Fair Housing Notice

Rentals In Southold

    to
     
     
     
    Property Criteria
    Features
    •  
    Display Tools
    Search

    97  properties match your search;

    97 with Multiple photos ;  5 with Virtual Tour ;  0 with Videos

    Save Search
    Showing 11 - 20 of 97 results| view:  results per page« 1|2|3|4|5|...|last »
    • Discover the finest rental property in the charming hamlet of Orient, on Long Island’s desirable North Fork. Built in 2017, this exceptional home combines a clean, contemporary aesthetic with breathtaking architectural detail, perfect for discerning guests.The first floor features an open-concept living space with soaring ceilings, anchored by a gourmet chef’s kitchen with premium appliances and a spacious island, ideal for cooking and entertaining. A cozy fireplace in the living room and a sophisticated dining area make for a warm, inviting atmosphere. The main level also includes a luxurious primary suite with an ensuite bath showcasing a carved vanity, as well as a small, convenient office.The upper level offers two light-filled bedrooms and a beautifully crafted stone bathroom, perfect for family or guests. The exquisitely finished lower level provides a relaxing escape with its sauna, another stone bathroom, and a spacious open area complete with a dining table and sectional seating-an ideal space for entertaining or unwinding. Step outside to the oversized, private yard, thoughtfully screened with mature evergreens. The outdoor amenities include a stunning 20 x 50 heated gunite saltwater pool, a wood deck for lounging, and a charming pool house finished with barn siding, slate flooring, and its own bathroom. This luxurious home is the ultimate North Fork retreat for those seeking beauty, privacy, and sophistication. 23
      2620 Orchard Street Orient, NY 11957
      $50,000
      3 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 2800.00:#
      Single Family For Rent ML# 3589919
      Discover the finest rental property in the charming hamlet of Orient, on Long Island’s desirable North Fork. Built in 2017, this exceptional home combines a clean, contemporary aesthetic with breathtaking architectural detail, perfect for discerning guests.The first floor features an open-concept living space with soaring ceilings, anchored by a gourmet chef’s kitchen with premium appliances and a spacious island, ideal for cooking and entertaining. A cozy fireplace in the living room and a sophisticated dining area make for a warm, inviting atmosphere. The main level also includes a luxurious primary suite with an ensuite bath showcasing a carved vanity, as well as a small, convenient office.The upper level offers two light-filled bedrooms and a beautifully crafted stone bathroom, perfect for family or guests. The exquisitely finished lower level provides a relaxing escape with its sauna, another stone bathroom, and a spacious open area complete with a dining table and sectional seating-an ideal space for entertaining or unwinding. Step outside to the oversized, private yard, thoughtfully screened with mature evergreens. The outdoor amenities include a stunning 20 x 50 heated gunite saltwater pool, a wood deck for lounging, and a charming pool house finished with barn siding, slate flooring, and its own bathroom. This luxurious home is the ultimate North Fork retreat for those seeking beauty, privacy, and sophistication.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • Stunning Orient retreat with a private heated gunite pool; enjoy an ideal location with a beach and village just down the block. This tranquil home features soaring ceilings, two fireplaces, four ensuite guest rooms, a private office, an enormous eat-in kitchen, a light-filled dining room, a hotel-like master suite with a second-floor balcony, charming front porch, two living rooms, and beautiful design details at every turn. This home is as stylish as it is comfortable and is the perfect summer rental to host family and friends. Mature trees and landscaping dots the exterior with a large outdoor shower. Garage with flex rec room space. Plenty of parking. Just minutes to Greenport Village and all the best amenities Orient and the North Fork has to offer. 35
      400 Youngs Rd Orient, NY 11957
      $50,000
      4 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 3300.00:#
      Single Family For Rent ML# 3585970
      Stunning Orient retreat with a private heated gunite pool; enjoy an ideal location with a beach and village just down the block. This tranquil home features soaring ceilings, two fireplaces, four ensuite guest rooms, a private office, an enormous eat-in kitchen, a light-filled dining room, a hotel-like master suite with a second-floor balcony, charming front porch, two living rooms, and beautiful design details at every turn. This home is as stylish as it is comfortable and is the perfect summer rental to host family and friends. Mature trees and landscaping dots the exterior with a large outdoor shower. Garage with flex rec room space. Plenty of parking. Just minutes to Greenport Village and all the best amenities Orient and the North Fork has to offer.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • Available for 2024! Newly constructed modern farmhouse with 4 bedrooms, all with ensuite baths. Get away from it all in this hotel-like Orient home. Open concept kitchen, dining, living with beautiful light filled bedrooms. Enormous blue stone patio leads to in-ground pool and beautifully landscaped yard beyond. Minutes from the private association beach, Orient State Park and Duryeas Restaurant & Bar. Past tenants all loved their stay at this home!! June 40k, July 45k, Aug 50k 16
