Holiday rentals with beach access in Shelter Island

4.85 out of 5 average rating, 156 reviews

Home in Hampton Bays

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

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Guesthouse in Southampton

A charming outdoor area features a black cottage in the background, with large glass doors reflecting the surroundings. The deck is adorned with potted red geraniums and wooden seating. A hot tub is positioned adjacent to the cottage, emphasizing a tranquil retreat atmosphere.

4.97 out of 5 average rating, 119 reviews

5 Star Rated Private Cottage Southampton/Sag Hrbr

The Honeycomb Cottage is a little retreat located on a lush acre of evergreens in Southampton rated 5 Star by every guest that has stayed. One block to Peconic Bay Beach - perfect for a day in the sun. A cozy space with TV, WiFi and Sun Deck. Luxury soaps provided, amazing shower and crisp white linens. Exclusive use of the Hot Tub for Cottage guests. Easy parking and located 15 minutes drive to Sag Harbor or Southampton Village. Koi pond with waterfall will sooth the mind and spirit.

WalkabilityBeachPool

4.93 out of 5 average rating, 134 reviews

A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.

Home in Mattituck

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

BeachWalkabilityPets

4.94 out of 5 average rating, 154 reviews

A wooden tray is centered on a neatly made bed, featuring a book and a coffee cup. The bed is dressed with a white quilt, and a softly textured pillow is placed against the headboard. A bedside lamp provides gentle illumination.

Guest suite in Southold

Comfortable Suite, a walk to the beach

Keep it simple at this spacious and peaceful home. Built in 2019, this home was specially designed for sustainable, green living; ground-source heating, and super insulation allow for minimal environmental impact and provide a quiet and comfortable stay. About a five minute walk to McCabe’s Beach. Very near to wineries, farms, and the quaint shops and bakeries of Southold and Greenport. Little Fish restaurant and oyster sales all down the street. Short drive from Sparkling Pointe vineyard.

BeachViewLong stay

4.98 out of 5 average rating, 181 reviews

A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.

Cottage in Riverhead

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

ViewWalkabilityFamily

4.98 out of 5 average rating, 237 reviews

A cozy living area is shown with two comfortable sofas and a coffee table. Natural light enters through two windows adorned with bamboo shades. A flat-screen television is mounted on the wall, and a decorative rug adds warmth to the wooden flooring.

Apartment in Sag Harbor

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

BeachWalkabilityAccess

4.95 out of 5 average rating, 154 reviews

A serene beach scene captures a golden sunset reflecting on calm waters. The sandy shore leads to gentle ripples, while distant land silhouettes frame the horizon. A tranquil ambiance is created as the sun descends, providing a peaceful setting for evening strolls.

Apartment in Southold

Bright, Southold Studio Apt near beach & town

Pied a terre on the North Fork, in the heart of Southold village. Gorgeous bay beach 5 minute walk, as are farmstands, supermarket, Historic Southold Village with quaint shops, Hampton Jitney & LIRR. Lots of light, new contemporary space featuring full bathroom with bathtub. Perfect for one, suitable for a couple for weekend getaway. Small kitchenette perfect for simple food prep, morning coffee/tea. Chickens on property, fresh pastured eggs in your kitchenette upon arrival!

BeachWalkabilityValue

4.91 out of 5 average rating, 356 reviews

A neatly arranged bedroom features a spacious bed dressed in white linens and accented with a textured throw pillow. Two windows provide natural light, flanked by simple wall sconces. A small shelf and minimal decor enhance the serene atmosphere.

Guest suite in Greenport

The Greenport Suite—private entry + near the beach

Welcome to The Greenport Suite! With its separate entrance, secluded outdoor patio space and ideal location, this newly-redesigned private suite in our contemporary Village home is perfect for enjoying a North Fork getaway. We are located just a few short blocks from bay beaches, the harbor, and public transport, while the area's celebrated wineries are a short drive or bike ride away. Come see why Forbes named Greenport one of the 11 prettiest villages in the United States!

