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Vacation rentals in Southampton

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Top-rated vacation rentals in Southampton

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

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A private outdoor space is showcased with a wooden deck, featuring two lounge chairs and a dining table shaded by an umbrella. Potted flowers add color, while a path leads through the well-maintained garden, enhancing the serene atmosphere of the yard.

Guesthouse in Hampton Bays

4.97 out of 5 average rating, 198 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 heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.

Home in Hampton Bays

4.96 out of 5 average rating, 111 reviews

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

Stylish+Modern Cape Beach House nestled in Hampton Bays South of the highway, 5 min drive to beaches. Heated Saltwater Pool. 4 Bedrooms+Crib room & Office. 2 Bathrooms. Outdoor deck w/family dining+BBQ. Fully fenced tree-lined back yard w/ beautiful sunsets. Upstairs King bedroom w/ensuite bthrm + Twin bedroom directly off master. Main floor has another King bedroom+Twin bedroom, master bath, lounge+kitchen w/huge sit-around island. TV Den. Central AC. 15 min walk/ 2 min drive to shops+train.

A cozy living space features a brown leather sofa and a white coffee table on a geometric patterned rug. A large window allows natural light to fill the room, showcasing a wall-mounted fish decor and colorful accents. A decorative plant sits on the table.

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 serene waterfront view features a sailboat gliding across calm waters. Lush green grass borders the shoreline, reflecting the tranquility of the environment. The clear blue sky stretches overhead, enhancing the peaceful atmosphere of the setting.

Home in Hampton Bays

5 out of 5 average rating, 129 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

A charming cottage is framed by lush greenery and well-maintained landscaping. The light-colored exterior features large windows and a welcoming green door. A stone walkway leads to the entrance, while a gravel driveway curves around, enhancing the natural setting.

Cottage in Southampton

4.96 out of 5 average rating, 193 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.

Top guest favorite

Apartment in Hampton Bays

4.96 out of 5 average rating, 391 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.

The airy living space features white shiplap walls and a high ceiling, accented by natural light from multiple windows. A gray sofa is paired with a glass coffee table, while a decorative fireplace adds charm. A ceiling fan provides airflow, 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 –

Top guest favorite

A charming cottage exterior features wood shingles and white trim. An American flag hangs proudly from the front, while window boxes with greenery add a touch of color. The light blue front door complements the natural elements, inviting guests inside.

Home in Westhampton Beach

4.99 out of 5 average rating, 142 reviews

Luxury Hamptons Home with Heated Saltwater Pool

Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.

The living area is characterized by high vaulted ceilings and large windows allowing natural light. A sofa with light cushions is centered around a wooden coffee table on a neutral rug. A decorative fireplace is framed with a modern mantle, adding warmth to the space.

Home in Southampton

4.83 out of 5 average rating, 212 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!

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, 112 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 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, 294 reviews

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

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

Southampton beach vacation rentals

A spacious living room features wooden beams across the ceiling and a cozy seating area around a brick fireplace. Various artworks adorn the walls, while a central coffee table is surrounded by small plants and decorative items. A bookshelf displays a selection of books.

Home in Sag Harbor

Summer Deal!

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.

Apartment in North Fork

4.94 out of 5 average rating, 103 reviews

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

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

4.9 out of 5 average rating, 31 reviews

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

An outdoor dining area is visible, featuring a glass-top table surrounded by six chairs beneath a large umbrella. A grill sits nearby, with a view of the water and lush greenery in the background, creating a relaxing setting for meals and gatherings.

Home in Hampton Bays

4.98 out of 5 average rating, 113 reviews

Hamptons Beachfront- Relax & Getaway- On the bay

Top guest favorite

A bright bedroom is complemented by natural light from windows with soft beige blinds. A spacious bed with white bedding and a decorative pillow is positioned against the wall. A bedside table holds a small stack of books, and a door leads to a grassy outdoor area.

Private room in Sag Harbor

5 out of 5 average rating, 33 reviews

Designer bedroom in the heart of the Hamptons

A serene beach scene is depicted with soft waves lapping against the shore. The horizon showcases a gradient of warm colors as the sun sets, creating a tranquil atmosphere over the water. A sandy beach extends along the coast, leading to distant islands.

