Long Island, NY Houses for Rent with Pool

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  /20

  $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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  /32

  $15,000 per month

  • 5 Beds
  • 3 Baths
  • House for Rent

  220 Cottage Walk, Ocean Beach, NY 11770

  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 chairs, 2 beach umbrellas & 2 wagons. Home has everything you could imagine for the perfect beach

  Mary Mallott Netter Real Estate Inc

  220 Cottage Walk, Ocean Beach, NY 11770
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  /25

  $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 Farmfield. 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 One

  Thomas McCarthy Thomas J McCarthy Real Estate

  3400 Youngs Ave, Southold, NY 11971
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  /22

  $12,000 per month

  • 4 Beds
  • 3 Baths
  • House for Rent

  352 Surf Rd, Ocean Beach, NY 11770

  Lovely 4 bedroom, 3 bath home in Ocean Beach. Includes in ground pool, outside shower, BBQ, beach chairs, umbrella, & wagon., Additional information: Weekly Rent Amt:12000

  Robin Citriniti Netter Real Estate Inc

  352 Surf Rd, Ocean Beach, NY 11770
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  /17

  $8,000 per month

  • 4 Beds
  • 1.5 Baths
  • House for Rent

  12 Seneca Walk, East Northport, NY 11731

  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., Additional information: Weekly Rent Amt:8000

  Lisa Campbell Netter Real Estate Inc

  12 Seneca Walk, East Northport, NY 11731
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  /30

  $30,000 per month

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

  3655 Pequash Ave, Cutchogue, NY 11935

  New to Market FLEET's NECK Rental! Walk to Beach from your Private FABULOUS SUMMER 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 with Both Living and

  Deirdre Fedun Fedun Real Estate Inc

  3655 Pequash Ave, Cutchogue, NY 11935
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  /20

  $10,000 per month

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

  60 Aspatuck Rd, Westhampton Beach, NY 11978

  60 Aspatuck is the perfect summer rental with 4 bedroom, 3 baths, close proximity to Westhampton Beach Main Street, access to Rogers and Lashley beaches, central air, and a heated pool. Enter to a light-filled open and airy living room, a dining room with french doors to the bluestone patio and heated pool, a newly refreshed kitchen, and a den with a 60-inch television. Enjoy maximum privacy with

  Dawn Litel-Murphy Corcoran

  60 Aspatuck Rd, Westhampton Beach, NY 11978
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  /18

  $21,690 per month

  • 2 Beds
  • 2 Baths
  • 1,116 Sq Ft
  • House for Rent

  21 Clark St Unit 1305, Brooklyn Heights, NY 11201

  CONTEMPORARY - COMFORTABLE - CONVENIENT - SENIOR LIVING COMMUNITY Apt 1305 Independent Living The Watermark at Brooklyn Heights is a senior living community located in the historic and beautifully renovated Leverich Towers Hotel. Independent Living, Assisted Living and Memory Care accommodations with award winning programming for a senior living community. Residents enjoy multiple dining venues,

  Shelley Wasserman Compass

  21 Clark St Unit 1305, Brooklyn Heights, NY 11201
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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

  Permit 816. Beautiful New Construction In Private Beach Community. Creekfront Beach Access Along With 20x40 Heated Saltwater Pool. Ideal For Large Groups & Perfect For Entertaining, This Property Has It All. 8 Bedrooms And 7 Bathrooms Set On Lush Manicured Grounds, Provides Spacious Accommodations For Up To 16 Guests. Spend Afternoons Lounging By The Pool & Evenings Gathering With Family And

  Colin McCarthy Thomas J McCarthy Real Estate

  650 Pine Ave, Southold, NY 11971
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  $50,000 per month

  • 4 Beds
  • 5.5 Baths
  • 5,000 Sq Ft
  • House for Rent

  Unlisted Address

  Nantucket-style waterfront home on the North Fork with creek access to/from Peconic Bay - 600 feet of waterfront, floating dock and a 1200 sq. ft. deck. The home offers ample ways to enjoy the outdoors - lounge poolside and enjoy a dip in the 20x40 pool and pool house amenities. Kayak or paddle board to a secluded bay front beach. Bring your boat or rent a captain, and go fishing any day you

