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Vacation rentals in Southampton

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Quick stats about vacation rentals in Southampton

  • Total vacation rentals

    Explore 610 vacation rentals in Southampton

  • Nightly prices starting at

    Southampton vacation rentals start at G$14,645 GYD per night before taxes and fees

  • Verified guest reviews

    Over 8,940 verified reviews to help you choose

  • Family-friendly vacation rentals

    530 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 240 rentals that welcome pets

  • Vacation rentals with a pool

    450 properties feature pools

  • Rentals with dedicated workspaces

    370 properties have a dedicated workspace

  • Wi-Fi availability

    590 of Southampton vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Southampton rentals

  • 4.9 Average rating

    Southampton stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Southampton

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

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Guest favorite
A spacious living area features a large sectional sofa arranged around an inviting coffee table. Natural light fills the room through multiple windows, highlighting a minimalist design with neutral tones and carefully placed decorative elements. A staircase leads to the upper level, creating an airy ambiance.
Home in Shinnecock Hills

Modern Southampton home, heated pool, pickleball

A modern style and freshly renovated Southampton home with waterfront views. 5 minutes from Southampton village & Coopers Beach. The house features 5 bedrooms, 4 bathrooms, including 2 ensuites. Brand-new kitchen with large Restoration Hardware dining table that seats 12 (+8 around the oversized counter). Expertly styled. Two fireplaces. Perfect for couples and/or families (equipped with 2 cribs, pack and play,xl playpen,toys,high chair). Total beach vibes with a heated pool and new patio area.

ValueFamilyBackyard

4.96 out of 5 average rating, 55 reviews
Guest favorite
Home in Shinnecock Hills

Chic Southampton Home. Mins to Village and 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.

ValueFamilyView

4.87 out of 5 average rating, 79 reviews
Guest favorite
A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.
Home in Mattituck

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

LocationFamilyCheckout

4.93 out of 5 average rating, 138 reviews
Guest favorite
A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.
Home in Hampton Bays

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views and sunset from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Our pool will close on September 15th, 2026 and will reopen May 29, 2027.

LocationFamilyGetting around

4.87 out of 5 average rating, 141 reviews
Top guest favorite
Home in Southampton

Brand New Sun Filled Home

OUR HOUSE A beautiful newly renovated Southampton two story home with spectacular light, offering the best of indoor-outdoor living. A large deck off of the kitchen with small porches off of two primary suites and a small sitting area off the first floor junior suite. On almost one acre of land, there is plenty of peaceful space. Very central - two miles from the beach and town. Two car garage with built in electric vehicle charger. Gas fireplace. All appliances are brand new.

LocationFamilyLong stay

4.96 out of 5 average rating, 24 reviews
Top guest favorite
A cozy living area features a comfortable sofa adorned with neutral-toned cushions. A large television is mounted on the wall. Natural light filters through multiple windows, brightening the space. A small side table and an armchair complement the seating arrangement, creating an inviting atmosphere.
Apartment in Southampton

Southampton apt walk to village

Enjoy easy access to everything from this perfectly located apartment in Southampton Village. You are just a 10-minute walk to downtown and 1.5 miles to our glorious village beaches. We are centrally located to all of the Hamptons, Sag Harbor, Montauk, and the North Fork. Ideal for nature lovers, our garden is a pollinator sanctuary home to birds, 🐝, 🦋, and other wildlife. We love pets, so your furry baby is welcome!

