Rentals In Southold

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    Showing 31 - 40 of 97 results| view:  results per page« first|...|2|3|4|5|...|last »
    • Mattituck, NY 11952
      $24,000
      3 Bedrooms 2 Full Baths Sq. Ft. 1800.00:#
      Single Family For Rent ML# 3513356
      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 room/kitchen with terrace access, large living room for rainy day enjoyment. Upstairs are 2 more bedrooms and full bath. Large, level and private lot conveniently located by area vineyards, popular Love Lane and both LI Sound and Bay beaches. Immaculate and awaiting your stay. Flexible dates; pets on individual basis; no smoking. Southold Town Rental Permit #1022., Additional information: Appearance:Diamond, Interior Features:Guest Quarters, Lease Term:August-Labor Day, Flexible, July, July-August, June, Memorial-Labor, Off Season
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • 75 Gillette Drive East Marion, NY 11939
      $22,500
      6 Bedrooms 4 Full Baths 1 Half Bath
      Single Family For Rent ML# 3593132
      2025 Rates: Memorial Day-Labor Day $87, 500, June $22, 500, July $32, 500, July-August $67, 000 and August-Labor Day $35, 000. Looking for a resort like retreat just outside of bustling Greenport Village? Look no further! This 6 bedroom, 4.5 bathroom stunner offers everything you could ask for and more. From 3 en-suite bedrooms to an open floor-plan with high-end appliances and a killer in-ground pool/hot tub combo, this property serves as the ideal summer rental. This rare offering is also just a short walk to a sugar sand bay beach, close proximity to Islands End Golf Course, local wineries, farm stands and much more!, Additional information: Appearance:Pristine, Interior Features:Guest Quarters
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • 935 Southern Cross Rd Cutchogue, NY 11935
      $22,500
      4 Bedrooms 4 Full Baths
      Single Family For Rent ML# 3371622
      Available 2025: April: $12, 000, May: $17, 500, June: $22, 500, July: $35, 000, August: $40, 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 floor features 2 bedrooms with 2 full baths with glass sliders leading out to the deck. Downstairs has 2 more ensuite bedrooms with glass sliders leading out to a patio. Soak up the sun and relax by the saltwater pool, rinse of the sand with the spacious outside shower or enjoy the patio where there is plenty of room to entertain throughout any time of the day.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • 1800 Village Lane Orient, NY 11957
      $22,000
      3 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 2200.00:#
      Single Family For Rent ML# 3524519
      Village Lane summer house - full season rental - historic charm seamlessly blended with modern amenities. Water views. Hardwood floors, lots of light, unique architectural interest with sophisticated decor for the discerning traveler. Rent reflects MD-LD.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • 25 Moose Trail Cutchogue, NY 11935
      $22,000
      4 Bedrooms 2 Full Baths Sq. Ft. 2600.00:#
      Single Family For Rent ML# 3505394
      Spectacular updated Cape with a heated pool at 25 Moose Trail, Cutchogue. Enjoy the chefs’ kitchen & many spacious living and entertaining areas, including dining room, game room with pool table & arcade games, bedroom, & a full bath on the first floor, all tastefully furnished. Outside you have an expansive deck off the kitchen that takes you to the heated pool surrounded by a paver patio & professionally landscaped yard. This home also has beach rights to a beautiful sandy bay beach and park. Many wonderful vineyards, restaurants, and farm stands are close by. This is the perfect home for entertaining & family gatherings! RP# 0422 , AVAILABLE 2025 June $12, 000, July $22, 000, August is RENTED ., Additional information: Appearance:excellent, Lease Term:August-Labor Day, July, July-August, June, Memorial-Labor
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • 905 Stephensons Rd Orient, NY 11957
      $20,000
      4 Bedrooms 4 Full Baths 2 Half Baths Sq. Ft. 4500.00:#
      Single Family For Rent ML# 3555837
      Escape the hustle and bustle of everyday and spend a month in Orient’s most coveted beachfront estate enclaves. You will be captivated by the breathtaking 180-degree water views and grand sunsets that greet you at every turn in this beautifully designed and expertly built home by the sea. With 4800 square feet of living space, this beachfront retreat offers an abundance of room for relaxation and family entertainment. Begin your day in the private gym and sauna, offering a sanctuary for health and well-being. Channel your inner chef in the state-of-the-art kitchen. Entertain with ease in the grand greet room, boasting a wood-burning fireplace and floor to ceiling windows overlooking the gorgeous beach. Just outside is expansive decking and a beautifully furnished large screened Mahogany porch for relaxing with friends and dining al-fresco overlooking the beachfront. Inside you will find four spacious bedrooms and additional guest suite with big water views; each featuring full baths ensuite for added convenience and privacy. After a day of seaside adventures, unwind in the movie room or den, where relaxation meets entertainment in unparalleled luxury. There is a well appointed office for those times you will need a professional atmosphere, but with the same captivating beach views. This home offers a peaceful retreat and an idyllic setting for memorable gatherings in Orient for those who love that one of a kind beachfront experience. Whether hosting family gatherings or entertaining guests, this haven provides the perfect setting for unforgettable moments by the sea. Close Jitney and Ferry, several farm stands, Orient’s historic district, Yacht club, Golf course, Village lane shops, Duryea’s, private fish charters, world class vineyards and Zagat rated restaurants. 5 minutes to Greenport with ferry service to the Hamptons. Only available August 1st - August 14th, 2025 $20, 000. Rental Permit# 1135
