Holiday rentals with a kayak in Shelter Island Heights

The image captures a spacious outdoor area featuring a large heated pool with a fountain and surrounding stone patio. Nearby, lounge chairs are arranged for relaxation, while a generous lawn stretches in the background, accompanied by a well-designed home nestled among trees.

4.77 out of 5 average rating, 142 reviews

Sprawling Hamptons Estate with Hot Tub & Amenities

Spacious & private Hamptons Oasis. High speed WiFi. Family friendly. Massive home on 1.4 acres hosts 15 guests across 6 bedrooms, 8 beds, 4 full baths plus crib & pack 'n play. Gorgeously decorated by Judy Posey Large heated gunite pool (42 x 20 feet) hot tub and sundeck. Fireplace, over-sized kitchen w/ 3 fridges, electric wood-fired grill, huge yard, firepit, bar/lounge, Golden Tee arcade™, bikes & kayaks. Just 2 miles from towns of East Hampton and Amagansett and several white sand beaches

A weathered wooden sign is attached to a large tree, directing visitors towards the beach. The sign is marked with the words 'TO THE BEACH' and is surrounded by a grassy area with additional trees in the background, offering a sense of calm and connection to nature.

4.95 out of 5 average rating, 61 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.

A beachfront house with a wooden exterior is depicted, featuring multiple windows adorned with green planters. Soft sand covers the area in front, leading to the water, which reflects the clear blue sky. A small chair is visible on the sand, emphasizing the serene beach setting.

4.89 out of 5 average rating, 28 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!

The exterior of a modern cottage is presented with a black wood facade and multiple windows. A front porch is seen, partially enclosed with slatted wood. Lush green grass and shrubbery frame the entrance, creating a welcoming approach to the home.

4.9 out of 5 average rating, 41 reviews

Waterfront NoFo Cottage w/ public beach access

Enjoy this waterfront cottage overlooking Marion Lake surrounded by lush landscape and wildlife. Experience the local Vineyards, take a leisurely stroll in downtown Greenport, ferry to Shelter Island, drive to Orient, or discover local hiking trails. Savor the culinary delights at the area's great restaurants, with fresh seafood and farm-to-table dining. Nestled between Greenport and Orient Point, East Marion provides access to all the North Fork has to offer. Rental Permit #1060

4.99 out of 5 average rating, 108 reviews

An aerial view captures a cozy cottage surrounded by lush greenery, featuring large windows that glow warmly in the evening light. A stone patio is visible, with outdoor seating and a fire pit. Nearby, a well-maintained lawn and a parking area with vehicles can be seen.

Cottage in Guilford

Waterfront Joshua Cove Cottage with private beach.

Beautiful architecturally designed 1 Bedroom + loft Cottage on Joshua Cove in Guilford. The sunsets are spectacular from your own private beach. Enjoy Fall Foliage, swimming, fishing, and some of the best Kayaking from this perfect setting. Minutes from the Guilford train station, restaurants, shopping, and historic town green. The property is just 15 minutes from New Haven, and the Yale campus. The Thimble Island cruise, and the Ct. river steam train/cruise are nearby as well.

4.96 out of 5 average rating, 49 reviews

A charming blue house is framed by lush green trees, with a welcoming front porch. Large windows invite natural light, while a white picket fence complements the tranquil outdoor setting. The spacious yard features vibrant grass, enhancing the peaceful atmosphere.

Home in Greenport

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 ༄Equipped kitchen w/blender, coffee, waffle maker + more! 𓇼Bathrooms w/heated floors + a clawfoot soaking tub (Please note there is only 1 shower) ☼Family Friendly: Board games, packNplay, high chair, beach chairs + toys ༄Kayak + bikes 𓇼Smart TVs

A view of the waterfront area features a private dock with a small wooden boat. White chairs are arranged on the grass near the house, which has a welcoming front porch. Lush greenery and a rustic shed complement the serene setting.

4.94 out of 5 average rating, 32 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 (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

4.86 out of 5 average rating, 116 reviews

A spacious living area features exposed wooden beams and a cozy brick fireplace. Comfortable seating includes a brown sofa and recliner, with decorative pillows adding warmth. A glass coffee table stands on a colorful area rug, while large windows overlook the greenery outside.

