Holiday houses in Southampton

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Top-rated holiday rentals in Southampton

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Top Guest favourite
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, 158 reviews

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

Take a bike ride to Havens Beach and feel the sand in your toes. Walk to explore the shops, restaurants and bars on the quaint Main Street of Sag Harbor. Repair to your sun drenched home away from home to enjoy a relaxed meal alfresco on the deck. Unwind under the umbrellas on the expansive deck surveying the private fenced in backyard. Take in all the amenities of a newly renovated home situated in the Hampton - recent updates include a furnished basement, ping pong table, smart TVs and sound system. Extra touches include beach towels, beach chairs, bikes, cooler, games and more. This beautifully renovated 3 BR, 2 Bath home is situated on a quiet street, with a fenced half acre yard. It is located less than a mile to the shops, bars and restaurants of Main Street and the Hampton Jitney stop with service to NYC. The open floor plan boasts an abundance of natural light with 4 skylights and large windows to bring the outdoors in. Brand new appliances, custom kitchen cabinets, large center island with bar stools are perfect for hosting friends & family. Central AC/forced air heating controlled by the Nest ensure your complete comfort. The master BR features a king bed and ensuite Bath with custom tile shower. The guest BRs have a queen bed and full bed respectively and share the hall bathroom with tub/shower. The large deck runs the length of the home and is perfect for al fresco dining & entertaining. Totally furnished with everything you need to enjoy yourself from the second you enter the home! We have four brand new adult bikes, helmets and locks for your enjoyment. Explore the village, bike to the beach or get some exercise while you're here. If you prefer to stay in, you'll find a games console / DVD player in the front room with a good selection of games and movies. Additionally, we provide 4 beach chairs, beach towels and a small cooler for your use. Enjoy! Guests have access to the entire house, backyard, deck, garage and driveway parking. We can be reached via cell or email and are very responsive. We will also have a friend who is local to the area who will be able to assist with any issues. Sag Harbor is the coolest, most authentic town in the Hamptons. Home to household names, the town retains its small-town charm and rustic maritime vibe. Browse the artsy, eclectic stores and strike up conversations in the coffee shops and local bars. Sag Harbor is a quaint, walkable town on the wharf with great restaurants and bars. The house is located less than a mile's walk into the main street. Beaches are accessible via bike or car. The Jitney stop from Manhattan is located on Main Street less than a mile from the house. There are taxis in the area available via phone for pick up. We provide four adult bikes, helmets and locks for your use.

Guest favourite
Home in Hampton Bays
4.86 out of 5 average rating, 130 reviews

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Top Guest favourite
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
4.97 out of 5 average rating, 414 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.

Top Guest favourite
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
5 out of 5 average rating, 50 reviews

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Chic, 5-bedroom, 3.5 half-bath home is close to the water and the village of Southampton. The sparkling pool has a beautiful backdrop of a lushly landscaped garden. Southern exposure in the backyard brings an abundance of sunshine inside and out. The home includes an outdoor sauna, fire pit and rock garden perched above the pool for your very own spa retreat. The inside of the home is thoughtfully designed with a relaxed, chic & luxury feel making it the perfect Hamptons getaway.

Top Guest favourite
A dining set featuring a large wooden table with eight matching chairs is positioned under a spacious umbrella, offering shade. Lush greenery and a serene waterfront view are visible nearby, providing a peaceful outdoor setting.
Home in North Sea
4.98 out of 5 average rating, 105 reviews

Breezy Waterfront Home With private Dock

This charming waterfront home is the ideal getaway for the active family with the Hamptons' largest natural 'saline pool' (the Peconic Bay) just footsteps away. This home easily sleeps 7 - with 3 bedrooms and 3 separate kids' sleeping cabins. You can jump on our standup paddle board right off our private dock, jog along wide stretches of pebble beach, have a swim race to our floating swim platform or simply relax in the hammock. 2 bathrooms indoors and 1 private outdoor shower,

Top Guest favourite
A modern kitchen space features a granite countertop with high-backed bar stools positioned for dining. Glass-front cabinets display dishware, and a sliding door opens to a sunny outdoor area with a pool and patio seating.
Home in Southampton
4.97 out of 5 average rating, 267 reviews

Stunning 3 bed 2 bath home W Pool

Nestled on a serene an acre off a tranquil lane, this contemporary, designer-updated residence provides an idyllic Hamptons retreat. With 3 delightful bedrooms, 2 sleek bathrooms, and a seasonal heated pool amidst mature landscaping, you're promised a calming respite. We kindly ask that you familiarize yourself with the detailed disclosures, & guidelines. We maintain a strict policy against events, parties, and smoking. our home and property grouds are smoke-free.

Top Guest favourite
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
4.96 out of 5 average rating, 459 reviews

Tiny Home in Prime Spot in Southampton Village

Price drop! Located in the heart of Southampton Village, this intimate cottage is the perfect getaway! Nestled in an 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 or 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.

Top Guest favourite
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, 125 reviews

Winter Getaway 2 miles from Ocean Beaches

Entire House! Large fenced in yard, great for pets. Two bedrooms, one song ride away from Ponquogue Beach. Have the beach to yourself for walks and exercise! Perfect place to get away and Unwind. The house is located on a quiet residential street close to the hamlet of Hampton Bays. Enjoy the patio and fire pit (use non-windy days) on 1/4 acre property. Still plenty to do here, we are 20 minutes from Wine Country and Tanger Outlets.

Guest favourite
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
4.95 out of 5 average rating, 228 reviews

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

Top Guest favourite
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, 119 reviews

Elegant Modern Artist's Residence

This simple and serene home is set against a farm preserve, exposed to beautiful light and views and biking distance to the beach. Very relaxing - a terrific, creative space for a couple or small group. A large vegetable garden is maintained on the property and is available for guests to harvest as they like. Fresh salad greens, herbs, vegetables for you to enjoy!

Guest favourite
A living area features a large brown sectional sofa adjacent to a flat-screen TV. Natural light enters through a window covered with light curtains. A round, black-and-white patterned ottoman sits in the center of the room, complemented by an ornamental plant nearby.
Loft in North Sea
4.88 out of 5 average rating, 107 reviews

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 .

Top Guest favourite
A private entrance features a white door set against a backdrop of textured wooden siding. Colorful purple irises bloom along the stone pathway, complemented by lush greenery, contributing to the inviting exterior of the studio apartment.
Apartment in Southampton
4.88 out of 5 average rating, 143 reviews

Southampton Village Studio

Location, Location, Location!!!! New renovated stand along Studio Apartment in the heart of Southampton Village. Private with lots of light, Cable TV and living room area. Located in wonderful Southampton Village location, only 1 mile to village shops and 2 miles Coopers Beach. Wi-Fi

Popular amenities for Southampton holiday rentals

When is the best time to visit Southampton?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$730 AUD$730 AUD$753 AUD$822 AUD$1,022 AUD$1,168 AUD$1,345 AUD$1,458 AUD$980 AUD$803 AUD$874 AUD$873 AUD
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.

Quick stats about holiday rentals in Southampton

  • Total holiday rentals

    Explore 490 holiday rentals in Southampton

  • Nightly prices starting at

    Southampton holiday rentals start at $131 AUD per night before taxes and fees

  • Verified guest reviews

    Over 8,950 verified reviews to help you choose

  • Family-friendly holiday rentals

    420 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 220 rentals that welcome pets

  • Holiday rentals with a pool

    380 properties feature pools

  • Rentals with dedicated workspaces

    300 properties have a dedicated workspace

  • Wi-Fi availability

    480 of Southampton holiday 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!

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