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • 260 Orchard Street Orient, NY 11957
      $20,000
      3 Bedrooms 1 Full Bath 1 Half Bath
      Single Family For Rent ML# 3554131
      Nantucket beauty with pool. Steps from Village Lane shops, bay and sound front swimming beaches. Spend your vacation in the coveted Orient Village. This pristine home is beautifully designed and decorated with details you will appreciate throughout. Lovely floor plan, professional chef’s kitchen and dining room, living room with wood burning fireplace, den, and 2 bedrooms with deck overlooking garden and pool and additional 3rd bedroom and 1.5 full Lux baths. Large poolside decking and gorgeous gardens. Well appointed home and yard that will make your summer stay just fabulous. Rental Permit# 0866
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • 5220 Stillwater Avenue Cutchogue, NY 11935
      $20,000
      4 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 2500.00:#
      Single Family For Rent ML# 3546762
      This charming 4-bedroom, 2.5-bathroom home offers the perfect blend of comfort, convenience, and seaside serenity. As you step inside, you’ll notice the beachy feel that permeates every corner of this home. The spacious living areas invite you to relax and unwind, with ample room and a well-appointed Chef’s Kitchen for gatherings and entertaining. Each bedroom is designed to offer tranquility and functionality, featuring windows that flood the rooms with natural light and offer glimpses of the surrounding natural beauty. Venture into the backyard, and you’ll discover your own private paradise. A gunite saltwater pool offers a refreshing escape during hot summer days, accompanied by an outdoor shower. The Dave Allison Park is just a short stroll away. Its playground and sandy community beach are ideal destinations for picnics, games, and waterfront fun. East Creek Beach, a private haven, is also within walking distance, offering secluded shores and tranquil waters for swimming and sunbathing. With its unbeatable location and irresistible amenities, this home is the ultimate retreat for those seeking the perfect blend of comfort and coastal living on the North Fork. Within minutes to world-renowned vineyards and local farms! Don’t miss your chance to make memories in this seaside sanctuary on the North Fork - Now available in Summer 2025 and off-season.
      Presented By: Nest Seekers International LLC  631-354-3547
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • East Marion, NY 11939
      $20,000
      4 Bedrooms 2 Full Baths Sq. Ft. 3000.00:# Square Feet
      Single Family For Rent ML# 3361257
      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 with many access points to southeast facing deck/terrace. Incredible sunrises - and sunsets reflected on the lighthouse and bay. Living room w/fireplace, sunroom/office, EIK with upscale appliances; DR w/sliders to terrace for outdoor dining. Waterside master suite w/full bath, 3 additional bedrooms w/guest bath. Large 3+ car garage for cars and summer toys. Private yard space for playing and pickinking. The ultimate North Fork beach house rental for you and your guests. Home sleeps up to 12 people comfortably. Life doesn’t get better than at Tara-by-the-Bay. Close proximity to area farmstands, lavender fields, wineries and destination restaurants in Greenport. Permit #0248
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • 300 Marion Place East Marion, NY 11939
      $19,000
      3 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3546433
      Private, peaceful home on a serene acre of property. Just renovated, featuring open modern Kitchen/Dining combo for casual entertaining. Separate family room across open foyer with fireplace and loads of puzzles & games. Charming covered front porch looks out onto front yard. Back deck with grill overlooks pool and backyard. Three bedrooms: 1 Queen, 2 full beds and primary with king bed and en-suite bathroom with large shower. Hall bathroom with tub. Laundry in basement. Tasteful furnishings, all the basics & wifi together make this an easy place to settle in and retreat to for a great vacation & workplace away from the everyday home office. Treadmill for workouts. Beach rights at the end of the Bay Avenue. The surrounding area has it all: vineyards, farm stands, restaurants, beaches, downtown Greenport and more. Avail for use: Fire Pit - Solo Stove, 3 bikes.
      Presented By: Prime Properties Long Island  631-427-9600
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
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