Cabin in North Fork

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

Welcome to nature's retreat, our secluded North Fork haven where 2+ acres of wild beauty and private beach access promise unparalleled relaxation. Delight in our hot tub's warmth under the stars, unwind on swings, or glide on bay waters with our kayak. With enchanting porch views, an invigorating outdoor shower, and nearby organic farms, our cabin is an idyllic escape. Experience the local charm with vineyard tours and return to a haven of comfort and adventure.

4.86 out of 5 average rating, 138 reviews

A spacious living room features a large sectional sofa adorned with colorful cushions, offering comfort and relaxation. A sleek television is mounted on the wall, while natural light streams through wide windows, illuminating a wooden coffee table and a decorative fireplace in the corner.

Home in Mastic

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

A modern cottage is set amidst lush greenery, featuring a spacious rear deck and a lower patio area with two lounge chairs. The second story includes a covered deck with an awning, while large windows invite natural light into the interior.

4.92 out of 5 average rating, 112 reviews

Walk to Breakwater Beach in Heart of Wine Country

Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.

Cottage in Shelter Island

A traditional New England-style house features a front porch supported by white columns. Two white chairs and a small table are arranged on the porch, complemented by a dark front door. Large windows allow natural light to fill the space, surrounded by green landscaped areas.

4.97 out of 5 average rating, 116 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...

An expansive deck features a picnic table and Adirondack chairs under a large umbrella, providing shade. The calm waters of East/Eugenes creek are visible in the background, with lush greenery and occasional boats contributing to the serene setting.

5 out of 5 average rating, 27 reviews

The Bay Breeze

Beautiful waterfront beach cottage in the heart of wine country. A true North Fork experience. IG @themelodytoo

Popular amenities for kayak rentals in Shelter Island Heights

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

A calm outdoor patio area features a round table surrounded by four white chairs. An umbrella stands in the center of the table, and potted plants add greenery. The view overlooks a serene pond framed by trees and a cloudy sky.

4.97 out of 5 average rating, 38 reviews

July 19k Perfect Days SouHptn A+ Cottage on pond

4.83 out of 5 average rating, 42 reviews

Bright Hamptons Getaway ☀️ Pool▪︎ Beach▪︎FamilyFun

5 out of 5 average rating, 52 reviews

A wooden deck overlooks serene waters, with tall grasses gently swaying in the breeze. The horizon is painted with soft hues of orange and blue as the sun sets, offering a tranquil view of the surrounding natural landscape.

Home in Mastic Beach

Waterfront home with amazing views

A charming cottage-style home is set amid lush greenery, featuring a covered porch with white railings. A gravel pathway leads to the entrance, surrounded by manicured shrubs and a well-kept lawn. The exterior is finished with natural wood siding and a sloped gray roof.

5 out of 5 average rating, 6 reviews

Hamptons Waterview Cottage

4.93 out of 5 average rating, 61 reviews

Home in Shirley

Designer Bayfront Oasis with Epic Sunsets

4.99 out of 5 average rating, 85 reviews

A spacious deck is furnished with a wooden table surrounded by six white chairs, offering ample space for relaxation. Two large umbrellas provide shade, while a view of the calm water and distant horizon can be seen in the background.

Home in Shirley

Stunning sunset charming waterfront home 4 seasons

An outdoor deck features a large dining table surrounded by multiple chairs, shaded by a sun umbrella. In the background, beach chairs and an umbrella are set on the sand, with calm waters extending toward the horizon.

5 out of 5 average rating, 35 reviews

Hang by the (Chel)SEA

4.95 out of 5 average rating, 56 reviews

A two-story house is elevated on stilts, showcasing large windows that allow natural light to fill the interior. A gravel driveway leads to the house, bordered by flowering plants. Scenic salt marsh views are visible in the background, enhancing the home's inviting presence.

Home in Morgan Point

Spectacular Waterfront Home on Private Sandy Beach

Cottage rentals with a kayak

Cottage in Shelter Island

Two wooden chairs are positioned on a grassy area overlooking the calm water. A fire pit sits in between the chairs, and a swing hangs from a nearby tree. In the background, a dock extends into the water, framed by trees.

