Apartment vacation rentals in Sag Harbor

A historic two-story house with a dark wooden exterior is framed by neatly trimmed hedges. A white picket fence leads to the entrance, while trees provide a natural backdrop. Views of the water can be glimpsed beyond the property, highlighting the waterfront location.

4.87 out of 5 average rating, 148 reviews

Whaling Captain Pierson's Apartment

Whaling Captain Pierson's Apartment is at a waterfront property. An apartment in one of the contributing homes which define Sag Harbor as a historic village. The house is a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only house and apartment offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets. (See my other listings of Whaling Captain Pierson's Apartment TOO and Whaling Captain Pierson's Cottage).

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.

4.96 out of 5 average rating, 163 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

4.96 out of 5 average rating, 306 reviews

A spacious outdoor deck is shown with a round table and four chairs shaded by a purple umbrella. Nearby, a cozy seating area is arranged with cushions. Lush green trees provide privacy along the perimeter, enhancing the tranquil atmosphere.

Apartment in East Quogue

The House of the Mermaid aka La Casa della Sirena

Welcome to The House of the Mermaid! Come stay in this newly renovated and decorated basement apartment in my house in a quiet and residential area of Hampton Bays. Close to all that you could ever want; restaurants, bars, shopping, and beaches. Perfect getaway for any season. The Hamptons are known for their amazing Summers at the beach, but don't forget about all that Long Island has to offer throughout the seasons. Shopping at Tanger Outlets, apple/pumpkin picking, and the N.F. vineyards!

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.

4.99 out of 5 average rating, 207 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!

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.

4.97 out of 5 average rating, 414 reviews

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.

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.

4.93 out of 5 average rating, 136 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 .

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.

4.89 out of 5 average rating, 174 reviews

Sag Harbor Village Oasis

Bright and spacious second floor apartment in historic Sag Harbor Village. 10 minute walk to historic Sag Harbor Village Main Street. Five minute walk to Bay beach. Super comfy king bed. Fully self contained with private entrance and hallway. Parking on street close to entrance. Kitchen with stovetop, refrigerator, sink, coffee and tea kettle. No pets - owner is allergic. No infants/children.

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.

4.98 out of 5 average rating, 130 reviews

Walk to Bay and Ocean-Newly Renovated

Newly renovated! Walking distance to beautiful bays , ocean beaches, restaurants and bars. Perfect Hamptons vacation getaway. Wine Country and Montauk are great day trips from this centrally located spot. Easily access Hampton Bays with public transportation via LIRR or Hampton Jitney, than a 3-5 minute Uber to apartment. Monthly stays will have cleaning service provided every two weeks.

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, 228 reviews

Sunny Southampton Studio

Newly renovated sun drenched, spacious studio in Southampton. Five minute drive to Main Street, while still in close proximity to some of the most beautiful beaches. Queen size bed and queen size pull out couch. Full kitchen with new appliances and full bathroom. BEACH PASS for Coopers beach is available upon advanced request—please let me know the day before you arrive

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, 259 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

A bright living area is depicted, featuring a sleek sofa, a wooden coffee table, and a round dining table surrounded by red chairs. The space incorporates a large potted plant, and light streams through a nearby window, illuminating the whitewashed wood floors.

4.97 out of 5 average rating, 129 reviews

Renovated Guest Cottage close to E.Hampton Village

This modern beach guesthouse has white washed wood floors, all new stainless steel appliances , central air, and very conveniently located . We are a short walk to East Hampton Village and 1.9 miles to the nearest beach.There is a private back patio with a cedar outdoor shower and sitting area in a serene setting .

4.88 out of 5 average rating, 143 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

Location, Location, Location!!!! New renovated stand along Studio Apartment in the heart of Southampton Village. Private with lots of light, Cable TV and living room area. Located in wonderful Southampton Village location, only 1 mile to village shops and 2 miles Coopers Beach. Wi-Fi

Popular amenities for Sag Harbor apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

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.

4.98 out of 5 average rating, 80 reviews

Newly Renovated 2-BR Apartment

Two bright orange chairs are positioned beside a small wooden table adorned with a potted plant and books. A cozy atmosphere is created in a well-lit space featuring light-colored flooring and natural light from the nearby window.

5 out of 5 average rating, 72 reviews

Hampton Studio

A cozy living area features wood-paneled walls and a neutral sofa positioned near a lamp and a chair. Natural light floods through the windows, illuminating a patterned rug on the hardwood floor. A television is mounted on the wall opposite the entrance.

