Village Of Southampton
$110,000
Village of Southampton, NY
Rental
Bedrooms: 3
Bathrooms: 3
Web ID: 737486
Perfect location South of the Highway on a prestigious block between the Village and the ocean combine to create an ideal summer retreat. The beautiful French mansard is positioned on 1.5-acres of manicured landscaping, complete with a heated swimming pool. The elegant, immaculate interior features a living room with fireplace, dining area, large kitchen, 3 bedrooms, 3 baths and a den. Listing ID: 737486
July / Aug Rental: $110,000
Gertrud Hoertnagl-Pereira
(631) 204-2425
East Hampton
$110,000
East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 3.5
Web ID: 859865
Rental Reg. # 23-555 Beautifully refurbished 5 bedroom home on 4 acres with pool, tennis and finished basement. This bright, airy home is a wonderful respite from the hustle and bustle of the rest of the world, with fresh air and mature trees transporting you to leisure and relaxation. The open floor plan welcomes family and friends and the numerous gathering sites make entertaining exciting for all. Summertime finds the over-sized deck, large pool and tennis court enticing visitors to enjoy all that summer has to offer. The game room in the basement, with pool table and ping pong table offers even more fun. Listing ID: 859865.
MD - LD Rental: $110,000
Year Round: $150,000
Anthony C Cerio
(631) 903-6151
Mitchel L Natter
(631) 903-6154
Beach Road
$110,000
Westhampton Beach, NY
Rental
Bedrooms: 6
Bathrooms: 6
Web ID: 817271
This classic Hampton's home is located in the heart of Westhampton Beach Village and offers close proximity to Main Street and Rogers Beach and other Dune Road beaches. The expansive kitchen is perfect for entertaining and has a large granite island and countertops, stainless steel appliances, breakfast nook and convenient desktop if needed. Easy to entertain with an adjoining formal dining room. The living room has a wood-burning fireplace and game table for your relaxing comfort. The private adjoining office provides a comfortable space for both leisure and work activities. Relax in the shade on the spectacular front porch or swim in the heated new gunite pool. There are six bedrooms and five-and-a-half baths with a private downstairs primary-suite or an upstairs primary-suite, and another guest room with private bathroom, as well as three other bedrooms (one has 2 sets of bunk beds). The heated new gunite pool is a...
Margaret A. Kisla
(5164461416) ) ) ) ) ) ) ) ) )
57 Big Fresh Pond Road
$110,000
Southampton, NY
Rental
Bedrooms: 5
Bathrooms: 4
Web ID: 918583
After departing from your dock and floating in your boat during sunset, the pinks, purples and golden hues bounce off the water from Big Fresh Pond. Upon returning, it is beautiful to dine, barbeque, and entertain on the deck with those awesome views. This renovated, multi-level house offers 5 bedrooms, 4 full bathrooms, with an open living plan with fireplace on the main floor and another common entertaining area on the above grade lower level which leads out to the dock. The ponds purity level is high for swimming, fishing and boating. Perched above Big Fresh, this property comes with a boat and bicycles for the total enjoyment of this beautifully natural area.
March Rental: $7,000
April Rental: $7,000
November Rental: $7,000
December Rental: $7,000
Winter Rental: $14,000
Year Round: $110,000
Andrea L Ackerman
(631) 537-4340
Elizabeth A Phenis
(631) 537-4357
55 Old Town Crossing
$110,000
Village of Southampton, NY
Rental
Bedrooms: 6
Bathrooms: 4.5
Web ID: 904679
Located in the most desirable location between Wyandanch Lane and Little Plains Road, sits this 6 bedroom, 4.5 bathroom classic home spanning 3,620 s/f over 3 levels. With a luxurious open space interior design boasting an abundance of natural light and furnished with meticulous detail. Featuring a captivating and fully-equipped chef's kitchen with state-of-the-art stainless steel appliances, central air conditioning and a music room with equipment for those that want to entertain and play. Outdoors, the spacious backyard features a patio, perfect for entertaining with ease, a beautiful landscape offering mature estate privet hedges with a manicured garden and a 44 x 20 heated gunite pool with outdoor shower. With only a short distance to world class shopping and world famous ocean beaches, this is an opportunity for living the Hamptons life you won't want to miss. Listing ID: 904679
August - LD Rental: $110,000
John P Vitello
(631) 204-2407
312 Ocean Road
$110,000
Bridgehampton, NY
Rental
Bedrooms: 5
Bathrooms: 4.5
Web ID: 755480
Come experience everything the Hamptons has to offer in this gorgeous 5 bedroom, 4.5 bathroom traditional in the estate section of Bridgehampton. This completely restored farmhouse set on .73 acre of picture perfect landscaping and gated entry. It is tastefully decorated with wide-plank floors, 2 fireplaces, a large living room, formal dining room, eat-in kitchen, and breakfast area with french doors leading to the pool. Outback, enjoy the 20x40 heated gunite pool, pool house with the fourth full bath, a back porch and patio, for classic Hamptons entertaining, accessed through the quintessential farm style kitchen. Head down the pristine and famous Ocean Road to world renown white sand ocean beaches and dunes indigenous to the Hamptons or make your way up the street to Bridgehampton's Main Street filled with History, restaurants with abundant outdoor dining and local shops for a magnificent summer get-a-way. Listing ID:755480
Custom Rental: $250,000
July Rental: $110,000
July / Aug Rental: $210,000
August - LD Rental: $110,000
September Rental: $60,000
Cynthia R Barrett
(631) 537-4322
14 Maple Street
$110,000
Village of Southampton, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 919236
Centrally located Southampton Village homes for rent in the most convenient location imaginable. Fully renovated and restored in 2006, the home provides 21st century dependability within the details of its architectural past. Enter into the unique brick-floored foyer and then onward into its spacious living and dining rooms with bright windows all around. French doors that open onto a deck that overlooks the pool and garden beyond. A new granite kitchen and full bath service the household and pool area. The second floor contains a junior primary suite plus two guest rooms with shared bath. Above, a large primary suite enjoys the full advantage of its quiet third floor perch, where dramatic ceilings rise to the peaks of its Gambrel frame. This charming one-of-a-kind home sits amid banks of hydrangea and lush plantings. You'll appreciate its central air conditioning, two sets of washer/dryers, basketball hoop, gas grill with close proximity...
