Vacation Rentals By Owner In Shelter Island, NY

When you turn the corner off the main road and see the house on the hill surrounded by over an acre of manicured lawn and gorgeous landscaping, you will be so happy to know your vacation starts in this beautiful property. The home is spotless, upscale, comfortable with attention to details. All new bedding and bath towels, high end appliances. Decorated with high end furniture, cable tv, completely air conditioned, meticulously cared for inside and out. The south breezes off the bay, the sunsets, the beautiful nature complete this very special house. Enjoy the private community dock directly across the street. Fish, swim, sail or paddle board. The kitchen is completely stocked with dishes, pots and pans, coffee maker, tea pot, microwave and utensils. The spacious, living room is on the south side of the house with lots of windows that will delight you with tree top views, beautiful sunsets, and a peek a boo view of the bay. Spend your time enjoying the nature that abounds as you relax on the back porch. Enjoy alfresco dinners and evenings around the fire pit. Hone your skills on the regulation size Ping Pong table located on the lower floor of the house. Friends or family will be so comfortable private on-suite bedroom furnished with 2 beds, coffee bar, and a full bath. All completely decorated upscale and very comfortable.brThis home is located close to Crescent Beach and Shell Beach and is in a private neighborhood away from the traffic.brEnjoy everything that Shelter Island has to offer and know that you can come home to a private, quiet magical oasis.

Shelter Island 3 bed 2 1/2 bath, 1.3 acres private, quiet water view bay access.

Shelter Island, New York, United States

Bed

Bath

Sleeps

$1874.8

Take the singular Shelter Island drive over Ram Island’s renowned causeways to this meticulously renovated and expanded 1933 charming, waterview home of stone and cedar on the most sought after Big Ram Island block. 5 bedrooms, 6 bathrooms and large living spaces flow seamlessly with the outdoors, thanks to the expansive covered porches off the living room and large patio connecting the pool and hot tub with the kitchen and family room. Every detail was considered in the home in terms of beauty, function and experience. It’s owner, a veteran in the home decor industry, designed all fabrics and wallpapers and spec’ed every detail. The house sits on 1.4 acres of land, with a large lawn, wraparound porches to take in the views and space for everyone to enjoy, lounge, play or explore. brbrBask in the sparkling sunshine on Coecles Harbor, take in the sunset from the two hanging porch-beds, or waterview-dine on the covered veranda. Swim in the heated pool, relax in the grotto-like hot tub or infrared sauna, or paddleboard, sail, fish or kayak just out your front door off the small beach that’s shared by the neighbors. Paddleboards stay parked here, and morning dips are mandatory in this idyllic spot. Off the beach, 37 Tuthill has a boat mooring, useable by renters. A short walk to the end of Tuthill Drive brings you to Reel Point, a sand peninsula lined with osprey nest platforms and blankets of seashells. brbrCoecles Harbor is a protected deep-water harbor that faces Mashomack Preserve, with over 2000 acres of interlacing tidal creeks, woodlands and freshwater marshes, easily accessible by paddleboard off our beach. The harbor is prized by sailors, swimmers and fishermen for its pristine, protected waters. The island enjoys a similar sense of peace and tranquility. brbrPerfect for everything from a relaxing couples getaway to a fun-filled family or friends gathering, this is fantastically special home designed for making cherished memories, in a magical corner of the world.br

NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT

Shelter Island, New York, United States

Bed

Bath

Sleeps

$549.4

Sleeps 4 adults (max) or total of 6 with kids.brPerfect family getaway.brShelter Island Rental License #: 2023-V-0018br**PLEASE DO NOT PUT IN A BOOKING REQUEST UNTIL WE HAVE HAD A CONVERSATION ON THIS SITE. MESSAGE ME ABOUT YOUR STAY AND I WILL RESPOND QUICKLY**brWeekly and Monthly Discounts for Winter Rentals!brbrStay at our newly renovated, light filled home! In the warmer months lounge by the heated pool in the private tree-filled yard, relax in the hot tub that overflows into the pool, nap in the shade of the pool house, then rinse off in the outdoor shower. Read a book in the hammock or on the porch rocking chairs. BBQ on the big back deck and hang out by the outdoor fire pit to roast marshmallows in the evening. **Pool & hot tub CLOSED NOVEMBER - MAY. brIn the colder months, stay in the mid-century modern style living room, play board games and watch a movie on Netflix with a roaring fire in the stone fireplace or walk to the best sledding on the island. Cook in our well appointed kitchen and eat while watching the sunshine and stars through the dining room skylight. You will never have to leave the house for an incredibly relaxing vacation! Perfect for a family get away any time of year (we also have toys, pool toys, and a Wii with lots of games) or for a place just to get away from it all. brbrAnd when you want to get out to explore Shelter Island - we are less than 1 mile from beautiful Sunset Beach! Beach by day, have a cocktail at the bar to watch the sunset in the evening! Walking distance to the public golf course. Or take the Ferry to Greenport or Sag Harbor for an easy trip! Ride the bikes to town for lunch. From the house it's an easy walk to the ice cream shop and Ice Pond Park. brbrThe house is situated on a very quiet, dead-end street with a beautiful, tree filled, and large yard. We have privacy for relaxing, but are close enough to Shelter Island Heights, the North Ferry to Greenport, the South Ferry to the Hamptons, and other conveniences to make this the perfect vacation location.brbrWe'll provide you with maps and tips for exploring the island's beaches and restaurants. Before purchasing this house we rented on Shelter Island for many years, so our goal is to make your stay as perfect as we can.brbrIMPORTANT: br- PLEASE DO NOT PUT IN A BOOKING REQUEST UNTIL WE HAVE HAD AN EMAL EXCHANGE ON VRBO. br-**Must be 30 years or older to rent the house. Families encouraged. 4 adults maximum. Hot Tub and Pool are Closed November - Mid May. brbrbrHouse Details:brbrCentral Air and Ceiling Fans in each room. brBedroom 1 - 1 Queen Bed (sleeps 2); private back deck; full bathroom with shower brBedroom 2 - 1 full bed (sleeps 2)brBedroom 2 - 1 twin bunk bed, 1 twin bed, 1 expandable twin bed (from Bo Concept) (sleeps 3 children)brBathroom 2 - clean and renovated with bathtub and showerbrPool - Heated and beautiful. Open Mid May - October **Note: Swimming only. There is no diving. The pool is not deep enough.**brHot Tub - Open Mid May - OctoberbrPool House with Outdoor Shower - Open May - OctoberbrWasher/DryerbrKitchen with Stainless Steel appliancesbrWiFi, basic cable and Apple TV with NetflixbrbrThe premises are equipped with exterior security cameras. Cameras are not monitored for guest safety in any way and should not be relied on by guests for personal security or security of their belongings. Cameras may be used to enforce and verify compliance with rental policies.

NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!

Shelter Island, New York, United States

Bed

2

Bath

6

Sleeps

$793.88

Newly renovated, spacious, 4 bedroom, 3.5 bath house on 1.25 acres in the Hay Beach neighborhood of Shelter Island overlooking the private golf course. You’ll want for nothing in this stylish modern on Shelter Island. Now taking inquiries for Summer of 2024. Monthly or seasonal rentals, only.

Spacious Modern on wooded lot - 5 min from beach!

Shelter Island, New York, United States

Bed

Bath

8

Sleeps

$1392.1

Summary:brbrWelcome to Sandpoint, a Rove Travel Home! brbrbrbrRove offers curated, luxury residences with the quality and care of a 5-star hotel.brbrbrbrThe Space:brbrWelcome to Sandpoint by Rove Travel, an exclusive Shelter Island retreat recently built on 1.4 acres, just a stone's throw from a sandy beach and across from a 12-acre preserve. This stunning home features five bedrooms, including two master suites and one room with twin beds. Sunlit and spacious, the heart of the home is a well-equipped kitchen with an oversized island overlooking a large pool and landscaped grounds. Sandpoint offers a serene 20x40 gunite pool, making it an unparalleled tranquil retreat on Shelter Island.brbrbrbrThe pool is currently closed, and will be guest-ready starting May 4, 2026.brbrbrbrTo finalize your reservation, all guests must pass a mandatory third-party screening process.brbrbrbr---brbrpbRoom Configuration:/b/pbrbrPrimary Bedroom: 1 king bedbrbrSecond Bedroom: 1 king bed, 1 cribbrbrThird Bedroom: 1 king bedbrbrFourth Bedroom: 1 king bedbrbrFifth Bedroom: 2 twin bedsbrbrGuest House: 1 queen bedbrbrbrbrpbAmenities:/b/pbrbrpbWork From Home:/b/p High-speed Wi-Fi, dedicated workspacebrbrpbLiving:/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/pbrbrPlease note that playing loud music is not allowed at this property. Additionally, we ask guests to keep backyard noise to a minimum, especially if traveling with children, to ensure a respectful environment for neighbors.brbrbrbrThe entire property, including the main house, guest house, and pool house, is exclusively accessible to guests.brbrbrbrIf you would like the pool heated during your stay, there is an additional fee of $75. This covers 8 hours of pool heating scheduled during the daytime.brbrbrbrThe pool will open on May 4, 2026. The pool is open seasonally. If weather permits, it may remain open through the end of September and potentially into mid-October.brbrbrbrOur pool is cleaned and chemically balanced weekly. As an open-air pool, natural debris from wind and breeze are normal between service visits — a skimmer net is available for your convenience. Our team is always happy to assist if needed.brbrbrbrThe Neighborhood:brbrNestled between the North and South Forks (although technically classified as part of the North Fork region) is Shelter Island. A tiny island accessed only by ferry from either Greenport on the North Fork, or North Haven on the South Fork, Shelter Island is known for its natural beauty, hiking, biking, bird-watching and some of the most breathtaking kayaking in Suffolk County. The entire island is approximately 27 square miles.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.

