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House holiday rentals in Southampton

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Top-rated house rentals in Southampton

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

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Home in Woodmont

4.92 out of 5 average rating, 26 reviews

Light-filled Beach House Steps from the Sand

Located in prime Bayview Beach, a one min stroll to the sandiest beach in Milford. Two floors with private patio. Main level: half-bath, Cooks kitchen with a 6 person dining area, living room with flatscreen. Upstairs: master w/king size bed & en-suite bath, kids bedroom w/ bunkbed, another full bath w/ tub. 3rd bedroom with queen bed and trundle twin. If you want a get-a-way from the city, or just an escape then come to this tucked-away home. Enjoy all that this coastline gem has to offer.

Guest favourite

Home in North Fork

5 out of 5 average rating, 9 reviews

Stylish Beach Getaway: pool & walking location

Perfectly located within walking distance to shops, beaches, and restaurants, our designer home offers comfort, luxury amenities, and privacy. Interested in a long term rental? Message us! Enjoy a beautifully landscaped backyard with pool, chefs kitchen for hosting, and nearby beach farms & wineries. Bedrooms boast organic linens and bathrooms offer Bathing Culture products. Kitchen is stocked with local organic pantry staples and stainless steel appliances to cook or grill on the patio.

Guest favourite

Home in East Hampton

4.95 out of 5 average rating, 228 reviews

Private beach, fully updated cottage, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this harbor oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

Guest favourite

Home in North Fork

4.98 out of 5 average rating, 100 reviews

Designer's Dream - Charming Boathouse

An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's, and recently & lovingly fully renovated and restored. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

Guest favourite

Home in Hampton Bays

4.92 out of 5 average rating, 119 reviews

Hamptons "Get Away" Near Beach/Wineries/Golf

Located in Hampton Bays-the heart of The Hamptons surrounded by water! Close to beaches, waterfront restaurants, wineries, golf & wedding venues. Open floor plan w/ modern flair. 4 bedrooms, 2 full baths, eat-in kitchen, spacious living room and lower level recreation area/ foosball. Enjoy amenities including smart TVs/appliances, EV Charger, 2 fireplaces, 1Gb WiFi, large deck w/ string lites, BBQ, firepit, & outdoor shower. Great for families, couples, coworkers and friends!

Guest favourite

Home in North Fork

4.93 out of 5 average rating, 107 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

Home in Westhampton Beach

5 out of 5 average rating, 4 reviews

Summer Main Home plus cottage close to Main Street

Come relax and enjoy! Beautifully updated Main home with separate cottage. Perfect for in-laws and guests. Each home has its own kitchen, living space, washer/dryer, and outdoor seating. Main house: 4 Br, 3 ba Cottage: 2 Br, 1 ba Outdoor shower for an after beach rinse, 2 patios, pergola, hammock, bbq. A two person kayak available for use; beach passes included. Games, internet, tv... Walk to coffee shops, restaurants, worship, and marina. Bike to beach.

Guest favourite

Home in Montauk

4.99 out of 5 average rating, 101 reviews

6 minute walk to Ditch Plains Beach

IMPORTANT: From Memorial Day 2024 - Labor Day 2024: weekly (1 week/2 week/3 week rentals must start and end on Saturdays. Monthly rentals can start on the first of the month regardless of the day of the week. Great beach house close to Ditch Plains beach with 3 bedrooms and 2 bathrooms. 2 queen beds and 2 bunk beds, deck, barbecue, outside shower, huge yard, recreation room. Spend your days at the beach and grill at night. Wifi, tv, and outdoor fire pit.

