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Vacation Rentals In Shelter Island, NY

Showing 20 Of 81 Vacation Rentals

We Have 81 Vacation Rental Offers Available In Shelter Island. Average Price Per Night Is $234.58. Find Your Vacation Home Today.

  • Property-1 Image 1
    Exceptional
    (1)
    Cottage
    Silver Beach, 3 Bedroom cottage w/ pool
    Shelter Island, New York, United States

    Enjoy summer on Shelter Island in this 3 bedroom, 2 bathroom, freshly painted and well equipped MCM ranch house on 3/4 of an acre. Located at the end of a private road, it's in walking distance to Shell Beach, town landings and a beautiful sunset viewing spot. Brand new, heated, inground pool w/ color changing light, central air, deck, fire pit and BBQ make this a great vacation home. Read More

    3 Bed
    2 Baths
    Sleeps 7
    $700 / Nightly
  • Property-2 Image 1
    Agritourism
    Waterfront farmhouse with dock and south and west sunset view.
    Shelter Island, New York, United States

    Offering 400’ of waterfront and southwest exposures, this classic home was just completely renovated and designer decorated to offer modern Hamptons luxury inside and out. The home features a gorgeous living room, formal dining room, chefs kitchen, and brand new stainless steel appliances. Upstairs all four bedrooms offer water views . Boating, swimming, paddle boarding, kayaking are the possibilities with your own private dock. Just minutes to the south ferry and Sag Harbor or Greenport. Read More

    4 Bed
    4 Baths
    Sleeps 6
    $900 / Nightly
  • Property-3 Image 1
    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. Read More

    3 Bed
    3 Baths
    Sleeps 6
    Select Dates for Price
  • Property-4 Image 1
    Exceptional
    (12)
    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 ! Read More

    3 Bed
    5 Baths
    Sleeps 6
    $374 / Nightly
  • Property-5 Image 1
    Exceptional
    (5)
    Private Vacation Home
    Mid-century on idyllic pasture like setting with pond
    Shelter Island, New York, United States

    This mid-century modern home sits on over an acre of land overlooking a tranquil pond. Located in the Shorewood section of Shelter Island just steps from a private beach and a 10 minute walk to the popular Wades Beach and access to a private tennis court across the street makes this a great summer escape. The open planned living room, dining room and kitchen with vaulted windowed ceiling adds great light by day and stargazing by night. All three bedrooms have sliding glass doors accessing the back deck and backyard. brbrThe furnishings are a mix of mid-century and modern, with white Egyptian cotton bedding in all three bedrooms. The master bedroom has a king bed, on suite bath and lots of windows and light. The second bedroom has a queen bed and lounging chair and the third bedroom has a twin sleep sofa, writing desk and chair, both rooms share a bath with shower in main hallway. Central air and ceiling fans in every room, make your stay comfortable. Read More

    3 Bed
    2 Baths
    Sleeps 5
    $750 / Nightly
  • Property-6 Image 1
    Exceptional
    (7)
    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. 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. Dog friendly! Read More

    4 Bed
    4 Baths
    Sleeps 10
    $1,500 / Nightly
  • Property-7 Image 1
    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. Read More

    4 Bed
    2 Baths
    Sleeps 8
    $350 / Nightly
  • Property-8 Image 1
    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. Read More

    1 Bed
    1 Baths
    Sleeps 3
    $280 / Nightly
  • Property-9 Image 1
    Private Vacation Home
    Peaceful Shelter Island sanctuary with heated gunite saltwater pool
    Shelter Island, New York, United States

    This property is extremely quiet and peaceful sitting on almost an acre of beautifully landscaped gardens and backing onto a serene nature preserve. It was completely renovated in 2019, in a minimal mid century style. The home is extremely comfortable and easy to use with new state of the art appliances, heated gunite, saltwater pool and upgraded air conditioning. The open plan kitchen opens onto a beautiful mahogany deck with outdoor dining and views of the pool, garden and the nature preserve. The property is a short walk to a community beach where kayaks and paddle board are provided for your use. The house is extremely child friendly and safe, with a fenced in pool and quiet cul de sac. Read More