MD - LD Rental: $110,000
Robert M Lohman
(631) 204-2404
Honeysuckle Lane
$105,000
East Quogue, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 822507
Look no further for your perfect Summer Rental Compound! With exceptional amenities including Heated Pool, Tennis, and Basketball... this is truly a MUST SEE! Nestled on a quiet street in East Quogue, conveniently located to the village and South Hampton's beautiful beaches, you will find the ultimate balance of luxury, tranquility and endless recreation. This 1.85-acre property also proves to be an entertainer's dream with expansive grounds for outdoor dining on the patio, lounging by the pool or simply enjoying the comfort and privacy within this magnificent Estate. The interior boasts 4,800+ square feet with 4 spacious Bedrooms and 4.5 Bathrooms, including a serene Primary Suite, with a private deck for your very own sanctuary. The inviting, contemporary floor plan expands across three levels and is flooded with natural light, accenting its soaring, vaulted ceiling across the living and dining areas. Recent updated features include a state-of-the-art AC system for consistent...
Kathleen Doubleday
(6316556238) ) ) ) ) ) ) ) ) )
Wainscott
$104,500
Wainscott, NY
Rental
Bedrooms: 6
Bathrooms: 4.5
Web ID: 737760
Rental Registration #: 24-114 (Feb 2, 2026)• Dynamic great room with two story vaulted ceilings • 1st floor master bedroom suite with fireplace • 6 bedrooms • 4 1/2 bathrooms • 3 fireplaces • Cook's kitchen featuring Wolf stove, Subzero refrigerator and wine refrigerator, Bosh dishwasher and Scotsman ice machine • Covered bluestone patio with ceiling fans and dining and seating area for entertaining with fire pit • 2 washing machines and 2 dryers • Indoor/outdoor sound system • Central air conditioning and heating (Nest Thermostat) • Heated 20 X 40 gunite pool (Jandy pool heater with iPhone control) • Beautiful landscaping including extensive privacy screening • Nest locks and thermostat • Housekeeping, handy-person and chef available on request • Town water connection with top-of-the-line water filtration system; garbage disposal • Dogs allowed with owner permission. Listing ID: 737760
MD - LD Rental: $264,000
June Rental: $82,500
July Rental: $104,500
August - LD Rental: $110,000
Year Round: $440,000
David Blumenfeld
(631) 537-4329
Water Mill
$100,000
Water Mill, NY
Rental
Bedrooms: 5
Bathrooms: 5.5
Web ID: 758247
This 5,000 +/- sf gambrel home on 1+/- acre in the heart of Water Mill is moments away from Bridgehampton Main Street and less than 5 miles away from ocean beaches. This open-concept 5 bedroom, 5.5 bath home is filled with natural light. The first floor features a great room with double-height ceilings, a gourmet eat-in kitchen with stainless steel appliances, a formal dining room, a spacious primary suite, 2 additional bedrooms with a shared bath, and walls of glass leading to the spacious back deck. The second level features 3 ensuites with renovated marble baths. The fully finished basement offers 2 game rooms and ample storage. The grounds feature lush landscaping, a heated pool, and a har-tru tennis court. This exquisite, one-of-a-kind summer rental is not to be missed.
April Rental: $40,000
May Rental: $60,000
MD - LD Rental: $275,000
June Rental: $65,000
July Rental: $100,000
July / Aug Rental: $220,000
August - LD Rental: $120,000
September Rental: $70,000
Christopher J Burnside
(516) 521-6007
Aubri Peele
(631) 252-5434
Village Of Southampton
$100,000
Village of Southampton, NY
Rental
Bedrooms: 5
Bathrooms: 7.5
Web ID: 735873
Oceanfront property with ocean and bay views. Private master bedroom suite with 2 fireplaces, 2 baths, sauna, sitting room, oceanfront and bayfront balconies with gorgeous views. Guest wing with 4 en-suite bedrooms and an additional sauna. Multiple entertaining spaces. Flat screen TVs throughout. Heated gunite pool and hot tub. Listing ID: 735873
Short Term Weekly: $100,000
John P Vitello
(631) 204-2407
Bridgehampton
$100,000
Bridgehampton, NY
Rental
Bedrooms: 5
Bathrooms: 4.5
Web ID: 736789
Conveniently located and close to Bridgehampton Village. You must see this pristine traditional in a great Bridgehampton location. This home features 4100 sq. ft.-4 bedrooms/4.5 baths...Sheek Dining Room, Living Room with Fireplace, Gourmet Kitchen, 2 Master suites, Den, plus finished lower level with den, Game Room, and Wine Cellar. When you need a break from our beautiful beaches, relax by the tastefully furnished pool area and spa. The landscaped grounds set the stage for an enchanted evening of dining under the pergola. It's simply perfect!
July Rental: $100,000
August Rental: $120,000
Two Week Rental: $50,000
Christopher J Burnside
(516) 521-6007
Aubri Peele
(631) 252-5434
Village Of Sag Harbor
$100,000
Village of Sag Harbor, NY
Rental
Bedrooms: 6
Bathrooms: 7.5
Web ID: 897595
Close to the Village, within a few blocks to a private community beach, and less than 1.5 +\- miles to Havens Beach in Sag Harbor, this stunning, modern farmhouse features 6 bedrooms and 7- and one-half baths across 3,800+\- sf. Multiples of sleek windows and oversized sliders create walls of glass in the grand, double-height living room with a fireplace that opens to the formal dining room and a designer chef's kitchen with a center island and counter dining. The spectacular primary en suite includes a vaulted-tray ceiling, a gas fireplace with a flat screen, and access to a large mahogany deck overlooking the back grounds. A separate guest wing on the 2nd level is accessed across the gallery bridge. Additional guestrooms and bathrooms are well-appointed with marble and contemporary fixtures. An extensive covered mahogany deck includes lounge and dining space, ceiling fans, an...
March Rental: $21,000
April Rental: $30,000
May Rental: $40,000
July Rental: $100,000
August Rental: $125,000
September Rental: $50,000
October Rental: $40,000
November Rental: $21,000
December Rental: $21,000
Sharman S Peddy
(631) 903-6171
Dennis Gallagher
(631) 771-5309
Hill Side Lane
$100,000
East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 7
Web ID: 3552889
Situated on over 3/4 of an acre, this extraordinary custom-built home is surrounded by stunning natural scenery and lush landscaping with stone walls. The upper level features an expansive great room with a open kitchen, fireplace, dining room, and sliding doors to two separate entertaining areas. The primary suite and a powder room are also on this level. The large east-facing upper deck offers beautiful sunset views and stairway to the pool and pool house. The main level includes three additional spacious bedrooms (two en suite), a fourth full bath, a laundry room, and a large family room with sliding doors to a covered deck, an outdoor shower, a heated gunite pool, and a pool house with a Air Conditioning and a full bath. The finished lower level boasts an attached two-car garage, large windows, a sixth full bath, space for an office, gym, or media room. This remarkable property...
Brandon Vazquez
(6318711993) ) ) ) ) ) ) ) ) )
Highview Drive
$100,000
Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 6
Web ID: 810042
Every detail of this stunning home has been thoughtfully designed to offer a luxurious and peaceful escape in the heart of the Hamptons. Located just minutes from the charming Sag Harbor Village and Bridgehampton, the property is perched on a rise, providing rare, lovely water vistas of Noyac Bay from its rooftop living platform. This five-bedroom, five-and-a-half-bathroom masterpiece is tailored for pure enjoyment, relaxation, and indulgence. Enjoy a beautiful modern home with great amenities.
Joseph T. Van Asco
(6313531043) ) ) ) ) ) ) ) ) )
Shinnecock Hills
$100,000
Shinnecock Hills, NY
Rental
Bedrooms: 3
Bathrooms: 3
Web ID: 912250
RP# 230614. With stunning views of Shinnecock Bay and the Atlantic ocean, be the first to enjoy this renovated contemporary featuring 3 bedrooms and 2 baths with a seamless open floor plan, new flooring and furnishings. The large living room with fireplace, vaulted ceilings and glass windows throughout inundate the space with a natural light which connects the indoors with the outdoor landscaping and the serenity of all its surroundings. Enjoy the incredible 180 degree panoramic water views in every room. There is also a loft area with a den/office to complete this wonderful home. Enjoy entertaining viewing the water on the south facing deck which is perfect for lounging with family and friends surrounded by nature and all its beauty. Paradise and tranquility, this is the ideal retreat for the perfect Hamptons getaway. Listing ID: 912250
Year Round: $100,000
Cristina Matos
(631) 204-2408
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