Suffolk County, NY Homes for Rent with Private Pool

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  $40,000 per month

  • 4 Beds
  • 3.5 Baths
  • 2,250 Sq Ft
  • House for Rent

  2430 Dignans Rd, Cutchogue, NY 11935

  Cutchogue North Fork: Spend August-LD 2027 in this beautifully appointed & very private Long Island Sound front home at 2430 Dignans Road, Cutchogue: come find out why the owners call it North Cliff. Spectacular decks & pool set high on the cliffs overlooking the LI Sound - private easy steps to beach. On the other side forever views of Oregon Road farmland. Published in international Fashion

  Nicholas Planamento William Raveis New York LLC

  2430 Dignans Rd, Cutchogue, NY 11935
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  $60,000 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  355 Windjammer Dr, Southold, NY 11971

  This soothing beach house is so Zen, you will feel like you are at a spa retreat! Peaceful and perfectly appointed, the backyard features a fabulous lagoon style pool, with a waterfall and hot tub, an amazing outdoor kitchen and bar, bathroom and outdoor shower! 3 bedrooms, 2 baths, including a spacious primary suite with a gorgeous spa like bathroom. All this and steps to the association beach!

  Sheri Winter Parker Corcoran

  355 Windjammer Dr, Southold, NY 11971
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  $22,000 per month

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • House for Rent

  Unlisted Address

  Mattituck, North Fork: Sunshine and solace await you in this immaculate and recently renovated vacation home with a brand NEW, heated, saltwater pool (16x34 gunite)! Large open and bright rooms with lots of natural light allow you to relax in comfort and enjoy your time off. Home accommodates a maximum of 6 guests and features first floor bedroom with luxurious bath, open concept dining

  Nicholas Planamento William Raveis New York LLC

  Unlisted Address
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  $20,000 per month

  • 4 Beds
  • 2 Baths
  • 2,600 Sq Ft
  • House for Rent

  25 Moose Trail, Cutchogue, NY 11935

  Discover the perfect blend of comfort and luxury in this stunning 4-bedroom Cape, ideally situated in the heart of Cutchogue. Designed for both relaxation and entertainment, this home features a chef’s kitchen and an array of spacious living areas, including a formal dining room, game room with a pool table and arcade games, plus a first-floor bedroom and full bath—all tastefully furnished. Step

  Jeanmarie Bay William Raveis New York LLC

  25 Moose Trail, Cutchogue, NY 11935
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  $15,000 per month

  • 5 Beds
  • 3 Baths
  • House for Rent

  220 Cottage Walk, Ocean Beach, NY 11770

  This Home is Available To Rent Weekly For $15,000 NOT a month. Fire Island is a vacation destination. Fantastic opportunity to rent this fabulous pool house, which is close to the beach. The interior of the home offers 5 bedrooms, 3 full baths & central air. Out back is a true oasis; pool surrounded by lounge chairs, hot tub, kitchen with island & flat screen TV. Included are: 6 bikes, 4 beach

  Mary Mallott Netter Real Estate Inc

  220 Cottage Walk, Ocean Beach, NY 11770
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  $7,500 per month

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  3400 Youngs Ave, Southold, NY 11971

  Permit #493 Newly Renovated Farmhouse Centrally Located In Southold With Easy Access By Bus, Train or Car. Enjoy Your Morning Coffee As The Sun Rises Over The Farm Field. Spend An Afternoon Exploring The Beauty of the North Fork, Soak in the Sun at one of the Beautiful Peconic Bay or Long Island Sound Beaches, Enjoy Live Music at Numerous Wineries and/or Breweries, Browse unique local finds at

  Thomas McCarthy Thomas J McCarthy Real Estate

  3400 Youngs Ave, Southold, NY 11971
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  $12,000 per month

  • 4 Beds
  • 3 Baths
  • House for Rent

  352 Surf Rd, Ocean Beach, NY 11770

  This Home is Available To Rent Weekly For $12,000 NOT a month. Fire Island is a vacation destination. Lovely 4 bedroom, 3 bath home in Ocean Beach. Includes in ground pool, outside shower, BBQ, beach chairs, umbrella, & wagon.