  Marie Beninati Beninati Associates

  Unlisted Address
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  /14

  $22,500 per month

  • 3 Beds
  • 2.5 Baths
  • House for Rent

  44 Legend Ln, Jamesport, NY 11947

  Remodeled to perfection! This beautiful home features an open floor plan with wood flooring throughout, a cozy living room with bay windows and a fireplace, 3 bedrooms including 1st floor primary bedroom ensuite, screened in porch, large backyard with 16x32 heated, salt water IG pool and a fire pit, perfect for family gatherings! Don't miss out on this beauty! Surrounded by North Fork award

  Sheri Winter Parker Corcoran

  44 Legend Ln, Jamesport, NY 11947
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  /11

  $4,000 per month

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • House for Rent

  2420 Plum Island Ln, Orient, NY 11957

  Year Round ONLY $4000 Per Month!! Welcome To Plum Island Lane In The Much Sought After Community Of 'Orient By The Sea' - Which Is A Stones Throw From The Private Beach! This Perfect Get Away Home Consists Of 3 Large Bedrooms, 1.5 Bathrooms, A Spacious EIK, Bright Open-Plan Living Room, Laundry And Recently Installed In-Ground 20 x 40 Saltwater Swimming Pool! This Gem Of A Home Was Completely

  Pete Halpin Douglas Elliman Real Estate

  2420 Plum Island Ln, Orient, NY 11957
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  /4

  $17,500 per month

  • 5 Beds
  • 3 Baths
  • House for Rent

  240 Wilmot Rd, Ocean Beach, NY 11770

  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!, Additional information: Weekly Rent Amt:17500

  Robin Citriniti Netter Real Estate Inc

  240 Wilmot Rd, Ocean Beach, NY 11770
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  /31

  $12,000 per month

  • 8 Beds
  • 7.5 Baths
  • 8,500 Sq Ft
  • House for Rent

  1060 Noyac Path, Water Mill, NY 11976

  Stunning and Private 8-Bedroom Property on 5 Acres, Featuring Har-Tru Tennis court, beautiful pool, mahogany deck, and Fully Equipped Gym with Peloton Equipment. This Gorgeous estate Includes a Main House with 5 Bedrooms and Attached 3-Bedroom Carriage House, Perfect for Large Families, Friends, or Live-In Staff. Enjoy Extra Rooms in the Finished Basement for Added Space and Privacy. Ideal for

  Diana Rafailova ALEPH REALTY BROKERAGE LLC

  1060 Noyac Path, Water Mill, NY 11976
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  /23

  $29,000 per month

  • 4 Beds
  • 3.5 Baths
  • 2,599 Sq Ft
  • House for Rent

  59 N Captains Neck Ln, Southampton, NY 11968

  Estate-like, lush privet hedges surround this immaculate, traditional situated on a beautiful .46-acre property on a tranquil lane in Southampton Village. Stylish, light-filled rooms, include a spacious living room, a cozy den/family room with fireplace and a separate formal dining room. A recently-renovated open kitchen with new stainless steel appliances, includes a breakfast area with sliding

  Cristina Matos Brown Harris Stevens Hamptons

  59 N Captains Neck Ln, Southampton, NY 11968
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  /22

  $250,000 per month

  • 5 Beds
  • 4.5 Baths
  • 3,900 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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  /21

  $18,620 per month

  • 2 Beds
  • 2 Baths
  • 1,073 Sq Ft
  • House for Rent

  21 Clark St Unit 1307, Brooklyn Heights, NY 11201

  CONTEMPORARY - COMFORTABLE - CONVENIENT - SENIOR LIVING COMMUNITY Apt 1307 Independent Living The Watermark at Brooklyn Heights is a senior living community located in the historic and beautifully renovated Leverich Towers Hotel. Independent Living, Assisted Living and Memory Care accommodations with award winning programming for a senior living community. Residents enjoy multiple dining venues,

  Shelley Wasserman Compass

  21 Clark St Unit 1307, Brooklyn Heights, NY 11201
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  /31

  $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.