      505 Plum Island Lane Orient, NY 11957
      $50,000
      4 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 2600.00:#
      Single Family For Rent ML# 3526488
      Available for 2024! Newly constructed modern farmhouse with 4 bedrooms, all with ensuite baths. Get away from it all in this hotel-like Orient home. Open concept kitchen, dining, living with beautiful light filled bedrooms. Enormous blue stone patio leads to in-ground pool and beautifully landscaped yard beyond. Minutes from the private association beach, Orient State Park and Duryeas Restaurant & Bar. Past tenants all loved their stay at this home!! June 40k, July 45k, Aug 50k
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • Sprawling Nassau Point estate with open floor plan, 4 ensuite bedrooms and beautiful pool area. Enjoy summer days by the pool or beach directly across the street. 1st floor features an open floor plan with living, dining and large chef’s kitchen. Also on the 1st floor, a large great room for gathering or watching movies. The hotel-like primary bedroom features peek-a-boo water views and a large primary ensuite bath. Plenty of room to stretch out and relax while retreating to the North Fork summer! Private mooring is available for guests’ use. 18
      4800 Nassau Point Rd Cutchogue, NY 11935
      $48,000
      4 Bedrooms 5 Full Baths Sq. Ft. 5500.00:#
      Single Family For Rent ML# 3532390
      Sprawling Nassau Point estate with open floor plan, 4 ensuite bedrooms and beautiful pool area. Enjoy summer days by the pool or beach directly across the street. 1st floor features an open floor plan with living, dining and large chef’s kitchen. Also on the 1st floor, a large great room for gathering or watching movies. The hotel-like primary bedroom features peek-a-boo water views and a large primary ensuite bath. Plenty of room to stretch out and relax while retreating to the North Fork summer! Private mooring is available for guests’ use.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • Impeccably restored and updated 1850’s Farmhouse in the heart of Orient Village. Featuring a great room with open floor plan - gourmet kitchen/dining/living room, a second-floor master bedroom with sitting room, full bath, and walk-in closet for a total of 3-bedrooms 2.5 baths in the main house. There is a separate Cottage with kitchenette, bedroom, and full bath, perfect for guests. Lovely private grounds with gardens, grand lawn, and heated salt water gunite pool. Walking distance to all village amenities, beaches, and marinas. Available June $25, 000; July $45, 000; Aug $45, 000; Sept $25, 000. Permit # 1019. 24
      400 King Street Orient, NY 11957
      $45,000
      4 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 3000.00:# Square Feet
      Single Family For Rent NEW ML# 812326
      Impeccably restored and updated 1850’s Farmhouse in the heart of Orient Village. Featuring a great room with open floor plan - gourmet kitchen/dining/living room, a second-floor master bedroom with sitting room, full bath, and walk-in closet for a total of 3-bedrooms 2.5 baths in the main house. There is a separate Cottage with kitchenette, bedroom, and full bath, perfect for guests. Lovely private grounds with gardens, grand lawn, and heated salt water gunite pool. Walking distance to all village amenities, beaches, and marinas. Available June $25, 000; July $45, 000; Aug $45, 000; Sept $25, 000. Permit # 1019.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • 3 Bedroom/2 Bath Home with Heated Inground Pool and Several Beaches Nearby. Open Floor Plan and Vaulted Ceilings. Enjoy the Days of Summer on the Back Deck, Fenced Lawn and Pool. Several Nearby Beaches Too! Summer 2025 - Memorial Day to Labor Day $45, 000; June $12, 000; July $16, 000; August to Labor Day $20, 000; Weekly $4, 000 Per Week with Two Week Minimum. Permit #0586. 21
      3045 Rocky Point Rd East Marion, NY 11939
      $45,000
      3 Bedrooms 2 Full Baths Sq. Ft. 2025.00:# Square Feet
      Single Family For Rent ML# 806080
      3 Bedroom/2 Bath Home with Heated Inground Pool and Several Beaches Nearby. Open Floor Plan and Vaulted Ceilings. Enjoy the Days of Summer on the Back Deck, Fenced Lawn and Pool. Several Nearby Beaches Too! Summer 2025 - Memorial Day to Labor Day $45, 000; June $12, 000; July $16, 000; August to Labor Day $20, 000; Weekly $4, 000 Per Week with Two Week Minimum. Permit #0586.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • Summer rental in Orient. Beautifully renovated inside and out featuring 4 bedrooms, 2.5 baths, plus a spacious backyard with pool. Available for August-LD. RP# 0930 5
