Apartment holiday rentals in Shelter Island Heights

A charming view is displayed through a large window, overlooking a green lawn that leads to a serene waterway. A decorative piece resembling a swan rests on a small table, casting a soft shadow as sunlight streams in.

4.91 out of 5 average rating, 181 reviews

Whaling Captain Pierson's Cottage

Whaling Captain Pierson's Cottage is at a waterfront property. A unique environmental experience, nestled in nature but only a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only cottage offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets and a private low-tide beach. (See my reviews from my other listings entitled, "Whaling Captain Pierson's Apartment" and "Whaling Captain Pierson's Apartment TOO".)

LocationValueWalkability

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.

4.98 out of 5 average rating, 241 reviews

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!

ValueLocationAmenities

4.95 out of 5 average rating, 156 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!

FamilyLocationQuiet

4.92 out of 5 average rating, 145 reviews

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

We are centrally located in a quiet neighborhood within blocks from the heart of Greenport Village, Peconic Bay Beach, LIRR/Jitney, restaurants, shopping, Mitchell Park, and more! Explore local farms, wineries, breweries and all the North Fork has to offer. Beautifully furnished, ground floor apt with private entrance & patio area comfortably sleeps four, features a queen Tempur-Pedic mattress & convertible couch. Friendly, housetrained pets are welcome for an additional charge.

LocationValueCleanliness

Apartment in Hampton Bays

A calm waterfront scene shows a serene body of water reflecting the sky. A sandy beach is visible, framed by natural vegetation, with a wooden barrier along the shoreline. The peaceful setting invites relaxation and enjoyment of the outdoors.

Private & Cozy Cottage with short walk to beach!

Walking distance to Bay Beach & Rumba, & short drive to town & ocean. Quiet neighborhood, great for couples, King bed upstairs, bit of a steep staircase, so may not be suited for anyone with mobility challenges. Kayaks, paddle-boards, available to enjoy. Dog friendly with fenced in patio and doggy door. Private outdoor patio, with charcoal grill. A/C & Heat for year-round enjoyment. Easy to get in/out from the city. Close drive to visit Westhampton and Southampton Main Streets.

LocationValueQuiet

4.97 out of 5 average rating, 442 reviews

A welcoming living area features a plush gray sofa and a light-colored armchair, accompanied by a rustic wooden coffee table. A dining table is visible in the background, and a well-equipped kitchen area is accessible. Natural light filters through multiple windows, enhancing the space.

4.95 out of 5 average rating, 272 reviews

Greenport Village View - Walk Downtown 2BR/1BA

Located in the heart of Greenport Village with easy walking access to restaurants, shops, Greenport Brewery, Kontakasta Winery, and much much more! Originally from Greenport, we look forward to hosting you and sharing our local favorites to make your stay memorable. Please note this rental may not suitable for small children due to the staircase. A new baby gate has been installed at the top of the stairs. Village of Greenport Short Term Rental Permit #R26-021.

LocationFamilyParks

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.

4.94 out of 5 average rating, 247 reviews

Harbor Heights

100% Walking Score 1 block away from Village 3 blocks away from Beach. 1 block away from Shelter Island Ferry. Around the corner from Hampton Jitney & LIRR Newly renovated 2-Family Home! This is for rental of 2nd floor apartment (only) plus cabana, plus outdoor jacuzzi. Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy.

FamilyValueSleep quality

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.

4.95 out of 5 average rating, 130 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.

ValueFamilyCheckout

A bright and airy great room combines kitchen, dining, and living areas. Light wood cabinetry and stainless steel appliances complement the open layout. Soft white sofas with navy pillows are arranged around a wooden coffee table, and a round mirror enhances the natural light from multiple windows.

4.96 out of 5 average rating, 178 reviews

Upscale Newly Constructed Apartment

Upscale 2- story building offers 3 bedrooms, 2 baths spacious apartment in the heart of Greenport. A vaulted ceiling in the great room (kitchen, dining & living room) with large windows and hardwood floors with plenty of natural light. Utilities included. CAC, Laundry. Less than a mile to a public beach, public transportation, restaurants, shops and Mitchell park. Off street parking for 2-3 cars.

FamilyLocationKitchen

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.

4.97 out of 5 average rating, 136 reviews

Lovely 2-bedroom apartment in a historic home

Restored apartment in a Victorian home, centrally located in the Village of Greenport. Short, few minutes walk to restaurants, shops, cafes in town. Also, conveniently located (10 minute walk) to the Hampton Jitney bus stop, LI Railroad and Shelter Island Ferry as well as local beaches. Enjoy the charm of a historic home, with all the convenience of modern amenities!

ValueLocationAccuracy

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.

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

ValueFamilyAir conditioning

4.9 out of 5 average rating, 271 reviews

A bright bedroom features white shiplap walls and large windows allowing natural light. A spacious bed is adorned with a textured white blanket and colorful decorative pillows. A vibrant area rug adds warmth, alongside a small table, a cozy armchair, and decorative plants.