  Constance Porto Douglas Elliman Real Estate

  25 Exchange Place, Westhampton Beach, NY 11978
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  /16

  $7,500 per month

  • 3 Beds
  • 1 Bath
  • House for Rent

  647 Ocean Breeze, Ocean Beach, NY 11770

  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., Additional information: Lease Term:Monthly,Weekly

  Lisa Campbell Netter Real Estate Inc

  647 Ocean Breeze, Ocean Beach, NY 11770
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  /18

  $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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  /35

  $55,000 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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  /35

  $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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  /23

  $90,000 per month

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

  271 Flying Point Rd, Southampton, NY 11968

  Located South of the Highway in Southampton Village, "THE WAVE" is a sprawling, updated and turnkey modern home that is the ideal retreat for year-round Hamptons living. With a southern exposure providing an abundance of natural light, the bright, open living spaces are ideal for entertaining. The 4 bedroom, 4 bath home benefits from oversized panels of glass that look out over the 1.30+/- acre

  John Vitello Brown Harris Stevens Hamptons

  271 Flying Point Rd, Southampton, NY 11968
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  $15,000 per month

  • 7 Beds
  • 8.5 Baths
  • 8,250 Sq Ft
  • House for Rent

  421 Edge of Woods Rd, Water Mill, NY 11976

  WATER MILL SECLUDED COMPOUND Down a long driveway, this wonderfully appointed home situated on 2.5+/- acres offers exceptional privacy and seclusion in Water Mill. The compound features a beautiful main house, a guest cottage, and a pool house, this newly-updated traditional offers 7 bedrooms and 8.5 baths. The main house features an oversized gourmet kitchen with stainless steel appliances with

  Cristina Matos Brown Harris Stevens Hamptons

  421 Edge of Woods Rd, Water Mill, NY 11976
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  /10

  $12,000 per month

  • 4 Beds
  • 3 Baths
  • House for Rent

  334 Dehnhoff Walk, Ocean Beach, NY 11770

  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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  $13,000 per month

  • 4 Beds
  • 3 Baths
  • 2,300 Sq Ft
  • House for Rent

  215 Northfield Ln, Southold, NY 11971

  Permit 681- Enjoy This Beautifully Renovated 4 Bedroom, 3 Bath Ranch Style Home With Heated Pool. Open Floor Plan Includes LR With Cathedral Ceilings, High End EIK, Dining Area & Outdoor Shower. Plenty of Room For The Whole Family & Guests. Beautiful Goose Creek Beach Just 0.2 Miles Down The Road. Minutes To Local Wineries, Shopping & Dining. BOOK NOW FOR SUMMER 2025. Terms: May $13,000, June

  Mitch Pickman Thomas J McCarthy Real Estate

  215 Northfield Ln, Southold, NY 11971
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  /18

  $15,000 per month

  • 4 Beds
  • 2.5 Baths
  • House for Rent

  748 Ocean Breeze, Ocean Beach, NY 11770

  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,Weekly Rent Amt:15000

  Lisa Campbell Netter Real Estate Inc

  748 Ocean Breeze, Ocean Beach, NY 11770
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  /23

  $22,500 per month

  • 4 Beds
  • 4 Baths
  • House for Rent

  935 Southern Cross Rd, Cutchogue, NY 11935

  Available 2025: April: $12,000, May: $17,500, June: $22,500, July: $35,000. 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 gatherings. The first

  Mariah Mills Daniel Gale Sothebys Intl Rlty

  935 Southern Cross Rd, Cutchogue, NY 11935
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  $25,000 per month

  • 4 Beds
  • 5 Baths
  • 5,000 Sq Ft
  • House for Rent

  2055 Grandview Dr, Orient, NY 11957

  2025 Rates: June $25,000, Amazing North Fork home with heated salt water gunite pool located in Grandview Estates featuring 4 bedrooms (1st floor bedroom with ensuite, 2 ensuite guest bedroom on the second floor with 1 additional guest bedroom and guest bathroom) office/den also located on the second floor with a large sitting area and balcony at the landing of the second floor, large, finished

  Justin Concannon Compass Greater NY LLC

  2055 Grandview Dr, Orient, NY 11957
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  /17

  $14,400 per month

  • 4 Beds
  • 1 Bath
  • House for Rent

  329 Surf Rd, Ocean Beach, NY 11770

  New To The Market! Beautifully Renovated 2 Story Contemporary With A Pool & Beautiful Views Of The Bay. Rates fluctuate from $13,000 to $14,400 per week.

