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Vacation rentals in Southampton

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Top-rated vacation rentals in Southampton

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Cottage in Southampton

4.95 out of 5 average rating, 88 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.

Top guest favorite

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.

Guesthouse in Hampton Bays

4.97 out of 5 average rating, 194 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.

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.

Guesthouse in Southampton

4.95 out of 5 average rating, 442 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 sandy beach extends alongside calm waters, with two white lounge chairs positioned for relaxation. Lush green grass borders the beach, while a distant shoreline showcases trees and buildings under a clear blue sky.

Home in Hampton Bays

5 out of 5 average rating, 128 reviews

Hamptons Waterfront- Great Location- On the bay

Amazing Beachfront vacation home located directly on a private sandy beach on Shinnecock Bay. Stunning waterfront views- sunrises/sunsets. Have a bbq and relax right on the back deck and watch the boats pass by or take a quick walk or shuttle boat to some of the Hamptons best restaurants. No worries about having a drink and getting home. You’ll love my place because of the location and the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids).

Top guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 188 reviews

Secluded Southampton Cottage w/Pool & Spa

*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.

A spacious living area is illuminated by natural light from large windows. A comfortable sofa and armchair are arranged around a low coffee table. A dining table with six chairs sits adjacent, while the kitchen is visible in the background. A staircase leads to the upper floor.

Home in Hampton Bays

4.95 out of 5 average rating, 131 reviews

5BR Hamptons Retreat • Near Beach • Sleeps 10

🌟 Rated 4.95 with over 130 glowing reviews – book with confidence! Escape to this stylish 5BR retreat in the heart of Hampton Bays—just minutes from beaches, dining, and shops. Enjoy open-concept living, a finished basement with a ping pong table, home gym, and a spacious backyard for relaxing or entertaining. Perfect for family getaways or group trips, this modern home offers comfort, convenience, and Hamptons charm. Close to some of the Hamptons' most popular beaches and attractions.

A gravel driveway curves through a manicured green lawn, surrounded by tall trees. A black car is parked to the side, indicating convenient parking. The scene suggests a quiet outdoor environment, enhancing the feeling of seclusion and tranquility.

Cottage in Southampton

4.96 out of 5 average rating, 143 reviews

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

The exterior of the cottage features a charming design with a gray shingle façade. An outdoor patio is equipped with a dining table and black chairs, accompanied by a large umbrella for shade. Light pours in from expansive glass doors, enhancing the inviting atmosphere.

Home in Southampton

4.89 out of 5 average rating, 275 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 –

The gunite pool is surrounded by manicured grass and framed by flowering white hydrangeas. Tall green trees provide a natural backdrop, enhancing the tranquil setting. Clear blue water reflects the sunlight, creating an inviting atmosphere for relaxation and leisure.

Cottage in Southampton

4.97 out of 5 average rating, 32 reviews

Newly Renovated Towd Point Beach Treasure

This stylish modern chic beach home is situated by the waters edge and one of the most idyllic beaches in the Hamptons. Make this home your summer escape and enjoy the cozy interior with brand new furniture throughout, hand selected by a renowned Hamptons interior designer. Outside, relax in the gunite pool or take the scenic walk to the shore. Along Towd Point, you'll find gorgeous beach homes, friendly neighbors, summer vibes and sunsets that will create lifelong memories!

A sandy pathway leads through grass-covered sand dunes towards a tranquil beach, framed by wooden fencing. The calm ocean waves gently lap at the shore under clear skies, inviting moments of relaxation and reflection.

Home in Southampton

4.83 out of 5 average rating, 210 reviews

Chic Southampton Retreat – Near Beaches & Village

Chic & cozy Hamptons retreat just minutes from Southampton Village and beaches! Enjoy a private backyard with sundeck, hot tub, fire pit, outdoor shower, and indoor fireplace. Next door to world-famous Shinnecock Hills Golf Club and 15 mins to Poxabogue public course. Close to Wölffer Estate, Duck Walk, and Channing Daughters wineries. Walk the nearby Scallop Pond Preserve or Elizabeth Morton Wildlife Refuge. Perfect year-round getaway!

A close-up view of a small plant is featured on a wooden surface, with soft natural lighting illuminating its leaves. The background is softly blurred, allowing the greenery to stand out, creating a calming and natural atmosphere.

