Vacation rentals in Southampton

4.95 out of 5 average rating, 86 reviews

Modern Southampton Cottage | Heated Pool & Peloton

Modern Hamptons cottage with mid-century modern interior, our 3 bedroom/ 2 bathroom cottage is set on manicured grounds and perfectly equipped for your stay. Heated gunite pool (summer months only) with retractable cover, Peloton bike and Central Air throughout. Newly renovated kitchen with high end appliances, large outdoor deck perfect for entertaining with new Weber grill. Private driveway accommodates 4 cars. 4 adult bicycles. 8 min ride to Southampton village. 15 min to Coopers Beach.

An ornate wrought-iron gate is set within a textured brick archway, leading to a landscaped garden. A brick pathway is visible, lined with greenery. A tall stone planter sits beside the gateway, adding character to the outdoor space.

5 out of 5 average rating, 13 reviews

Southampton Village Near Ocean & Shops - Suite "A"

Our suite "A" features location, location, location! You are so close to everything, you can leave your car behind! Just two blocks from historic Main Street. Ocean beach is less than a mile at the end of the road. Brand new lower level apartment. Private entrance. Enjoy sipping wine outdoors in a private sitting area. Off street parking for one car available. Level 2 EV charger w/J1772 plug available for overnight charging. On the premises for use is a heated gunite pool & outside shower.

Guesthouse in The Hamptons

A private outdoor deck features two lounge chairs facing toward a lawn, accompanied by a round dining table with four chairs and an umbrella for shade. Surrounding greenery provides a serene setting, complemented by wooden siding on the cottage's exterior.

4.97 out of 5 average rating, 190 reviews

WELCOME TO THE LOVE SHACK BY THE SEA

Escape the city, work in nature! Totally private cottage with garden views , central air and heated floors. 1 mile from pristine beaches and center of town, LIRR, Hampton Jitney, 3 large grocery stores, Starbucks, organic market, shopping & restaurants. King bed, cable TV, refrigerator w/ice, microwave, outdoor grill, private yard, Perfect for couples, solo, 1-2 small kids. We welcome small dogs for a $100 fee. Please message us with the size and type. Working couple/owners in main house.

Guesthouse in The Hamptons

A compact kitchen corner features a light blue microwave alongside a silver toaster. A decorative tray displaying a map of the Hamptons adds a local touch to the granite countertop, which reflects the kitchen’s clean, modern design.

4.95 out of 5 average rating, 440 reviews

Tiny Home in Prime Spot in Southampton Village

Located in the heart of Southampton Village, this intimate, centrally-located cottage is the perfect getaway! Nestled in an easily accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station and a 5 min. walk to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet!

A modern dining area is highlighted by an oval black marble table at its center, accompanied by sleek chrome chairs. Soft cushions line a nearby nook, with natural light flooding in through large windows that offer a view of the outdoor surroundings.

4.91 out of 5 average rating, 44 reviews

Summer in the Hamptons! SH Gem mins from the Beach

Welcome to your perfect Hamptons getaway! This sun-filled, architecturally unique home is ideal for a summer retreat or a cozy weekend escape. Offering modern furnishings, and an open floor plan, this space is perfect for small groups. Whether you're enjoying the crisp evenings of early spring, sun-drenched summer days, or the vibrant fall season, this home is a serene escape year-round. Cozy up by the fire, relax on the sun-soaked balconies, or unwind in the beautifully renovated pool house.

A rustic wooden sign reading 'SUMMER COTTAGE' is mounted above an intricately designed metal decoration. The decoration features a symmetrical pattern of swirls and curls, adding detail to the light-colored wooden wall.

4.96 out of 5 average rating, 385 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.

Guesthouse in The Hamptons

An exterior view of a contemporary structure is presented, featuring natural wood siding and neatly trimmed hedges. A stone pathway leads to the entrance, bordered by lush greenery. Soft sunlight illuminates the area, creating a serene atmosphere in the surrounding garden.

4.98 out of 5 average rating, 60 reviews

Southampton Modern Barn, Private Hot Tub and Pool

This magical getaway delivers peace and relaxation. Wake up to coffee on your private deck with bucolic views. Play in your heated, saltwater pool, and relax under the stars in your hot tub (open year round). During your stay, these amenities and more will be for your personal use. Stroll to the owner’s dock on Big Fresh Pond, for paddle boarding, kayaking and sunsets. You can also drive 8 minutes to Southampton Village for shopping, restaurants, art galleries and Ocean Beaches.

