Rentals In Southold

    to
     
     
     
    Property Criteria
    Features
    •  
    Display Tools
    Search

    93  properties match your search;

    Save Search
    Showing 21 - 30 of 93 results| view:  results per page« 1|2|3|4|5|...|last »
    • 3655 Pequash Avenue Cutchogue, NY 11935
      $30,000
      4 Bedrooms 2 Full Baths Sq. Ft. 2400.00:#
      Single Family For Rent ML# 3477027
      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 Dining/BBQ Spaces, 2 Spacious Bedrooms and a Full Bath with Walk-In Shower. Lower level has 2 Additional Bedrooms and a Large Full Bath with Separate Living/Entertaining/Gaming Area for more Informal Fun! Air Hockey, FOOSBALL, & Large Flat Screen TV! Two-Car Garage and Plenty of Guest Parking. Bedrooms provide own TVs and plenty of closet space. PLUS: Fenced-in Sprawling Summertime Fun & Relaxation Spot. 20x40 Heated, Lighted, Saltwater Pool, with 4 In-Pool Chaise Loungers, and steps to separate Jacuzzi Spa to warm up before you Cool Down. Also enclosed is an Outdoor BBQ Pavillion with Bar Area and Kitchenette, as well as Outdoor Living Room complete with Wide Screen TV, and outdoor lighting. Live Your Best Life Here or walk a short distance to Bay Beach at End of Street, or a Short Drive to Long Island Sound and Ocean Beaches, and Local Marinas. Nearby to Gourmet Restaurants, Wineries, Breweries, Golf, Shopping, and NF Farm Stands & Easy Access to the LIRR or NYC Jitney. 3rd Story Master Suite and Attic Off-Limits to Tenants. Utilities Not included in Rental Amounts. Landlord takes care of Pool and Lawn; Tenants to Reimburse for Utilities for the Term; One Month Security Deposit and Utility Deposit (50% of Estimated Term) Lease and Proof of Renters Insurance Required and Satisfactory Credit Approval., Additional information: Appearance:Outstandin, Interior Features:Combo Kitchen, Guest Quarters, Lease Term:1-6 Months, August-Labor Day, Flexible, July, July-August, June, Memorial-Labor, Off Season
      Presented By: Fedun Real Estate Inc  631-722-5000
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • 1429 Peconic Bay Boulevard Laurel, NY 11948
      $25,000
      4 Bedrooms 2 Full Baths 1 Half Bath
      Single Family For Rent ML# 3575176
      Escape to your own piece of paradise in this stunning bayfront home, offering the ultimate in relaxation and luxury. Nestled on the scenic North Fork, this charming 4-bedroom, 2-bath residence boasts breathtaking bay views and direct access to your very own private beach. Imagine unwinding on the expansive deck, sipping your morning coffee while gazing at the tranquil waters, or heading down to the beach to dip your toes in the sand. This home is a true oasis, perfect for outdoor entertaining and water activities. Whether you’re swimming, kayaking, paddleboarding, or simply lounging on the giant anchored raft, there’s something for everyone. The lush, hydrangea-filled gardens provide a sense of privacy and serenity, making this retreat incredibly enticing. With two spacious living areas and options for dining indoors or out, this home is designed for both relaxation and entertainment. Enjoy cozy evenings by the beach or star gazing, roasting marshmallows over a fire and making memories to last a lifetime. Discover the perfect North Fork getaway, where charm, character, and coastal living come together in harmony.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-298-4130
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • 1080 Lands End Rd Orient, NY 11957
      $25,000
      4 Bedrooms 3 Full Baths Sq. Ft. 4000.00:#
      Misc For Rent ML# 3550345
      Very spacious, sunlight filled custom built beauty just 3 minutes to gorgeous LI Sound beach. 44’ x 24’ heated, saltwater pool. Open concept LR/DR/KI with sliders to expansive deck overlooking private, fully fenced, park-like yard and pool area. Upstairs has a large, 2nd living room with billiards, foosball, tv area & sliders to another deck. 2 primary bedrooms - one on each level. 2nd floor primary has living room, wet bar, refrigerator and wall of sliders to deck. Home impeccably maintained and tastefully furnished throughout. Fine dining & state park just down the road. A scenic 9 mile drive to bustling downtown Greenport. Rental Permit #1117. Exp. 5.6.26.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • 1300 Parkview Lane Orient, NY 11957
      $24,000
      4 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 2400.00:#
      Single Family For Rent ML# 3567118
      Welcome to your ideal summer getaway! This charming 4-bedroom, 2.5-bathroom home offers 2400 sq ft of living space on a sprawling 41818 sq ft lot. Prepare to dive into relaxation as this home features a saltwater pool and deck for al fresco dining, with plenty of open space for indoor entertaining. This summer rental is the perfect haven for your seasonal escape!
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631) 339-9090, or  Email: Hartford Homes Estates of Long Island
    • 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
      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
    Showing 21 - 30 of 93 results| view:  results per page« 1|2|3|4|5|...|last »

    Contact Us

    Submit