Home in Sag Harbor

5 out of 5 average rating, 11 reviews

Oh Buoy! Charming Cottage Steps to Beach | Firepit

Top guest favorite

A spacious deck features white lounge chairs and a circular dining table surrounded by seating. A large umbrella provides shade. The serene view overlooks Shinnecock Bay and captures distant boats on the water, creating a relaxing outdoor space.

Home in Hampton Bays

4.96 out of 5 average rating, 51 reviews

Hamptons Beach House- Sun, Sand & Relax-Beachfront

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, 143 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Southampton house rentals

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

A modern home is showcased with a unique angular design, featuring a combination of wood and glass. The surrounding lawn is spacious and well-maintained, with natural landscaping, including grasses and a small tree, contributing to the serene outdoor setting.

Home in East Hampton

4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

A welcoming living area features a comfortable sofa adorned with coral-patterned pillows. A rustic coffee table sits at the center, surrounded by natural light from large windows. A view of the open space and kitchen area can be seen in the background.

Home in Sag Harbor

4.97 out of 5 average rating, 149 reviews

Relax into Coastal Life at a Sun-Drenched Sag Harbor Home

An outdoor dining area features a wooden table surrounded by several chairs, set on a gravel surface. A large umbrella provides shade, while lush greenery lines the background, enhancing the spacious fenced yard.

Home in Southampton

4.97 out of 5 average rating, 32 reviews

Minutes from the beach, brand new 4 bedroom

A covered patio area showcases comfortable outdoor seating, with a soft-toned sectional sofa facing the water. Lounge chairs are positioned nearby, offering unobstructed views of the tranquil ocean under a cloudy sky. The deck is lined with protective railings for safety.

Home in Hampton Bays

4.85 out of 5 average rating, 79 reviews

Hamptons Oceanfront Oasis

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, 442 reviews

Silver House: 3BR Home with Private Beach Access

An outdoor patio features multiple wooden lounge chairs arranged around a central fire pit. A gunite pool with clear water reflects the surrounding greenery. The main house, visible in the background, showcases a classic design with white siding and large windows.

Home in Sag Harbor

4.86 out of 5 average rating, 270 reviews

Exclusive Sag Harbor Compound

An inviting outdoor seating area features multiple lounge chairs and a central table surrounded by manicured grass. A heated inground pool is visible in the background, framed by lush greenery and a blue sky. Colorful cushions add a touch of comfort to the space.

Home in Southampton

5 out of 5 average rating, 7 reviews

Perfect SouthHampton getaway

Beach house rentals in Southampton

Two striped armchairs are positioned beside a small round table. A vase filled with sunflowers rests on the table, adding a touch of color. Light filters through a window adorned with sheer curtains, creating a relaxed and inviting space.

Home in North Fork

Orient Country Home

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 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| Fireplace|Firepit

Aerial view of a waterfront community features several quaint houses along a serene creek. Lush greenery surrounds the area, with water gently reflecting the sky. A dock extends into the water, offering access for outdoor activities.

Home in Southampton

Roy's Cottage

A hot tub is featured with luminous blue lighting, casting an ethereal glow over the bubbling water. The water jets create dynamic patterns as the surface ripples, inviting relaxation. The surrounding deck area is visible, enhancing the outdoor ambiance.

Home in Hampton Bays

5 out of 5 average rating, 31 reviews

Beach House -Walk to Beach -Live Band -Hot Tub

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, 237 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 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
650 properties
Nightly prices starting at
R179 ZAR before taxes and fees
Total number of reviews
8.1K reviews
Family-friendly rentals
420 properties are a good fit for families
Pet-friendly rentals
270 properties allow pets
Rentals with a pool
380 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 290 vacation rentals in Southampton featuring dedicated workspaces. Stay connected and productive 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 270 vacation rentals for guests traveling with pets.
Are there Southampton vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 380 vacation homes with pools in Southampton, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in house rentals in Southampton?
Experience the best of Southampton with our house rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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 house rentals in Southampton have self check-in?
Absolutely! We offer over 80 house rentals with self check-in in Southampton. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Southampton?
Enhance your stay in our House Rentals with the most popular amenities: over 70 homes with a gym, over 150 homes with a bbq area, over 80 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore