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Newest Homes for Rent in Southold, NY

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  • /31

    $4,500 Per Month

    • 4 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    65 Lake Dr, Southold, NY 11971

    Two week minimum rental. Available in July and August, $4,500 / week. August 16 through Labor Day, $5,500/week. 3% discount for rentals longer than 3 weeks. Perfectly situated in one of the North Fork's most desirable beach communities, this welcoming 4-bedroom, 2-bath, 2-story beach bungalow is just a 3 minute stroll to the sandy shoreline of Kenney's Beach, 7 minutes to the Great Pond, a 10

    Jon Tomlinson Daniel Gale Sothebys Intl Rlty

    65 Lake Dr, Southold, NY 11971
  • /29

    $10,000 Per Month

    • 2 Beds
    • 1.5 Baths
    • 940 Sq Ft
    • House for Rent

    1825 Main Bayview Rd, Southold, NY 11971

    Clean and Tidy 2 Bedroom/1.5 Bath Cottage with North Fork Character and Charm, Located Near Bay Beach and Farmstand. Nice Yard and Deck for Enjoyable Outdoor Living. July $8,000 (or $2,000 per week with two week minimum); August to Labor Day $10,000 (or $2,000 per week with two week minimum); Labor Day thru September $6,000 (or $2,000 per week with two week minimum); October $6,000. Rental Permit

    Paul Loeb Douglas Elliman Real Estate

    1825 Main Bayview Rd, Southold, NY 11971
  • /18

    $3,700 Per Month

    • 3 Beds
    • 1 Bath
    • 1,500 Sq Ft
    • House for Rent

    2380 S Harbor Rd, Southold, NY 11971

    YEAR ROUND - Monthly Rate $3,700 STARTING OCTOBER 1 - ALSO AVAILABLE AS SEASONAL RENTAL. The Yellow House sits on five secluded acres in Southold on the North Fork of Long Island, offering sweeping vineyard views and stunning sunsets. One of the North Fork's best bay beaches is just a five-minute stroll to the end of the road. The home has been newly painted and furnished and features central air

    Sheri Winter Parker Corcoran

    2380 S Harbor Rd, Southold, NY 11971
  • /18

    $16,000 Per Month

    • 3 Beds
    • 1 Bath
    • 1,500 Sq Ft
    • House for Rent

    2380 S Harbor Rd, Southold, NY 11971

    Available: July $16K, August $19.5K, Oct 1, 2026 to Sept 30, 2027 - Monthly Rate $3,700. The Yellow House sits on five secluded acres in Southold on the North Fork of Long Island, offering sweeping vineyard views and stunning sunsets. One of the North Fork's best bay beaches is just a five-minute stroll to the end of the road. The home has been newly painted and furnished and features central air

    Sheri Winter Parker Corcoran

    2380 S Harbor Rd, Southold, NY 11971
  • /21

    $30,000 Per Month

    • 4 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • House for Rent

    1225 Leeton Dr, Southold, NY 11971

    Summer is here, and this home has vacation written all over it. Enjoy spectacular sunset water views of the Long Island Sound from the spacious wrap-around deck or from the bright, open-concept living spaces inside. Perfect for entertaining, the layout features 4 bedrooms and 2 full bathrooms, offering a beautiful oasis for relaxation and togetherness. The lifestyle here is effortless: Kenny's

    Mackenzie Needham Daniel Gale Sothebys Intl Rlty

    1225 Leeton Dr, Southold, NY 11971
  • /43

    $14,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,693 Sq Ft
    • House for Rent

    4525 S Harbor Rd, Southold, NY 11971

    2026 Availability: July $12,000; August $14,000. Newly renovated Southold home offering 3 bedrooms and 2 full baths, ideally located just 0.2 miles from South Harbor beach. An open concept kitchen and living room, anchored by a fireplace and filled with natural light offers the perfect place to unwind after a day of exploring the North Fork. Outdoors, a patio with dining area, built in barbecue,