4.92 out of 5 average rating, 12 reviews

Sugarloaf Annex

A warm wood-paneled interior features a cozy bed adorned with a white quilt and decorative pillows. A small yellow bench sits at the foot of the bed. A bathroom entrance is visible in the background, and a landscape painting hangs above a nightstand with a lamp.

5 out of 5 average rating, 26 reviews

US OPEN 2026: 5 Miles Away The Vineyard Studio

5 out of 5 average rating, 22 reviews

A spacious bedroom is featured with a large bed, flanked by two nightstands. A cozy couch offers additional seating, and a light fixture adds warmth to the space. Soft curtains frame a window, allowing natural light to fill the room, complemented by a decorative area rug.

Apartment in Springs

Springs Plaza

The kitchen features light grey cabinets with white countertops, complemented by stainless steel appliances. A small dining table with two stools is positioned near the window, allowing natural light to brighten the space. Hardwood flooring provides a warm touch to the modern design.

4.96 out of 5 average rating, 23 reviews

Charming 2 Bedroom Apt in Dwntwn Greenport

5 out of 5 average rating, 5 reviews

Apartment in Water Mill

Lower level space

4.84 out of 5 average rating, 31 reviews

2Br Hampton Family Escape: Beaches, kayaks, BBQ

Private apartment rentals

The exterior of a three-story house features light grey siding with turquoise shutters. A welcoming front porch contains multiple windows, and the entrance is accentuated by a small flight of stairs. Lush greenery surrounds the property, enhancing its appeal.

4.83 out of 5 average rating, 126 reviews

House on First

Apartment in Bridgehampton

A spacious bedroom is featured with a comfortable king-sized bed, adorned with soft linen and decorative pillows. Nightstands with stylish lamps provide gentle illumination, complementing the calm color scheme of the room.

4.96 out of 5 average rating, 80 reviews

Hamptons Elegant and Comfortable Apartment

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, 166 reviews

Upscale Newly Constructed Apartment

4.79 out of 5 average rating, 34 reviews

Peaceful getaway in the Hamptons

4.94 out of 5 average rating, 139 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

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, 118 reviews

Lovely 2-bedroom apartment in a historic home

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, 263 reviews

Greenport Village View - Walk Downtown 2BR/1BA

A cozy living area features a comfortable gray sofa adorned with patterned pillows. A light-colored side table and an illuminated lamp create a soft glow. A decorative coffee table sits in front, accompanied by a potted plant in the corner, adding a touch of greenery.

4.92 out of 5 average rating, 121 reviews

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

Family-friendly apartment rentals

A spacious living area is equipped with a sectional sofa, a coffee table, and a vintage popcorn machine. Natural light enters through sliding glass doors, which provide a view of the outdoor space. The room features a neutral color palette and modern lighting.

Comfortable & clean apt in Sag

A bright living area is presented with a dark coffee table at the center. Natural light enters through sliding glass doors, leading to an outdoor space. A television is mounted on the wall, and a compact workspace is visible near the kitchen area, featuring a refrigerator.

4.89 out of 5 average rating, 9 reviews

Basement apartment near circle beach

5 out of 5 average rating, 93 reviews

Uber Clean Studio Apartment

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.

4.96 out of 5 average rating, 101 reviews

Swimming pool w/Hot tub Fire Pit Coffee Bar

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.

4.83 out of 5 average rating, 185 reviews

Quiet Neighborhood and only steps to Town

A spacious living area showcases a light grey sectional sofa and a matching loveseat arranged around a wooden coffee table. A striped area rug adds a pop of color to the dark flooring. Shelves line the walls, and large windows allow natural light to fill the room.

4.79 out of 5 average rating, 345 reviews

Amazing Greenport Village Apartment in CENTER!

A secluded outdoor space features a clean, rectangular pool surrounded by a manicured lawn. Lounge chairs are positioned near the pool, offering a relaxing atmosphere. Trees provide shade, enhancing the serene environment with a wooden fence enclosing the area.

5 out of 5 average rating, 8 reviews

Casa Greenport 1st Floor

A cozy living area features a dark blue sofa adorned with decorative cushions. A small striped ottoman is positioned in front of the sofa, alongside a wooden side table topped with a lamp and a decorative vase. Natural light filters through the window shades.