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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 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.

Home in Southampton

5 out of 5 average rating, 4 reviews

Charming- In village/bike2beach

Cottage escape spans 1/2 acre; blocks from town & bike ride to Coopers. Gourmet kitchen, livingroom/fireplace, queen-size bedroom downstairs, with laundry and bath. Upstairs: master and guest bedrooms. Outdoors, lush gardens, pool, pergola, cabana, which offer an enchanting sanctuary for relaxation & alfresco living. Whether strolling among fragrant blooms, lounging by the pool, or enjoying outdoor bbq. Timeless charm & contemporary luxury! Month rental -Only avail for aug. + Security deposit

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, 100 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 Southampton

4.94 out of 5 average rating, 270 reviews

Southampton Village Classic-Summer Special!

Beautiful Southampton Village property, walk to shops, restaurants, train & jitney, no car needed! Main house includes 4 bedrooms, 3 beautiful baths, high-end kitchen and plenty of old-world charm, accommodating 8. Large deck for lounging, a seasonal heated pool and beach nearby. Quintessential Hamptons experience. Bonus cottage included, accommodating 3 more, bringing the total to 11. Summer Special- 10% of weekly rental!

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$.

Guest favourite

Home in North Fork

4.98 out of 5 average rating, 175 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

Guest favourite

Home in Hampton Bays

5 out of 5 average rating, 25 reviews

Convenient 2 Bedroom Hampton’s Getaway

Your family will be close to everything when you stay at this centrally-located beach house . Close to beaches, restaurants and shopping. Biking and walking distance to Town and Ocean. You can also take advantage of our close proximity to the North Fork and the wineries. Montauk is about 35 miles east.

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Popular amenities for Southampton house rentals

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, 101 reviews

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

Guest favourite

Home in East Hampton

5 out of 5 average rating, 35 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 Manorville

4.98 out of 5 average rating, 246 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

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!

Guest favourite

Home in East Hampton

4.83 out of 5 average rating, 30 reviews

Private East Hampton Estate

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 North Fork

4.98 out of 5 average rating, 183 reviews

Nofo Bungalow-In The Heart of Greenport Village

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!

Guest favourite

Home in Shirley

4.9 out of 5 average rating, 135 reviews

Cope near the beach

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 Sagaponack

4.94 out of 5 average rating, 280 reviews

Amazing Home close to Everything -

Guest favourite

Home in Madison

4.87 out of 5 average rating, 23 reviews

Historic Beachside Glamour

Private house rentals

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 31 reviews

Pretty East Hampton Village Fringe - Hansom Hills

Guest favourite

Home in North Fork

4.88 out of 5 average rating, 123 reviews

The Perfect North Fork Escape

Home in East Hampton

4.88 out of 5 average rating, 110 reviews

Gorgeous East Hampton Getaway

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 East Hampton

4.92 out of 5 average rating, 144 reviews

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

Guest favourite

Home in Montauk

4.71 out of 5 average rating, 21 reviews

The Raffle Beach House

Quick stats about house rentals in Southampton

Total rentals
390 properties
Nightly prices starting at
$160 AUD before taxes and fees
Total number of reviews
5.2K reviews
Family-friendly rentals
350 properties are a good fit for families
Pet-friendly rentals
180 properties allow pets
Rentals with a pool
310 properties have a pool

Destinations to explore