35 Best Southampton Estates on Holiday Lettings - Apartments

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36 Vacation rentals

20

Vacation home in Southampton

Hamptons / Southampton

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Pet friendly
Located in Southampton, this 6 bedroom home is 8 km from Agawam Park. Southampton 6 Bed with Pool features a grand entrance, kitchen area with marble counters, stainless steel appliances and French doors with an outside seating area. The living room offers an archway w …see more

from $1546 / night

$10816 / week

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avg. 3 hours 34 minutes

from $1546 / night

28

Southampton Vacation home rental

Hamptons / Southampton

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
***PLEASE INQUIRE FIRST (EMAIL OWNER) BEFORE INSTANT BOOKING!!.. 631 - 365 - 3828 Located east of the canal on the beautiful Peconic Bay, over 100 feet of sandy beach, walk down the shore to for food, drinks and entertainment! Beautiful, crystal clear water, 5000 sq ft …see more

from $3400 / night

$23800 / week

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avg. 1 hour 0 minutes

from $3400 / night

28

Vacation home in Southampton

Hamptons / Southampton

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Welcome to your private Hamptons escape! Featuring 4 bedrooms, 5 bathrooms, and enough space to comfortably sleep up to 7 guests, this immaculate Southampton vacation rental house is sure to provide the perfect spot for families or a close group of friends traveling tog …see more

from $849 / night

$5944 - $10500 / week

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avg. 1 hour 0 minutes

from $849 / night

37

Vacation home in Southampton

Hamptons / Southampton

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
A family place with wrap-around windows and skylights gives you the best of the Hamptons. Big beautify yard and gardens, magical garden-set pool, hot-tub and plenty of room for privacy, makes it a family dream. Backyard. 3 decks. Pool set amongst Maples and hibiscus. …see more

from $675 / night

$6000 - $8101 / week

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avg. 2 hours 31 minutes

from $675 / night

24

Home rental in Southampton with shared pool

Hamptons / Southampton

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
In the front is a beautiful woodland garden with rare woodland flowers and ferns, moss-covered boulders and miniature ponds. In the rear is a Japanese garden, complete with a moon bridge over a babbling brook, a waterfall you can swim behind, a pond house with a deck yo …see more

from $300 / night

$2100 / week

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from $300 / night

6

Vacation cottage in Southampton

Hamptons / Southampton

2 2 2 nights min

  • 2 bedrooms
  • Sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden
This private and quiet waterfront cottage is the perfect Hamptons retreat for one or two people. A short drive to the ocean beach or Main Street in the village for strolling and dining. Located near Southampton Village, the cottage is convenient for wine tasting excurs …see more

from $550 / night

$3850 / week

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avg. 3 hours 34 minutes

from $550 / night

14

Southampton Vacation home rental

Hamptons / Southampton

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Ask about children
  • Ask about pets
The Space Located in Southampton less then a half a mile from the quite beaches of Peconic Bay, this house is also just a 10 minute drive to Sag Harbor or Southampton Villages. Close to ArtHampton (5 mi), Art Market (5 mi) and Hampton Classic Showgrounds (6.5 mi)! Th …see more

from $434 / night

$3034 / week

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from $434 / night

22

Home rental in Southampton with swimming pool

Hamptons / Southampton

3 8 6 nights min

  • 3 bedrooms
  • Sleeps 8
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Step inside this stylish, recently renovated 3 bedroom, 3 bath Southampton home, and the stage is set for a perfect Hamptons summer vacation. Gorgeously appointed and sun-lit, the open floor plan encompasses a great room with fireplace, a screened three-season dining ar …see more

from $1500 / night

$10000 / week

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from $1500 / night

12

Home rental in Southampton

Hamptons / Southampton

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
Price: $36,000 (June 15 to Labor Day) $17,000 (June) $18,000 (July) $29,000 (July through Labor Day) $20,000 (August through Labor Day) Neighborhood: Flanders Centrally Located West of Shinnecock Canal. Minimal traffic! Easy access to NYC and airports. Town of Southamp …see more

