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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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Rental unit in Sag Harbor

4.83 out of 5 average rating, 183 reviews

Pet friendly Apt. Plus cabin, EV charger & sauna.

Artists apartment and cabin located on quaint cul-de-sac just outside Sag Harbor Village, minutes from Long Beach, pet friendly beaches are even closer. Centrally located for easy commutes to all towns and even ocean beaches. Free bikes, surf boards, 3 stand up paddle boards and 2 canoes. Life vests for you and pets A large tick free, shaded, shaded dog run. The cabin is a separate sleeping space from the apartment and has a 2 person SAUNA recently installed. WIFI AC and heat but No bathroom!.

Home in East Haven

4.96 out of 5 average rating, 132 reviews

The Breakaway - a waterfront gem.

Located next to historic Lighthouse Park, this Morgan Point, California-style bungalow overlooks a lighthouse and breakwater that protect New Haven Harbor. Prepare oceanfront dinners in your modern kitchen; relax to sunrises, sunsets, & the sound of waves. A quiet beach is steps from the door for swimming and kayaking. New Haven sights, restaurants, & nightlife are only minutes away. Picturesque coastline communities, local vineyards, breweries, fall foliage, & commuter rail to NYC are nearby.

Home in Old Saybrook

4.97 out of 5 average rating, 118 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

Home in New London

4.89 out of 5 average rating, 117 reviews

Beauty and the Beach!

Welcome to Beauty and the Beach, where you can come and relax with the whole family or come alone to get away from the busynesses of life! The property is located within an 8 minute walk to Ocean Beach Park and a block away from Alwife cove. With all year recreation. we are located within a short distance to: - Coast Guard Academy -Navy Sub Base -Mohegan Sun -Historic Mystic -Shopping and Great Dining Experiences! -Scenic hiking trails Come and embrace the New England Salty Life!

Home in Southampton

4.95 out of 5 average rating, 151 reviews

Waterview, DogsStayFree! Kayaks, Ping-Pong

Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of the Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

Home in Rocky Point

4.89 out of 5 average rating, 216 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.

Cottage in Guilford

4.93 out of 5 average rating, 259 reviews

The Cottage at Indian Cove

A charming original turn of the century cottage that was recently renovated. One main room plus a full bathroom and Ikea kitchen. It includes a back porch that gets a perfect amount of late afternoon sun. The cottage has electric baseboard heat for cool nights. We are located in Indian Cove beach Association with a two block walk to the beach. You are welcome to enjoy our kayaks, bikes to tour the area and a fire pit.

Home in Shelter Island

4.9 out of 5 average rating, 115 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!!!

Home in Montauk

4.88 out of 5 average rating, 146 reviews

Waterfront House on Fort Pond, MTK

Spacious house right on Fort Pond with relaxed bohemian vibe. Enjoy the open kitchen, reclaimed wood beams, and hand crafted furniture. Access directly to the water from the back yard. There are two other cottages that are two bedrooms each on property as well. We do live on the property full time and enjoy making our space a safe and clean environment.

Cottage in Groton

4.95 out of 5 average rating, 299 reviews

Restored Historic Schoolhouse, Mystic River Views

This newly renovated, historic 1 BR/1 Bath former school house, is located directly on the Mystic River with amazing River views. . It started life as a one room school house. In 1857, it was moved to it's current location. Our design team meticulously furnished to create a unique historic atmoshpere.

Cottage in Shelter Island

4.96 out of 5 average rating, 104 reviews

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

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Popular amenities for Shelter Island Heights kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Port Jefferson

4.8 out of 5 average rating, 298 reviews

The Hilltop Harborview

Home in Montauk

5 out of 5 average rating, 29 reviews

House on Napeague Harbor, Amagansett

Home in North Fork

5 out of 5 average rating, 16 reviews

Waterfront with private dock & bocce court

Home in Clinton

5 out of 5 average rating, 6 reviews

Boulder Lake House Retreat

Home in Essex

4.96 out of 5 average rating, 68 reviews

4-Bedroom Farmhouse *Comfort and Privacy*

Home in Madison

5 out of 5 average rating, 42 reviews

Writer's Retreat & Explorer's Adventure!

Home in Old Saybrook

5 out of 5 average rating, 37 reviews

Great Hammcock Getaway, Nearby beaches, Hot tub

Home in East Hampton

4.97 out of 5 average rating, 29 reviews

Designer Waterfront Cottage on Gerard Dr

Cottage rentals with a kayak

Cottage in North Fork

5 out of 5 average rating, 12 reviews

Lovely North Fork Beach Cottage (2 BR/2 bath)!

Cottage in Guilford

4.99 out of 5 average rating, 96 reviews

Waterfront Joshua Cove Cottage with private beach.

Cottage in East Lyme

4.98 out of 5 average rating, 57 reviews

Little Gem Waterfront beach home/ cottage

Cottage in East Hampton

5 out of 5 average rating, 6 reviews

Charming Cottage in East Hampton

Cottage in North Fork

4.98 out of 5 average rating, 43 reviews

Stunning waterfront modern farmhouse with dock.

Cottage in North Fork

5 out of 5 average rating, 24 reviews

The Bay Breeze

Cottage in Clinton

4.98 out of 5 average rating, 98 reviews

Guest House at the Marina

Cottage in Old Lyme

4.97 out of 5 average rating, 33 reviews

Cottage with Roger’s Lake Views

Quick stats about vacation rentals with a kayak in Shelter Island Heights

Total rentals
30 properties
Nightly prices starting at
$200 before taxes and fees
Total number of reviews
600 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool

Destinations to explore