Home in Southampton

4.96 out of 5 average rating, 171 reviews

Waterview+Pool, FreeForDogs! Kayaks/PingPong/Bikes

Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of the Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

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 Hampton Bays

4.97 out of 5 average rating, 111 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

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Popular amenities for Southampton vacation rentals

Laptop-friendly workspace

Stay near Southampton's top sights

Cooper's Beach, Southampton56 locals recommend

Parrish Art Museum50 locals recommend

Duck Walk Vineyard26 locals recommend

House rentals in Southampton

A contemporary home is depicted with a clear blue pool in the foreground, surrounded by a spacious wooden deck. Lush greenery and autumn foliage frame the property, while sliding glass doors provide views of the interior.

Home in Hampton Bays

4.94 out of 5 average rating, 132 reviews

Peaceful Retreat in Immaculate Architect’s House

An English cottage is featured with a white exterior and multiple windows framed by shrubs and flowering plants. A well-maintained lawn surrounds the house, complemented by tall trees at the edges, creating a serene and inviting setting.

Home in Southampton

4.76 out of 5 average rating, 74 reviews

Southampton Village, Pool, Walkable, Close 2 Beach

Top guest favorite

A spacious living area features a white sectional sofa and leather armchairs, arranged to face large glass doors that provide views of the beach. Natural light fills the room, highlighting warm wood paneling and a cozy, inviting atmosphere. A dining table is visible in the background.

Home in North Fork

5 out of 5 average rating, 13 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

The exterior of a two-story home is visible, featuring large glass windows that promote natural light. A spacious wooden deck hosts a dining area with a white umbrella. Lush green grass and trees surround the area, creating a serene outdoor setting.

Home in Water Mill

4.92 out of 5 average rating, 108 reviews

Elegant Modern Artist's Residence

Top guest favorite

A sunset scene is captured over a sandy landscape, where vibrant shades of orange and pink fill the sky. Silhouettes of beach fencing and grassy dunes are visible in the foreground, complemented by a wooden structure to the right.

Home in Hampton Bays

4.99 out of 5 average rating, 107 reviews

Full House Two miles from the Ocean

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 East Hampton

4.95 out of 5 average rating, 438 reviews

Silver House: 3BR Home with Private Beach Access

A welcoming living area is illuminated by natural light from large windows. A comfortable gray sofa is complemented by light-colored armchairs and a coffee table adorned with books and decorative items. The neutral color palette is accentuated by indoor plants and a textured rug.

Home in Sag Harbor

4.96 out of 5 average rating, 293 reviews

Sag Harbor Cottage, Walk to the Beach!

The outdoor area features a rectangular pool surrounded by a brick patio. Several lounge chairs are arranged around the pool, complemented by a blue umbrella. A two-story house with large windows overlooks the pool, and lush greenery enhances the setting.

Home in Southampton

5 out of 5 average rating, 20 reviews

Walk to the village! Charming modern farmhouse.

Southampton beach vacation rentals

A bright and airy living area is enhanced by large windows allowing natural light to fill the space. A comfortable white sofa is positioned at the center, accompanied by decorative pillows. Two stylish pendant lights hang above, and a coffee table sits atop a textured rug, creating a welcoming atmosphere.

Home in North Fork

5 out of 5 average rating, 3 reviews

Orient cottage in the Village

A charming beach home is showcased, featuring a neatly maintained exterior with an American flag displaying at the front. Greenery surrounds the house, complemented by colorful potted plants and a small stone pathway that leads to the welcoming entrance.

Cottage in Fenwick

4.92 out of 5 average rating, 39 reviews

SeaStar Beach House Old Saybrook

Top guest favorite

A two-story cottage features horizontal siding and a distinctive light blue front door. A large window is positioned above the entrance, allowing natural light to enter. The garage is on the ground level, with a small staircase leading to the entryway.

Cottage in Milford

4.92 out of 5 average rating, 51 reviews

Salty Kisses Beach Cottage Milford CT

An expansive hallway features arched doorways and rustic wooden beams overhead. Potted plants add greenery, while large windows dressed with floral curtains allow natural light to illuminate the stone floor. Comfy seating arrangements are positioned along the walls, creating inviting spaces for relaxation.

Condo in Montauk

4.89 out of 5 average rating, 28 reviews

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

A view of the exterior of the blue house, showcasing a white lattice railing along the patio. Steps lead down to the water, with a calm blue surface reflecting the sky. Potted plants add a touch of greenery to the space.

Home in Guilford

5 out of 5 average rating, 27 reviews

Charming 2BR Beach House, Overlooking the Water

Top guest favorite

A private deck overlooks a tranquil marsh, framed by vibrant flowers in terracotta pots. A shaded seating area includes a couch with cushions and a small table, inviting relaxation while enjoying the serene view of the water and surrounding natural greenery.