  Robin Citriniti Netter Real Estate Inc

  352 Surf Rd, Ocean Beach, NY 11770
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  $5,412 per month

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Apartment for Rent

  201 Jerusalem Hollow Rd, Manorville, NY 11949

  Generously sized 3bedroom, 2 bath in Heritage Pine Hills Country Club. High-end floor plans including patio or balcony. Country club amenities featuring two pools, a fitness center, state-of-the-art playground, covered picnic area, Active spaces include tennis courts, beach volleyball courts, deck hockey, a turf soccer field, and a basketball court. Inspiring views of pristine golf course.$50

  Brian Hickey Hickey & Smith REALTORS

  201 Jerusalem Hollow Rd, Manorville, NY 11949
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  /15

  $3,995 per month

  • 3 Beds
  • 2.5 Baths
  • 1,670 Sq Ft
  • Apartment for Rent

  201 Jerusalem Hollow Rd, Manorville, NY 11949

  Generously sized 3 bedroom, 2.5 Townhouse in Heritage Pine Hills Country Club. High-end floor plans including patio or balcony. Country club amenities featuring two pools, a fitness center, state-of-the-art playground, covered picnic area. Active spaces include tennis courts, beach volleyball courts, deck hockey, a turf soccer field, basketball court.views of pristine golf course, Additional

  Brian Hickey Hickey & Smith REALTORS

  201 Jerusalem Hollow Rd, Manorville, NY 11949
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  $8,000 per month

  • 4 Beds
  • 1.5 Baths
  • House for Rent

  12 Seneca Walk, East Northport, NY 11731

  This Home is Available To Rent Weekly For $8,000 NOT a month. Fire Island is a vacation destination. Fun in the Sun! Enjoy a Pool & a Hot Tub. 4 Bedrooms, 1 1/2 Baths. Secluded Yard with Huge Deck. Includes 6 bikes, 12 beach chairs, wagon & 2 umbrellas.

  Lisa Campbell Netter Real Estate Inc

  12 Seneca Walk, East Northport, NY 11731
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  $30,000 per month

  • 4 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • House for Rent

  3655 Pequash Ave, Cutchogue, NY 11935

  GORGEOUS SEASONAL (and Off-Season) RENTAL AVAILABLE -- FLEET's NECK! Walk to Beach from your Private FABULOUS OASIS. 4 Bedroom and 2 Full Bath Contemporary Home on tucked away Lot Set Well-Back from Road on 1 + acres. Offers Sleek Main Floor Living Area with Fireplace, Chandeliered Dining Area, Foyer, Light Bright Kitchen with All Stainless-Steel Appliances, that leads to a Furnished 2-Level Deck

  Deirdre Fedun Fedun Real Estate Inc

  3655 Pequash Ave, Cutchogue, NY 11935
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  $10,000 per month

  • 4 Beds
  • 3 Baths
  • 2,150 Sq Ft
  • House for Rent

  60 Aspatuck Rd, Westhampton Beach, NY 11978

  60 Aspatuck Road is the ideal Westhampton Beach Village rental, offering 4 bedrooms, 3 baths, central air, a heated pool, and coveted proximity to Main Street, with Rogers and Lashley Beach rights. Enter into a light-filled, open living room that flows effortlessly into the dining room, where French doors lead out to a bluestone patio and the heated pool. The newly refreshed kitchen and a

  Dawn Litel-Murphy Corcoran

  60 Aspatuck Rd, Westhampton Beach, NY 11978
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  $24,500 per month

  • 3 Beds
  • 3 Baths
  • 2,800 Sq Ft
  • House for Rent

  43 Bridle Path, Westhampton Beach, NY 11978

  One Story Contemporary in the Heart of the Village Offering Open Living- Dining Area with Marble Fireplace, Eat-in-Kitchen with Granite Counters, Primary Suite and Bath with Jacuzzi Tub, plus 2 Bedrooms, Den and 2 Additional Full Bathrooms. Private, Fenced Yard with Heated Swimming Pool, 2,000 sq ft of Decking, Hot Tub and Enclosed Outdoor Shower. Access to Village Beach! Available 2026: May

  Dana Stachnik Hampton Properties

  43 Bridle Path, Westhampton Beach, NY 11978
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  $30,000 per month

  • 8 Beds
  • 7 Baths
  • 5,400 Sq Ft
  • House for Rent

  650 Pine Ave, Southold, NY 11971

  A masterfully crafted resort style property, where coastal luxury meets effortless living. Tucked within a coveted private beach community with beach access, this resort-style property was designed for gathering, entertaining, and unwinding in total privacy. The home features a show-stopping 20’ x 40’ heated saltwater pool, framed by lush, manicured grounds that feel both serene and indulgent.