ValueLocationHospitality

5.0 out of 5 average rating, 47 reviews
Guest favorite
A well-maintained outdoor pool area is surrounded by a wooden deck and lush greenery. Lounge chairs are positioned along the pool, with a shaded area provided by a large tree. The clear blue water of the pool reflects the sunlight, inviting relaxation.
Home in Water Mill

Astounding Watermill 5 Bedroom home with Pool

Situated off of a quiet lane on a half-acre of land, updated, modern residence offers a peaceful and quiet Hamptons getaway. 5 bedrooms / 3 modern bathrooms offers a relaxing escape. Large open kitchen leads out to the back garden, pool and indoor-outdoor eating areas. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

ValueLocationIndoor spaces

4.94 out of 5 average rating, 167 reviews
Guest favorite
Home in Water Mill

Beach Barn w/ Heated Pool & Sauna - Dog Friendly

@WaterMillBeachBarn Dog friendly (upon approval) Hampton Beach Barn with pool and infrared sauna. POOL OPEN - May 1st - October 23, 2026 This impressive house, nestled within a rustic, woodland plot, promises a tranquil stay. Eclectic designer decor is complemented by striking rustic touches, such as Dutch-style farm doors, exposed beams, and vintage wood-burning stove.

LocationValueGetting around

4.93 out of 5 average rating, 143 reviews
Guest favorite
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.
Apartment in Shinnecock Hills

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

LocationValueBathroom

4.95 out of 5 average rating, 244 reviews
Guest favorite
A solar-heated pool is surrounded by a spacious bluestone patio, offering various lounge chairs and shaded areas. A brick fireplace is visible alongside a dining space, all framed by mature landscaping and trees, enhancing the outdoor relaxation experience.
Home in Shinnecock Hills

Dream Home with a wonderful heated pool in SH

Situated on a half-acre of land, this designer, updated, modern residence offers a peaceful and quiet Hamptons getaway. 4 wonderful bedrooms 3 modern bathrooms and a solar heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

LocationFamilyLaundry

4.96 out of 5 average rating, 225 reviews
Guest favorite
A bright and airy outdoor space features a long pool bordered by lounge chairs and greenery. The white house stands in the background, with large windows reflecting the blue sky. An umbrella provides shade beside the pool, promoting relaxation.
Home in Shinnecock Hills

Luxe Southampton Home w/Pool 5 Min To Town & Beach

Enjoy a stylish experience at this centrally-located home. Modern, spacious, airy home with 3 Bedrooms and 3 Bathrooms. Beautiful pool and deck with BBQ. Only 5 minute drive to Southampton Village and Cooper Beach. The perfect Summer escape. Pool is OPEN from May 1st until end of September. Pool is not heated.

LocationValueDecor

4.98 out of 5 average rating, 61 reviews
Top guest favorite
Apartment in Southampton

Oasis Hampton getaway

Located in the heart of southampton. 3miles away from main shopping areas.Room is newly remodeled and furnished . All upscale Ammenities. Electric toilet ,free WiFi, free Netflix , use of pool and bbq grill, fire pit, living room with 52”flat screen tv, kitchenette and dining area and driveway parking .

LocationValueKitchen

4.9 out of 5 average rating, 130 reviews

Popular amenities for Southampton vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

Stay near Southampton's top sights

Cooper's Beach, Southampton

237 locals recommend

Parrish Art Museum

326 locals recommend

Duck Walk Vineyard

103 locals recommend

Southampton Arts Center

50 locals recommend

Agawam Park

50 locals recommend

Hank's Pumpkintown

43 locals recommend

House rentals in Southampton

Top guest favorite
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

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

FamilyValueCondition

4.97 out of 5 average rating, 156 reviews
Guest favorite
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

Sag Harbor Cottage, Walk to the Beach!

FamilyLocationLaundry

4.95 out of 5 average rating, 324 reviews
Guest favorite
Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

LocationValueWalkability

4.96 out of 5 average rating, 187 reviews
Guest favorite
Home in Southampton

Southampton Village Escape

FamilyLocationWalkability

4.91 out of 5 average rating, 11 reviews
Top guest favorite
Home in Southampton

Charming House In The Village

LocationFamilyBathroom

5.0 out of 5 average rating, 50 reviews
Guest favorite
A sparkling pool reflects the clear blue sky, surrounded by a sleek stone patio. Lounge chairs are positioned nearby, inviting relaxation. Lush greenery and vibrant gardens frame the space, enhancing the private outdoor setting.
Home in Shinnecock Hills

