Holiday rentals with a kayak in Shelter Island Heights

4.78 out of 5 average rating, 143 reviews

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.

Home in East Hampton

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

Outdoor spacesLocationComfort

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.

4.96 out of 5 average rating, 67 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.

LocationValueHospitality

4.9 out of 5 average rating, 29 reviews

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.

Home in Greenport

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!

Outdoor spacesValueHospitality

5.0 out of 5 average rating, 113 reviews

A spacious backyard is framed by mature trees, featuring a fire pit surrounded by white Adirondack chairs. A children’s playground with swing set is visible nearby, while the home, illuminated by warm lights, stands invitingly in the background.

Villa in Southampton

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

[FOLLOW US on 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. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

LocationValueBeach

4.91 out of 5 average rating, 43 reviews

Lakefront NoFo Cottage, walkable to public beach

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

LocationOutdoor spacesCheck-in

4.96 out of 5 average rating, 57 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 Southold

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

Outdoor spacesLocationQuiet

A spacious balcony extends along the side of the house, offering unobstructed views of the shimmering water. Weathered wooden benches provide seating, while the gentle waves can be observed lapping against the shore in the distance.

4.89 out of 5 average rating, 44 reviews

North Fork Sound Front Home with Pool

This Long Island Sound front property on nearly three acres of land with an inground, custom designed, gunite pool is the perfect vacation home. Walk down the ramp to your private beach for a kayak, paddle board or swim in the summer and enjoy a luxurious outdoor shower afterwards. In the fall and winter months, enjoy the extensive book collection and stay cozy by the fireplaces. Spacious and bright, this home has a unique aesthetic and can accommodate 8 guests comfortably.

LocationOutdoor spacesLong stay

4.87 out of 5 average rating, 123 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.

ValueOutdoor spacesDecor

4.87 out of 5 average rating, 137 reviews

A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.

Home in Hampton Bays

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views and sunset from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Our pool will open May 23, 2026 and close on Labor Day.

LocationValueHospitality

4.87 out of 5 average rating, 147 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

LocationValueHot tub

4.85 out of 5 average rating, 20 reviews

A sunlit seating area features a wooden bench adorned with colorful cushions. A round area rug is centered on the terracotta floor. A large mirror reflects light, while a doorway leads to a well-lit bedroom, accented by a photo and a decorative tub nearby.

Apartment in Sag Harbor

Artists pet friendly apartment and cabin, sauna.

Full apartment with full bathroom 10 minutes to all Hampton towns. Quiet property Walking distance to free SUP boards and canoes and only 2 minute drive to a dog friendly beaches. Extra bedroom is a Cabin in the middle of the property and was a recording studio, now has queen bed, wifi, fridge, micro wave, heat and AC, TV and DVD player but no bathroom. You have your own parking spots, entrance and outdoor dining area and outdoor shower.

LocationOutdoor spacesHospitality

4.95 out of 5 average rating, 203 reviews

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.

Home in Shinnecock Hills

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong

Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of 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.

LocationValueWi-Fi

Popular amenities for Shelter Island Heights kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.85 out of 5 average rating, 114 reviews

A charming cottage exterior is presented, featuring a light yellow facade with contrasting black shutters. A vibrant red door provides a welcoming entrance. Lush green shrubs and seasonal flowers frame the walkway, enhancing the overall appeal of the front yard.

Home in Hampton Bays

Heart of the Hamptons

ValueOutdoor spacesAccuracy

A serene waterfront scene captures a vibrant sunset, showcasing a blend of orange, pink, and purple hues reflected on calm water. A wooden dock extends into the water, while silhouettes of people can be seen engaging at the water's edge.

4.91 out of 5 average rating, 11 reviews

Sag Harbor Village Waterfront Cottage

Outdoor spacesLocationAmenities

5.0 out of 5 average rating, 45 reviews

A spacious backyard is featured, with a circular stone fire pit surrounded by several colorful Adirondack chairs. Lush green grass extends towards a charming white house in the background, bordered by trees under a clear blue sky.

Home in Southold

Private Waterfront Access + Hot Tub + Scenic Yard

LocationOutdoor spacesBackyard

4.96 out of 5 average rating, 48 reviews

Luxe Beach Cottage-Steps to Water-Firepit

ValueLocationNearby

4.9 out of 5 average rating, 41 reviews

Home in Southold

Coastal Cottage on the Water

LocationOutdoor spacesWalkability

The exterior of the cottage is presented, showcasing its wooden shingle design and large windows. The surrounding grassy area is well-maintained, with lounge seating visible on a stone patio. Trees provide privacy on the property, enhancing the peaceful environment.

5.0 out of 5 average rating, 9 reviews

Modern Cottage with a View

LocationOutdoor spacesCondition

4.68 out of 5 average rating, 31 reviews

An outdoor space features a modern freestanding soaking tub surrounded by wooden decking. The area is bordered by wooden walls and adorned with a potted plant, adding a touch of nature. A bright sky and trees can be seen in the backdrop.

Home in Amagansett

Amagansett walk-to-the-bay Beach House

Outdoor spacesLocationAccess

4.89 out of 5 average rating, 18 reviews

A serene river scene is captured under a partly cloudy sky. Tall grasses line the water's edge, while trees provide shade along the bank. The calm water reflects the surrounding landscape, creating a peaceful atmosphere.

Home in Springs

Private Beach Community with exceptional light

LocationOutdoor spacesBathroom

Cottages with a kayak

4.94 out of 5 average rating, 69 reviews

An outdoor deck features a dining table surrounded by six chairs, positioned over the water. The scene includes a marina with boats and lush greenery. A tranquil sunset casts soft hues across the landscape, enhancing the serene environment.

Cottage in Flanders

Bayside bliss - Charming 2bdrm on the water w dock

Outdoor spacesLocationHospitality

A modern kitchen is presented with sleek cabinetry and stainless steel appliances. A large island with a marble countertop is surrounded by several cushioned stools. Natural light floods in from a nearby window, illuminating a small vase of blue hydrangeas on the island.

5.0 out of 5 average rating, 53 reviews

Renovated 2-Bedroom Cottage on the North Fork

Outdoor spacesLocationComfort

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.

5.0 out of 5 average rating, 29 reviews

The Bay Breeze

LocationOutdoor spacesBeach

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, 60 reviews

Stunning waterfront modern farmhouse with dock.

Outdoor spacesValueComfort

5.0 out of 5 average rating, 33 reviews

A spacious outdoor deck features a dining table accompanied by seating and an umbrella. The deck is surrounded by sand and greenery, with a grill positioned nearby. A flowering tree adds a pop of color, enhancing the outdoor space's ambiance.

Cottage in Amagansett

Amagansett Beach Cottage - Short Walk to the Ocean

Outdoor spacesLocationBathroom

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.

4.94 out of 5 average rating, 32 reviews

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

Outdoor spacesValueWi-Fi

Cottage in Westhampton Beach

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.

4.98 out of 5 average rating, 54 reviews

Westhampton Beach cozy cottage, walk to all

LocationValueTV

Cottage in Shelter Island Heights

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

LocationValueCheck-in

Other holiday rentals with a kayak

5.0 out of 5 average rating, 4 reviews

Cabin in Springs

Modern Cabin near the Beach

LocationCleanlinessHospitality

5.0 out of 5 average rating, 66 reviews

A spacious studio apartment is presented, featuring a large circular mirror and light-colored furnishings. Two separate sleeping areas are visible, with one prominent bed framed by bamboo-style headboards. Natural light filters in through sliding glass doors, enhancing the welcoming ambiance of the room.

Apartment in Sag Harbor

Spacious apartment in Sag Harbor

Outdoor spacesLocationBiking

Guesthouse in Southampton

A modern two-story building is viewed from the well-maintained lawn. The heated saltwater pool features clear water surrounded by lounge chairs under colorful umbrellas. Lush green trees provide a natural backdrop, creating a peaceful outdoor space for relaxation.

4.99 out of 5 average rating, 76 reviews

Southampton Modern Barn, Private Hot Tub and Pool

ValueLocationHot tub

A charming Italianate villa is framed by verdant trees and lush grass. The exterior, painted in soft hues, features a welcoming porch with decorative columns. A path leads through the manicured lawn towards the entrance, promoting a sense of tranquility in a private setting.

4.96 out of 5 average rating, 56 reviews

The Captain's Crib

LocationOutdoor spacesCheck-in

5.0 out of 5 average rating, 37 reviews

A spacious deck is furnished with comfortable seating and a dining table, overlooking a marina with various boats. The water reflects clear blue skies, creating a serene atmosphere. A patterned area rug adds a touch of style to the outdoor space.

Home in Hampton Bays

2.5 Miles from the 2026 U.S OPEN, Waterfront

LocationOutdoor spacesNearby

The house features a wraparound porch with a wooden railing and steps leading to a spacious deck. Ample windows allow for natural light, and a patio umbrella provides shade over outdoor seating. Lush greenery surrounds the exterior, contributing to a serene environment.

5.0 out of 5 average rating, 63 reviews

Beach House on the Bay

Outdoor spacesLocationBarbecue

4.98 out of 5 average rating, 44 reviews

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.

Home in Southampton

Southampton swim/pond/ocean Aug/deal 18-22 $500day

ValueLocationCleanliness