  Colin McCarthy Thomas J McCarthy Real Estate

  650 Pine Ave, Southold, NY 11971
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  $17,500 per month

  • 5 Beds
  • 3 Baths
  • House for Rent

  240 Wilmot Rd, Ocean Beach, NY 11770

  This Home is Available To Rent Weekly For $17,500 NOT a month. Fire Island is a vacation destination. This beachfront features 5 bedroom, 3 full bath home and is currently being renovated and will be an utter showstopper! With breathtaking ocean views, and a pool, you're not going to want to leave!

  Robin Citriniti Netter Real Estate Inc

  240 Wilmot Rd, Ocean Beach, NY 11770
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  /22

  $275,000 per month

  • 5 Beds
  • 4.5 Baths
  • 3,600 Sq Ft
  • House for Rent

  120 Swans Neck Ln, Water Mill, NY 11976

  Newly-renovated and presiding over an estate of 2.50 acres featuring living room with fireplace, dining room, eat-in kitchen, 5 bedrooms (including first-floor master), 4 baths and a powder room. Additional amenities include central air-conditioning, sound system and a heated 20' x 40' pool. Mature landscaping and a picturesque setting, this property is privately situated on a cul-de-sac and

  John Vitello Brown Harris Stevens Hamptons

  120 Swans Neck Ln, Water Mill, NY 11976
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  $10,000 per month

  • 5 Beds
  • 3 Baths
  • 2,620 Sq Ft
  • House for Rent

  25 Exchange Place, Westhampton Beach, NY 11978

  Down the road from Rogers Beach and Main Street sits this beautiful home with amazing water views. The perfect location for you to enjoy all. Available for winter rental and short term during the summer. Also available during summer for two week minimum rentals. Call for pricing., Additional information: Appearance:mint,Weekly Renta Amt:10000

  Constance Porto Douglas Elliman Real Estate

  25 Exchange Place, Westhampton Beach, NY 11978
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  $7,500 per month

  • 3 Beds
  • 1 Bath
  • House for Rent

  647 Ocean Breeze, Ocean Beach, NY 11770

  This Home is Available To Rent Weekly For $7,500 NOT a month. Fire Island is a vacation destination. Enjoy Your Sunny Days On Fire Island At This Spectacular 3 Bedroom, 1 Bath Fully Updated Poolhouse. This Immaculate, Bright and Airy Cottage Includes Pool, Outside Shower, Sperate Entrances, 5 Bikes, 8 Beach Chairs, 2 Beach Umbrellas, and a Wagon.

  Lisa Campbell Netter Real Estate Inc

  647 Ocean Breeze, Ocean Beach, NY 11770
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  $30,000 per month

  • 6 Beds
  • 3.5 Baths
  • 3,114 Sq Ft
  • House for Rent

  4 White Ln, Hampton Bays, NY 11946

  This one of a kind, furnished, 6 bedroom, 3.5 bath expanded ranch sleeps 12 effortlessly and comfortably. w 2 Additional dens for a few extra guests. Large eat in Kitchen with double oven, dishwasher and Television as well as formal dining room. Home features HEATED IN-GROUND POOL, above ground 6-SEAT JACUZZI. 6 cable boxes (Kitchen, TV Room and 4 bedrooms) as well as Sonos speakers throughout.