    Bridget Elkin Compass Greater NY LLC

    4525 S Harbor Rd, Southold, NY 11971
  • /20

    $20,000 Per Month

    • 3 Beds
    • 4 Baths
    • 2,600 Sq Ft
    • House for Rent

    2045 Lake Dr, Southold, NY 11971

    Offered June $10,000 ($2,500/wk); July $20,000 ($5,000/wk); Aug $25,000 ($6,250/wk); Sept $12,000 ($3,000/wk); Oct $10,000 ($2,500/wk). Two-week minimum. This contemporary waterfront home on Great Pond enjoys sunrise over the water and spectacular sunsets over Long Island Sound from its hilltop setting in one of the North Fork’s most distinctive beach communities. Surrounded by native plantings

    Janet Markarian Daniel Gale Sothebys Intl Rlty

    2045 Lake Dr, Southold, NY 11971
  • /26

    $12,500 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,500 Sq Ft
    • House for Rent

    16125 Soundview Ave, Southold, NY 11971

    Available 2026: September $12,500; October $12,500; November $8,500Experience the very best of the North Fork in this extraordinary soundfront retreat, where miles of pristine Long Island Sound beachfront become your backyard and sunsets RSVP nightly just for you. Wake each morning in the primary suite to panoramic water views that stretch to the horizon, framed by floor-to-ceiling glass that

    Sheri Winter Parker Corcoran

    16125 Soundview Ave, Southold, NY 11971
  • /16

    $2,600 Per Month

    • 1 Bed
    • 1 Bath
    • 530 Sq Ft
    • Apartment for Rent

    55075 Main Rd Unit Youngs Bldg 3, Southold, NY 11971

    Newly renovated and pristine year-round rental in the heart of Southold's beautiful Colonial Village, an exclusive 55 an over adult community. This inviting ground level one bedroom, one bath apartment offers comfort and convenience boasting a modern eat-in kitchen with granite countertops, all new stainless steel appliances and cabinetry; spacious living room & bedroom; ample storage; hardwood

    Thomas McCarthy Thomas J McCarthy Real Estate

    55075 Main Rd Unit Youngs Bldg 3, Southold, NY 11971
  • /22

    $3,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    440 Longview Ln, Southold, NY 11971

    Experience effortless one-level living in this immaculate Southold retreat. Set in the coveted Terry Waters community with its own sandy beach just down the road, this clean, airy home offers comfort, privacy, and classic North Fork charm. A welcoming front porch opens to an inviting living room and a spacious den featuring hardwood floors and a wood-burning fireplace. The dining area flows into

    Ryan McQueeney True North Realty Luxury Homes

    440 Longview Ln, Southold, NY 11971
  • /20

    $6,000 Per Month

    • 2 Beds
    • 3 Baths
    • 1,000 Sq Ft
    • Apartment for Rent

    345 Old Cove Blvd, Southold, NY 11971

    Seasonal Rental. Set directly across from Town Beach in Southold, this beautifully maintained seasonal rental captures the best of North Fork coastal living with unobstructed water views, direct beach access, and a relaxed indoor-outdoor lifestyle. Located within a private home built approximately six years ago, the apartment offers its own private side entrance from the patio area, complete with

    Basil Boziotis Compass Greater NY LLC

    345 Old Cove Blvd, Southold, NY 11971
  • /17

    $3,200 Per Month

    • 2 Beds
    • 1 Bath
    • 606 Sq Ft
    • House for Rent

    1385 Old Shipyard Ln, Southold, NY 11971

    Charming year-round rental in coveted Founders Landing! Just moments from a sugar sand Bay beach and a marina with deep water access. Nestled on a spacious 1/4 acre parcel perfect for outdoor activities. Featuring two cozy bedrooms and a well-appointed bath, this home offers plenty of room for entertaining while being easy to maintain. Conveniently close to shops, beaches, and dining. Don't miss

    Andrea Parks Douglas Elliman Real Estate

    1385 Old Shipyard Ln, Southold, NY 11971
  • /20

    $14,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,572 Sq Ft
    • House for Rent

    465 Tarpon Dr, Southold, NY 11971

    August Rental $14,500: This elegant mid-century coastal charming North Fork rental is nestled in Southold Shore Community with a bayfront beach, marina and water access for launching a kayak. This chic and sophisticated modern home has been completely renovated and sits on a private road with a manicured front lawn and a two car garage. Enjoy your cup of coffee or lunch on the beautiful large