4.84 out of 5 average rating, 200 reviews

Quiet Neighborhood and only steps to Town

Walk the 5 min into town with restaurants and bars, shops and cafes or enjoy the quiet neighbourhood and take a stroll down the block to watch the sailboats cruise into Sterling Harbor. This sunny apartment is situated on the second floor of a 1860's house on one of Greenport's prettiest streets. Its the true couples getaway!

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Popular amenities for Shelter Island Heights apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

A bright living area features two windows, allowing natural light to fill the space. A white sofa and an accent chair are positioned around a small coffee table. Artwork adorns the walls, complementing the light color palette. A dining table with two chairs is visible in the corner.

4.9 out of 5 average rating, 185 reviews

Sag Harbor Village Oasis

LocationValueWi-Fi

Apartment in Hampton Bays

A well-lit living area is highlighted by a cream-colored sofa with nautical-themed pillows. A wooden coffee table features shells and a vase of flowers. Display shelves in the background hold decorative items, with natural light streaming through large windows.

Vacation at the Beach: Entire Home

FamilyLocationHospitality

4.84 out of 5 average rating, 150 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.

4.94 out of 5 average rating, 155 reviews

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

LocationValueDecor

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.

Sunny Southampton Studio

LocationFamilyQuiet

4.95 out of 5 average rating, 244 reviews

4.96 out of 5 average rating, 319 reviews

Apartment in East Quogue

The House of the Mermaid aka La Casa della Sirena

LocationFamilyCleanliness

4.97 out of 5 average rating, 114 reviews

A cozy living area features a grey sofa adorned with decorative cushions, along with a white accent chair. Natural light floods in from two large windows, casting a warm glow on the wooden floor. An American flag decorates the wall, adding character to the space.

Apartment in Southampton

Stunning Garage Apartment!

FamilyValueNearby

4.88 out of 5 average rating, 163 reviews

A private entrance features a white door set against a backdrop of textured wooden siding. Colorful purple irises bloom along the stone pathway, complemented by lush greenery, contributing to the inviting exterior of the studio apartment.

Apartment in Southampton

Southampton Village Studio

FamilyValueTV

Apartment in Hampton Bays

Charming Maritime Apartment Steps from the Beach

FamilyLocationAccuracy

4.9 out of 5 average rating, 531 reviews

Private apartment rentals

4.76 out of 5 average rating, 196 reviews

Apartment in Ridge

Spacious 1Bedroom Apartment By Wineries & Beaches

FamilyValueAccess

4.88 out of 5 average rating, 141 reviews

Apartment in Montauk

Recharge at our Renovated ocean front unit

FamilyValueIndoor spaces

4.99 out of 5 average rating, 107 reviews

A cozy living area is presented, featuring a full-size couch and love seat in soft brown fabric. A round black coffee table sits at the center, complemented by a patterned area rug. Natural light enters through a skylight and glass doors, creating a warm ambiance.

Apartment in Shirley

Welcome to Bill & Debbies AirBnb

FamilyLocationHospitality

A two-story dwelling is depicted, featuring a soft green exterior with white accents. A wooden deck and railing provide access to the entrance door, while surrounding plants and a clean pathway add to the welcoming appeal. Nearby utility lines are present in the background.

4.96 out of 5 average rating, 79 reviews

Vintage 1880 Victorian gem.

ValueFamilyBeach

A charming Victorian home features a blue exterior with white accents and a welcoming porch. Lush greenery surrounds the entrance, enhancing the inviting atmosphere. The property includes a second-story balcony, providing outdoor space to enjoy the surrounding neighborhood.

4.94 out of 5 average rating, 66 reviews

Lovely 1st floor of farmhouse, wineries/downtown

ValueFamilyBathroom

4.88 out of 5 average rating, 26 reviews

A spacious bedroom is furnished with a large bed featuring a light-colored striped duvet. Soft blue walls complement the natural wood accents, while a chandelier adds elegance. A mounted television is visible, and sliding glass doors lead to a private balcony surrounded by trees.

Apartment in North Fork

Waterfront Greenport Getaway

ValueLocationOutdoor spaces

4.82 out of 5 average rating, 11 reviews

Apartment in Southold

1BR Apartment - Beach Access - Wineries, Vineyards

ValueFamilyKitchen

The charming two-story building features a light-colored exterior with shingle accents. A covered porch spans the front, supported by tall white columns. Large windows invite natural light, while blooming trees enhance the inviting street view.

4.97 out of 5 average rating, 98 reviews

Newly Renovated 2-BR Apartment

ValueLocationLong stay

Apartment rentals with a hot tub

4.96 out of 5 average rating, 109 reviews

A vibrant pool scene is captured, featuring a colorful unicorn float positioned on the water. Lush hydrangea blooms frame the area in shades of pink, complementing the surrounding greenery and the wooden fence that provides privacy.

Apartment in Southampton

Swimming pool w/Hot tub Fire Pit Coffee Bar

ValueLocationCleanliness