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Vacation rentals with a kayak in Shelter Island

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Shelter Island

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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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

Guest suite in Old Lyme

4.93 out of 5 average rating, 14 reviews

Marina 1 bedroom apartment with on-water facility

Take it easy at this unique and tranquil getaway located directly on the Great Island Salt Marsh national sanctuary. This second floor marina apartment is a sportsman's paradise, overlooking the waterways, and giving you access to all of the water sports we offer at Black Hall Outfitters in pristine Old Lyme CT. Kayak, Paddle board, and relax and unwind while overlooking the Long Island Sound at the Mouth of the CT. River. The apartments sleeps 4 comfortably, and has a spacious open floor plan.

Home in North Fork

4.95 out of 5 average rating, 21 reviews

Coastal Cottage on the Water

A coastal cottage on the water surrounded by vineyards and farm stands on the North Fork. Unwind in the backyard with a private view of the Goldsmith's Inlet where you can watch the sunrise, bird watch, and admire our local swans. A quick 5-minute walk to the Long Island Sound where you can sunbathe, swim, kayak, and watch the beautiful sunset. Conveniently located near Greenport, Orient, and Southold. *IMPORTANT* Kayaks and grill are only available from May 1st to September 30th.

Cottage in Flanders

4.9 out of 5 average rating, 39 reviews

Bayside bliss - Charming 2bdrm on the water w dock

Lovely 2 bedroom cottage located on the water with your own private dock. 2 queen beds, 1 bathroom, and full kitchen. Enjoy a swim and outdoor shower after a blissful kayak along the shores of the Peconic Bay. Easy access to the North and South Forks of Long Island, famous wine trails, Ocean Beaches, and amazing farms. 2 kayaks included in the rental. Experience the food, drink, and beautiful scenery with a short drive to all of the Hamptons.

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!!!

Cottage in Old Saybrook

5 out of 5 average rating, 93 reviews

Cozy Waterfront Retreat

Serene waterfront retreat! Direct waterfront property on Oyster River perfect for kayaking, fishing, paddle boarding or just soaking up the sun. This cozy cottage with views of stunning sunsets allows guests to relax and unwind. Minutes to local restaurants and shopping, walking/bicycling distance to the towns best beaches; close to outlets and casinos. Quaint, charming cottage with beach decor throughout.

Rental unit in Branford

4.95 out of 5 average rating, 22 reviews

Ocean front 1 bedroom apartment

This charming apartment is across the street from LI sound and has an outdoor shower for your use. It has been completely remodeled, including appliances and is large at 1300 sq ft. This is the ideal location for 2 people to unwind and get away from it all and enjoy the beach, put your kayaks in 50’ from property or enjoy the excellent restaurants and attractions along the Connecticut shore line.

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.

Rental unit in Sag Harbor

4.69 out of 5 average rating, 55 reviews

Sag Harbor Suite by the Beach

*Private Beach Access - 7 min walk - 0.4 mi Parking in Driveway Private Entrance Outdoor Patio 1 BR Apartment with common area with sleeper sofa (2 queen beds) Kitchenette - Fridge, Toaster Oven, Coffee/Tea, Microwave Plates, Bowls, Cups, Utensils (2) Bikes available (1) Kayak available (4) Beach Chairs provided (4) Beach towels provided Games to play

Guesthouse in Hampton Bays

5 out of 5 average rating, 21 reviews

2 Bedroom Hamptons Waterfront Cottage Rental

This incredible 2 Bedroom, 1 Bath 750 sq ft Cottage is steps from an inlet leading out to Peconic Bay. The cottage sleeps 4 adults comfortably. Bedroom 1 currently has 2 Twins, Bedroom 2 has a queen Bed, but 2 twins can be requested. The cottage has a private entrance and private deck with BBQ, kitchen, and living area.

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Popular amenities for Shelter Island kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Branford

5 out of 5 average rating, 50 reviews

Beach House in Private Community on LI Sound

Home in Shelter Island

5 out of 5 average rating, 29 reviews

Family Friendly Oasis Steps to Water - Heated Pool

Home in Mastic Beach

5 out of 5 average rating, 42 reviews

Waterfront home with amazing views

Home in Southampton

4.95 out of 5 average rating, 151 reviews

Waterview, DogsStayFree! Kayaks, Ping-Pong

Home in Madison

5 out of 5 average rating, 24 reviews

Waterfront Beach House with pool

Home in Clinton

4.7 out of 5 average rating, 79 reviews

Year-Round Waterview 4 Bds/2Bths, Sleeps 13 Linens

Home in Shirley

4.98 out of 5 average rating, 63 reviews

Stunning sunset charming waterfront home 4 seasons

Home in North Fork

5 out of 5 average rating, 10 reviews

Hang by the (Chel)SEA

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 North Fork

4.89 out of 5 average rating, 28 reviews

Pumpkins & Sunflowers! Cozy Cottage in the Fall!

Cottage in East Hampton

5 out of 5 average rating, 6 reviews

Charming Cottage in East Hampton

Cottage in Guilford

4.93 out of 5 average rating, 259 reviews

The Cottage at Indian Cove

Cottage in North Fork

4.98 out of 5 average rating, 43 reviews

Stunning waterfront modern farmhouse with dock.

Cottage in Clinton

4.97 out of 5 average rating, 30 reviews

Cottage at the Marina

Cottage in Branford

4.95 out of 5 average rating, 43 reviews

Ret's Coastal Cottage w/ Private Association Beach

Cottage in East Haven

4.93 out of 5 average rating, 29 reviews

Cozy Cottage with Water Views Steps to the Sand

Quick stats about vacation rentals with a kayak in Shelter Island

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

Destinations to explore