from $567 / night

$3967 / week

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from $567 / night

12

Vacation cottage in Southampton

Hamptons / Southampton

4 7 30 nights min

  • 4 bedrooms
  • Sleeps 7
  • 30 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Charming century-old wood-frame and shingled cottage located in a former artists' colony in Southampton, NY, close to beaches, shopping and sight-seeing. Has been well-maintained and steadily upgraded to respond to modern expectations. Tenants may bring a dog. I am loo …see more

from $330 / night

$2310 / week

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from $330 / night

(2) Excellent 

32

Vacation home rental

Hamptons / Southampton

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Experience the exquisite relaxation of upper Long Island, New York by staying at this luxurious 4-bedroom, 4-bathroom Southampton vacation rental home, which sleeps 8! With incredible upscale amenities, an alluring private pool, wraparound deck with bay views, exclusive …see more

from $700 / night

$4900 - $17500 / week

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avg. 1 hour 0 minutes

from $700 / night

28

Southampton Vacation home rental

Hamptons / Southampton

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Newly build home, no expense spared. Beautiful pool and outdoor dining and cooking/BBQ area. The prefect home for entertaining and relaxing. Fully equipped kitchen for cooking and dining, plenty of space for entertaining. Master bedroom is fit for royalty, 4 more beauti …see more

from $1500 / night

$10500 / week

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avg. 2 hours 16 minutes

from $1500 / night

16

Home rental in Southampton

Hamptons / Southampton

5 12 14 nights min

  • 5 bedrooms
  • Sleeps 12
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Newly Renovated Private Contemporary on 2 Acres of Privacy offers 5 Bedrooms 4 Bathrooms, Heated Pool, Hot Tub and All Weather Tennis Court. Bright and Airy lots of Glass & skylights with Glass doors to beautiful Bluestone patio perfect for Entertaining! Lush gardens …see more

from $1929 / night

$13500 / week

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from $1929 / night

24

Vacation townhouse in Southampton

Hamptons / Southampton

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Bishops Pond is a new high-end condo development in Southampton Village. The clubhouse offers a pool, fitness center, billiards, outdoor tennis court, and more. This beautiful and comfortable second floor level home located on the far south east corner of the developme …see more

from $184 / night

$1284 / week

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from $184 / night

24

Southampton Vacation home rental

Hamptons / Southampton

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Pack your bags for an unforgettable East Coast escape at this 3-bedroom, 2.5-bathroom Southampton vacation rental house. Boasting 2,500 square-feet of luxurious living space, this home offers sleeping accommodations for up to 6 guests, a covered front porch and a spacio …see more

from $425 / night

$2975 - $4750 / week

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avg. 1 hour 0 minutes

from $425 / night

11

Vacation cottage rental

Hamptons / Southampton

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Enjoy the best of both worlds! Wake up and take your kayak or stand up paddle board across the street and out in the beautiful N. Sea Harbor & then head into nearby Southampton village for a nice relaxing lunch. Finish the day by soaking in the hot tub with a glass of w …see more

from $400 / night

$2800 / week

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from $400 / night

15

Vacation cottage rental

Hamptons / Southampton

4 10 14 nights min

  • 4 bedrooms
  • Sleeps 10
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Getaway to this charming Cottage on the water with spectacular views!! 3 Bedrooms & Baths in the main house with a separate guest cottage with Bedroom, Kitchen & Bathroom. Heated water front Gunite Pool, Hot Tub, Dock plus Kayaks & Bikes. Close to the village of Sout …see more

from $4500 / night

$10500 / week

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from $4500 / night

7

Home rental in Southampton

Hamptons / Southampton

5 16 7 nights min

  • 5 bedrooms
  • Sleeps 16
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets
You can rent this weekly, bi-weekly or full summer season. Summer 2015 weekly rentals start at $7000/week for any weeks in June, $8750/week for any weeks in July and $9200/week for any weeks in August. You can rent for as little as a week in the summer season or monthly …see more