    Maryse Bransfield William Raveis New York LLC

    465 Tarpon Dr, Southold, NY 11971
  • /14

    $25,000 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,300 Sq Ft
    • House for Rent

    2662 Paradise Shores Rd, Southold, NY 11971

    Your quintessential North Fork summer starts here. Tucked away in the quiet beach community of Paradise Shores, this Bayfront cottage is the summer retreat you’ve been dreaming of. Positioned directly on Southold Bay with unobstructed views of Shelter Island, this charming cottage offers the best scenery on the North Fork. Whether you're hosting a sunset dinner or just enjoying a quiet morning,

    JoAnn Wind Daniel Gale Sothebys Intl Rlty

    2662 Paradise Shores Rd, Southold, NY 11971
  • /18

    $7,908

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,194 Sq Ft
    • Condo for Rent

    155 Sound Ave Unit SI FL3-ID1521494P, Mattituck, NY 11952

    The advertised rate of $7,908/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 14, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    155 Sound Ave Unit SI FL3-ID1521494P, Mattituck, NY 11952
  • /6

    $15,000 Per Month

    • 1 Bath
    • 230 Sq Ft
    • Condo for Rent

    52325 County Road 48 Unit 8, Southold, NY 11971

    Waterfront Studio Condo in Southold property features living room / kitchen combo with 1 Queen Size bed and 2 pull out trundle beds which can become 1 full size bed. outdoor area includes BBQ area on grounds free laundry room.Seasonal Condo Use Only Open from April - November then the condo closes for season.

    Peter Vekiarellis ERealty Advisors Inc

    52325 County Road 48 Unit 8, Southold, NY 11971
  • /20

    $8,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • House for Rent

    1050 Pine Ave, Southold, NY 11971

    North Fork summers are defined by sun-soaked beach days, vineyard hopping, and slow evenings spent cooking under the open sky—and this charming 3-bedroom, 2-bath cottage captures it all. Tucked away in Southold, this inviting rental places you right in the heart of the North Fork, perfectly positioned to experience everything the area has to offer. Spend your mornings browsing Southold’s curated

    Kieran Collings Douglas Elliman Real Estate

    1050 Pine Ave, Southold, NY 11971
  • /29

    $12,612

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 3,196 Sq Ft
    • Condo for Rent

    1345 Long Creek Dr Unit SI ID1512339P, Southold, NY 11971

    The advertised rate of $12,612/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 21, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    1345 Long Creek Dr Unit SI ID1512339P, Southold, NY 11971
  • /18

    $22,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • House for Rent

    2845 Hobart Rd, Southold, NY 11971

    Mint mid-century modern cottage offering 3 bedrooms and 2 baths, ideally located just 100 yards from sandy Founders Landing beach. The interior features clean, modern lines, anchored by a fireplace and expansive picture windows that fill the space with natural light and capture beautiful water views. Outdoors, your backyard with fire pit and outdoor shower creates an ideal setting for summer

    Eric Elkin Compass Greater NY LLC

    2845 Hobart Rd, Southold, NY 11971
  • /17

    $6,000 Per Month

    • 4 Beds
    • 4 Baths
    • 1,800 Sq Ft
    • House for Rent

    215 Leon Rd, Southold, NY 11971

    Enjoy this spacious vacation rental located just a short distance from Southold Town Beach. With room for the whole family, this home features three en-suite bedrooms plus an additional bedroom and full bath. The well-equipped kitchen opens to the dining and living rooms, where a cozy fireplace adds charm and warmth. Sliding glass doors lead to a deck overlooking a large backyard, perfect for

    Jeanmarie Bay William Raveis New York LLC

    215 Leon Rd, Southold, NY 11971
  • /10

    $4,000 Per Month

    • 2 Beds
    • 1 Bath
    • 750 Sq Ft
    • House for Rent

    8515 Soundview Ave, Southold, NY 11971

    Tucked away on the peaceful edge of freshwater Great Pond in Southold, this delightful 2-bedroom, 1-bath cottage offers the perfect blend of comfort and charm. Enjoy quiet mornings with water views and spend your days kayaking, paddle boarding, or fishing right from your backyard. Barbecue and dine on the spacious deck with a sunset view of the lake. Ideally situated just moments from Kenny's