    4 Bed
    3 Baths
    Sleeps 8
    $450 / Nightly
  • Property-10 Image 1
    Exceptional
    (1)
    Private Vacation Home
    NEW RENTAL! Gorgeous Traditional w/ Pool, 2 minutes from Beaches, Golf, Tennis
    Shelter Island, New York, United States

    Traditional Hamptons style home with beautiful details, all impeccably renovated. Wrap around porch overlooks expansive front yard. Roomy bedrooms, jetted tubs with separate showers in every bathroom. The primary bedroom suite has a balcony that overlooks the large pool and 6+ acres of natural preserved land. Formal living room with baby grand piano; bright private office with large window seat; breezy screened in sun room,; large 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 pool, two reclining couches, full wet bar, pool table with ping pong topper. Adjoining spa-like bathroom with double sinks, jetted tub for two, and very generously sized shower. 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 golf courses, hiking trails, tennis, restaurants, bars, 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! Read More

    4 Bed
    4 Baths
    Sleeps 8
    $1,229 / Nightly
  • Property-11 Image 1
    Agritourism
    Beautifully renovated Farmhouse sitting on a lush property
    Shelter Island, New York, United States

    This classic farmhouse just got completely renovated with attention to all details from the bathrooms outfitted with Waterworks and Lefroy Brooks to the kitchen with high-end appliances including a LaCornue range for the chef in you. The queen-size bedrooms are all upstairs. Right in front of the kitchen are an outdoor dining and seating area with a gas grill. The house sits back from the street and is very quiet, the perfect place to relax. Close to the wonderful beaches of Shelter Island. Read More

    3 Bed
    3 Baths
    Sleeps 6
    $1,330 / Nightly
  • Property-12 Image 1
    Private Vacation Home
    Waterfront Treehouse with Pool
    Shelter Island, New York, United States

    Designer family home perched atop a hill in Shelter Island with beautiful covered deck overlooking the water. The house includes a pool, outdoor bath tub, sauna, kids bunk bed with toys, gas fire pit, treehouse and much more. This house has everything needed for an incredible vacation. Note that one of 4 the bedrooms has a bunk bed that is only suitable for children. Wades beach and Crescent beach within a five minute drive. Salt Marina and Restaurant within walking distance. Read More

    4 Bed
    3 Baths
    Sleeps 7
    $1,000 / Nightly
  • Property-13 Image 1
    Private Vacation Home
    Water views Beach and pool!
    Shelter Island, New York, United States

    Spacious entertainment, relax by the fireplace or relax in the closed porch , Private Beach on the corner of property. Enjoy the 18x36 saltwater heated pool …. 3 Bedrooms/2 Bath, Sleeps 8-10. Reasonable rental offers considered. Read More

    4 Bed
    3 Baths
    Sleeps 10
    Select Dates for Price
  • Property-14 Image 1
    Private Vacation Home
    Chic modern mid century home with saltwater pool and expansive views
    Shelter Island, New York, United States

    Natural luxury and relaxation at its best. Minutes walk to uncrowded beach, or relax in new gunite pool, enjoy peaceful expansive golf course views. Indoor/outdoor feel, designer upscale furnishings throughout, nature and natural light inspire full relaxation.brGourmet kitchen, master suite with pool and sunrise views, 4th bedroom on main level with ensuite bathroom, perfect for families.brBikes, barbecue, 2 outdoor lounging area, hammock, ping pong and birds. You'll love this light uplifting home and its designer interiors, open layout , and its quiet peaceful vibe. Read More

    4 Bed
    3 Baths
    Sleeps 8
    $924 / Nightly
  • Property-15 Image 1
    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. Read More

    5 Bed
    3 Baths
    Sleeps 7
    $598 / Nightly
  • Property-16 Image 1
    Private Vacation Home
    Hilltop Cottage Privacy Abounds
    Shelter Island, New York, United States