The exterior of the cottage is presented, featuring a light wood shingle facade and large glass doors. Two windows above frame a warm interior illuminated against the evening sky. A patio area with a table and chairs is set, accompanied by an umbrella for shade.

4.89 out of 5 average rating, 272 reviews

PICTURE PERFECT SOUTHAMPTON HOME-

Picture Perfect 3 bedroom 1.5 Bath Cottage located in the heart of Southampton. The home is conveniently located close to Southampton, Bridgehampton and Sag Harbor towns. Additionally, there is close access to both Bay and Ocean Beaches. The Newly renovated home gives you a peaceful and serene feeling everyday. Dogs are accepted on a case by case basis. Cats are not permitted. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

A well-maintained outdoor space features a gunite pool with a soothing waterfall. Surrounding greenery provides privacy, while a section of the pool deck is fitted with lounge chairs. Bright sunlight helps illuminate the serene scene.

4.93 out of 5 average rating, 30 reviews

Charming Village home in the heart of Southampton

Designer decorated home in the heart of Southampton Village. Conveniently located minutes to town and ocean beaches, this sun-drenched gem offers a primary ensuite and two guest rooms with shared bathroom. Eat-in kitchen features Viking and Sub-Zero appliances. Dining room is adjacent to the open concept living room. Separate TV room is furnished with a sofa that converts to a double-sized bed. Outdoor oasis is surrounded by mature landscaping and gunite pool with waterfall.

A bathroom countertop showcases a washbasin alongside neatly stacked white towels. A decorative dish holds a bar of Dove soap, while a small bowl displays pink artificial flowers. A bottle of liquid soap and additional items are arranged in a stylish tray.

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 .

A bright, inviting pool with clear blue water reflects the surrounding greenery. The pool is framed by a wooden deck and bordered by shaded trees and garden plants, creating a peaceful outdoor space for relaxation.

4.81 out of 5 average rating, 21 reviews

Enchanting Cottage in the Heart of Southampton Vil

Enchanting Cottage in the Heart of Southampton Village Escape to this delightful cottage nestled in the heart of Southampton Village, offering a perfect blend of charm, comfort, and convenience. Situated just moments away from the beach, restaurants, and entertainment, this retreat boasts private gardens and access to a refreshing pool. 🛏️ Bedrooms: Studio 🛁 Bathrooms: 1 🌳 Outdoor Space: Private gardens 🏊 Pool Access: Available (open MDW -LDW) 🚘 Two Parking Spaces

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.

4.97 out of 5 average rating, 109 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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Popular amenities for Southampton vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Southampton's top sights

Cooper's Beach, Southampton55 locals recommend

Parrish Art Museum49 locals recommend

Duck Walk Vineyard26 locals recommend

Other great vacation rentals in Southampton

A sunlit living area features large windows with views of the tranquil pond. Modern furniture includes comfortable seating and a glass coffee table. Fresh flowers add a touch of color, while a countertop with a decorative bowl sits in the foreground.

5 out of 5 average rating, 32 reviews

Perfect So. Hampton Home on pond Enjoy July 4 now

4.88 out of 5 average rating, 24 reviews

SPA DEPARTURES NEAR THE SEA

A serene outdoor space features a white hammock gently swaying beneath a tree, adjacent to a sparkling salt-water pool. Lush green grass surrounds the pool, and neatly trimmed hedges provide privacy, creating a tranquil environment for relaxation.

4.94 out of 5 average rating, 17 reviews

Designer Home w/ Heated, Salt-Water Pool

A spacious living area features large glass doors that open to a waterfront deck, allowing for ample natural light. A comfortable lounge area is complemented by soft decorative cushions. A dining table, seating six, is positioned nearby, enhancing the space's functionality.

5 out of 5 average rating, 10 reviews

Waterfront home next to the beach in Southampton !

4.9 out of 5 average rating, 59 reviews

Bay View Cottage- Short Walk to Private Beaches

An inviting outdoor space features a blue swimming pool surrounded by a well-manicured lawn. A spacious deck is equipped with comfortable seating and a grill. The two-story home is visible in the background, framed by trees and shrubs.

4.97 out of 5 average rating, 106 reviews

Southampton beach cottage with pool- open in May

A shared balcony area is presented with multiple seating options, including a large sectional sofa and individual chairs, all arranged around a coffee table. Decorative cushions add comfort, while green plants provide subtle natural touches amidst a backdrop of nearby greenery.

5 out of 5 average rating, 8 reviews

Southampton apt walk to village

A spacious wooden deck is featured, adorned with a large picnic table and benches. The deck offers a view of the surrounding trees, creating a calm outdoor space for relaxation. The weathered wood adds a rustic charm to the area.