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

LocationFamilyIndoor spaces

4.98 out of 5 average rating, 55 reviews
Guest favorite
A spacious backyard is highlighted by a large in-ground pool featuring a floating toy. Surrounding the pool are several lounge chairs on a tiled patio. A gazebo sits to the left, framed by meticulously maintained greenery, creating a serene outdoor entertaining area.
Home in Southampton

Home in the Village Home w/Fenced in Pool

LocationFamilyQuiet

4.95 out of 5 average rating, 78 reviews
Superhost
Home in Southampton

Southampton Village - Walk to Train

LocationBathroomKitchen

5.0 out of 5 average rating, 3 reviews

Other great vacation rentals in Southampton

Guest favorite
A heated salt water pool is surrounded by a stone patio, reflecting sunlight on its clear surface. A Japanese Maple tree provides shade along one edge, enhancing the serene outdoor space. Lush green grass and a white fence enclose the area, creating a private setting.
Villa in Shinnecock Hills

Just renovated Southampton retreat w/ heated pool

ValueFamilyPets

4.95 out of 5 average rating, 87 reviews
Guest favorite
A serene outdoor space showcases a heated saltwater pool framed by neatly trimmed hedges. Comfortable lounge chairs are arranged beside the water, while a large umbrella provides shade. A two-story house is visible in the background, surrounded by greenery.
Guesthouse in Southampton

3 Bedroom Guest House in Southampton

FamilyLocationOutdoor spaces

4.96 out of 5 average rating, 23 reviews
Top guest favorite
A spacious lawn is bordered by tall trees, providing a natural frame for the cottage. The vibrant green grass leads to a serene waterfront, where the lake reflects the sunlight. The peaceful setting invites relaxation and outdoor activities.
Cottage in Water Mill

Head of Pond House - Waterfront Cottage

FamilyLocationView

4.98 out of 5 average rating, 80 reviews
Top guest favorite
Cottage in Sag Harbor

Hamptons Waterfront Getaway – Stylish & Serene

FamilyLocationQuiet

5.0 out of 5 average rating, 18 reviews
Guest favorite
A bright living room is featured with a large flat-screen television mounted above a modern fireplace. A bay window offers views of greenery, complemented by a cozy seating area. Elegant decor includes a stylish mirror and a decorative table, enhancing the inviting ambiance.
Cottage in Southampton

SPA DEPARTURES NEAR THE SEA

FamilyValueView

4.88 out of 5 average rating, 32 reviews
Guest favorite
Cottage in Hampton Bays

Swim into Fall & Hot Tub through Winter!

LocationFamilyAmenities

5.0 out of 5 average rating, 15 reviews
Luxe
An aerial view of the Mid Century Modern home is showcased, surrounded by lush greenery. The spacious yard features a heated pool, deck chairs, and a large checkered game board. A shaded seating area is positioned nearby, offering a perfect gathering spot amidst the natural landscape.
Villa in East Hampton

Luxe|Pool|Games|Movie|HotTub|Firepit|MegaChess

ValueLocationAmenities

4.99 out of 5 average rating, 70 reviews
Top guest favorite
Home in Hampton Bays

Walk to Beach | Rooftop Bay Views |Fully Fenced In

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 7 reviews

When is the best time to visit Southampton?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$138,086 GYDG$128,671 GYDG$122,813 GYDG$134,947 GYDG$190,809 GYDG$235,373 GYDG$192,692 GYDG$209,012 GYDG$140,387 GYDG$115,071 GYDG$125,323 GYDG$125,114 GYD
Avg. temp0°C1°C4°C10°C15°C21°C24°C23°C19°C13°C8°C3°C

Frequently Asked Questions

  • What are the best places to stay in Southampton?

    Vacation rentals near the beach, village area, and residential neighborhoods are frequently suggested. Many homes have easy access to local shops, green spaces, and coastal walks.