Sandpoint by Rove Travel | 6BR Family Home w/ Pool

Shelter Island, New York, United States

Bed

Bath

Sleeps

$1221.06

Please note that a reservation for this property needs to be approved before it is confirmed.brbrEast Brander EscapebrbrLovely Shelter Island cottage with panoramic bay views, secluded, screened porch, cedar outdoor shower, steps to the beach, access to kayaks and bikesbrbr4BR/2BA - waterview, screened in porch perfect for dining inside and out, cedar outdoor showerbrbrGently tucked on a quiet street and steps to West Neck Harbor, a picture perfect Cape summer retreat full of Shelter Islands charm, sweeping bay views and beautiful outdoor space that is sure to be an unforgettable stay in Shelter Island. With direct access to the bay, prepare for outdoor activities galore including kayaking, canoeing, biking, picnics, nature walks or simply basking in the sun.brbrSpanning over 2,200 square feet, this contemporary home features a light-filled, open floor plan curated with cool blue hues, warm neutrals, panoramic water views and contemporary finishes sure to make you feel at home. The spacious living and dining room features a cozy fireplace to spend time with family and friends in. Settled just off of the living room is a peaceful den perfect for reading or quiet time. Showcase your skills or hire a private chef to come and prepare a lavish meal for the home as the gourmet kitchen includes your main cooking essentials. There are four tranquil bedrooms prepared with your warmth and comfort in mind. Each room includes fresh linens, plush towels and your main bath essentials. Additional amenities include a wood fire pit, beach chairs/umbrella and gas grill for summer BBQs.brbrStart and finish your day outdoors as you are surrounded by the tranquility of natures beauty and Shelters island relaxing ambiance. Wake up to your natural alarm clock and enjoy the sunrise from your cozy screened porch then head down the trail for fun in the sun. When youre ready to head into town, grab one of the bikes available and explore the North Fork. Conveniently located you are near a wide array of stellar local shops and restaurants as well as minutes from Shell, Crescent and Crab Creek Beach. East Brander Escape makes for the perfect summer enjoyment.brbrSeparate ResidencebrPlease note, there is a separate cottage on the property where the owner will likely be staying.brbrPlease note: the sliding doors off the deck need to be pulled firmly to open.brbrThis property has a max occupancy of 6brbrBedroomsbrbrBedroom 1: One Queen Bed, 2nd Floor, Air Conditioning, Standard ClosetbrbrBedroom 2: One Queen Bed, 2nd Floor, Air Conditioning, ClosetbrbrBedroom 3: Two Twin Single Beds, 2nd Floor, Air Conditioning, ClosetbrbrBedroom 4: Two Twin Single Beds, First Floor/Main Floor, Air Conditioning, ClosetbrbrAdditional Sleeping Space: One Sleep Sofa, First Floor/Main Floor, Air ConditioningbrbrBathroomsbrbrBathroom 1: Full Bath, First Floor/Main Floor, Shower, TubbrbrBathroom 2: Full Bath, 2nd Floor, ShowerbrbrOutdoorsbrBeach Chairs (10 Chairs), Beach Umbrella, Outdoor Shower (Hot + Cold Water), Deck/Patio (Covered), Patio Furniture (Table, Chairs), Bicycle (4 Adult Bikes), Grill (Gas), Kayak/Canoe, Fire Pit (Wood-Burning), Cooler, Fence Around The YardbrbrAmenitiesbrBed Linens, Bath Towels, Pool/Beach Towels, Air Conditioning (Window Units), Heating, Hot Water, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Usable Fireplace (Wood-Burning), Internet (Wifi), Microwave, Coffee (Pot, Other, Keurig), Dishes and Silverware, Pots and Pans, Toaster, Speaker System (Bluetooth Speaker), Television, Private Entrance, Living Room, Parking (4 Cars In Driveway), Pack 'n Play/Travel Crib, Kitchen, Stove, Oven, Refrigerator, Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Dishwasher, Cable TV, Essentials, Blender, Laptop-Friendly Workspace, Pots and PansbrbrSpecial FeaturesbrFull waterview, across the street from the beach. Kayak access across the street. Very close to shell beach. Located in a corner lot, on a very quiet part of Shelter Island/Silver Beach.brbrLocationbrbrNearby Beaches:brShell Beach, Crescent Beach, Crab Creek Beach.brbrNearby Grocery Stores:brIGA on IslandbrbrNearby Restaurants and Bars:brDan Brock's Barbecue at Ellie's country store excellent sides and puddings in mason jarsbrbrMarie Eiffel- in the Heights a wonderful french patisserie with great take out food.brbrRam's Head Inn-- always special even just for cocktails on the beautiful lawn in adirondeck chairs.brbrKyles- fantastic homemade jelly and cinemon 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 has decent pizza.brbrOther Location Information:bryou don't need a parking sticker for the first half of crescent beach, which is about two miles away and also has a food truck.brbrOther FAQ'sbrbrEstimated Square Footage: 2,200brbrRental Registration: 19S-0025.brbrSuitability: Not handicap accessible.brPrimary renter must be at least 35 years old.brbrPet Policy: One hypoallergenic, non-shedding dog of 50 lbs or less is permitted for an additional $250.00 per booking. Non hypoallergenic/shedding dogs or any dogs over 50 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:brUtility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $70.00 per night 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.brbrOff-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking.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.