    Nicole Fitzgerald Signature Premier Properties

    8515 Soundview Ave, Southold, NY 11971
  • /28

    $9,500 Per Month

    • 3 Beds
    • 3 Baths
    • 2,280 Sq Ft
    • House for Rent

    205 Pine Ave, Southold, NY 11971

    A relaxed North Fork summer retreat with a private beaches, a pool for long afternoons, and easy access to vineyards, farmstands, and waterfront dining. Summer on the North Fork begins at 205 Pine Avenue!Located within the coveted Goose Bay Estates private beach community, this beautifully maintained Southold home offers access to two private beaches at the end of the street—perfect for

    Barbara Poliwoda Douglas Elliman Real Estate

    205 Pine Ave, Southold, NY 11971
  • /8

    $5,000 Per Month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    8415 Soundview Ave, Southold, NY 11971

    Step inside this charming 2 bedroom, 1 bath bungalow nestled on the serene shores of Great Pond in Southold. This cozy waterfront retreat offers tranquil water views and is just around the corner from Kenny's Beach and the popular Little Fish restaurant. Enjoy kayaking, paddle boarding, and fishing right from your backyard. Centrally located in the heart of the North Fork, you're perfectly

    Nicole Fitzgerald Signature Premier Properties

    8415 Soundview Ave, Southold, NY 11971
  • /41

    $14,950 Per Month

    • 6 Beds
    • 3.5 Baths
    • 3,500 Sq Ft
    • House for Rent

    100 W Shore Dr, Southold, NY 11971

    Set in the highly sought-after Reydon Shores community, 100 W Shore Dr, Southold is a rare dog-friendly North Fork waterfront seasonal rental with your own private, sandy beach and sweeping bay views to Shelter Island. This renovated classic offers three levels of living with a great room and sunroom, 6 bedrooms, 3.5 baths, two wood-burning fireplaces, and a huge Trex deck built for sunset

    Basil Boziotis Compass Greater NY LLC

    100 W Shore Dr, Southold, NY 11971
  • /32

    $44,000 Per Month

    • 4 Beds
    • 4.5 Baths
    • 2,500 Sq Ft
    • House for Rent

    70 Arshamomaque Ave, Southold, NY 11971

    Southold, North Fork AUGUST 1-14, 2026 Rental: Heaven Off Main. Chic new retreat with ultra vacation vibe. 4 en suite bedrooms, each with a different theme and a full bath, complement the 'public' rooms designed for entertaining. Home opens up to poolside terrace and gorgeous sun! Located in the private bayfront beach community of Beixedon. Book your stay today. Pets on an individual basis.

    Nicholas Planamento William Raveis New York LLC

    70 Arshamomaque Ave, Southold, NY 11971
  • /29

    $27,000 Per Month

    • 4 Beds
    • 4.5 Baths
    • 3,100 Sq Ft
    • House for Rent

    590 Soundview Ave, Southold, NY 11971

    This Spacious Open Floor Plan Home Features Two Separate Living Areas, a Treetop Waterview Deck, A Chef's Kitchen with Pantry and a Large Stylish Dining Table. This Inviting Home's Layout Offers Comfortable Gathering Spaces. The Resort-Style Outdoor Living Area is Highlighted by an Inground Pool with a Built-In Hot Tub and Elegant Bluestone Pool Surround. Generous Seating Area Including Hammock,

    Paul Loeb Douglas Elliman Real Estate

    590 Soundview Ave, Southold, NY 11971
  • /47

    $45,000 Per Month

    • 6 Beds
    • 5.5 Baths
    • 6,600 Sq Ft
    • House for Rent

    57305 Route 48, Greenport, NY 11944

    Spectacular, contemporary seasonal rental home with pool and Jacuzzi on the Long Island Sound front. 150 feet of direct waterfront and beach, with incredible view. Meticulously renovated and professionally designed. 6 bedrooms, 5.5 bathrooms. Hamptons luxury in North Fork. Home situated on 1 acre, 6,600 square feet. One master bedroom has jacuzzi and steam room and two extra bedrooms with full

