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Vacation rentals with beach access in Shelter Island Heights

Find and book unique beach access rentals on Airbnb

Top-rated beach access rentals in Shelter Island Heights

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An aerial view captures the oceanfront condos nestled along the coastline, surrounded by lush greenery and a sandy beach. The serene waters and well-maintained grassy area enhance the natural beauty of the setting.

Condo in North Fork

4.84 out of 5 average rating, 135 reviews

Seaside Summer Escape: 2BR Waterfront Condo w/Pool

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on a private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

Two blue Adirondack chairs are positioned on a manicured lawn, facing a vibrant sunset over the ocean. The sky displays pink and orange hues as the sun sets on the horizon, creating a serene outdoor setting.

Condo in North Fork

4.92 out of 5 average rating, 139 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

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 North Fork

4.91 out of 5 average rating, 315 reviews

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!

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 The Hamptons

4.93 out of 5 average rating, 121 reviews

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

Top guest favorite

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 North Fork

4.94 out of 5 average rating, 186 reviews

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

The spacious patio is shaded by a vine-covered pergola, featuring a round dining table surrounded by black chairs. Lounge chairs are positioned nearby, and the yard extends beyond, showcasing green grass and a variety of plants, contributing to an inviting outdoor space.

Home in North Fork

4.93 out of 5 average rating, 113 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

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 South End

4.94 out of 5 average rating, 127 reviews

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. Less than 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, and Love Lane.

A spacious two-story apartment building is surrounded by well-kept greenery and manicured lawns. A paved pathway leads to the entrance, with colorful landscaping enhancing the inviting exterior. Two bright orange lounge chairs are positioned under trees on the side, offering a peaceful outdoor seating area.

Guest suite in North Fork

4.92 out of 5 average rating, 156 reviews

GREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH

4-6 GUEST MAXIMUM PLEASE. Cozy 2 BR and 1 BTHRM apartment in private home in Greenport NY. Total privacy and separation of unit!! Perfectly situated on 1.75 acres. 3 minute drive, or easy walk, to the center of Greenport village, 2 minute ferry ride to quaint Shelter Island, and a 6 minute drive to tip of Orient. So right in the middle of the action with the peace and serenity of living outside the village. Private beach a short walk/ride down the street.

A clear blue saltwater pool is surrounded by a landscaped yard featuring green grass and shrubs. Several lounge chairs are positioned nearby under light blue umbrellas, providing shade. A two-story house is visible in the background, framed by tall trees.

Home in North Fork

4.9 out of 5 average rating, 214 reviews

Greenport Beach house Mini Resort Spa & Catering

Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).

An open living area features a comfortable gray sofa facing a flat-screen TV. A black coffee table sits on a textured rug, while a wooden dining table with chairs is positioned nearby. Sunlight filters through the blinds of the dual doors leading to the outside.

Apartment in North Fork

4.96 out of 5 average rating, 103 reviews

Junior 1-BR in the heart of Greenport Village

Beautiful junior one bedroom in the heart of Greenport Village. Located in the historical district, our basement apartment is walking distance (2-Blocks) to downtown Greenport. Perfect for a couples weekend, girls trip, or for a small family. Our apartment includes one queen bed and a twin day bed with trundle underneath. (Sleeps 4 total) TV with streaming service and WiFi are included. W/D are available upon request.

A rocky shoreline is framed by a silhouetted tree against a colorful sunset. Clouds display shades of pink and orange as the sun sets over the water, creating a serene atmosphere. The beach area offers a peaceful view of nature.

Home in Shelter Island

4.9 out of 5 average rating, 116 reviews

There's a 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. Cleaning fees for winter stays are 0$.

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.

Apartment in Shelter Island Heights

4.91 out of 5 average rating, 247 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

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Quaint homes, peaceful surroundings

Popular amenities for Shelter Island Heights beach access rentals

Free parking on premises

Air conditioning

Apartment rentals with beach access

An outdoor dining area features a round wooden table surrounded by four wooden chairs. A bright red umbrella provides shade, while a view of the ocean and lush greenery is visible in the background.

Apartment in The Hamptons

4.9 out of 5 average rating, 220 reviews

Montauk Beach Bungalow West

A charming two-story house is nestled among lush greenery, with large windows reflecting sunlight. The wooden exterior features shingle siding, and a gentle slope of grass leads up to the entrance. Surrounding trees create a serene, private atmosphere.

Apartment in The Hamptons

4.96 out of 5 average rating, 154 reviews

Hamptons Hills Escape

A glass desk is positioned beside large windows, offering views of the water and sky. A cozy chair with a fluffy seat cover complements the desk. A stack of books, binoculars, and a soft-lit lamp are arranged on the desk, enhancing the workspace atmosphere.

Apartment in Stonington

4.95 out of 5 average rating, 289 reviews

Mystical Ocean View in Historic Stonington Borough

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 South End

4.95 out of 5 average rating, 120 reviews

Bright, Southold Studio Apt near beach & town

Top guest favorite

A serene garden area is seen, featuring lush green grass and vibrant flowerbeds with orange blooms. A tranquil pond is visible in the background, surrounded by trees and natural landscaping, creating a peaceful outdoor setting.

Apartment in Milford

4.98 out of 5 average rating, 104 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

Top guest favorite

A sandy path leads through beach grass, flanked by wooden fencing, toward a tranquil ocean beyond. Clear blue skies complement the scene, where gentle waves are visible on the horizon.

Apartment in The Hamptons

4.97 out of 5 average rating, 109 reviews

Walk to Bay and Ocean-Newly Renovated

An expansive view of the ocean stretches across the horizon, framed by wooden sliding doors. Gentle waves wash onto a sandy beach, with greenery in the foreground. A potted plant rests on the railing, adding a natural touch to the serene scene.