Lovely Shelter Island cottage with panoramic bay views, secluded, screened...

Shelter Island, New York, United States

Bed

Bath

Sleeps

$1013.36

* Please Read House Rules And Policy's Before Booking*br*Check In And Check Out Times Are Firm*brbrPerfect For Families!! Dogs Welcome! Located within close proximity to resort areas, Sunset / Crescent beach & Crab Creek with sunsets galore, Shelter Island Heights Town is jus a short bike ride away. This neat-as-a-pin home has all the ingredients for an exciting summer vacation. Tucked behind evergreens, the rooms are sun-filled in an open plan. Just inside the foyer the living room has a extra large Queen sized sleeper sofa beautiful windows out to the veranda, fireplace and entry to a well equipped kitchen, which then flows into the dining area which has French doors to the entertainment deck. Down the hall is a full bath, a guest bedroom with bunk bed w/ trundle, a second guest bedroom with a queen sized bed, home office area and door to the pool deck, plus the primary en-suite bedroom. The lower level has a projection screen media room, comfy recliner chairs and laundry area. The grounds are what summer is all about, with an in ground Gunite pool and adjacent outdoor shower, dining area off the kitchen with Pizza Oven and Gas Grill, covered lounge area, fire pit with Adirondack chairs and S'mores Station , Vegetable / herb cutting garden, pool cabana with pool / ping pong table, smart TV, Blue tooth indoor / outdoor speakers, extra refrigerator, food and beverage area and lounge chairs. Fully Fenced In Yard !brCable (All Premium Channels)brNest Controlled Central AC, brADT Alarm System / Ring front door bellbrPool Maintenance , brLawn Maintenance brand Garbage Pick UpbrKayak, Baby Stroller(s), Jogging Stroller, Pack and Play, Child Gate, Pool / Door Alarm, Pool Floats and Clamming Nets, Skate Board, Scooters, Adult, Teen and Child Bicycle's All ready and Available.brDog FriendlybrbrThis Is a Quiet Family Neighborhood Please Be Respectful...brNO PARTIES, NO SMOKING, NO EXCEPTIONS!brMax 4 Adultsbr*Incense and candles are not permitted inside or outside the house due to fire hazards.* br• Smoking is not permitted br• Supervise children on pool deck and around the firepit. br• Guests and visitors should park only in our driveway, not the main road. br• When leaving house, please always lock all doors—including pool house French doors and garage doors br• Before checkout, dispose all garbage in outdoor trash bins. br• Report any damages and/or breakages. Guests are responsible for any damage reported by the house manager they cause to the property and household items that. brbr• Please pick up after your dog, especially around the grounds of the house.br*Dogs Welcome $200 pet fee*brbr*Bunk Beds Are For Ages 13 and Under*

