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Southold Rentals

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162 Results

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Price: high to low

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162 Houses

PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES

Southold house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$430

Private Waterfront W Beach, New Renovation

Southold house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$836

Shorecrest Beach House, 4 bedroom private beach front, new renovation

Southold house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$908

Steve's Place Well Furnished 3 BR Southold Home Heated Pool, Town Near Beach

Southold house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$832

Brand New Apartment Across From Town Beach

Southold apartment

2 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$398

2BR North Fork Southold Private Cottage Beach steps to beach 10min Greenport

Southold cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$382

Private waterfront home w Dock Kayaks town of Southold, near Greenport,

Southold house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$832

Sea Breeze & Sunsets, Beach house steps to Beach & Vineyards

Southold house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$1,009

3BR Goose Creek cottage Southold near beach & Greenport

Southold house

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$832

Great rentals within 20 miles that match your search

Perfect Hamptons Rental with Pool and Tennis

Bridgehampton house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$1,648

Hampton Accommodations 3 / FREE BIKE RENTALS

East Hampton b&b

1 bedroom / 2 bathrooms / sleeps 2

Price per night from

$313

Hampton accommodations 2

East Hampton b&b

1 bedroom / 2 bathrooms / sleeps 2

Price per night from

$284

Majestic Southampton Waterfront Estate

Southampton villa

7 bedrooms / 5 bathrooms / sleeps 18

“Best alternative to Fire Island” My partner and I wanted to try something new, we originally always go to Fire Island and although we will always love that place, I can't express how expensive it is just to go for a weekend with friends not to mention that we can't help but feel stranded in a way (we don't drive) because once the ferry leaves, that's it! You will be staying whether you want to or not. I would have never thought that I would find a house of this size, with amenities such as linens, towels, beach chairs, hot tub, and pool included for such a reasonable price at the Hamptons none the less...I thought it had to be a mistake, I literally had to call to confirm the rates. The owner was very prompt in her responses whether it would be through phone and or email, and she definitely went out of her way to make sure we were properly accommodated as well as gave awesome recommendations to nearby shops and restaurants. I never had such a pleasant and smooth experience. It was a one, two, three transaction and was very pleased with the outcome, will be coming back next year for sure!

Price per night from

$1,380

Great Rates in 2019- No Increases In Rates and Over Holiday Weeks

Hampton Bays house

3 bedrooms / 2 bathrooms / sleeps 6

“Hamptons” Dear Jackie and al, we had a wonderful time in your house. The service was perfect. We had everything in the house we needed. It is a in nice area . There are shops and restaurants near by. Thanks for everything Ina and family

Price per night from

$455

Classic Hamptons Home in beautiful Water Mill - Minimum 2 week rental

Water Mill house

5 bedrooms / 4 bathrooms / sleeps 13

Price per night from

$1,705

Waterfront Southampton Gem! Sailboat On Grounds - Travertine patio and Hot Tub

Water Mill house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$773

Spectacular Family Resort in Hampton Bays, NY

Hampton Bays house

7 bedrooms / 5 bathrooms / sleeps 18

“Hamptons Heavenly Honeymoon” My fiancé and I wanted to go somewhere amazing for our honeymoon. We decided that we wanted to spend our honeymoon in the Hamptons. We spent two lovely weeks in august of 2013 at this lovely home. There is nothing bad that I could say about this house. It was spacious, clean, well kept, and well decorated. This house was in the perfect location. It was close enough to the town of Hampton Bays but also close enough to Riverhead. The owner of the house was very cooperative, if we had a question she would answer all of them without hesitation. During the stay my fiancé and I spent most of our time outside. It was so quite and peaceful. We would sit by the pool and enjoy a glass of wine. I would highly recommend this house to anybody. My fiancé and I were talking and once we start a family we are going to make coming to this house a tradition.

Price per night from

$813

Luxury Hamptons Quogue Village 4BR Modernist Retre

Quogue house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,705

East Hampton shingle style home

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$853

Amagansett House with Pool near Village & Beach

Amagansett house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,299

SOUTHAMPTON POOL & TENNIS

Southampton house

5 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$3,246

Hamptons Summer Getaway

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$682

Serene & Private East Hampton Summer Rental w/pool

East Hampton house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$974

East Hampton Village Classic , South of Highway

East Hampton house

7 bedrooms / 9 bathrooms / sleeps 12

Price per night from

$4,870

East End Retreat - Steps to the beach! - Northfork - Monthly Rentals Available!

Baiting Hollow house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$1,022

Amagansett Estate 3 BR 60ft Pool

Amagansett house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,364

Quaint Seaside Retreat With Full Gym

Hampton Bays house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 6 minutes

Price per night from

$1,364

Beautiful Estate home in the Hamptons, New York

Water Mill villa

7 bedrooms / 7 bathrooms / sleeps 10

Price per night from

$6,817

Amagansett Estate 5 Bedroom 60ft Pool

Amagansett villa

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,591

Bishops Pond Southampton NY

Southampton townhouse

4 bedrooms / 10 bathrooms / sleeps 8

Price per night from

$146

SOUTHAMPTON NEW YOK LUXURY RENTAL

Southampton house

4 bedrooms / 11 bathrooms / sleeps 8

Price per night from

$2,030

Amagansett Estate 4BR 60ft Pool

Amagansett manor house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,193

Southampton Water Front Retreat

Southampton cottage

4 bedrooms / 10 bathrooms / sleeps 10

Price per night from

$3,246

Brand New Southampton Condo

Southampton condo

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$488

Summer in a Hamptons Cottage

Bridgehampton house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$488

CHIC RETREAT!! Walk to Desirable Bay BEACH!!

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 7 minutes

Price per night from

$2,500

Relaxing East Hampton Summer Getaway

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 49 minutes

Price per night from

$370

Dream house vacation on the Long Island Sound

Orient house

5 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,080

Viewing 38 of 162
rentals in Southold

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