from $1286 / night

$9000 / week

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from $1286 / night

11

Vacation villa in Southampton

Hamptons / Southampton

6 12 14 nights min

  • 6 bedrooms
  • Sleeps 12
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Fabulous Bay Front Villa on a private acre in Southampton close to village & Beaches. Beautiful fountain to greet you and your guests to the water front retreat with high end finishes. Vaulted ceilings, Professionally decorated and 6 Bedrooms with 4 1/2 baths with Jette …see more

from $5500 / night

$12000 / week

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from $5500 / night

24

Vacation cottage in Southampton

Hamptons / Southampton

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This 3 bedroom waterfront cottage is a perfect family getaway. Located in a small beach community between Southampton and Sag Harbor, it is surrounded by water - from the dining room you look right out onto a serene lake, from the first floor you can see both lake and t …see more

from $921 / night

$6450 / week

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from $921 / night

19

Vacation villa in Southampton

Hamptons / Southampton

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ask about children
  • Ask about pets
The quintessential Infamous Hamptons showcases the posh, yet understated style characteristic to this legendary holiday destination. In an area of New York renown for its five star restaurants and VIP night clubs, there’s actually more to a holiday in Southampton than a …see more

from $1750 / night

$12250 / week

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avg. 2 minutes

from $1750 / night

18

Vacation home in Southampton

Hamptons / Southampton

4 8 14 nights min

  • 4 bedrooms
  • Sleeps 8
  • 14 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden
THIS SOUTHAMPTON HOME OFFERS PRIVACY, LUXURY ,SERENITY AND IS EXQUISITELY DECORATED ,THIS RENTAL HAS EVERYTHING ONE WOULD ASK FOR AS THE OWNER.I LIVE THERE PART TIME AS WELL AND HAVE GIVEN THE UTMOST ATTENTION TO EVERY DETAIL IN THE HOUSE FOR ONES COMFORTS THIS HOUSE …see more

from $1786 / night

$12500 / week

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from $1786 / night

14

Vacation private room with shared pool in Southampton

Hamptons / Southampton

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 12 mi
  • Swimming pool
  • Air conditioning
Newly renovated house with nice spacious rooms with comfortable new double beds. Double occupancy room /private bathroom/entrance, queen size bed newly renovated 4 bedroom-3 bathroom home in prime Southampton location. Close to bay, beach and town. Directly across the s …see more

from $250 / night

$1750 / week

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avg. 22 minutes

from $250 / night

11

Vacation cottage with shared pool in Southampton

Hamptons / Southampton

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
Chic Sunny Private 2 bedrm Cottage (93 miles frm NYC) that step out on to your own secluded patio w/outdoor furniture + gas grill for easy BBQ meals. Cottage guests hv their own gate entry to the pool. You are minutes from World Famous Cooper's Beach, convenient to Vi …see more

from $350 / night

$2200 / week

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from $350 / night

22

Vacation villa in Southampton

Hamptons / Southampton

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
ONE-OF-A-KIND VILLA NESTLED ALONG THE SHORE OF THE GREAT PECONIC BAY, with 180 degree views. The newly renovated and newly furnished (indoor as well as out) with all white interior consists of an open kitchen, living and dining area which lead to french doors, opening o …see more

from $893 / night

$6250 / week

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from $893 / night

(3) Excellent 

20

Vacation home rental

Hamptons / Southampton

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 12 mi
  • Swimming pool
  • Ask about children
This well-appointed and maintained 2,200 sq.ft., 4 bedroom, 3 bath Contemporary has a bright sunlit breakfast area directly off the gourmet kitchen, Situated on a sprawling manicured acre with a 20x40 sparkling swimming pool and directly across the street from the fasci …see more

from $643 / night

$4500 - $7000 / week

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avg. 22 minutes

from $643 / night

4

Vacation home in Southampton

Hamptons / Southampton

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
The Modern Cottage is perfect for a few friends or family. It is just 5 minutes from Southampton Village center and is a quick ride up to the bay or to the ocean beaches. There is sliding glass door to the large cedar deck with big teak table and BBQ grill. A lower d …see more