  Dionicio Neblett Panache Realty Co

  4 White Ln, Hampton Bays, NY 11946
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  $60,000 per month

  • 4 Beds
  • 6 Baths
  • 3,465 Sq Ft
  • House for Rent

  18 Remsen Ln, Remsenburg-Speonk, NY 11960

  18 Remsen Lane has everything you need for the ideal getaway: Tennis, Pickleball, Pool and more: four bedrooms (with an extra bedroom and room for ten), newly resurfaced court,, pathway to a natural pond, game room, media room with 85-inch screen, eat-in cook's kitchen, light-filled open living areas great for entertaining and relaxing. Completely renovated in 2018 from top to bottom including

  Kristen Smyth Corcoran

  18 Remsen Ln, Remsenburg-Speonk, NY 11960
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  $30,000 per month

  • 6 Beds
  • 6.5 Baths
  • House for Rent

  157 Dune Rd, Quogue, NY 11959

  Step into a realm of pure Resort Style living and waterfront splendor within this newly designed Hamptons Bayfront masterpiece. Behind the estate gate, graciously situated on a serene and meticulously maintained 1.4 acres, ensconced by vibrant gardens and exquisite specimen plantings, this distinguished Bayfront residence finds its place along the illustrious Dune Road. Here, where luxury living

  Robert Canberg Nest Seekers International LLC

  157 Dune Rd, Quogue, NY 11959
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  $75,000 per month

  • 6 Beds
  • 4.5 Baths
  • 4,600 Sq Ft
  • House for Rent

  15 Montclair Ave, Shelter Island, NY 11964

  Enjoy all The Hamptons have to offer in this newly recreated waterfront home in the heart of West Neck Harbor! Complete with a boat and complimentary captain at the end of your private dock. Every detail was masterfully thought through by a leading design team. The floor plan offers a first-floor primary suite, four additional private guest bedrooms with two gracious common living spaces, a

  Margot Reutter Corcoran

  15 Montclair Ave, Shelter Island, NY 11964
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  $12,000 per month

  • 4 Beds
  • 3 Baths
  • House for Rent

  334 Dehnhoff Walk, Ocean Beach, NY 11770

  This Home is Available To Rent Weekly For $12,000 NOT a month. Fire Island is a vacation destination. Brand New Top of The Line Appliances- All the Bells and Whistles! Includes Pool, Heat, Central Air, Outside Shower, Separate Entrances, 4 Beach Chairs, Beach Umbrellas, and Wagon.

  Mary Mallott Netter Real Estate Inc

  334 Dehnhoff Walk, Ocean Beach, NY 11770
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  $15,000 per month

  • 4 Beds
  • 2.5 Baths
  • House for Rent

  748 Ocean Breeze, Ocean Beach, NY 11770

  This Home is Available To Rent Weekly For $15,000 NOT a month. Fire Island is a vacation destination. Great Space for a Large Group. Features a Heated Swimming Pool and Sectional Outdoor Seating. Upstairs has a Spacious Master En Suite with a Balcony. Additional information: Appearance: Great

  Lisa Campbell Netter Real Estate Inc

  748 Ocean Breeze, Ocean Beach, NY 11770
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  $22,500 per month

  • 4 Beds
  • 4 Baths
  • House for Rent

  935 Southern Cross Rd, Cutchogue, NY 11935

  Available 2026: April: $12,000, May: $17,500, June: $22,500, July: $35,000. August Rented. Vacation at this spectacular, completely renovated 4 en suite bedroom home this summer located in the desirable Fleet's Neck neighborhood with 2 gorgeous beaches moments away! Entertain in the open concept living area featuring a large island overlooking the family and dining area, perfect for large

  Mariah Mills Daniel Gale Sothebys Intl Rlty

  935 Southern Cross Rd, Cutchogue, NY 11935
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  $14,400 per month

  • 4 Beds
  • 1 Bath
  • House for Rent

  329 Surf Rd, Ocean Beach, NY 11770

  This Home is Available To Rent Weekly For $13,000 - $14,400 NOT a month. Fire Island is a vacation destination. New To The Market! Beautifully Renovated 2 Story Contemporary With A Pool & Beautiful Views Of The Bay.

  Lisa Campbell Netter Real Estate Inc

  329 Surf Rd, Ocean Beach, NY 11770
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  $13,000 per month

  • 4 Beds
  • 3.5 Baths
  • House for Rent

  265 Cottage Walk, Ocean Beach, NY 11770

  This Home is Available To Rent Weekly For $13,000 NOT a month. Fire Island is a vacation destination. Newly renovated and immaculate home with pool and relaxation area. Home includes the following; 4 Bikes, 8 Beach chairs, Beach Umbrella, and a Wagon.