    Private Hilltop Cottage on 1.5 acre lot bordering horse farm. Feel the stress melt away. brCentrally located within walking distance to restaurants, golf, and beach. Clean, cozy, 3 bedroom with 2 full baths, wood stove, grill, washer & dryer, full kitchen, and dining room. Bikes and games, too. Read More

    3 Bed
    3 Baths
    Sleeps 6
    $475 / Nightly
  • Property-17 Image 1
    Excellent
    (38)
    Private Vacation Home
    Renovated and Spacious Summer Home with Water View on Picturesque Island.
    Shelter Island, New York, United States

    Steps from the beach, this beach house is the perfect destination to enjoy beautiful Shelter Island. Recently renovated summer home across a private beach with large windows, and a sizable garden. The property is two-story with five bedrooms, three bathrooms, a fireplace, two spacious private decks, and a view of the waterfront and a dock for your boat. Ideal for families, couples or single people. The Island has several several beaches, opportunities for boating, fishing, golf, rafting, tennis, music, etc. It is ideal for biking, bird watching, runners. brbrThere are bikes at the house, a grill, wifi, games, TV and internet, Xbox etc. You wake up to the sound of birds chirping and nature.brbrGreat promotion on prices for the months of July-NovemberbrbrAsk for the special prices and get a great place to stay.brbr5 Bedroom, 3 Bath 8-10 Sleeps . Read More

    4 Bed
    3 Baths
    Sleeps 10
    $552 / Nightly
  • Property-18 Image 1
    Wonderful
    (16)
    Private Vacation Home
    Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve
    Shelter Island, New York, United States

    3 bedroom, 2 bath house in Shelter Island offers many amenities including pool, dock, private beach access and great coastal hiking in the 2,000 acre Mashomack Preserve. Close to the south ferry with easy access to Sag Harbor and the Hamptons. It is the perfect house to get away from the hustle of the city to relax, soak in the sun and enjoy the gourmet chef’s kitchen and herb garden and 2 grills.brThe open plan house has a granite eating counter, dining room and a large deck overlooking the pool with an outdoor dining and lounging. brThe large property comes with a paddle board and 4 bikes to explore the beautiful island.brThere are 3 bedrooms, including a master en suite. Read More

    3 Bed
    2 Baths
    Sleeps 6
    $289 / Nightly
  • Property-19 Image 1
    Exceptional
    (3)
    Private Vacation Home
    Private heated pool and spacious yard. 5 minute walk to the beach.
    Shelter Island, New York, United States

    Enjoy this newly renovated home on Shelter Island. A gorgeous, well-stocked gourmet kitchen with vaulted ceiling great room allows the chef(s) to be a part of the fun. Sliders out to the pool and tons of outdoor seating provide plenty of options for a relaxing experience. The outdoor shower makes for an easy post-beach or pool refresher. Master bedroom with en suite bathroom gives everyone their own space. brIndoor dining options feature 3 seats at the counter and a pub-height dining table that expands to seat 12. Outdoor dining with table & umbrella along with a Weber grill.brbrPrivate backyard, large 20x40 heated gunite pool with Hollywood steps and a deep water bench make pool days a dream. Stroll to the beach to watch the sunset in less than 5 minutes. Biking, kayaking, boating, golf and beaching are the joys of Shelter Island, along with it's farmers markets, local shopping and wonderful local seafood, casual and fine dining restaurants. Brief ferry rides to Greenport or Sag Harbor gives you plenty of "off-island" entertainment options, too! Summer by the sea never looked better than from this clean, comfortable home.brbr* Other amenities:br Bose wireless stereo systembr Nespresso coffee makerbr Fully stocked kitchen br Washer & Dryer / Separate Laundry Roombr Full Cable / WiFi / Internetbr Smart TVs in 3 bedrooms & LRbr Twin bedroom easily converts to an office, if preferredbr Extra full-size fridge in the attached garagebr Two person kayakbr Bicycles, beach chairs and cooler providedbr Room in the attached garage to store and protect the toys br you bring with you.br Driveway parking Read More

