Apartment holiday rentals in Southampton

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.

4.93 out of 5 average rating, 166 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".)

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.

4.97 out of 5 average rating, 170 reviews

A modern living area features a dark sectional sofa accented by cushions and a stylish area rug. In the background, a dining space with four chairs and a kitchen area is visible. Natural light enters through multiple windows, creating a bright, inviting environment.

Apartment in Patchogue

Charming 2 Bedroom apartment

Enjoy our charming 2 Bedroom apartment that is in a quiet and friendly neighborhood in a cul-de-sac. Private entrance on first floor of our house with 2 Bedrooms, 1 Bathroom, Living room, Dining area, and a Kitchen. Close to: Main highways (Sunrise HWY/Long Island Expressway), Grocery stores, Winery & Vineyards, Davis park ferry, Downtown Patchogue village (Restaurants, bars, breweries, shopping), Beaches, Top Golf, MacArthur airport, Long Island Community Hospital, St Joseph’s College.

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.

4.94 out of 5 average rating, 109 reviews

Modern Montauk retreat with wood stove by Harbor

Scandinavia meets Montauk in this sophisticated, comfy, all-season getaway with open-plan interior & large, private fenced yard. • 950 sq ft, 2 BRs (compact but comfy), 1 Ba, full high-end kitchen, W/D, A/C • Wood stove, Solo stove, patio, outdoor shower, high-end linens & furnishings/decor • Steps to LI Sound & Harbor. 3 mi to ocean/Town • Owner is in a private studio w/ own entrance in the house. No shared spaces! • Ask about dogs & flexible rental periods CLICK MORE for IMPORTANT INFO!

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, 197 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, 411 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.

4.95 out of 5 average rating, 136 reviews

A cozy living area features a plush gray couch adorned with decorative pillows. Vibrant blue walls complement the stylish kitchen cabinetry in the background. A large flat-screen television displays a scenic beach image, while a sleek desk sits nearby. Soft lighting adds to the inviting ambiance.

Apartment in Shirley

Boho Beach Vibez Retreat! Private entrance

"Experience a different kind of stay with our unique Airbnb, the 'Boho Beach Vibez” This cozy 1-bedroom apartment , that’s approximately 500sqft is situated on the first level of our home with a separate entrance . Located in a prime area of our town, you'll find yourself just minutes away from all the stores, restaurants, highways, and within walking distance of hiking trails, the Carman’s river, and 5 miles from Smith Point beach. NOTE : hosts live on top level .

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, 224 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

4.94 out of 5 average rating, 169 reviews

A tranquil backyard setting features a well-maintained pool surrounded by greenery and decorative lighting. Flower pots and a trellis adorned with plants enhance the space, while a stone pathway leads to the area. Trees provide a natural backdrop, creating a serene atmosphere.

Apartment in Rocky Point

North shore Guest Room.

This apartment is our guest room with outside private entrance and off street parking. Apartment has a refrigerator, microwave, coffee maker, and toaster oven. Queen bed and a twin pullout couch bed is provided. The place is appropriate for a short stay as an affordable alternative to hotel stay.

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.

4.88 out of 5 average rating, 143 reviews

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

An expansive ocean view is showcased from the studio, featuring calm waters that reflect the sunlight. Soft waves gently lap at the sandy shore, while lush greenery lines the foreground, contrasting with the clear blue sky above.

4.92 out of 5 average rating, 105 reviews

Ocean View Studio with King Bed

The sun, the sand, and the surf meet at the Wavecrest Resort to offer a magical holiday to our guests. This unique, fully renovated studio offers a king bed w/ a Loft bed for a small child, kitchenette, beautiful ocean view.

Popular amenities for Southampton apartment rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

A cozy studio apartment features a spacious Murphy bed with a light-colored comforter, neatly folded against the wall. A dark sofa is positioned adjacent to a dining table with two chairs. Natural light illuminates the room through window blinds.

4.91 out of 5 average rating, 11 reviews

Instant Book: Fall Foliage Escape in WHB, NY

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

Apartment in Middle Island

A modern kitchen is featured, showcasing gray cabinetry and stainless steel appliances. A dining table set for two includes black chairs and glassware, with a small vase of flowers at the center. A window allows natural light to brighten the space.

4.97 out of 5 average rating, 86 reviews

Modern Farmhouse Decor With Washer/Dryer

The sleeping area features a plush bed with white bedding and two neatly arranged pillows. Warm light from the wall-mounted lamps illuminates the space, while green foliage is visible through the large windows on either side, creating a soothing atmosphere.

4.97 out of 5 average rating, 38 reviews

The Hideaway | Clearwater Beach

Apartment in Center Moriches

An open studio space features a spacious bed with a light duvet and decorative pillows. A leather couch complements the area, while large windows provide natural light, framed by white blinds. A bedside table and warm lighting create a cozy ambiance.