      20 Vincent Street Orient, NY 11957
      $45,000
      4 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 2300.00:#
      Misc For Rent ML# 3488219
      Summer rental in Orient. Beautifully renovated inside and out featuring 4 bedrooms, 2.5 baths, plus a spacious backyard with pool. Available for August-LD. RP# 0930
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • Stunning vineyard views! Nestled in the heart of the North Fork’s first vineyard is this sprawling, historic beauty. Steeped in history but with all the modern comforts and conveniences is the generous estate. Don’t miss the one-of-a-kind North Fork sunrises from the primary suite or the picturesque sunsets from the gunite pool. Experience life on a working farm, while enjoying the seclusion and serenity of nearly 66 acres of a classic North Fork vineyard. Completely renovated, never lived in, and to be professionally furnished with designer grade places! July $40, 000 - August-LD $40, 000 36
      4782 Alvah’s Lane Cutchogue, NY 11935
      $40,000
      6 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 3000.00:# Square Feet
      Single Family For Rent ML# 805043
      Stunning vineyard views! Nestled in the heart of the North Fork’s first vineyard is this sprawling, historic beauty. Steeped in history but with all the modern comforts and conveniences is the generous estate. Don’t miss the one-of-a-kind North Fork sunrises from the primary suite or the picturesque sunsets from the gunite pool. Experience life on a working farm, while enjoying the seclusion and serenity of nearly 66 acres of a classic North Fork vineyard. Completely renovated, never lived in, and to be professionally furnished with designer grade places! July $40, 000 - August-LD $40, 000
      Presented By: Century 21 Albertson Realty  631-765-3800
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • Cutchogue North Fork: Spend August-LD 2025 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 Magazines. Chique but casual Summer home. Inside Outside living. Endless beaches to take in and at night follow the lights from Horton’s Lighthouse over the crescent coastline. Primary Suite with gorgeous long water views from large private sundeck. August-LD $40, 000 RP# 0579 26
      2430 Dignans Rd Cutchogue, NY 11935
      $40,000
      4 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 2250.00:# Square Feet
      Single Family For Rent ML# 3518964
      Cutchogue North Fork: Spend August-LD 2025 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 Magazines. Chique but casual Summer home. Inside Outside living. Endless beaches to take in and at night follow the lights from Horton’s Lighthouse over the crescent coastline. Primary Suite with gorgeous long water views from large private sundeck. August-LD $40, 000 RP# 0579
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • CHIC RETREAT! A glamorous getaway! You won’t know if you are tucked away in Tuscany or the South of France! This recently renovated modernist home is nestled amongst your own private vineyard with incredible farm vistas, imparting a spa retreat vibe. A large pool reaching out towards the horizon. Cozy up by the firepit or have lunch alfresco under the vineyard pergola and enjoy incredible privacy! 3 bedrooms, 2.5 baths, Minutes to the best of everything the North Fork has to offer - local farm stands, beaches, renowned restaurants, (check out Duryea’s) Village Lane, Orient State Park and Greenport Village! This Could Be You! Either 8/8-8/22 or 8/10-8/24 available at: $38, 500.00. Permit #1128 Additional information: Appearance:Mint+++, Interior 25
      27840 Main Road Orient, NY 11957
      $38,500
      3 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 2110.00:#
      Single Family For Rent ML# 3560540
      CHIC RETREAT! A glamorous getaway! You won’t know if you are tucked away in Tuscany or the South of France! This recently renovated modernist home is nestled amongst your own private vineyard with incredible farm vistas, imparting a spa retreat vibe. A large pool reaching out towards the horizon. Cozy up by the firepit or have lunch alfresco under the vineyard pergola and enjoy incredible privacy! 3 bedrooms, 2.5 baths, Minutes to the best of everything the North Fork has to offer - local farm stands, beaches, renowned restaurants, (check out Duryea’s) Village Lane, Orient State Park and Greenport Village! This Could Be You! Either 8/8-8/22 or 8/10-8/24 available at: $38, 500.00. Permit #1128 Additional information: Appearance:Mint+++, Interior
      Presented By: Corcoran  631-848-7730
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    Showing 11 - 20 of 97 results| view:  results per page« 1|2|3|4|5|...|last »
    Hartford Homes
    (631) 339-9090

    475 Route 25A Rocky Point, NY 11778

    Contact Us

     Submit