  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

  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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  /35

  $20,000 per month

  • 4 Beds
  • 2 Baths
  • 3,000 Sq Ft
  • House for Rent

  Unlisted Address

  2025: $6k Winter, balance of September or October $20k or BOOK 2026 NOW: Various Rates All Year Long: East Marion, North Fork - Coveted and rare rental (Rates: Season 2026 $87k; June $20k, Aug-LD $40k; Bal of Sept OR Oct $20k; off Season Winter $6k per mo etc) on the bay in private setting overlooking Bug Light and Long Beach. Spectacular setting with heated, waterside pool. One floor living

  Nicholas Planamento William Raveis New York LLC

  Unlisted Address
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  /36

  $230,000 per month

  • 6 Beds
  • 5.5 Baths
  • 5,496 Sq Ft
  • House for Rent

  140 Ox Pasture Rd, Southampton, NY 11968

  Full of charm and ideally situated less than a mile to the heart of Southampton Village and just up the street from world-renowned ocean beaches, this contemporary with gated driveway is the ideal place to call home for the summer. Sitting on just over 1.9 acres of manicured grounds, the home offers 6 bedrooms, one of which is a small children's room with bunk beds, 5.5 baths, large foyer,

  Cristina Matos Brown Harris Stevens Hamptons

  140 Ox Pasture Rd, Southampton, NY 11968
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  /15

  $9,200 per month

  • 4 Beds
  • 2 Baths
  • House for Rent

  17 Bungalow Walk, Ocean Beach, NY 11770

  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. Rates fluctuate from $9,200 to $10,000 per week.

  Robin Citriniti Netter Real Estate Inc

  17 Bungalow 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

  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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  /12

  $14,000 per month

  • 5 Beds
  • 3 Baths
  • House for Rent

  335 Surf Rd, Ocean Beach, NY 11770

  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., Additional information: Weekly Renta Amt:14000

  Robin Citriniti Netter Real Estate Inc

  335 Surf Rd, Ocean Beach, NY 11770
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  /21

  $13,000 per month

  • 4 Beds
  • 2.5 Baths
  • House for Rent

  109 Bungalow Walk, Ocean Beach, NY 11770

  Stunning Recent New Build On Fabulous Beach Block! Includes Pool, Screened-In Porch, Outside Shower, 4 Bikes, 8 Beach Chairs, Beach Umbrella, and Wagon., Additional information: Weekly Renta Amt:13000

  Robin Citriniti Netter Real Estate Inc

  109 Bungalow Walk, Ocean Beach, NY 11770
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  /24

  $12,500 per month

  • 4 Beds
  • 2.5 Baths
  • House for Rent

  207 Wilmot Rd, Ocean Beach, NY 11770

  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., Additional information: Weekly Renta Amt:12500

  Lisa Campbell Netter Real Estate Inc

  207 Wilmot Rd, Ocean Beach, NY 11770
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  /25

  $85,000 per month

  • 4 Beds
  • 6 Baths
  • 3,800 Sq Ft
  • House for Rent

  134 Middle Pond Rd, Southampton, NY 11968

  SOUTHAMPTON WATERFRONT RENTAL Just renovated!! Spectacular 4 bedroom, 4.5 bath Post-Modern home on a private waterfront 1.60-acre +/- property. Features include a heated gunite pool with spa, chef's kitchen, 2 car garage, 2 fireplaces, central air-conditioning, 3,800 square-feet of living space, and designer bathrooms. Magnificent water views all the way to the Ocean. Quiet an private location.

  Amelia Doggwiler Brown Harris Stevens Hamptons

  134 Middle Pond Rd, Southampton, NY 11968

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