  Robin Citriniti Netter Real Estate Inc

  265 Cottage Walk, Ocean Beach, NY 11770
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  /22

  $7,500 per month

  • 2 Beds
  • 2 Baths
  • House for Rent

  61 Ocean Rd, Ocean Beach, NY 11770

  This Home is Available To Rent Weekly For $7,500 or $26,000 a month. Fire Island is a vacation destination. Located Seven Houses From the Beach. Includes Outside Shower,10x20 Heated Pool, Jacuzzi/Hot Tub, Wood-Burning Stove, A/C, Heat, Extra Refrigerator, 5 Bikes, 4 Beach Chairs, Beach Umbrella, and Wagon.

  Robin Citriniti Netter Real Estate Inc

  61 Ocean Rd, Ocean Beach, NY 11770
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  $9,200 per month

  • 4 Beds
  • 2 Baths
  • House for Rent

  17 Bungalow Walk, Ocean Beach, NY 11770

  This Home is Available To Rent Weekly. Rates fluctuate from $9,200 to $10,000 per week. NOT a month. Fire Island is a vacation destination. In Addition to this Lovely Home, There is a Brand New Swimming Pool, Deck & Outdoor Shower. Renovated Home Near Town and Beach. Perfect for a Vacation! Includes 4 Bikes, 8 Beach Chairs, and Wagon.

  Robin Citriniti Netter Real Estate Inc

  17 Bungalow Walk, Ocean Beach, NY 11770
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  $14,000 per month

  • 5 Beds
  • 3 Baths
  • House for Rent

  335 Surf Rd, Ocean Beach, NY 11770

  This Home is Available To Rent Weekly For $14,000 NOT a month. Fire Island is a vacation destination. Newly Built, Two Primary Bedrooms, And Views of the Bay, Lovely Pool, Wine Fridge and Extra Icemaker. Also Includes 7 Bikes, 8 Beach Chairs, BBQ, Beach Umbrella, Wagon, Outdoor TV and Shower.

  Robin Citriniti Netter Real Estate Inc

  335 Surf Rd, Ocean Beach, NY 11770
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  $13,000 per month

  • 4 Beds
  • 2.5 Baths
  • House for Rent

  109 Bungalow Walk, Ocean Beach, NY 11770

  This Home is Available To Rent Weekly For $13,000 NOT a month. Fire Island is a vacation destination. Stunning Recent New Build On Fabulous Beach Block! Includes Pool, Screened-In Porch, Outside Shower, 4 Bikes, 8 Beach Chairs, Beach Umbrella, and Wagon.

  Robin Citriniti Netter Real Estate Inc

  109 Bungalow Walk, Ocean Beach, NY 11770
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  $12,500 per month

  • 4 Beds
  • 2.5 Baths
  • House for Rent

  207 Wilmot Rd, Ocean Beach, NY 11770

  This Home is Available To Rent Weekly For $12,500 NOT a month. Fire Island is a vacation destination. Experience this stunning 2 story offering 4 bedrooms, 2 1/2 baths, generously sized bedrooms with a primary ensuite, a pristine brand new pool, and expansive decks.

  Lisa Campbell Netter Real Estate Inc

  207 Wilmot Rd, Ocean Beach, NY 11770
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  $13,000 per month

  • 5 Beds
  • 3 Baths
  • House for Rent

  345 Dehnhoff Walk, Ocean Beach, NY 11770

  This Home is Available To Rent Weekly For $13,000 to $15,000 NOT a month. Fire Island is a vacation destination. Lovely, NEW, five bedroom, three full bathroom home with pool. Close to the beach and town! Book your Summer 2025/2026 rental fast!