Shelter Island Retreat With Pool ...Close To Beach & Pet Friendly

Shelter Island, New York, United States

Bed

Bath

Sleeps

$746.84

Great house in great location. 3 bedrooms (including one with bunk bed and additional bed) . Open floor plan with updated kitchen and bathrooms. In addition to large pool, great yard and outdoor shower. Short walk to nearby beach or bike to Sunset or Shell Beach. Very friendly quiet neighborhood. Ideal for families with 2-4 kids. We hope our house feels like your home for the time you are here!

Charming updated home with pool on quiet street. Near Silver Beach

Shelter Island, New York, United States

Bed

Bath

Sleeps

$1076.93

Enjoy the best that Shelter Island can offer at this renovated 2 bedroom waterfront gem. brNestled on West Neck Bay, this one-of-a-kind home is just 20ft from the water with sweeping views.brWake up to the amazing dawn rising above the water and flooding the patio outside the master bedroom.brTake a morning stroll to bootleggers' beach or simply hang out on the dock. brAfter breakfast, sit and enjoy the views or rent some Kayaks and explore the bay and beyond. brThen there's swimming off the dock (no diving though as the water is shallow), clamming, reading, relaxing...And so it goes on until it's time for a picnic or an outdoor BBQ with your friends who've just sailed over from Sag Harbor and anchored off your dock.brAnd of course, if you can tear yourself away from this little piece of heaven there's the whole of Shelter Island and beyond to explore before coming back to evening cocktails on the porch, more views and dinner around the table. brYou may never need it, but just in case there's also cable TV, stereo and all that. brBe warned - you may never want to leave :-)brbrLicense 014 - twenty seventeenbr

Shelter Island, Waterfront, Lazy Days With Stunning Views

Shelter Island, New York, United States

Bed

Bath

Sleeps

$1196.63

Light-filled retreat with 5 sliding glass doors between indoor/outdoor space with heated poolbrbrLocated in landscaped setting on pastoral Shelter Island, enjoy the island lifestyle at this new, completely gut renovated, mid-20th century home with modern 4 bedroom/2.5 bathroom addition and heated, gunite pool. It will serve as both your quiet sanctuary away from city life and a place to entertain. Large deck with skid-resistance Italian porcelain tile, cedar pergola and wrap around patio bench seating for you and your guests. Find easy access to beaches, local cuisine, farmers' markets and seafood shops. Savor the excellent restaurants or make your own home-cooked meals on the 5-burner Jenn-Air gas stove or outdoor gas grill. Full kitchen with all amenities including granite center island with stools; Electrolux Icon refrigerator/freezer, Microwave and Oven, Bosch dishwasher. There is a large capacity washer/dryer off kitchen. Lounge on the large, sectional sofa in the living room with gas fireplace. The house features 2 systems for central heat and A/C with Nest thermostats. Sleeping 8, the bedrooms consist of one King Bed in Primary Bedroom with en suite Carrera marble bathroom; 2 twin beds in 2nd bedroom with full bathroom, shower and tub and 3rd bedroom with comfortable, Queen sleeper sofa. A 4th Bedroom on lower level features a Queen Bed and home office. The lower level also features a kitchenette, living area and ping pong table. A half-bath is off the main kitchen and dining room. Play your favorite songs on 2 Sonos systems in the living room and pool deck. A T-shaped driveway provides ample parking for up to 5 cars. Available Memorial Day to Labor Day and off-season as well, bi-weekly, weekly or monthly. 7- day minimum rental.brDiscount of 5% applied for 7 nights or morebrDiscount of 10% applied for more than 28 nights

