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Vacation rentals with a kayak in Shelter Island

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Top-rated kayak rentals in Shelter Island

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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!.

Villa in Southampton

5 out of 5 average rating, 92 reviews

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

*Follow Us: Insta @29watersedge* 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. Return home to a backyard that has it all: a large dock, fire pit, swing/playset, hammock, grill, and oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village and Sag Harbor.

Home in East Haven

4.96 out of 5 average rating, 131 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 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.

Cottage in North Fork

4.98 out of 5 average rating, 43 reviews

Stunning waterfront modern farmhouse with dock.

Relax with the whole family or a group of friends at this peaceful, waterfront cottage. Perfect spot to bring a group for a country retreat in the heart of stunning vineyards, spectacular restaurants and stunning waterscapes. Our home’s interior is beautifully appointed where you will be comfortable both inside and outside on our patio, or deck with a breathtaking waterfront view. Peaceful, relaxing and magical place in an idyllic spot.

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!!!

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.

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 kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in North Fork

5 out of 5 average rating, 16 reviews

Waterfront with private dock & bocce court

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, 150 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

4.69 out of 5 average rating, 77 reviews

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

Home in North Fork

5 out of 5 average rating, 10 reviews

Hang by the (Chel)SEA

Home in East Haven

4.94 out of 5 average rating, 52 reviews

Spectacular Waterfront Home on Private Sandy Beach

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 Guilford

4.99 out of 5 average rating, 96 reviews

Waterfront Joshua Cove Cottage with private beach.

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 East Patchogue

4.89 out of 5 average rating, 57 reviews

Bellport Beach Estates Private Cottage with Pool

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