  Robin Citriniti Netter Real Estate Inc

  345 Dehnhoff Walk, Ocean Beach, NY 11770
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  $8,000 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  400 Wells Rd, Laurel, NY 11948

  ** RENTED JULY 5th - AUGUST 21st. ** Adorable 3-bed, 2-bath rental with a pool in the fenced in back yard and close to a bay beach! Available Off Season (Jan-May23): $4,000/mo, June: $8,000, July: $9,000, August: $10,000, July & August: $18,000, Memorial Day - Labor Day: $26,000, September (not including LBD): $6,000, October: $6,000, November: $5,000 and December: $5,000. *Unavailable 6/28/26 -

  Mariah Mills Daniel Gale Sothebys Intl Rlty

  400 Wells Rd, Laurel, NY 11948
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  $10,000 per month

  • 4 Beds
  • 2.5 Baths
  • House for Rent

  1275 the Esplanade, Southold, NY 11971

  STUNNER 4BR DESIGNER HOME ~ PET FRIENDLY, HEATED POOL & BEACH!Fabulous Lux Vacations on the coveted Esplanade in "Angel Shores", with a deeded sandy bay beach and heated freeform lagoon pool with a waterfall. Property is fully fenced and private, with many lounge areas for sunning, a shady pergola when needed, and a great new outdoor shower. We offer a pet friendly policy, rare for an

  Kate Carpluk William Raveis New York LLC

  1275 the Esplanade, Southold, NY 11971
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  $13,000 per month

  • 5 Beds
  • 3 Baths
  • House for Rent

  386 Dehnhoff Walk, Ocean Beach, NY 11770

  This Home is Available To Rent Weekly For $13,000 NOT a month. Fire Island is a vacation destination. Beautiful Home With 5 Bedrooms, 3 Baths, Outdoor Shower And A Pool! Home Includes 7 Bikes, Wagon, And 6 Beach Chairs For Your Use! Home Is Great For The Family Trip! Additional information: Lease Term: August - Labor Day, July, July - August, Memorial - Labor Day, Monthly, Weekly, Weekly Rent

  Robin Citriniti Netter Real Estate Inc

  386 Dehnhoff Walk, Ocean Beach, NY 11770
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  $15,000 per month

  • 4 Beds
  • 3.5 Baths
  • House for Rent

  929 Dune Rd, Westhampton Beach, NY 11978

  Available for Spring Summer of 2026. One month rental for July or August $65,000 plus fees

  Irwin Krasnow Area Real Estate Assoc Inc

  929 Dune Rd, Westhampton Beach, NY 11978
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  $30,000 per month

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • House for Rent

  42 Oak St, Westhampton Beach, NY 11978

  Down a long private driveway sits this secluded and charming Westhampton Beach Village Summer rental home that has been completely renovated with a Contemporary flair and style. Enjoy your summer vacation with this updated 3 Bedroom, 2 Bath home, with vaulted ceilings, stone fireplace, Gourmet Kitchen, new heated pool with bluestone patio, outdoor stone BBQ/Bar, outdoor shower, and newly

  James Salandino Compass Greater NY LLC

  42 Oak St, Westhampton Beach, NY 11978
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  $80,000 per month

  • 7 Beds
  • 7.5 Baths
  • 6,500 Sq Ft
  • House for Rent

  10 Jones Rd, East Hampton, NY 11937

  Graceful and refined living in Georgica, South of the Highway in East Hampton, takes place on one-and-a-half acres. As you enter the foyer, a bright blue living room with fireplace greets you as well as the formal dining. There is an intimate study for quiet reading in front of a cozy fireplace. Toward the back of the house is the stunning kitchen with an open living space with fireplace fronted

  Noel Mason Brown Harris Stevens Hamptons

  10 Jones Rd, East Hampton, NY 11937
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  $150,000 per month

  • 3 Beds
  • 3 Baths
  • 2,500 Sq Ft
  • House for Rent

  5 Cowhill Ln, Wainscott, NY 11975

  Contemporary Luxury Living in the Heart of WainscottExperience serene Hamptons living in this turnkey contemporary retreat, ideally set on a quiet lane just behind Wainscott Village. Sun-filled and thoughtfully designed, the residence offers approximately 2,500 square feet of stylish living space on 0.52 acres, blending modern architecture with a relaxed coastal living and seamless

  Angela Boyer Sothebys Int'l Realty Hamptons

  5 Cowhill Ln, Wainscott, NY 11975

Showing Results 401 - 440, Page 11 of 12