Guest favourite

Home in Montauk

5 out of 5 average rating, 6 reviews

Hilltop Bright Home w/New Pool Summer 2024

Home is professionally managed by Montauk Rental Management Group. Your family will be close to everything when you stay at this centrally-located Montauk home. Short drive to Town and Beaches. This home was recently painted and updated, it's clean, bright and the perfect family rental! -4 bedrooms -3 bathrooms -Spacious deck with water views -Outdoor dining & seating -Grill -Peaceful, quiet location perched on a hill Rental Registry 23-780

Guest favourite

Home in Milford

5 out of 5 average rating, 100 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌟 Special Discounts on Early Birds, Last-Minute Stays & 7+ Nights! 🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

Home in North Fork

4.64 out of 5 average rating, 11 reviews

Queen Vic Beach House: 5 Mins to Vineyards & Farms

Queen Vic Beach House is a 5 bedroom house that sleeps up to ten guests with 3.5 bathrooms. This one-of-a-kind home has everything you need for a vacation/holiday to remember! Perfect home for a family reunion or friend get-together. Many of the rooms have stained glass windows giving the house character and charm. There is also a conservatory/patio to relax and read while looking out at the waves.

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Holiday rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Flats

Convenient locations with everyday essentials

Popular amenities for house rentals in Southampton

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Amagansett

4.95 out of 5 average rating, 40 reviews

Wonderful Amagansett Home - Bay View & Heated Pool

Guest favourite

Home in East Hampton

4.87 out of 5 average rating, 103 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

Guest favourite

Home in Southampton

5 out of 5 average rating, 14 reviews

Pool&Spa open till December

Guest favourite

Home in East Hampton

5 out of 5 average rating, 36 reviews

Stunning Central E. Hampton Home w/ gunite pool.

Guest favourite

Home in East Hampton

5 out of 5 average rating, 5 reviews

The Hideaway

Guest favourite

Home in Hampton Bays

4.89 out of 5 average rating, 85 reviews

Perfect Hamptons Summer Rental with Pool

Home in East Hampton

4.94 out of 5 average rating, 16 reviews

Walk to Water. Stunning Home with Gorgeous Pool & Grounds.

Guest favourite

Home in Mastic Beach

4.93 out of 5 average rating, 120 reviews

Gorgeous Waterfront and Indoor Pool Family Oasis!

Weekly house rentals

Home in Hampton Bays

4.78 out of 5 average rating, 99 reviews

Jacuzzi & pool. Fenced in property.

Guest favourite

Home in Water Mill

4.92 out of 5 average rating, 125 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

Guest favourite

Home in North Fork

4.97 out of 5 average rating, 247 reviews

The Greenport Bungalow

Guest favourite

Home in Montauk

5 out of 5 average rating, 20 reviews

Montauk beach house!

Home in Shirley

4.87 out of 5 average rating, 137 reviews

Cope near the beach

Guest favourite

Home in Southampton

4.93 out of 5 average rating, 61 reviews

Southampton Quiet Private Home/Pool 6min to Villag

Guest favourite

Home in Shelter Island

5 out of 5 average rating, 29 reviews

Family Friendly Oasis Steps to Water - Heated Pool

Guest favourite

Home in Madison

4.87 out of 5 average rating, 23 reviews

Historic Beachside Glamour

Private house rentals

Guest favourite

Home in North Fork

4.88 out of 5 average rating, 123 reviews

The Perfect North Fork Escape

Guest favourite

Home in Sag Harbor

4.95 out of 5 average rating, 93 reviews

Sag village, 4 en-suite BRs, hot tub, beach 5 mins

Home in East Hampton

4.86 out of 5 average rating, 28 reviews

Salt Pool 4 Bed Sanctuary w/ Private Beach Access

Home in East Hampton

4.74 out of 5 average rating, 89 reviews

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend

Guest favourite

Home in Water Mill

4.99 out of 5 average rating, 84 reviews

Pristine 5 bedroom Home - South of the Highway

Guest favourite

Home in North Fork

4.91 out of 5 average rating, 11 reviews

Private Beach access along the Wine Trail

Guest favourite

Home in Southampton

4.92 out of 5 average rating, 114 reviews

Serene 3 Bed 2.5 Bath House w/Heated Pool

Guest favourite

Home in East Hampton

4.92 out of 5 average rating, 144 reviews

Heated pool, games room, near beach, kid-friendly

Quick stats about house rentals in Southampton

Total rentals
380 properties
Nightly prices starting at
₹6,929 before taxes and fees
Total number of reviews
5.3K reviews
Family-friendly rentals
340 properties are a good fit for families
Pet-friendly rentals
170 properties allow pets
Rentals with a pool
300 properties have a pool

Destinations to explore