    4 Bed
    3 Baths
    Sleeps 7
    $1,121 / Nightly
  • Property-20 Image 1
    Wonderful
    (7)
    Private Vacation Home
    Elegant Treetop Modern with Heated Gunite Pool Steps from Hay Beach
    Shelter Island, New York, United States

    Within 300 feet to wide sandy bay 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 connected to nearly unlimited propane. 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: Child protected stairs, kitchen access, pool access, and optional door knob protector for stair access to lower floor. Read More

    4 Bed
    4 Baths
    Sleeps 5
    $488 / Nightly
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Most popular vacation rentals in Shelter Island

  • thumb
    $ 545.00 avg/night
    4
    • 3 Beds
    • 3 Baths
    • 6 Guest(s)
    Sweet Retreat on Shelter Island Shelter Island, New York, United States

    Enjoy the serenity of this wonderful island while staying at our cozy 3BR, 3Bath ranch-style... Read More

  • thumb
    $ 933.00 avg/night
    1
    • 2 Beds
    • 2 Baths
    • 4 Guest(s)
    Shelter Island, Waterfront, Lazy Days With Stunning Views Shelter Island, New York, United States

    Enjoy the best that Shelter Island can offer at this renovated 2 bedroom waterfront gem. Nestled... Read More

  • thumb
    $ 600.00 avg/night
    13
    • 3 Beds
    • 2 Baths
    • 8 Guest(s)
    Charming updated home with pool on quiet street. Near Silver Beach Shelter Island, New York, United States

    Great house in great location. 3 bedrooms (including one with bunk bed and additional bed) .... Read More

  • thumb
    $ 900.00 avg/night
    9
    • 4 Beds
    • 3 Baths
    • 9 Guest(s)
    Waterfront Home Plus Separate Cottage/Dock Shelter Island, New York, United States

    Wake up to the beautiful Sunrises. Take your coffee and enjoy the porch views. Watch mother... Read More

  • thumb
    $ 374.00 avg/night
    12
    • 3 Beds
    • 5 Baths
    • 6 Guest(s)
    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... Read More

  • thumb
    $ 700.00 avg/night
    9
    • 4 Beds
    • 3 Baths
    • 6 Guest(s)
    Peaceful get away with Tranquil Salt Water Pool Shelter Island, New York, United States

    This 1960's A-Frame is flooded with natural light - open zen vibe and a tranquil backyard with a... Read More

  • thumb
    $ 826.00 avg/night
    1
    • 3 Beds
    • 2 Baths
    • 8 Guest(s)
    Magical and serene family compound walking distance to water and walking trails Shelter Island, New York, United States

    Welcome to Casa di Famiglia! Close to nature and the water, this family compound will rejuvenate... Read More

  • thumb
    $ 1121.00 avg/night
    3
    • 4 Beds
    • 3 Baths
    • 7 Guest(s)
    Private heated pool and spacious yard. 5 minute walk to the beach. Shelter Island, New York, United States

    Enjoy this newly renovated home on Shelter Island. A gorgeous, well-stocked gourmet kitchen with... Read More

  • thumb
    $ 300.00 avg/night
    1
    • 4 Beds
    • 2 Baths
    • 9 Guest(s)
    Rustic & spacious 4 bdrm renovated farmhouse in lovely Shelter Island, LI Shelter Island, New York, United States

    Just grab a swimsuit! Close to all the private beaches, (Wades, Hay, Silver) smack in the middle... Read More

  • thumb
    $ 442.00 avg/night
    1
    • 2 Beds
    • 2 Baths
    • 6 Guest(s)
    Cozy family cottage on Shelter Island Shelter Island, New York, United States

    Relax on Shelter Island. Enjoy a central location close to town and amenities within a short... Read More

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