Tranquility Base; Architect-Renovated, Modern Ranch With Heated Pool

Shelter Island, New York, United States

Bed

2

Bath

8

Sleeps

$952.42

Welcome to Shelter Island, your home away from home. A short ferry ride to a relaxing vacation at the beach. Our updated home is close to south ferry, Mashomack Preserve, beaches, restaurants and shops.brbrWhen you walk in, you will see an open dining and kitchen area perfect for everyone to gather after a day at the beach. There is a nice big porch with BBQ to enjoy outside and stargazing when the sun goes down. Be sure to keep a look out for the wild turkeys and deer!! brbrWe have two living rooms to relax, both with smart TV’s, one also has a sleeper sofa. Bedroom on first floor has queen. Four bedrooms upstairs: 1 with two twins and three with queen beds. Each floor has a full bathroom. We also supply all sheets, bath towels and beach towels.brbrThe renovated kitchen is equipped with all the necessary appliances, dishware and utensils. The central air conditioning ensures your comfort throughout your stay. Stay connected and entertained with high-speed internet throughout the house.brbrThe South Ferry Hills Association private community beach is around the corner with picnic benches, a boat launch and enclosed waters of Smith Cove for paddleboarding, kayaking and boating. brbrWe are close to the South Ferry and not far from Shelter Island's, restaurants (including Leon 1909, The Pridwin, Vine Street Cafe, The Chequit, Sunset Beach, Salt and The Rams Head Inn), public beaches, golf courses and Mashomack Preserve.brbrWe also have two paddleboards available for us during your stay.brbrWe also have a peloton, so bring your shoes.brbrIt is the perfect getaway and we hope you enjoy it as much as we do.

Spacious 5-bedroom house in delightful Shelter Island

Shelter Island, New York, United States

Bed

Bath

Sleeps

$1118.06

Beautiful Waterfront Home on West Neck Creek on Shelter Island. New deck overlooking West Neck Creek -Great for relaxing or entertaining. Bright & Airy vacation home on private road. Newly decorated with central air conditioning, pool/game room. Large picture windows throughout overlooking water – great vacation home for large family. Deep water dock, six and half feet at low tide on shallow end, for up to 60 boat. Swim, Fish, Sail, Boating. Commercial ice machine, 450 pounds of ice a day for beach, boating or your party!brbrRestaurants & Shopping, Marina, Golf, Beaches. Luxury home on water. Beautiful sunsets.br

Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock

Shelter Island, New York, United States

Bed

Bath

Sleeps

$752.47

Lovely three bedroom cottage centrally located. Cook's kitchen, cozy living room with fireplace, two bathrooms, southern light, and large, private yard. The perfect spot to read, relax, prepare meals and explore the natural beauty of Shelter Islabd. The cottage is close to all island beaches, nature preserve and restaurants. All of the charm and character of an original house on the island dating to the 1860’s but lovingly updated and very comfortable.

Cottage

Charming, Historic Cottage

Shelter Island, New York, United States

Bed

Bath

Sleeps

$1285.31

Completely renovated and updated 1929 Sear's kit home with beautiful views to Peconic Bay. Swim, fish for dinner, windsurf, Kayak or just take in amazing view over a bottle of wine from your private beach. This spectacular and desirable Silver Beach location features a 4 bedroom, 2 bathroom cape with country kitchen, living room with fireplace and dining area with french doors opening to a covered veranda with forever views. An outdoor shower and private enclosed yard plus sandy beach make this a picture perfect summer retreat.

Spectacular Waterfront-Best view on island-Tastefully renovated 1929 Cape.

Shelter Island, New York, United States

Bed

Bath

Sleeps

$776.88

Great location. Situated on 3/4 acre. Walk to Sunset/Crescent beach, ferry, restaurants, shops less than 1 mile. Ice cream parlor and public golf course across the street. 3 Bedrooms, (1 King Bed, 1 Queen Bed, 2 Twin Beds) Air conditioned. 2 bathrooms on 2nd floor, 1/2 bath on first floor, W/D, Living Room, Dining Room, Kitchen, Basement with air hockey and foosball. Large 18 X 42 Pool and patio for outdoor fun. Large outdoor deck. Front and side porch. Owner occupied separate apartment on premises accessible by entry at driveway location. Town beaches accessible online with a permit.

