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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, 87 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, 193 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, 441 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!

An open-concept living area features large windows allowing ample natural light. A spacious white sectional sofa, a wooden coffee table, and a fireplace create a relaxed setting. The decor includes artwork on the walls and a view of outdoor greenery visible through glass doors.

Home in Southampton

4.91 out of 5 average rating, 47 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 simple entry table made of light wood features a smooth marble surface. A decorative white conch shell is placed alongside stacks of books, topped by a glass vase holding fresh white flowers. A large, round mirror with a rope design hangs on the wall above.

Villa in Southampton

4.95 out of 5 average rating, 60 reviews

Just renovated Southampton retreat w/ heated pool

JUST RENOVATED! INQUIRE ABOUT MONTHLY RENTALS! Come and enjoy with family and friends your own beautiful house in Southampton. 5-minute drive to Cooper’s Beach and to Southampton Village. Enjoy beautiful ocean beaches, have brunch in the Village, swim in your 32’ heated salt water pool, enjoy a BBQ on your patio under the shadow of a Japanese Maple, indulge in a quiet evening with a book by the fireplace, or take advantage of the home office while your family & friends enjoy the property.

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 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 –

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.

Home in Southampton

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.

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 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.

Cottage in Southampton

4.84 out of 5 average rating, 25 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 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.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

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

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.

Home in Southampton

5 out of 5 average rating, 32 reviews

Perfect So. Hampton Home on pond Enjoy July 4 now

LucreciaRating, 5 stars9 months ago

We had a great time at Denise's house. The house is lovely , the garden and the pond are super relaxing and very nice , it gives the house a different touch. It is 5 min drive from Southampton Main Street

Cottage in Southampton

4.88 out of 5 average rating, 24 reviews

SPA DEPARTURES NEAR THE SEA

BrettRating, 5 stars4 weeks ago

Amy was fantastic from start to finish. The house has four good bedrooms. The bottom floor is very private. Great kitchen and we loved the fact there were cooking basics like olive oil, spices, etc all there.

A light-filled living area features a comfortable sectional sofa with decorative pillows. A coffee table rests on a textured area rug, accompanied by framed art on the white walls. Natural light enters through a window overlooking greenery, accentuating a serene environment.

Apartment in Southampton

4.89 out of 5 average rating, 38 reviews

Spacious One Bedroom Apartment, Close to Beaches

SenRating, 5 stars4 days ago

Rarely is it the case that an Airbnb blows away your expectations, but that is the case with this one. Spacious, clean, beautiful, quiet. Would highly recommend and we would love to come again!

Top guest favorite

An outdoor patio area features a wooden dining table surrounded by six white chairs, ideal for al fresco meals. A charcoal grill is situated nearby, along with lounge chairs, all framed by well-maintained greenery and expansive views of Gardiner's Bay under a clear blue sky.

Home in North Fork

5 out of 5 average rating, 13 reviews

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

SamanthaRating, 5 stars1 month ago

Can not recommend more! Beautiful house and perfect location! Would love to come back. Kids loved the beach and finding shells and little sea creatures in low tide!

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.

Apartment in Southampton

5 out of 5 average rating, 8 reviews

Southampton apt walk to village

RoshniRating, 5 stars2 weeks ago

Had a lovely stay! Beautiful apartment with private entrance. The living spaces, bathroom, kitchen and bedroom were modern, very clean and had all the necessary amenities for a comfortable stay. The place is within walking distance of the train station and village. Would absolutely stay here again.

A modern living area is presented with a spacious gray sectional sofa facing a wall-mounted television. Light-colored walls enhance the open feel, while natural light streams through large windows. A small chair and a coffee table add to the welcoming atmosphere.

Home in Southampton

4.97 out of 5 average rating, 29 reviews

Minutes from the beach, brand new 4 bedroom

DylanRating, 5 stars4 days ago

Thomas was super responsive and a pleasure to interact with. His home was lovely and the perfect house for my girlfriends!

A serene beach view is captured at sunset, with the sun positioned low on the horizon over the gentle waves of the water. The sandy path, framed by grassy edges, leads towards the pebbled shoreline.

Cottage in Sag Harbor

4.95 out of 5 average rating, 80 reviews

Steps to the Beach - Designer Cove House Cottage

KarinRating, 5 stars2 weeks ago

The house was great. Perfect location. The house is decorated beautifully. Perfect for a small group or family. Right across from Long Beach. If you don’t know the Hamptons, this is a big deal. To park at any beach, you need to have a parking permit only issued to home owners. A lot of people come out thinking they will spend their weekend at the beach and get very frustrated when that can’t happen. This location is perfect because you can walk to the beach, no sticker or parking needed and it’s the Bay which is much better for children.

An outdoor seating area is presented on a stone patio, featuring a wooden dining table surrounded by six chairs. A green lounge area with two cushions offers relaxation under a canopy of greenery. A metal fire pit is positioned centrally on the patio.

Home in Southampton

4.95 out of 5 average rating, 55 reviews

Scandinavian Cottage

SophieRating, 5 stars2 weeks ago

We enjoyed our stay at Cosmo’s place. It was exactly as described, clean, and clutter-free. We were in The Hamptons for work, so it was great with Wi-Fi and the ability to cook. We also found the location very convenient and easy to find, and we would love to rent Cosmo’s place next time we find ourselves in The Hamptons!

Quick stats about vacation rentals in Southampton

Total rentals
640 properties
Nightly prices starting at
$10 USD 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