Apartment in The Hamptons

4.86 out of 5 average rating, 111 reviews

Recharge at our Renovated ocean front unit

A serene view of Pattagansett Lake is presented, with gentle ripples reflecting the sky. Surrounding hills are adorned with trees displaying autumn colors, while fluffy clouds drift above. The calm waters enhance the tranquil atmosphere of the natural setting.

Apartment in East Lyme

4.97 out of 5 average rating, 231 reviews

Brand New Direct Lakefront - Panoramic Sunsets

House rentals with beach access

Top guest favorite

A stylish living area showcases a comfortable sofa and accent chairs arranged around a modern coffee table. Warm wood flooring complements the dark walls, and soft lighting is provided by a chandelier. Large windows are dressed with elegant drapes, inviting natural light into the space.

Home in North Fork

5 out of 5 average rating, 23 reviews

Elegant Greenport Victorian -Winter Harbor House

The exterior of a single-story home is set among lush greenery, featuring a varied facade with shingle and clapboard elements. Symmetrical landscaping includes neatly trimmed shrubs and a spacious lawn. A pathway leads to the front door, framed by tall trees providing natural shade.

Home in Shelter Island

4.89 out of 5 average rating, 28 reviews

Peaceful and Private 3 bedroom home in the woods

An outdoor patio features multiple wooden lounge chairs arranged around a central fire pit. A gunite pool with clear water reflects the surrounding greenery. The main house, visible in the background, showcases a classic design with white siding and large windows.

Home in The Hamptons

4.86 out of 5 average rating, 266 reviews

Exclusive Sag Harbor Compound

A bright living area features a light grey sofa paired with two black chairs, positioned around a glass coffee table. Large windows allow natural light to fill the space, while a minimalist fireplace offers visual interest. A small desk is visible against the wall.

Home in The Hamptons

4.95 out of 5 average rating, 432 reviews

Silver House: 3BR Home with Private Beach Access

A swimming pool with clear blue water is surrounded by a spacious deck. Lounge chairs with striped cushions are arranged for relaxation. Colorful umbrellas provide shade over outdoor sofas, and lush greenery in the background enhances the serene environment.

Home in The Hamptons

4.93 out of 5 average rating, 153 reviews

Large heated pool, games room, near private beach

Top guest favorite

The living area features a combination of modern and historic elements, including a cozy seating arrangement with leather chairs and a round coffee table. Stained-glass windows add color, while a 65" television is mounted above a brick fireplace. Natural light illuminates the hardwood floors.

Home in North Fork

5 out of 5 average rating, 12 reviews

The Olde Church in Greenport

An outdoor dining area is sheltered by a natural pergola adorned with greenery. A long, gray table is surrounded by wooden folding chairs. Sunlight filters through the leaves, creating dappled patterns on the stone floor, while white French doors lead into the house.

Home in North Fork

4.98 out of 5 average rating, 123 reviews

Stylish Farmhouse in North Fork

A spacious deck with multiple dining tables overlooks a private beach and calm waters. Flower pots line the railing, adding color to the relaxing coastal view. The sandy beach is visible in the distance, leading to rocky outcroppings under a clear blue sky.

Home in South End

4.94 out of 5 average rating, 34 reviews

Water front 3 bedrooms 2 bathrooms beach house.

Condo rentals with beach access

A private balcony is featured, overlooking the ocean with a clear blue sky. A small, round table is accompanied by four chairs in a light blue hue, creating a comfortable setting for outdoor relaxation.

Condo in The Hamptons

5 out of 5 average rating, 15 reviews

Second Floor Corner Unit Overlooking the Ocean

The private room features a queen bed with neatly arranged linens and towels. A wall-mounted TV is positioned above a microwave and refrigerator, enhancing functionality. Natural light filters through a small window, complementing the simple, clean design of the space.

Condo in Old Lyme

4.9 out of 5 average rating, 31 reviews

The Anchor at Soundview · Beach+Ocean+Sunrise

Two individuals are seen enjoying a swim in a calm body of water, with sunlight reflecting off the surface. Lush greenery is visible in the background, creating a serene natural setting.

Condo in Mount Sinai

4.8 out of 5 average rating, 74 reviews

1856 Trading House w/ walk to water

Condo in The Hamptons

4.89 out of 5 average rating, 9 reviews

Endless Summer Studio Condo w Balcony Bayview

A bright and airy living space is highlighted by skylights and white wooden beams. A spacious kitchenette is situated behind a dining table surrounded by light chairs. Large windows invite natural light, and a television sits on a white console between soothing tones of gray and cream.

Condo in The Hamptons

4.78 out of 5 average rating, 23 reviews

Waterfront Elevated Bungalow - Spectacular Views

A cozy living area is furnished with a beige sofa, a round wooden coffee table, and stylish light blue armchairs. A large window allows natural light to fill the space. Potted plants add a touch of greenery, creating a relaxed atmosphere.

Condo in Old Saybrook

4.89 out of 5 average rating, 73 reviews

Seashore getaway - CT shoreline

Top guest favorite

The exterior of a historic Tudor-style building is framed by large, blooming cherry blossom trees. The soft pink flowers create a vibrant contrast against the architecture. A paved pathway leads to the entrance, where benches are positioned for seating.

Condo in The Hamptons

4.95 out of 5 average rating, 120 reviews

Deluxe Studio Apt@The Montauk Manor

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.

Condo in The Hamptons

4.82 out of 5 average rating, 95 reviews

Beautiful Condo on the Ocean Bluffs

Quick stats about vacation rentals with beach access in Shelter Island Heights

Total rentals
200 properties
Nightly prices starting at
G$25,105 GYD before taxes and fees
Total number of reviews
8.3K reviews
Family-friendly rentals
160 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with a pool
70 properties have a pool

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