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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$14,644 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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Top guest favorite
Home in Southampton

Charming House In The Village

Keep it simple at this peaceful and centrally-located place in the Heart of Southampton Village Escape to this delightful house nestled in the heart of Southampton Village, offering a perfect blend of charm, comfort, and convenience. Situated just moments away from the beach, and walking distance to restaurants and entertainment. 🏠 Entire First Floor (Private) 🛏️ Bedrooms: 2
🛁 Bathrooms: 1
🌳 Outdoor Space: Private Garden 
🔥 Fire Pit and BBQ 🚘 Two Parking Spaces 👨‍🍳 Fully Stocked Kitchen

5.0 out of 5 average rating, 52 reviews
Guest favorite
An open-concept living space features a modern dining area with a wooden table set for six, complemented by sleek metallic chairs. A comfortable sectional sofa is positioned across from a wall-mounted television, with a fireplace and green outdoor views visible through large windows.
Cottage in Bridgehampton

Calf Creek Cottage (Water Mill/Bridgehampton)

Enjoy the peaceful seclusion of this charming, updated 3 bedroom, 2 bath cottage located on a private, acre-sized flag-lot south of the highway right on the border of Water Mill and Bridgehampton. Each bedroom (1 king, 2 queen) features ample closet space and new smart TVs . The new, fully-stocked kitchen, propane BBQ, outdoor dining table for 8, outdoor shower and spa with lounge furniture, and wood burning fireplace make it the perfect getaway for either summer or the winter season. Pets OK.

4.95 out of 5 average rating, 110 reviews
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 Cozy Cape - 5 min 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.

4.97 out of 5 average rating, 159 reviews
Guest favorite
The exterior of a modern two-story home features a sleek white facade with large windows allowing for ample natural light. A covered porch provides a welcoming entrance, alongside neatly arranged greenery and stone pathway leading to the front door.
Home in Southampton

Southampton Village Newly Built Gem

Enjoy a stylish experience at this 3765+ sq ft., just built, SH Village gem! Beautiful and bright spacious home with 5 well appointed bedrooms, multiple custom closets and 5.5 baths (4 ensuite). Luxurious lighting fixtures throughout the home. Living room fireplace, vaulted wooden beam kitchen ceiling with formal dining for 10 plus. Gunite pool and spa, with multiple outdoor seating areas. Expansive media room with 75 inch TV and room length comfy cloud sofa. Two sets of washers and dryers.

4.97 out of 5 average rating, 103 reviews
Top guest favorite
A calm waterfront scene shows a serene body of water reflecting the sky. A sandy beach is visible, framed by natural vegetation, with a wooden barrier along the shoreline. The peaceful setting invites relaxation and enjoyment of the outdoors.
Apartment in Hampton Bays

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.

4.97 out of 5 average rating, 449 reviews
Guest favorite
A spacious backyard is framed by mature trees, featuring a fire pit surrounded by white Adirondack chairs. A children’s playground with swing set is visible nearby, while the home, illuminated by warm lights, stands invitingly in the background.
Villa in Southampton

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge

[FOLLOW US on INSTA @29watersedge] 1-mile from the beach, this child-friendly waterfront Southampton home is a perfect family getaway. Ready for watersports: kayak, paddleboard, boat, or jet ski. Walk down to the beach for a swim in the bay. At home, the backyard has it all: large dock, fire pit, swing/playset, hammock, grill, & oversized deck to take in the views. Surrounded by nature and water, you are just minutes from restaurants and shopping in Southampton Village &Sag Harbor.

5.0 out of 5 average rating, 117 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.

4.87 out of 5 average rating, 144 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.

4.96 out of 5 average rating, 25 reviews
Superhost
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

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 –

4.89 out of 5 average rating, 312 reviews
Guest favorite
A spacious backyard is showcased with a large saltwater pool, featuring a floating inflatable and sun loungers arranged along the edge. The house stands in the background, framed by trees and an inviting grassy area, enclosed by a black fence.
Home in Hampton Bays

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

Unwind in Hamptons Bliss! A coastal oasis awaits at this exquisite vacation house. Immerse yourself in luxury, from the elegant interiors to the serene outdoor retreat including a massive fenced-in salt water heated pool (Memorial Day to Labor Day) that will leave you in awe. Indulge in beachside bliss, upscale shopping, and culinary delights. Create memories that will linger long after the sun sets over the horizon. Your dream Hamptons getaway starts here!

4.94 out of 5 average rating, 119 reviews
Guest favorite
A serene view of calm water featuring kayakers enjoying a sunny day. The distant shoreline is dotted with houses, creating a relaxed coastal atmosphere. Clear blue skies reflect on the water, enhancing the peaceful scene.
Home in Shinnecock Hills

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong

Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of 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.

4.95 out of 5 average rating, 206 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

4.95 out of 5 average rating, 244 reviews

Popular amenities for Southampton vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

Stay near Southampton's top sights

Cooper's Beach, Southampton

242 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 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

Luxury Hamptons Home with Heated Saltwater Pool

4.98 out of 5 average rating, 179 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!

4.95 out of 5 average rating, 325 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

4.94 out of 5 average rating, 139 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

4.94 out of 5 average rating, 167 reviews
Superhost
Home in Southampton

Southampton Village, Oversized Pool, Walk to All

4.71 out of 5 average rating, 85 reviews
Guest favorite
A large outdoor pool is surrounded by lounge chairs and umbrellas, inviting relaxation. Well-maintained gardens and trees frame the area, with a spacious deck along one side. The bright blue sky enhances the tranquil atmosphere of this inviting outdoor retreat.
Home in Shinnecock Hills

Spectacular Southampton Retreat!

4.95 out of 5 average rating, 62 reviews
Guest favorite
Home in Shinnecock Hills

Chic Southampton Home. Mins to Village and Beach!

4.86 out of 5 average rating, 80 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

4.98 out of 5 average rating, 62 reviews

Other great vacation rentals in Southampton

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

5.0 out of 5 average rating, 47 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

4.98 out of 5 average rating, 80 reviews
Guest favorite
An outdoor seating area features a round black table accompanied by a chair with a cushion. The tiny house is visible in the background, showcasing its modern black exterior and large windows, surrounded by trees and a gravel landscape.
Tiny home in Southampton

Hamptons Tiny House!

4.99 out of 5 average rating, 71 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

4.88 out of 5 average rating, 32 reviews
Top guest favorite
Cottage in Sag Harbor

Hamptons Waterfront Getaway – Stylish & Serene

5.0 out of 5 average rating, 20 reviews
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

4.95 out of 5 average rating, 87 reviews
Guest favorite
Cottage in Hampton Bays

Swim into Fall & Hot Tub through Winter!

5.0 out of 5 average rating, 16 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

4.96 out of 5 average rating, 23 reviews

When is the best time to visit Southampton?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$138,072 GYDG$128,658 GYDG$122,800 GYDG$134,934 GYDG$190,790 GYDG$235,349 GYDG$192,673 GYDG$208,990 GYDG$140,373 GYDG$115,060 GYDG$125,310 GYDG$125,101 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