from $1750 / night

$4500 - $8000 / week

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from $1750 / night

10

Vacation home in Southampton

Hamptons / Southampton

3 6 21 nights min

  • 3 bedrooms
  • Sleeps 6
  • 21 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
It's a 3 bedroom, 2 bath home. 2 Family room, one with a TV and one for reading and watching the sunset over Fish Cove through a large window. The master bedroom with en suite bathroom is located on one side of the house while the guest bedrooms are on the other side, …see more

from $400 / night

$2800 / week

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from $400 / night

14

Home rental in Southampton

Hamptons / Southampton

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Charming 3 bedroom Hampton's beach cottage, with cable and wifi available,private patio and garden. 3 minute walk to beautiful ocean beach, gas grill on patio, outdoor shower, fully equipped, kitchen with dishwasher, and all utensils. washer and dryer, all bed linens an …see more

from $572 / night

$4000 / week

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from $572 / night

5

Vacation home in Southampton

Hamptons / Southampton

4 8 90 nights min

  • 4 bedrooms
  • Sleeps 8
  • 90 nights min
  • Child friendly
  • Air conditioning
Newly updated 4 bedroom 2 bathroom house in Sag Harbor ! Stroll to town, restaurants, shops, cafés, Washer/dryer, central heat/AC, wrap around deck, outdoor gas grill, new appliances, 2 queen beds 2 twin beds, high end linens towels ect, plenty of cooking/kitchen utensi …see more

from $1000 / night

$4000 / week

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from $1000 / night

5

Southampton Vacation home rental

Hamptons / Southampton

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
Home is located on quiet road in Village of Southampton. A ten minute stroll to Main St. where there is wide choice of stores and restaurants. One mile from Ocean Beaches. The garden is gated and large and pool and deck wonderfully private. House design is open, tastefu …see more

from $572 / night

$4000 - $6000 / week

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from $572 / night

10

Home rental in Southampton

Hamptons / Southampton

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautifully renovated seven bedroom, five bath, two-story home that holds on to its 19th century architectural roots while embracing the conveniences of modern day. Well-appointed throughout, additional features include a state-of-the-art kitchen, formal dining room, th …see more

from $1000 / night

$7000 - $20000 / week

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avg. 13 minutes

from $1000 / night

23

Southampton Vacation villa rental

Hamptons / Southampton

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This two-story Southampton Traditional sits on nearly 3+/- acres and enjoys several magnificent amenities and attributes, including seven bedrooms and six and one half baths. The living room has a cathedral ceiling, a fireplace, windows rising nearly to the rooms full h …see more

from $2600 / night

$18200 - $35000 / week

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from $2600 / night

17

Vacation home in Southampton

Hamptons / Southampton

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Mint-renovated and newly decorated Southampton Village home offers a sunny living room, eat-in chef's kitchen and four bedrooms with two baths. Subzero and Wolf appliances, Waterworks fixtures, Cararra marble throughout. Enjoy the summer in our fully-fenced backyard sit …see more

from $1429 / night

$10000 / week

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from $1429 / night

7

Southampton Vacation home rental

Hamptons / Southampton

4 10 14 nights min

  • 4 bedrooms
  • Sleeps 10
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
water everywhere. bulkhead and dock. on wooley pond, southampton. bring your kayak or paddle and leave from your backyard, go into great peconic in short distance. large decks from various rooms in house, with water views. sit on your deck and bbq. 20x40 pool, lounges …see more

from $800 / night

$7000 - $12000 / week

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from $800 / night

21

Vacation condo in Southampton

Hamptons / Southampton

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Child friendly
  • Air conditioning
Large open 2 story unit with all brand new appliances and brand new furniture throughout the condo with a brand new 60" flat screen TV. The condo comes with an extra large master bedroom, and beautiful walk in closet and a nice size master bathroom. The second bedroom c …see more

from $429 / night

$3000 / week

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from $429 / night