    Zepur Diktas Compass Greater NY LLC

    57305 Route 48, Greenport, NY 11944
  • /22

    $30,000 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,233 Sq Ft
    • House for Rent

    1700 Cedar Dr, Southold, NY 11971

    2026 Availability: June $30,000. July RENTED. Perfect summer getaway with 5 bed, 4.5 bath in the heart of the North Fork. The home sits on 1.24 acres and features an open floor plan, large screened-in porch, full finished basement, wood burning fireplace, outdoor shower, and a saltwater, gunite pool. The primary bedroom has a large roof deck overlooking the pool and rear yard. Bedrooms and full

    Shane Hafer Compass Greater NY LLC

    1700 Cedar Dr, Southold, NY 11971
  • /24

    $15,000 Per Month

    • 3 Beds
    • 4 Baths
    • 1,800 Sq Ft
    • House for Rent

    935 Corey Creek Ln, Southold, NY 11971

    Experience the ultimate North Fork summer in this stunning new construction home, designed for effortless entertaining and elevated coastal living. Professionally decorated and impeccably finished, this residence offers three bedrooms, four full bathrooms, a bonus room, and a beautifully finished lower level with an additional private half bath. Step outside to your own private retreat featuring

    Melissa Principi Douglas Elliman Real Estate

    935 Corey Creek Ln, Southold, NY 11971
  • /26

    $30,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,350 Sq Ft
    • House for Rent

    485 Hickory Ave, Southold, NY 11971

    Impressive Goose Creek home with water views and large heated in-ground pool! This four bedroom, three bath house features a first floor primary bedroom with en-suite, a gourmet kitchen and open living space. The newly designed landscape with outdoor kitchen (not pictured) is ideal for entertaining or relaxing. Enjoy its large fire pit and BBQ grill after an afternoon of Kayaking. Close to

    Mackenzie Needham Daniel Gale Sothebys Intl Rlty

    485 Hickory Ave, Southold, NY 11971
  • /29

    $8,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,600 Sq Ft
    • House for Rent

    60 Water Terrace, Southold, NY 11971

    Settle into summer on the North Fork in this beautifully maintained and updated 4 bedroom, 3 full bath home located in the Angel Shores community of Southold. The layout is ideal for entertaining or just enjoying the lazy days of summer. This special home offers a 1st floor bedroom and full bath, along with a 2nd story spacious primary en-suite and 2 additional bedrooms to comfortably accommodate

    Natalie Hough Daniel Gale Sothebys Intl Rlty

    60 Water Terrace, Southold, NY 11971
  • /32

    $20,000 Per Month

    • 4 Beds
    • 4 Baths
    • 3,585 Sq Ft
    • House for Rent

    580 Gin Ln, Southold, NY 11971

    Wonderful opportunity to spend time in the wonderful Southold community of Bay Haven. Choose to spend the sunny days by your own pool, or head down the block to the community's private bay beach. There is more than ample space to host in this brightly renovated cape with room for everyone. The main level is comprised of a lounge area with fireplace and dry bar, an open kitchen and a large great

    Scott Bortzner Compass Greater NY LLC

    580 Gin Ln, Southold, NY 11971
  • /20

    $13,000 Per Month

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

    215 Northfield Ln, Southold, NY 11971

    Permit 0681- A 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 2026. Terms & Availability: May $13,000,

    Mitch Pickman Thomas J McCarthy Real Estate

    215 Northfield Ln, Southold, NY 11971
  • /21

    $22,500 Per Month

    • 4 Beds
    • 3 Baths
    • 1,800 Sq Ft
    • House for Rent

    270 N Sea Dr, Southold, NY 11971

    Southold, North Fork: Endless sunsets await at this exceptional vacation rental, available year-round with flexible terms and rates. Ideally located in the sought-after Kenny’s Beach community, this sun-drenched home is surrounded by wide sandy dunes perfect for walking, birdwatching, swimming, and relaxing days by the shore.Immaculately maintained, the residence offers 4 bedrooms and 3 full

