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Holiday Homes and Apartments Southampton, NY

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From
$160
Per Night
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1 / 34
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Studio, 1 Bathroom, Sleeps 4
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$2,301
Per Week
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1 / 16
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3 Bedrooms, 2 Bathrooms, Sleeps 7
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$639
Per Night
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1 / 25
6 Bedrooms, 3 Bathrooms, Sleeps 12
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$639
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1 / 44
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4 Bedrooms, 2 Bathrooms, Sleeps 10
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  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Located in Southampton's largest natural area - Big Fresh Pond. Treat yourself with abundance of nature, tranquility and available activities! 8000 sqft total of private space including 4000 sqft of private peaceful lakefront with dock and kayaks, 2000 sqft of indoor space and 2000 sqft of private... View all property information
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5 of 5 stars Reviewed 11 June 2014
Pavel was a wonderful host and gave us all the right tips to enjoy the area. The lake(one minute away walk) is wonderful(to swim /kayak or just hang out) and the house is also...
5 of 5 stars Reviewed 10 June 2014
We booked this quite last minute but it was all that we hoped for. Owner gave us some great tips on things to do in the area as well -
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From
$1,553
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1 / 55
7 Bedrooms, 5 Bathrooms, Sleeps 18
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Private Fishing...
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
This is extravagant living at its best. Picture yourself enjoying expansive water views and majestic sunsets. The park like setting lends itself to an idyllic outdoor paradise. This home has 7 huge bedrooms and 5 palatial bathrooms. The house boasts a wide-open floor plan with soaring cathedral... View all property information
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5 of 5 stars Reviewed 16 January 2015
This is a great location for families. Kayaks are available to rent nearby so you can explore the bay shore. You can fish from nearby docks or directly from the backyard and...
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$639
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1 / 43
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4 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Located in Southampton's largest natural area - Big Fresh Pond. Treat yourself with abundance of nature, tranquility and available activities! 8000 sqft total of private space including 4000 sqft of private peaceful lakefront with dock and kayaks, 2000 sqft of indoor space and 2000 sqft of private... View all property information
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4 of 5 stars Reviewed 5 August 2012
We stayed with three other couples after a week in NYC and this was the ideal break for us. The house is perfectly located just a 5/10 minute drive from Southampton centre. At...
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From
$8,949
Per Week
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1 / 13
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Enjoy the Hamptons! in this mint condition beautifully decorated and full equipped beach house. Located in Southampton, close to the Village and Beaches, this 4 BR open floor plan cedar shingle home is on almost 1 gorgeous acre on the border of a preserve with total privacy. Enjoy a first floor... View all property information
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$1,598
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1 / 52
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6 Bedrooms, 7 Bathrooms, Sleeps 14
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
25 year age limit...please don't inquire if you do not meet the age requirements, you will be wasting your time and ours. This luxurious Southampton estate is set on a large private plot of land. With close proximity to Southampton village and world famous Coopers beach, the location of this... View all property information
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From
$626
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1 / 24
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6 Bedrooms, 4 Bathrooms, Sleeps 15
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Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Ocean Views
  • Ping Pong Table
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Southampton estate with sprawling 3 acre property overlooking the bay is home to this totally renovated 1886 rambling 5,000 SF Historic home. Pottery Barn chic sparks images of family-style living spaces that are well-coordinated and comfortable. Our home's decor is styled after a Restoration... View all property information
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From
$1,023
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1 / 22
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Stunning four bedroom home on one plus park-like acre 5 minutes from Southampton and ocean beaches, This home has never been rented before. It boasts an oversized heated gunite pool, spa and cooks kitchen. Make your self at home outside by the pool or on one of the upper decks. Amenities... View all property information
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From
$5,960
Per Week
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1 / 24
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4 Bedrooms, 9 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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 development is exquisitely decorated,... View all property information
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From
$607
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1 / 23
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Lots of large windows and glass doors make this home bright and warm all year long. Art adorned walls and colorful original textile designs by the artist/designer, herself are throughout this home. The layout is both open and yet private, with a cathedral ceiling great room. The great room... View all property information
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From
$422
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1 / 12
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4 Bedrooms, 4 Bathrooms, Sleeps 7
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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 looking for seasonal or monthly... View all property information
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From
$1,214
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1 / 22
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4 Bedrooms, 4 Bathrooms, Sleeps 8
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Contemporary designer home for the well seasoned traveler. Enjoy a gourmet kitchen while your guests relax by the fireplace in the open dining area, in the large comfy entertainment room, or on the wood deck custom dining area for more than 10 people. Designer renovated split-level home offers 4... View all property information