4.85 out of 5 average rating, 100 reviews

Quiet and comfy studio near the Hamptons

Superhost

4.92 out of 5 average rating, 26 reviews

Peaceful getaway in the Hamptons

Superhost

A garden archway adorned with climbing greenery frames a stone pathway. The path leads through a flower-filled area, featuring a small seating arrangement made of natural stone and flowerpots. Lush foliage surrounds the space, contributing to a serene outdoor atmosphere.

4.81 out of 5 average rating, 21 reviews

Southampton Village Apartment

A cozy living area features a green patterned accent wall and a comfortable sofa. A television is positioned on a white media stand, while a rustic dining table and chairs are present. A bright red fridge adds a pop of color, and a lofted sleeping area is accessed by a blue-painted staircase.

4.94 out of 5 average rating, 65 reviews

Sunny 1 bedroom Guest Suite w/private entrance

Private apartment rentals

A studio suite features a spacious bed with a patterned quilt, paired with a comfortable gray sofa. A dining table with white chairs is positioned nearby. Large sliding doors reveal a view of the ocean, enhancing natural light in the room. Coastal artwork decorates the walls.

4.95 out of 5 average rating, 43 reviews

Luxurious Beachside Getaway Steps to the Ocean

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

5 out of 5 average rating, 12 reviews

Tranquil country garden retreat

A comfortable living area is furnished with a large gray sectional sofa and an armchair. A flat-screen TV is mounted on the wall opposite. Natural light floods through large windows, creating a relaxed atmosphere. A small table sits on the light-colored area rug, complementing the wooden floor.

4.83 out of 5 average rating, 76 reviews

Sunny and Spacious 1BR Apartment

The exterior of the two-story apartment is showcased, featuring grey siding and multiple windows with white trim. A defined driveway leads to the building, bordered by manicured greenery. Sunlight casts soft shadows across the landscape, enhancing the inviting atmosphere.

5 out of 5 average rating, 14 reviews

Beachside Bliss

A serene sleeping area features a spacious bed dressed in crisp white linens and accented by a dark throw pillow. Framed artwork adorns the walls, while stylish side tables complement the modern aesthetic. Floor-to-ceiling curtains in a neutral tone add a touch of elegance.

4.85 out of 5 average rating, 86 reviews

Private Newly built Modern East Hampton Apartment!

A vibrant sunset is captured over the Long Island Sound, with rich hues of orange and pink blending into the deep blue water. The shoreline is lined with lush greenery, while the sky is filled with soft, swirling clouds, creating a serene evening scene.

4.98 out of 5 average rating, 44 reviews

Waterfront Greenport Condo

A living area features a pair of black leather sofas positioned around a glass coffee table on a textured rug. A wooden TV stand holds a flat-screen television, with greenery visible in the background. Natural light filters through the window blinds.

4.89 out of 5 average rating, 54 reviews

Quiet idyllic getaway

Apartment rentals with a hot tub

An open-plan living area features a light-colored floor and walls, with a large sectional couch in a soft gray hue arranged around a simple coffee table. A dining table with white chairs is positioned nearby. Natural light illuminates the space, creating a bright atmosphere.

4.75 out of 5 average rating, 4 reviews

Elegant 2BR Beach Condo

A light-filled living area features a comfortable sofa and glass coffee table. A dining table for four is set beside a large artwork depicting calm ocean hues. Sliding doors provide access to the balcony, enhancing the open and airy feel of the space.

5 out of 5 average rating, 8 reviews

Updated 4 Bed, 1 Bedroom Waterfront Condo

A serene waterfront view showcases a private deck adorned with lush greenery and vibrant flowers. A saltwater hot tub and lounge area invite relaxation, while the expansive water stretches into the distance. Comfortable seating arrangements enhance the tranquil outdoor environment.

4.94 out of 5 average rating, 80 reviews

Hamptons Waterfront Escape/ Hot Tub/ Resort Style

4.88 out of 5 average rating, 8 reviews

Apartment in Shirley

A 1 BR home away from home to relax and unwind.

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, 100 reviews

Swimming pool w/Hot tub Fire Pit Coffee Bar

A spacious living area is captured, featuring a large flat-screen television mounted on the wall. A light-colored sofa and two armchairs are arranged around a round coffee table. A dining area with a wooden table and chairs is visible in the background, complemented by a kitchen area.

Oceanview Escape in Montauk

A spacious living area is shown with light-colored wooden flooring. Two comfortable leather sofas face a coffee table, complementing a dining table with black chairs. A well-equipped kitchen is partially visible in the background, illuminated by natural light from multiple windows.

Resort Living in Amagansett

The living area is seen featuring a light-colored sofa and armchair with soft textures. A small table holds decorative items and a woven basket. The kitchenette is visible, equipped with modern appliances and a window that allows natural light to brighten the space.