Holiday rentals with a kayak in Shelter Island Heights

4.78 out of 5 average rating, 146 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 spacesLocationKitchen

4.85 out of 5 average rating, 115 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

Peaceful 3 bedroom cottage in a quaint section of the Hamptons. Located on the south shore, closest to the ocean beaches you can get. Bay water at end of lane, ocean beach just over the Ponquogue bridge. Large backyard for games & BBQ grilling. Enclosed patio for morning coffee & evening dinners. The house is best suited for families & friends needing space & looking for simple, low key relaxation. Please click "Contact Host" if you have specific booking requests & I will look to accommodate.

LocationValueCondition

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, 70 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.

ValueOutdoor spacesAir conditioning

4.91 out of 5 average rating, 33 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!

ValueLocationCheckout

4.91 out of 5 average rating, 45 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 spacesCondition

4.87 out of 5 average rating, 141 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 close on September 15th, 2026 and will reopen May 29, 2027.

LocationOutdoor spacesPool

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.

4.97 out of 5 average rating, 60 reviews

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

LocationOutdoor spacesBackyard

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 spacesHospitality

4.87 out of 5 average rating, 151 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

Outdoor spacesValueCheckout

4.94 out of 5 average rating, 105 reviews

Apartment in Flanders

Hamptons Waterfront Suite | Private Hot Tub

✔ Separate private guest suite with its own entrance ✔ Entire back property exclusively yours (not shared) ✔ Year-round saltwater hot tub ✔ Private dock + 2-person kayak ✔ Fire pit, lounge chairs & beach towels ✔ Stunning waterfront sunrise & sunset views ✔ Private porch & outdoor shower ✔ 55" Smart TV & electric fireplace ✔ Self check-in & central air ✔ 19 minutes to Southampton Village ✔ Adults only – No pets – No children

Outdoor spacesValueNearby

Luxe

Home in Amagansett

Historic Designer Farmhouse - Warm Pool until Nov

Tucked away on a private lot, just minutes from East Hampton Village, Amagansett Village, and Indian Wells Beach, this 3-bedroom, 2.5-bath cottage features a heated saltwater pool & Mahogany outdoor open-sky shower - open May through October, fireside outdoor lounge area, and charming children’s playhouse - creating the perfect setting for relaxing days spent at home.

Outdoor spacesValueGetting around

4.99 out of 5 average rating, 274 reviews

4.92 out of 5 average rating, 118 reviews

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.

Home in Mattituck

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.

Outdoor spacesValueAmenities

Popular amenities for Shelter Island Heights kayak rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

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.

5.0 out of 5 average rating, 45 reviews

Private Waterfront Access + Hot Tub + Scenic Yard

Outdoor spacesLocationBarbecue

4.88 out of 5 average rating, 42 reviews

Coastal Cottage on the Water

LocationOutdoor spacesAccess

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

Outdoor spacesLocationPets

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.

5.0 out of 5 average rating, 45 reviews

Hang by the (Chel)SEA

Outdoor spacesLocationSolo travel

4.96 out of 5 average rating, 50 reviews

Home in Sag Harbor

Luxe Beach Cottage-Steps to Water-Firepit

ValueLocationSleep quality

4.92 out of 5 average rating, 48 reviews

A bright living room features large windows that showcase water views. Comfortable white sofas are arranged around a wooden coffee table, while a dining area is visible in the background. A ceiling fan and a wall-mounted TV add to the room's functionality.

Home in Sag Harbor

Wake up to Stunning Views at a Serene Waterfront Haven

LocationOutdoor spacesCleanliness

4.88 out of 5 average rating, 24 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

Outdoor spacesLocationHospitality

Superhost

5.0 out of 5 average rating, 4 reviews

New listing | 50ft Pool on 1.6 Private Acres

CheckoutIndoor spacesNearby

Cottages with a kayak

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, 63 reviews

Stunning waterfront modern farmhouse with dock.

LocationValueView

4.95 out of 5 average rating, 74 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 spacesLocationAmenities

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, 57 reviews

Renovated 2-Bedroom Cottage on the North Fork

LocationValueAmenities

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, 34 reviews

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

LocationOutdoor spacesHeating

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.

4.97 out of 5 average rating, 31 reviews

The Bay Breeze

LocationOutdoor spacesSleep quality

5.0 out of 5 average rating, 34 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

LocationOutdoor spacesAmenities

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.

Westhampton Beach cozy cottage, walk to all

ValueOutdoor spacesIndoor spaces

4.98 out of 5 average rating, 55 reviews

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.

Shelter Island Waterfront Getaway

LocationOutdoor spacesWalkability

4.97 out of 5 average rating, 115 reviews

Other holiday rentals with a kayak

5.0 out of 5 average rating, 6 reviews

Cabin in Springs

Modern Cabin near the Beach

LocationFamilyCleanliness

5.0 out of 5 average rating, 68 reviews

Apartment in Sag Harbor

Spacious apartment in Sag Harbor

Outdoor spacesLocationDecor

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.

Southampton Modern Barn, Private Pool and Hot Tub

Outdoor spacesLocationCondition

4.99 out of 5 average rating, 78 reviews

5.0 out of 5 average rating, 44 reviews

Home in Mattituck

Creek Front home w/heated pool & endless sunsets

LocationOutdoor spacesIndoor spaces

Superhost

Apartment in Hampton Bays

2Br Hampton Family Escape: Beaches, kayaks, BBQ

ValueLocationCheckout

4.85 out of 5 average rating, 53 reviews

5.0 out of 5 average rating, 22 reviews

A spacious heated swimming pool is surrounded by lush greenery and trees, creating a serene atmosphere. Lounge chairs are positioned at the poolside, and a shaded area with an umbrella provides additional seating. The clear water reflects the natural light and offers a refreshing retreat.

Home in Montauk

Mermaid Oasis - 5bd, Pool, Walk to Beach

LocationOutdoor spacesPool

Superhost

Home in Hampton Bays

Bright Hamptons Getaway ☀️ Pool▪︎ Beach▪︎FamilyFun

ValueLocationPool

4.85 out of 5 average rating, 47 reviews