Perfect Family Summer Vacation Home Close to beach 18x42 pool

Shelter Island, New York, United States

Bed

Bath

Sleeps

$1296.27

Wake up to the beautiful Sunrises. Take your coffee and enjoy the porch views. Watch mother nature at her best! Lovely new screened in Porch .brSend the kids down to the Dock where they can catch small crabs in their nets. Grab that fishing pole and try your luck at the end of Dock. Bring your boat! brEnjoy all your meals on the waterfront Deck. Take a bike ride or a stroll around the beautiful neighborhood. Shell Beach and Sunset Beaches are close by!brTake a good book and relax in the Hammock aahh!brThis is a special House with lots of charm. Three bedrooms plus an additional childs area with captains bed off the Master Bedroom. Master Bedroom w/Queen Bed / Shower. The other two guests bedroom share a bath and shower. In addition there is a lovely separate Guest Cottage w/Stone Fireplace, Bath/Laundry Room (a favorite of guests)brbr Main House there are Flat Screen TV's in the Living Room and the Master Bedroom. The house has Internet/ Cable . The Kitchen is fully stocked with a large walk in pantry. There is a Gas Viking Stove. Plenty of Dishes, Pots, Pans, Silverware and Glassware. brbrKeywords: Lovely Home on the Waterfront.brSituated on 2.1 Acres. Waterside Pool & DockbrbrNOTE: Tenant is required to pay electric charges and final cleaning which will be deducted from their Security Deposit.

Waterfront Home Plus Separate Cottage/Dock

Shelter Island, New York, United States

Bed

Bath

9

Sleeps

$632.82

Nestled in the woods just behind the Pridwin Hotel, walk to Crescent Beach, Perlman Music and Sunset Beach.br1930''s Shelter Island original structure recently renovated. brSurrounded by nature. br.......