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$767
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1 / 2
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3 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Farmhouse style house in the Village of Southampton within walking distance to train station, railway station, downtown, and bicycle to the beach. House has 2 1/2 bedrooms, 2 1/2 baths, heated swimming pool. NO GROUP Rentals single family only!!!!!!!!!! House only available for a monthly rental... View all property information
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From
$5,114
Per Week
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1 / 9
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4 Bedrooms, 2 Bathrooms, Sleeps 8
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Southampton, Luxury 4 Bed 2 Bath home with pool, minutes to everything! New 25 x 50 Salt Generated Pool, no maintenance and much easier on the eyes! 3 Minutes to Private Beach! Free Parking, NO Beach Passes needed! This 4 bedroom, 2 bath home is nestled on 1.5 acres which abuts a 10 acre... View all property information
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From
$639
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1 / 17
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
A very private and charming getaway minutes from the the ocean, the bay, and Southampton Village shopping and activities. Also centrally located to the other Hamptons villages and a ferry ride away to Shelter Island and the North Fork, our home is the perfect base from which to explore the beauty... View all property information
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From
$1,278
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1 / 24
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4 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Four bedroom.three bathroom house with heated pool on a wooded acre in Southampton. Granite kitchen, deck with grill, peaceful gardens and woodland views, very close to the village, ocean and bay. Previously rented by national magazine. View all property information
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From
$767
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1 / 16
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4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
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Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This prime home is large, rambling, comfortable. It's perfectly located. Beach: 7 minutes by bike or car. Bayr: across the street. Golf: 5 minutes. SH center: 7 minutes by bike or car. 'South of the Highway,' this spacious, open plan home with pool has space for family plus nanny. Garden... View all property information
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From
$447
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1 / 32
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Fireplace
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Beautiful 3 bedroom house located on top of the hill overlooking Peconic Bay. Full Winter Views and partial Summer Views. Downstairs has master bedroom and kitchen and Free Form Dining table with wrap around porch and outdoor seating. Upstairs has deck, large family room with pull out sofa, Large... View all property information
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From
$192
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1 / 3
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
SUCH A BEAUTIFUL LOCATION ! Come stay at our Beautiful Southampton guest house suite. Getaway and visit Southampton towns and shops Great restaurants. Centrally located near vineyards,minutes drive to Southampton town and Coopers beach, the bay beach is 2 minutes away, you can walk it about 1 mile.... View all property information
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From
$10,739
Per Week
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1 / 25
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6 Bedrooms, 5 Bathrooms, Sleeps 12
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Recently renovated, beautiful vacation home within a mile of Southampton Village restaurants and shops. It is located on a very quiet and private lane near two beautiful horse farms. This home features six large bedrooms and four and one half baths. The floor plan is open, bright and airy, with... View all property information
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From
$2,237
Per Night
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1 / 11
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6 Bedrooms, 4 Bathrooms, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
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 Jetted Tubs & Steam Shower. All... View all property information
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From
$1,598
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1 / 23
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7 Bedrooms, 7 Bathrooms, Sleeps 14
Booking
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
25 year age limit...please don't inquire if you do not meet the age requirements, you will be wasting your time and ours. This estate has 7 bedrooms and 6.5 bathrooms, all bathrooms are marble with high-end fixtures. All bedrooms have 32 inch HDTV's. Boasting 2 living rooms - 1 on the main floor... View all property information
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From
$2,301
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1 / 7
6 Bedrooms, 7 Bathrooms, Sleeps 14
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Hot Tub
  • Private Outdoor...
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
waterfront villa estate with;everything!!!!! Beds: 3 King Beds, 2 Queen Beds, 1 Double Bed, 2 Sofa Beds, 1 Crib View all property information
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From
$511
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1 / 24
4 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Hot Tub
  • Internet Access
  • Private Fishing...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
'This home is perfectly located in Southampton. It is a 4 Bedroom and it sleeps 10 people. The house is perfectly located in the heart of the Hamptons and has a large yard that is private and just beautiful. There is a nice HUGE built in Jacuzzi & Heated Pool in the yard for you to enjoy as well as... View all property information
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$5,960
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1 / 7
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5 Bedrooms, 10 Bathrooms, Sleeps 16
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Hot Tub
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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 or seasonal. In the... View all property information
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From
$15,980
Per Week
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1 / 18
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4 Bedrooms, 10 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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 HAS 4 BEDROOM TWO OF WHICH ARE... View all property information
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