BeachWalkabilityQuiet

Home in Shelter Island Heights

4.9 out of 5 average rating, 128 reviews

Hay Beach Family Home: Fire Pit, Playroom, Yard

Two blocks from Hay Beach, this family-and-dog-friendly 3BR sleeps 6 in a quiet Shelter Island neighborhood. Fenced yard, fire pit, playroom, crib, toddler toys, beach gear, and bikes included. The home was built for families: open living area with wood-burning fireplace, full kitchen, 2 full baths, basement playroom, and workout space. Outside: fully fenced yard, fire pit, sun loungers, propane grill, Big Green Egg. Winter stays: $0 cleaning fee Nov–Mar.

BeachWalkabilityParking

4.95 out of 5 average rating, 321 reviews

A welcoming living area is illuminated by natural light from large windows. A comfortable gray sofa is complemented by light-colored armchairs and a coffee table adorned with books and decorative items. The neutral color palette is accentuated by indoor plants and a textured rug.

Home in Sag Harbor

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

ViewWalkabilityWi-Fi

Guest suite in North Fork

The exterior of a historic Tudor home is shown, featuring a blend of brick and wood accents. A winding driveway leads to the entrance, surrounded by lush greenery and a decorative black fence. Trees provide shade, enhancing the serene outdoor setting.

4.88 out of 5 average rating, 737 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

WalkabilityViewParking

Apartment in Shelter Island Heights

A round wooden dining table is surrounded by four metal chairs. Natural light enters through two large windows, with framed black-and-white photographs arranged on the wall beside them. A decorative centerpiece is placed on the table, offering a rustic touch to the space.

4.9 out of 5 average rating, 270 reviews

Squire Chase House

Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone

WalkabilityViewLaundry

Popular amenities for Shelter Island Accommodation with Beach Access

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

Apartment in Shinnecock Hills

A wide sandy beach stretches towards the horizon, where soft waves gently lap at the shore. Tall lifeguard stands are positioned along the beach, with a few distant figures walking. The sky features a gradient of muted colors as the sun sets, creating a serene atmosphere.

4.95 out of 5 average rating, 242 reviews

Sunny Southampton Studio

WalkabilityBeachLong stay

4.97 out of 5 average rating, 133 reviews

The main bedroom features a spacious bed with a white comforter and dark accent pillows. Sunlight filters through sheer white curtains covering French doors, leading to the outdoors. Bright wooden floors add warmth, while a ceiling fan offers comfort.

Apartment in Greenport

Lovely 2-bedroom apartment in a historic home

WalkabilityViewComfort

4.85 out of 5 average rating, 214 reviews

A serene bedroom features a spacious bed dressed in light aqua linens, complemented by decorative pillows. Artwork showcasing botanical prints adorns the wall above the bed. A decorative ladder holds a turquoise throw blanket, while a small table beside the bed displays a flower arrangement.

Apartment in Sag Harbor

Village Studio a short walk to everything

BeachWalkabilityQuiet

4.94 out of 5 average rating, 155 reviews

A comfortable living room area is presented, featuring a light-colored sectional sofa arranged around a wooden coffee table. Natural light enters through a large window, illuminating a piece of artwork on the wall and adding a cozy touch to the space.

Apartment in Sag Harbor

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

WalkabilityBeachGetting around

4.95 out of 5 average rating, 135 reviews

An open living area features a comfortable sectional sofa and a large area rug, with natural light streaming through multiple windows. A dining table is visible, accompanied by stools, and the kitchen area includes modern appliances and a view into the outdoor patio space.

Apartment in Montauk

Modern Montauk retreat with wood stove by Harbor

BeachViewSleep quality

4.88 out of 5 average rating, 139 reviews

Apartment in Montauk

Recharge at our Renovated ocean front unit

BeachViewAccuracy

4.94 out of 5 average rating, 102 reviews

Apartment in Flanders

Hamptons Waterfront Suite | Private Hot Tub

ViewBeachCheckout

4.92 out of 5 average rating, 141 reviews

Apartment in Greenport

Private 1st flr apt w/ patio 3 blocks from beach

BeachWalkabilityAir conditioning

Holiday House Rentals with beach access

4.94 out of 5 average rating, 242 reviews

A cozy living area features a brown sectional sofa adorned with patterned throw pillows. A black coffee table sits on a striped area rug, providing a neutral contrast to the light hardwood flooring. Natural light filters through multiple windows, enhancing the welcoming ambiance.