Cottage in Branford

4.98 out of 5 average rating, 96 reviews

Enchanted Cottage on the Marsh, walk to beach

Top guest favorite

A charming cottage is set against a backdrop of lush greenery, with a spacious yard framed by trees. A gravel driveway leads to a white garage, while the cottage features a welcoming facade with well-maintained shrubs and a clear blue sky above.

Cottage in Madison

4.94 out of 5 average rating, 33 reviews

Adorable cottage close to beaches and downtown

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, 140 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Beach house rentals in Southampton

A patio overlooks the calm waters of Napeague Harbor, featuring two lounge chairs under large umbrellas. Surrounding plants and flower pots add greenery, while an American flag gently flutters in the breeze. The serene landscape is complemented by distant boats on the water.

Home in Montauk

5 out of 5 average rating, 30 reviews

House on Napeague Harbor, Amagansett

A serene beach scene is captured at sunset, featuring soft, warm hues in the sky blending with the calm water. The sandy shore curves gently along the edge, with distant islands visible on the horizon, creating a peaceful coastal atmosphere.

Home in Sag Harbor

4.95 out of 5 average rating, 20 reviews

Beach Cottage | Steps to Water | Firepit

A spacious living area features a modern sectional sofa adorned with decorative pillows. A large chandelier adds visual interest, while natural light enters through sliding glass doors, revealing a view of the outdoor space. Framed artwork is arranged on the adjacent wall.

Home in Sag Harbor

Newly Renovated Sag Harbor House

The kitchen showcases a modern design with white cabinetry and stainless steel appliances. A wooden dining table is surrounded by red metal chairs, while an open layout is enhanced by natural light streaming through large sliding doors leading to the outdoor space.

Home in Montauk

5 out of 5 average rating, 20 reviews

Family Friendly Designer 3bd Centrally Located

Top guest favorite

A charming cottage is set against a backdrop of lush greenery, featuring a welcoming front porch with a white railing. Natural light illuminates the exterior, showcasing the textured shingle siding and a gabled roof. The grassy area extends toward the tree line, creating a serene atmosphere.

Home in East Hampton

4.95 out of 5 average rating, 233 reviews

Private beach, fully updated house, on 2 acres.

The living room features vaulted cedar ceilings and large windows that allow natural light to fill the space. A stone fireplace serves as a focal point, and a comfortable seating arrangement includes a spacious sofa and stylish armchairs. A coffee table is surrounded by greenery and decorative accents.

Home in Southampton

5 out of 5 average rating, 14 reviews

Lakay-Porte Rouge (Shinnecock hills)of Southampton

A serene pool area is framed by vibrant hydrangeas and lush greenery. The sparkling blue water features two striped floaties. A paved patio extends around the pool, with a charming pergola visible in the background, inviting relaxation amidst the natural setting.

Home in Center Moriches

4.88 out of 5 average rating, 16 reviews

“It’s All Good” Hydrangea Hampton House

A spacious living room features a cozy seating area arranged around a brick fireplace. Exposed wooden beams add character to the high ceiling, while a decorative bookshelf holds various items. Natural light is provided by generous windows, complemented by vibrant artwork on the walls.

Home in Sag Harbor

4.93 out of 5 average rating, 14 reviews

Near Beach & Sag Harbor in the Heart of Hamptons!

Quick stats about vacation rentals in Southampton

Total rentals
640 properties
Nightly prices starting at
ﺩ.ﺇ37 before taxes and fees
Total number of reviews
7.8K reviews
Family-friendly rentals
400 properties are a good fit for families
Pet-friendly rentals
250 properties allow pets
Rentals with a pool
370 properties have a pool

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Southampton?
Yes! Work meets play with ease at over 280 vacation rentals in Southampton featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Southampton?
Experience the best of Southampton with our apartment rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Southampton?
Four-legged friends are welcome in Southampton. Choose from more than 250 vacation rentals for guests traveling with pets.
What are the most popular amenities for Apartment Rentals in Southampton?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with self check-in, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there Southampton house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 300 house rentals with pools in Southampton, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Southampton have a bbq area?
Absolutely! We offer over 150 house rentals with a bbq area in Southampton. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Southampton have a gym?
Absolutely! We offer over 70 house rentals with a gym in Southampton. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Southampton have self check-in?
Absolutely! We offer over 10 apartment rentals with self check-in in Southampton. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Southampton have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Southampton. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Southampton?
Southampton has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore