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Southold Rentals

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169 Results

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169 Houses

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

Southold house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$428

Private Waterfront W Beach, New Renovation

Southold house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$601

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

Southold house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$683

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

$1,241

Brand New Apartment Across From Town Beach

Southold apartment

2 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$399

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

Southold cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$155

3BR Beachwood private waterfront with Private 25ft Boat Dock!

Southold house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$229

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

Southold house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$861

3BR Newly renovated Southold Beach Cottage steps to beach close to Greenport

Southold house

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$495

Great rentals within 20 miles that match your search

North Fork House with Private Beach Access

East Marion house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$341

Hampton's Paradise sag Harbor, Southampton

Sag Harbor house

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$1,140

Ready for Summer 2021

Southampton house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,709

Fantasy Bay Front Country French Villa

Southampton villa

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$2,279

Hip & Stylish East Hampton Getaway

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

“Wonderful stay” Me, my husband and our daughter rented this nice house for a week. It was really great, Patricia was so nice and helpful from the start when we wanted to rent it until we left. The house is light, nicely furnished, comfortable beds with nice linen. The kitchen is really well equipped, also with an espresso machine so you can enjoy good coffee at home. We stayed by the house a lot and enjoyed the deck with the grill and the nice pool with the floating sunchairs. We liked that it had all the trees and it's in a quiet area. It's only 10-15 min. drive to East Hampton town and to the beaches nearby. We can really recommend this house and we would love to come back soon.

Price per night from

$977

Perfect Hamptons Rental with Pool and Tennis

Bridgehampton house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$1,254

Hampton Accommodations 3 / FREE BIKE RENTALS

East Hampton b&b

1 bedroom / 2 bathrooms / sleeps 2

Price per night from

$314

Hampton Bays, south of 27A

Hampton Bays house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 43 minutes

Price per night from

$456

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

$1,383

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

$456

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

Water Mill house

5 bedrooms / 4 bathrooms / sleeps 13

Price per night from

$1,709

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

Water Mill house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$775

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

$815

Luxury Hamptons Quogue Village 4BR Modernist Retre

Quogue house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,368

East Hampton shingle style home

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$855

North Fork 5 bed room home with forever farm view

Aquebogue house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$456

Cozy North Shore Beach House * Wine Country

Baiting Hollow house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$228

Amagansett Estate 3 BR 60ft Pool

Amagansett house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,026

Newly remodeled mid century modern

East Hampton house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$570

Quaint Seaside Retreat With Full Gym

Hampton Bays house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 49 minutes

Price per night from

$1,368

Beautiful Estate home in the Hamptons, New York

Water Mill villa

7 bedrooms / 7 bathrooms / sleeps 10

Price per night from

$6,836

Amagansett Estate 5 Bedroom 60ft Pool

Amagansett villa

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,328

SOUTHAMPTON NEW YOK LUXURY RENTAL

Southampton house

4 bedrooms / 11 bathrooms / sleeps 8

Price per night from

$2,035

Amagansett Estate 4BR 60ft Pool

Amagansett manor house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,197

Southampton Water Front Retreat

Southampton cottage

4 bedrooms / 10 bathrooms / sleeps 10

Price per night from

$3,255

Amagansett House with Pool near Village & Beach

Amagansett house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,303

SOUTHAMPTON POOL & TENNIS

Southampton house

5 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$1,900

East Hampton Dream House 'Serendipity' - Great Buy

East Hampton house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$570

Hamptons Summer Getaway

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$684

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