Home in Greenport

Harbor Heights

WalkabilityBeachBackyard

4.96 out of 5 average rating, 272 reviews

A modern kitchen space features a granite countertop with high-backed bar stools positioned for dining. Glass-front cabinets display dishware, and a sliding door opens to a sunny outdoor area with a pool and patio seating.

Home in Southampton

Stunning 3 bed 2 bath home W Pool

ViewWalkabilityParking

4.83 out of 5 average rating, 138 reviews

An outdoor area features a rectangular pool surrounded by a wooden deck. Lounge chairs are positioned along the pool's edge, and a shaded seating area is located nearby under an umbrella. Lush trees provide privacy and a natural backdrop.

Home in Springs

East Hampton Oasis - Pool and Hot Tub

WalkabilityBeachQuiet

4.95 out of 5 average rating, 263 reviews

A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.

Home in Springs

Private beach, fully updated house, on 2 acres.

ViewBeachAmenities

4.92 out of 5 average rating, 115 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

WalkabilityBeachFamily

4.99 out of 5 average rating, 211 reviews

A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.

Home in Greenport

Greenport Village walking distance to all

ViewBeachCheck-in

4.84 out of 5 average rating, 107 reviews

Home in Montauk

Montauk Private Beach Bungalow

BeachWalkabilityHiking

4.95 out of 5 average rating, 246 reviews

A comfortable living area features two light-colored sofas with decorative pillows, arranged around a central glass coffee table. A flat-screen TV is mounted on the wall, and large sliding doors provide scenic views of the outdoor greenery and natural surroundings.

Home in Springs

Ritz-East Hampton Cottage- 5 stars

ViewBeachQuiet

Holiday condos with beach access

An expansive view of the ocean under a bright blue sky, featuring wispy clouds. The shoreline is lined with gentle waves, and a grassy area is visible in the foreground, leading down to the water.

4.89 out of 5 average rating, 279 reviews

Sound Front Condominium

BeachViewBathroom

A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.

4.88 out of 5 average rating, 167 reviews

Waterfront Escape | Private Beach, Pool & Views

ViewWalkabilityBarbecue

The studio features a queen-sized bed adorned with a floral-patterned blanket. A comfortable sofa and armchair are positioned nearby, along with a small table. Natural light filters through a nearby door, illuminating the warm wood flooring.

4.84 out of 5 average rating, 211 reviews

Coastline View Studio

WalkabilityBeachWi-Fi

The living area features a spacious dark gray couch, a light wooden coffee table, and a white dining table with woven chairs. Natural light filters through the window with plantation shutters, while decorative elements like a round mirror and wall art create a welcoming ambiance.

4.89 out of 5 average rating, 196 reviews

Beautiful Waterview Condo on the North Fork of LI

WalkabilityBeachCleanliness

A spacious green lawn extends towards the ocean, with gentle waves visible in the distance. A multi-story building with defined balconies is situated to the left, surrounded by well-maintained bushes and trees, contributing to a serene coastal atmosphere.

4.85 out of 5 average rating, 110 reviews

Beautiful Condo on the Ocean Bluffs

ViewWalkabilityParks

A view from the balcony overlooks the pool area, featuring a clear blue pool surrounded by lounge chairs. Colorful umbrellas provide shade for several tables, while the surrounding buildings reflect a simple, two-story design.

4.8 out of 5 average rating, 246 reviews

Montauk Royal Atlantic Beach Resort North

WalkabilityViewCondition

5.0 out of 5 average rating, 93 reviews

Montauk Poolside Suite, Steps to Beach

WalkabilityViewBathroom