Vacation rentals with a kayak in Shelter Island Heights

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Top-rated kayak rentals in Shelter Island Heights

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Guest favorite

Home in Greenport

4.92 out of 5 average rating, 121 reviews

Beautiful Cottage Home W/ Beach & Dock Access

Beautiful, spacious beach side home situated within a block of a private beach. This cozy home is walking distance to Kontokosta Winery, Island's End Golf & Country Club, Lavender By the Bay and a five minute drive to the Village of Greenport. Replete with natural light and an open backyard perfect for outdoor dining and barbecues, this home is perfect for your stay in Greenport. Netflix/Hulu/Disney+ / ESPN+ / HBO MAX. Please note, 4 Bikes/1 Paddle Board/1 Kayak & Life Jackets provided May-Sept.

Sep 19 – 26

ﺩ.ﺇ3,213 per night

Guest favorite

Home in Greenport

4.95 out of 5 average rating, 40 reviews

The North Star: Greenport Waterview Beach Getaway

Welcome to our charming home in Greenport, NY. Right across the street from the private community beach! We are neighbors to the most famous wineries on the North Fork. 3 bedrooms, 2 baths, & a den that has a pull-out queen sleeper sofa. Private beach. Outdoor shower. Comes fully equipped with towels & linens. 2 miles from the town of Greenport. Perfect house for families/groups. DOG(s) FRIENDLY (w/ a pet fee) with fenced front yard & deck- sorry no cats! Looking for adults aged 30 or over.

Mar 25 – Apr 1

ﺩ.ﺇ2,402 per night

Guest favorite

Apartment in Sag Harbor

4.96 out of 5 average rating, 132 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

Jun 13 – 20

ﺩ.ﺇ1,114 per night

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Escape to your own private oasis at this charming beach house in Greenport. This beachfront home offers views of the ocean in every room. Inside, the living space gives plenty of natural light and sitting areas. The kitchen has everything you need to cook for family & friends. There are 4 beds to choose from, which can sleep 6 total. Outside, enjoy your own private beach as well as kayaks to use at your leisure. Located next to Greenport's best restaurants and wineries, book your stay today!

Nov 5 – 12

ﺩ.ﺇ2,402 per night

Guest favorite

Home in East Marion

4.87 out of 5 average rating, 15 reviews

Waterfront NoFo Cottage w/ public beach access

Modern and chic waterfront cottage overlooking Marion Lake. 2 bedroom, 1 bath home with an open plan living room/kitchen plus a breakfast nook and outdoor deck overlooking the lake. Observe Osprey, Snowy Egrets, Swans, waterfowl, turtles and other wildlife on the lake, walk 400 feet to the bay beach, drive 7 minutes to downtown Greenport or 10 minutes to Orient Point. Enjoy all the North fork has to offer including fishing, sailing, farm stands, vineyards, and fine dining. Rental Permit #1060

May 15 – 22

ﺩ.ﺇ1,466 per night

Superhost

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

𓇼Walk to the Beach! ༄Location: quiet oasis by nature preserve, vineyards, breweries, farm stands, restaurants + attractions, 5 min to Greenport Village + Southold 𓇼Firepit, outdoor dining with string lights, grill, beverage cooler ☼Outdoor games: volleyball, badminton, bocce ball ༄Equipped kitchen w/blender, coffee, waffle maker + more! 𓇼Bathrooms w/heated floors + a clawfoot soaking tub ☼Family Friendly: Board games, packNplay, high chair, beach chairs + toys ༄Kayak + bikes 𓇼Smart TVs

Sep 24 – Oct 1

ﺩ.ﺇ2,133 per night

Superhost

Home in Greenport

5.0 out of 5 average rating, 3 reviews

Waterfront Greenport Boathouse

Watch the boats go by from this waterfront 1840's Greenport boathouse. Step back in time with this home that was originally part of Greenport's working waterfront. It has been recently restored while retaining its wide-plank floors and exposed beams. Private dock and beach area for launching kayaks or paddle boards (provided in season). It has three bedrooms with queen sized beds as well as two full bathrooms. New central air-conditioning throughout house. Wifi, Smart TV, Bose stereo

Jan 3 – 10

ﺩ.ﺇ2,294 per night

Guest favorite

Apartment in Sag Harbor

4.84 out of 5 average rating, 172 reviews

Pet friendly, artists apartment & guest cabin.

Artists apartment and cabin located on quaint cul-de-sac just outside Sag Harbor Village, minutes from Long Beach. Centrally located. Free bikes, surf boards, 3 stand up paddle boards and a large canoe. Minutes from most beaches. A shaded, fenced in dog run. The cabin is a separate sleeping space from the apartment and has a 2 person SAUNA recently installed. Used if you bring more guests or if the two primary guests require separate rooms. WIFI AC and heat but No bathroom in the cabin.

May 31 – Jun 7

ﺩ.ﺇ1,167 per night

Superhost

Apartment in Greenport

4.78 out of 5 average rating, 46 reviews

2 Bedroom Greenport Waterfront Coastal Cottage

An amazing & unique experience on the North Fork of Long Island, New York. Sitting on a bluff 15’ above a huge private beach, this year-round multi-family property boasts panoramic views of the Long Island Sound. Amazing sunset/sunrise views, fishing, beach combing, swimming, wineries, restaurants, shopping. Huge 2nd story deck perfect for evening cocktails. Full kitchen, BBQ, loads of amenities. Completely updated inside & out. Private beach shared only with other guests of the property

Feb 10 – 17

ﺩ.ﺇ2,523 per night

Guest favorite

Home in Old Lyme

4.96 out of 5 average rating, 125 reviews

Cozy Beach Cottage with short walk to the beach

Relax with the whole family with all the best New England has to offer! The Beach Barn is located in the quiet neighborhood of Hawks Nest Beach and is a quick half-mile walk to the beach in a very family friendly neighborhood. From sipping on morning coffee at the beach to watching sunset with the ocean breeze - there is plenty to do in the area during every season. All you have to do is show up ready to relax, have fun, and enjoy your stay!

Jan 5 – 12

ﺩ.ﺇ1,142 per night

Guest favorite

Home in Rocky Point

4.91 out of 5 average rating, 179 reviews

The Katalpa House -by the beach

-Our beach is private, key and beach tag provided- (in brown shed) This 1000+ sf home, features a newly renovated kitchen, outdoor shower, and many quirks that come with a 90 year old home. The furnishings are eclectic and vintage. Most of the flooring is also new. The beach and bluffs are only about a 2 minute walk. The 1/4 acre lot is shared with a secondary unit as you can see in the photos which is occupied by my sister.

Dec 28 – Jan 4

ﺩ.ﺇ614 per night

Superhost

Home in Shelter Island

4.89 out of 5 average rating, 106 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Monday-Thursday stays February through June no cleaning fees!!!

Mar 19 – 26

ﺩ.ﺇ2,976 per night