    Nicholas Planamento William Raveis New York LLC

    270 N Sea Dr, Southold, NY 11971
  • /5

    $4,000 Per Month

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • House for Rent

    310 Old Shipyard Ln, Southold, NY 11971

    Southold Village Rental Charming and well-located, this 3-bedroom, 1-bath residence offers easy North Fork living just moments from the heart of Southold. A short distance to Southold Town, local shops, dining, and the waterfront, as well as close proximity to Founders Beach for swimming, sunsets, and seaside relaxation. The home features a comfortable layout with light-filled living spaces,

    Eric Frend Corcoran

    310 Old Shipyard Ln, Southold, NY 11971
  • /19

    $11,473

    Total Monthly Price

    • 3 Beds
    • 1.5 Baths
    • 1,097 Sq Ft
    • Condo for Rent

    810 Waterview Dr Unit SI ID1261529P, Southold, NY 11971

    The advertised rate of $11,473/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 22, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    810 Waterview Dr Unit SI ID1261529P, Southold, NY 11971
  • /46

    $12,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,900 Sq Ft
    • House for Rent

    110 Sleepy Hollow Ln, Southold, NY 11971

    Discover this stunningly renovated 4-bedroom, 3-bath home, offering an expansive open floor plan, a cozy den, and a versatile bonus room. Designed for both comfort and style, the chef’s kitchen includes a massive eat-in-quartz island and boasts top-of-the-line Fisher & Paykel appliances, including a double-drawer dishwasher, induction cooktop, and convection oven. Perfect for entertaining and

    Paul Loeb Douglas Elliman Real Estate

    110 Sleepy Hollow Ln, Southold, NY 11971
  • /26

    $15,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,700 Sq Ft
    • House for Rent

    1000 Rambler Rd, Southold, NY 11971

    Beautiful like new colonial just 500 feet from sandy bay beach. Four bedrooms plus a lovely sunroom. Fully Furnished. Enjoy your morning coffee on the bedroom balcony. Outside shower and gas grill off backyard deck. Bicycles and a kayak with trailer included. A perfect beach house. Available July $15,000, August-Labor Day $20,000, July-Labor Day $35,000, utilities included.

    Pamela Hunt Colony Realty

    1000 Rambler Rd, Southold, NY 11971
  • /20

    $55,000 Per Month

    • 5 Beds
    • 3.5 Baths
    • 2,750 Sq Ft
    • House for Rent

    7635 Main Bayview Rd, Southold, NY 11971

    Elegant Historic Home in Southold – Coastal Charm Meets Modern Luxury Escape to the North Fork and enjoy this beautifully restored historic Southold home, perfectly blending timeless elegance with every modern comfort. This spacious retreat features 5 bedrooms and 3.5 baths, ideal for families or groups seeking a serene getaway. Enjoy central air conditioning, high-speed internet, and five smart

    Mary Terry MCKENNASHEA LLC

    7635 Main Bayview Rd, Southold, NY 11971
  • /43

    $35,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,724 Sq Ft
    • House for Rent

    345 Colonial Rd, Southold, NY 11971

    Tucked away on a private setting in a peaceful North Fork neighborhood just minutes from Corey Creek, Croteaux Vineyards and Greenport Brewery, this exceptional colonial offers the perfect backdrop for an unforgettable summer. With approximately 2,700 sq. ft. of bright, inviting living space across two levels, there is ample room for family and friends to gather and create lasting memories. Step

    Gloria Scrocco STOEBE & CO

    345 Colonial Rd, Southold, NY 11971

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Frequently Asked Questions

How much does it cost to rent a home in Southold, NY?
The median rent for a home in Southold, NY is $12,250 per month, though prices vary by neighborhood, size, and property type. As of July 2026, condos tend to be the most affordable option while townhouses and single-family homes are currently more expensive.
How much do you need to make to afford rent in Southold, NY?
To comfortably afford the median rent in Southold, NY, a household needs to earn roughly $490,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $12,250 per month in Southold, NY, renters typically need to show $36,750 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Southold, NY?
In Southold, NY, the price-to-rent ratio is 6.5, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.

Rental Home Trends

Number of Homes for Rent
66
Median Rent
$12,250
Median Single Family Home Rent
$9,750
Median Townhouse Rent
$3,200
Median Condo Rent
$3,100
How to Rent a Home