$15,000 per month
530 Stillwater Ave, Cutchogue, NY 11935
Perfect summer getaway! 3 bedrooms, 2.5 bathrooms, in-ground pool, close to beach, business district, vineyards and restaurants. Two week minimum stay., Additional information: Appearance:very good
Erin Kaelin Signature Premier Properties
$6,000 per month
3 Meadow Way, Westhampton Beach, NY 11978
Living is easy in this perfect Hamptons getaway! Located in the estate section of Westhampton Beach, this south of the highway, one-level contemporary is private yet convenient to the beach and all that Westhampton Beach Village has to offer. This sunny home features four bedrooms, two full bathrooms, an open living/dining room with a fireplace, and central air-conditioning. The property includes
Dawn Litel-Murphy Corcoran
$20,000 per month
1460 Hillcrest Dr, Orient, NY 11957
This home has it all! Experience luxurious North Fork living with this incredible one-of-a-kind resort-style property. Gorgeous professionally designed 1-acre fully enclosed rear yard. Multiple tiers, huge 20x40 heated pool, outdoor shower, expansive rear patios with tons of seating and space to lounge, relax and have fun including a sports court - basketball and badminton, tree swing, fire pit,
Nicole Pappas Compass Greater NY LLC
$40,000 per month
2430 Dignans Rd, Cutchogue, NY 11935
Cutchogue North Fork: Spend August-LD 2026 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
$13,500 per month
155 Bridge St, Greenport, NY 11944
2025 Rates are as follows: May 1 - 22: $10,000 or $3,500 per week; May 23 - June 27: $20,000 or $5,000 per week; July 13-31 $20K; Sept 4 - 30: $20,000 or $5,000 per week: Rare new construction on a quiet side street in Greenport Village, this modern luxury home is the perfect base to explore the beaches, wineries, and farm-to-table dining of the North Fork. Walking distance to downtown Greenport
William Walters Daniel Gale Sothebys Intl Rlty
$20,000 per month
6 Ocean View Pkwy, Southampton, NY 11968
Secluded and amenity-filled, this Southampton property features an expansive 6000+/- sf of immaculate interior living space across 3 stories and multiple indoor and outdoor entertaining areas. This home has it all, from sprawling lush grounds to a luxurious, feature-rich home with a 3.5 car garage. All 6 bedrooms and 5.5 baths are well-appointed and drenched in natural light. The great room
Cristina Matos Brown Harris Stevens Hamptons
$35,000 per month
7 Plume Grass Way, Westhampton, NY 11977
Welcome to 7 Plume Grass Way. This Immaculate Post-Modern home has everything you would need for your Summer Rental. Once you drive down the beautifully manicured driveway, you can walk right into this 5 Bedroom and 5 Bath Summer Oasis. Look straight through the Vaulted Ceiling living room out to the large deck and Pool Area. Or walk through the open floorplan past the dining area and into the
Antonio Bottero Compass Greater NY LLC
$70,000 per month
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
$24,000 per month
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
$9,000 per month
39 Smugglers Path, Jamesport, NY 11947
Pristine and private post-modern home in Jamesport Now Available for the Off-Season 2025 from November 1, 2025 through April 30, 2026 for $9,000 Per Month. Summer 2026 Now Available for Booking! July for $35,000 and August for $40,000. Nestled away on a pin-drop quiet cul-de-sac and situated on a shy acre of meticulously landscaped property. All just around the corner from the coveted Iron Pier
Rene Giacobbe Douglas Elliman Real Estate
$20,000 per month
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
$15,000 per month
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
$7,500 per month
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
$12,000 per month
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
$8,000 per month
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
$30,000 per month
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
$10,000 per month
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
$19,500 per month
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
$30,000 per month
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
$50,000 per month
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
$22,500 per month
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
$4,000 per month
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
$17,500 per month
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
$12,000 per month
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
$29,000 per month
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
$10,000 per month
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
$7,500 per month
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
$30,000 per month
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
$55,000 per month
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
$30,000 per month
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
$75,000 per month
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
$90,000 per month
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
$15,000 per month
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
$12,000 per month
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
$15,000 per month
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
$22,500 per month
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
$25,000 per month
2055 Grandview Dr, Orient, NY 11957
Available for Sept. 3-30. $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 en suite 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,
JoAnn Wind Daniel Gale Sothebys Intl Rlty
$14,400 per month
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
$13,000 per month
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
$230,000 per month
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
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