks available and a grill on the patio. A short walk to shell beach, and on property access for up to two boats , we think our place will help you experience everything Shelter Island has to offer. Patio available in spring/summer
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Bath 3

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$1116.79

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Private Vacation Home

Updated Greek Revival home minutes to beaches and amenities

Shelter Island, New York, United States

Updated and renovated home convenient to all amenities Shelter Island has to offer. Home away from home with gourmet kitchen and new luxury baths.brStyled and furnished with chic casual furniture and decoration.
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Bath 2

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Sleep 7

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$1212.19

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Private Vacation Home

Haven on Glynn by Rove Travel | 3BR Coastal Luxury

Shelter Island, New York, United States

Summary:brbrWelcome to Haven on Glynn, a Rove Travel Home!brbrbrbrRove offers beautifully designed residences with the quality and care of a 5-star hotel.brbrbrbrThe Space:brbrWelcome to Haven on Glynn by Rove Travel, a serene luxury retreat on Shelter Island that captures the essence of modern coastal living. This bright and elegantly designed three bedroom, two and a half bath home, curated by a top design firm, is just minutes from Crescent and Sunset Beach, The Pridwin, Leon, and Wades Beach. Enjoy central A/C, multiple decks for al fresco dining and lounging, and a screened in porch perfect for morning coffee or evening gatherings. Inside, refined interiors feature designer furnishings from Serena & Lily, Pottery Barn, and West Elm, complemented by abundant natural light and coastal tones. brbrbrbrThe fully equipped kitchen offers premium appliances, high end cookware, and a Nespresso machine. While the home is technically three bedrooms, the finished basement is beautifully designed and functions as a fourth bedroom, providing extra comfort and flexibility for guests. Outdoors, relax on the spacious decks, enjoy grilling and dining under the stars, or take a short 5 minute walk to the private community beach. Guests have access to a beach, swimming area, dock, and a convenient spot to store kayaks or canoes, perfect for leisurely days on the water or admiring breathtaking sunsets over the bay.brbrbrbr___brbrpbRoom Configuration:/b/pbrbrPrimary Bedroom: 1 king bedbrbrSecond Bedroom: 1 queen bedbrbrThird Bedroom: 2 twin bedsbrbrBasement: 1 full pullout mattressbrbrbrbrpbAmenities:/b/pbrbrpbWork From Home:/b/p High-speed Wi-FibrbrpbLiving:/b/p Fully equipped chef’s kitchen, luxury linens, and premium bath productsbrbrpbSupport:/b/p 5-star service, housekeeping, maintenance, local recommendationsbrbrpbLaundry:/b/p In-unit washer/dryer availablebrbrpbPet policy:/b/p No pets allowedbrbrbrbrpbHome Truths:/b/pbrbrThis property requires owner approval for all reservations, and is subject to a background check after the booking is completed to confirm the reservation.brbrbrbrThe basement includes a pull out mattress, providing additional sleeping space.brbrbrbrThe Neighborhood:brbrNestled on sheltered, scenic Shelter Island, Haven on Glynn offers a quiet, refined coastal escape while remaining just minutes from several of the island’s most beloved beaches and landmarks. You’ll be only a short drive or pleasant walk from Crescent / Sunset Beach, The Pridwin, Leon, and Wades Beach, perfect for days of sun, sand, paddling, or seaside dining. The property also lies close to Shelter Island Heights, a charming historic area known for its Victorian homes and tranquil streets.brbrbrbrThe island itself is known for its low traffic, natural preserves, and sense of privacy, with nearly a third of the land held by conservation groups. You’ll enjoy easy access to the island’s public beaches, like Crescent and Wades, and the peaceful, nature rich character that sets Shelter Island apart from the busier South Fork crowds.brbrbrbrOther Things to Note:brbrPets are not allowed at this property. Rove requires a property rental agreement to be signed by the primary guest prior to arrival for all reservations at this home.brbrbrbrAs a reminder, smoking is not allowed anywhere on the property, in the home or in the outside areas of the home. Smoking will result in a odor removal fee of no less than $500 and up to $1,000 as well as possible removal from the property.brbrbrbrpbSecurity Deposit Policy:/b/pbrbrA refundable credit card hold of $1,000 is required as a security deposit for stays at this home to cover any property damage that may occur during your stay. A credit card is required for processing and the hold will be placed 48 hours prior to your arrival. The release of this hold will initiate 2 days after your departure following a departure inspection of the home by our local team.
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Exceptional(7)

$1234.94

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Private Vacation Home

Elegant Treetop Modern Steps from Hay Beach, Heated Gunite Pool

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 (bedroom) 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 bedroom-media room 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.brbrInquiries welcome with special rates for long term/annual renters.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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$661.42

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Private Vacation Home

SHELTER ISLAND YEARLY RENTAL - Perfect family home 4500 a month

Shelter Island, New York, United States

This 3-bedroom house on Shelter Island is perfect for your escape. With 3 queen beds, 2 bathrooms featuring a bathtub and shower, and amenities like AC, WiFi, and a washing machine, guests will feel right at home. The delightful and lovely atmosphere of this property will make the perfect yearly home. Great out door deck for all your meals plus an out side shower. ONLY AVAILABLE YEARLY
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Exceptional(16)

$677.34

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Private Vacation Home

Family friendly home near beach with wonderful deck!

Shelter Island, New York, United States

You can walk to the beach from this attractive home that comfortably sleeps 7. Enjoy cocktails and outdoor dining on the second floor wrap around deck. The second floor great room makes entertaining fun and relaxing. The kitchen, fully equipped with plates, cookware, silverware, glasses, etc, is open to the dining area and living area. The sunny master bedroom, furnished with a queen luxury mattress, is on the second floor and also has access to the deck. brThe first floor has 3 bedrooms, two with twin beds and one with a double bed, and a large common area where family members and guests can play and relax. There is a full bath on each floor.brThe house interior was painted in 2020 and has newer linens, rugs, and other amenities (all from 2020). brThe property has a large lawn where children can play.brYou are 10 minutes to golf and miniature golf, and to the grocery store. The beach is a 6 minute walk, around the corner. brShelter Island has a wonderful nature preserve minutes from the house as well.brWIFI available and TV.br
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Exceptional(53)

$1401.8

/ Nightly
Private Vacation Home

Work and Play Special! Extended Stay Discount

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 8 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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