4.97 out of 5 average rating, 115 reviews

Shelter Island Waterfront Getaway

A spacious great room is highlighted by a cathedral ceiling with exposed wooden beams. Comfortable sofas frame a central coffee table, while large windows provide natural light, accentuated by sheer white curtains. A cozy reading nook is positioned against the wall, complemented by a variety of books.

4.93 out of 5 average rating, 27 reviews

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

5 out of 5 average rating, 5 reviews

A beach cottage is presented with a wooden walkway leading from the sandy beach to the entrance. A deck with seating and a kayak is visible, with a backdrop of a clear blue sky and greenery completing the scene.

Cottage in Morgan Point

Caroline Beach Escape

A serene waterfront scene captures a vibrant sunset reflecting on calm waters. Silhouetted trees line the background, while a private dock extends into the water, featuring a railing. Warm hues of orange and pink fill the sky, creating a peaceful ambiance.

4.98 out of 5 average rating, 56 reviews

Stunning waterfront modern farmhouse with dock.

The scene captures a serene beachfront at sunset, with gentle waves lapping at the shore. Soft hues of orange and pink reflect on the calm water, while lush greenery frames the coastline. The atmosphere suggests tranquility and connection with nature.

4.76 out of 5 average rating, 59 reviews

Secluded Soundfront 1910 Rustic Getaway

4.97 out of 5 average rating, 63 reviews

Cottage in Short Beach

Ret's Coastal Cottage w/Private Association beach

A charming red cottage is framed by lush greenery, set back from a driveway leading to the entrance. A small white bench is visible on the left side of the well-maintained lawn, with flowering plants adding a touch of color in front of the house.

4.68 out of 5 average rating, 207 reviews

Lovely 2 BR Beach House No. Shore

4.98 out of 5 average rating, 46 reviews

A bright and airy living space features a light-colored sofa adorned with a decorative pillow. Two woven poufs are situated in front of the couch on a neutral rug. Sunlight enters through a large window, illuminating the room and providing a welcoming atmosphere.

Cottage in The Hamptons

Prime location, walk to all, cozy cottage WHB

Other holiday rentals with a kayak

Guest suite in North Fork

A private entrance is visible, featuring a light-colored wooden walkway leading to a white door. Flanking the entrance are two lattice panels with flowering plants beneath. Garden beds are arranged with green foliage and ornamental flowers, enhancing the welcoming atmosphere.

4.8 out of 5 average rating, 45 reviews

Garden Studio with private entrance

4.95 out of 5 average rating, 93 reviews

Flat in The Hamptons

Hamptons Waterfront Suite | Private Hot Tub

5 out of 5 average rating, 26 reviews

A warm wood-paneled interior features a cozy bed adorned with a white quilt and decorative pillows. A small yellow bench sits at the foot of the bed. A bathroom entrance is visible in the background, and a landscape painting hangs above a nightstand with a lamp.

Flat in The Hamptons

Hamptons The Vineyard Studio

4.85 out of 5 average rating, 33 reviews

Flat in The Hamptons

2Br Hampton Family Escape: Beaches, kayaks, BBQ

The backyard features a large, clear swimming pool complemented by lounge chairs and a shaded dining area under an umbrella. The ranch-style home and surrounding trees create a serene, private space. Soft blue skies and dappled sunlight reflect off the water, enhancing the inviting atmosphere.

4.93 out of 5 average rating, 40 reviews

NOFO Ranch Home in Wine Cntry 2 Beaches 5 Min Walk

A serene waterfront scene is presented, featuring a small boat docked alongside a gently flowing waterway. Wooden Adirondack chairs are positioned on sandy ground, surrounded by lush green grass and coastal plants, enhancing the connection to nature.

4.96 out of 5 average rating, 24 reviews

Peaceful Hamptons Waterfront 3 bedroom, 2 bath

A serene view of calm water featuring kayakers enjoying a sunny day. The distant shoreline is dotted with houses, creating a relaxed coastal atmosphere. Clear blue skies reflect on the water, enhancing the peaceful scene.