  • What are the best things to do in Southampton with kids?

    Kids often enjoy exhibits at the Children’s Museum of the East End, beach outings, and biking village paths. Seasonal events, local playgrounds, and parks add to the family fun.

  • What are some of the best things to do in Southampton?

    Enjoy the sandy stretches at Coopers Beach, browse local art at Southampton Arts Center, and learn history at the Southampton Historical Museum. In summer, farm stands and outdoor markets are frequently suggested stops.

  • How is the weather in Southampton?

    Southampton has chilly winters around 25–44°F (-4–7°C) with frequent rain, and warm summers near 66–83°F (19–28°C) with coastal breezes. Spring and fall have mild temperatures; bring layers for changing conditions.

  • When is the best time to visit Southampton?

    Late spring through early fall is often recommended for warmer beach weather, outdoor events, and lively markets. Off-season months have a quieter atmosphere and mild coastal walks.

  • What are the best places to visit in Southampton?

    Coopers Beach is often recommended for its sandy shoreline, and the Southampton Historical Museum shares local heritage. The Parrish Art Museum draws visitors with regional and contemporary art exhibits.

  • What are some hiking trails in Southampton?

    Explore shaded woodland trails at the Downs, stroll through nature on the Great Peconic Bay trails, or hike coastal paths around Mashashimuet Park. These areas have a mix of forest, beach, and freshwater views.

  • What are some family activities we can do in Southampton?

    Families often explore the Children’s Museum of the East End, play in park areas, and visit local farms for fresh produce and seasonal events. Beach days, mini-golf, and bike rides are frequently recommended.

  • What are some of the best day trip ideas from Southampton?

    Explore vineyard tours around Long Island, stroll antique shops in Sag Harbor, or enjoy nature preserves in nearby towns. Art museums and waterfront villages around the Hamptons region are frequently suggested.

  • Are there any pet friendly accommodations available in Southampton?

    Southampton has many vacation rentals that welcome pets, especially near the beach and in residential neighborhoods. Look for listings with outdoor spaces or walking paths nearby.

  • What are some local tips for visiting Southampton?

    Consider visiting farm stands early for fresh selections, use bikes to explore scenic local neighborhoods, and check village calendars for markets or arts events. Beaches can be busiest in summer, so arrive early for quieter moments.

  • What is Southampton known for?

    Southampton is known for its scenic beaches, vibrant arts scene, and historic districts. Visitors often explore elegant estates, local galleries, and areas shaped by maritime history.

  • What are the best hidden gems to explore in Southampton?

    Discover small art galleries tucked along village streets, quiet nature trails at Mashashimuet Park, and garden walks at the historic Rogers Mansion. Local bookshops and farm stands around Southampton invite relaxed browsing.

  • What are the best foods to try in Southampton?

    Seasonal seafood, farm-fresh produce, and classic local pies are frequently suggested. Many visitors also enjoy lobster rolls, clam chowder, and baked goods from neighborhood bakeries.

  • What should I bring for a trip to Southampton?

    Pack layers for changing coastal weather, comfortable shoes for exploring beaches and villages, and sun protection for outdoor activities. Consider bringing a rain jacket and reusable water bottle.

  • What is the nightlife in Southampton like?

    Southampton has a mix of relaxed lounges, music bars, and restaurants that fill up in summer. Village hotspots host live entertainment, while waterfront spots have outdoor patios and local wines.

  • What are the most popular events or festivals in Southampton?

    Southampton has arts fairs and seasonal film festivals, with farmers markets blooming in late spring and music events often filling summer weekends. Holiday parades and cultural celebrations are highlights around the village.

  • Are there family friendly vacation rentals in Southampton?

    Southampton has many family-friendly vacation rentals, especially around quiet neighborhoods and near beaches. Look for homes with spacious yards, multiple bedrooms, or easy access to parks.

Destinations to explore