Sea Pine Cottage

Shelter Island, New York, United States

2

Bed

1

Bath

Sleeps

$2109.33

Shelter Island GembrbrChic Shelter Island A-Frame with Private Pool, Stylish Interiors, and Resort-Style Outdoor Livingbrbr3BR/2BA: Private Heated Pool, Expansive Fenced Yard, Outdoor Dining & Shower, Fire Pit, Seamless Indoor-Outdoor LivingbrbrWelcome to a stunning blend of charm, sophistication, and coastal style at this impeccably designed Shelter Island A-Frame home. Perfectly situated in a central location, guests will find themselves just moments from the islands beloved restaurants, shops, bars, and pristine beaches. This elegant hideaway offers the ideal backdrop for families, groups, or anyone looking to truly escape daily life and immerse themselves in the relaxed spirit of Shelter Island. With three bedrooms, two bathrooms, and room for up to six guests, this residence boasts double-height ceilings, abundant natural light, a stylishly updated kitchen, and thoughtfully designed interiors. Equipped with all modern conveniences including WiFi, air conditioning, a washer and dryer, and a dedicated work-from-home space, this home masterfully combines comfort with luxury island living.brbrOutside, the private, expansive fenced-in yard creates a true sanctuary. Guests can bask in the sunshine by the private heated pool, where chaise loungers invite relaxation throughout the day. A charming pool house provides additional living space for lounging or quiet moments away from the main home. A beautiful wooden sundeck offers a seamless connection between indoor and outdoor living, complete with an outdoor shower with hot and cold waterperfect for rinsing off after a refreshing swim or beach day. Evenings are made magical around the fire pit with Adirondack chairs, ideal for cocktails, storytelling, and stargazing. Multiple outdoor seating areas encourage leisurely afternoons and intimate conversations, while outdoor dining spaces invite memorable alfresco meals. Ample free parking ensures convenience for all guests throughout their stay.brbrUpon entering the A-frame home, guests are greeted by an airy, open floor plan flooded with natural light. The main living area flows effortlessly into the dining space and kitchen, creating a communal atmosphere perfect for gathering. Sliding glass doors off the dining room open directly to the backyard oasis, further blending the indoors with the beauty of the surrounding outdoors. An additional sunroom, framed by walls of windows and furnished with two plush sofas, offers a cozy and serene spot to unwind, with direct access to the sun deck through sliding doors. The updated kitchen is fully equipped with everything needed to craft a home-cooked meal, including modern appliances, a coffee maker, and a complete array of cooking essentials. Every detail throughout the interiors has been carefully selected to offer a stylish, comfortable, and inviting environment.brbrThe home offers three beautifully appointed bedrooms and two sleek, modern bathrooms, ensuring every guest rests in absolute comfort. Two bedrooms are conveniently located on the main floor, each featuring a queen bed outfitted with fresh, luxurious linens and thoughtful touches for a restful night's sleep. A lofted third bedroom offers a charming and private retreat, also with a queen bed. The primary bedroom boasts direct access to the sun deck and an en-suite bathroom complete with a spacious walk-in shower. An additional hall bathroom, also featuring a walk-in shower, serves the other bedrooms. Both bathrooms are newly updated, fully stocked with plush towels, and equipped with all the essentials needed for a seamless stay.brbrBeyond the property, the heart of Shelter Island awaits. Guests can easily explore a variety of local treasures, many just a short drive or leisurely bike ride away. Discover charming boutiques, art galleries, and locally loved restaurants offering everything from farm-to-table fare to fresh-caught seafood. For those looking to connect with nature, Shelter Islands beautiful beaches provide the perfect escape for sunbathing, swimming, and water sports. Outdoor enthusiasts will appreciate nearby golf courses, scenic nature preserves, and hiking trails. The islands many farm stands and markets offer fresh, local produce to bring back and enjoy at the home. For wine lovers, several acclaimed wineries are within easy reach, offering tastings and tours in picturesque vineyard settings. Whether guests seek adventure or relaxation, this location offers something for every mood and moment.brbrThis Shelter Island A-frame invites you to slow down, breathe in the sea air, and create unforgettable memories in a setting that feels both luxurious and effortless. Your island escape awaits.brbrThis property has a max occupancy of 6brbrBedroomsbrbrBedroom 1 - Primary: One Queen Bed, First Floor/Main Floor, Air Conditioning, Ensuite BathroombrbrBedroom 2 - Guest: One Queen Bed, First Floor/Main Floor, Air Conditioning, TV, Standard ClosetbrbrBedroom 3 - Guest: One Queen Bed, 2nd Floor, Air ConditioningbrbrBathroomsbrbrBathroom 1 - Primary Ensuite: Full Bath, First Floor/Main Floor, Ensuite, Handicap Accessible, ShowerbrbrBathroom 2 - Hall: Full Bath, First Floor/Main Floor, Handicap Accessible, ShowerbrbrTVsbrbrBedroom 2 - GuestbrbrOutdoors & Pool/SpasbrDeck/Patio (Uncovered), Outdoor Shower (Hot + Cold Water), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Fence Around The Pool, Fence Around The Yard, Fire Pit (Wood-Burning), Private Pool (Heated, Outdoor, Saltwater)brbrAmenitiesbrBed Linens, Air Conditioning (Central Air), Dryer, Heating, Internet (Wifi), Washer, Hair Dryer, Living Room, Parking, Coffee (Other), Dishes and Silverware, Pots and Pans, Toaster, Speaker System (Sonos), Television, Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Fire Extinguisher, Essentials, Laptop-Friendly Workspace, Bath Towels, Pool/Beach Towels, Private Entrance, Blender, Smart TV, Privacy (Completely Private)brbrLocationbrbrNearby Beaches:brShell BeachbrWades BeachbrCrescent BeachbrbrNearby Grocery Stores:brHaven's Farmer's MarketbrSep's Farm StandbrElli's Country StorebrIGA Shelter IslandbrbrNearby Restaurants and Bars:brShelter Island Craft BrewerybrSALT Waterfront Bar & Grillbr18 BaybrOsprey Bar & LoungebrSunset BeachbrThe IslanderbrbrOther Location Information:brMashomack PreservebrFresh PondbrbrSuitability: Not handicap accessible.brPrimary renter must be at least 30 years old.brbrPet Policy: One dog of 50 lbs or less is permitted for an additional $250.00 per booking. Dogs over 50 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:brUtility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $100.00 per night 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: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking.brFor energy conservation purposes, the pool heater may only be operational from 8am to 6pm.brbrOff-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking.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.

Chic Shelter Island A-Frame with Private Pool, Stylish Interiors, and...

Shelter Island, New York, United States

Bed

Bath

Sleeps

$855.5

Brand new 4 bedroom 3 full bath home with porches overlooking the creek and a heated, saltwater, gunite pool and patio. (3 bedrooms up, with two full baths and 1 master suite down with a full bath as well). Kayaks, a peddle boat, BBQ, fire pit, all needed outdoor furniture as well as linens etc. are all included. The home has two master suites. There is also a deep water mooring!brbr* ** Please note: we have a 30 day minimum. Shelter Island ID#: 19-L-0002.brbrbr

Lovely home by the sea with dock and heated Gunite pool!

Shelter Island, New York, United States

Bed