Business.com made a record in 1999 when eCompanies, an Internet incubator, paid $7.5 million for the Web domain name, putting it on the list of the highest domain name transactions in history. Business.com is backed by venture capital firms Benchmark Capital and Institutional Venture Partners, as well as media giants Reed Business Information and McGraw-Hill. However, no one could have predicted that this domain would be worth 47 times more in just 8 years.

After Dow Jones and The New York Times attempted to purchase Business.com in the years after 1999, the domain's value skyrocketed. R.H. Donnelley, which publishes print and online phone directories, announced the acquisition of Business.com for $345 million in cash plus additional delayed payments. However, the buyer was unlucky in this specific domain name sale. Only two years after purchasing the domain, the third-largest print and online Yellow Pages publisher in the United States entered bankruptcy.

Price: $345 million

LasVegas.com was purchased in 2005 by VEGAS.com, LLC, which sought to link the two domains to ensure that both search phrases directed Las Vegas-based online traffic to the tourist agency. The big $90 million sale guarantees that this will go down in history as one of the most expensive website purchases.

Stephens Media, the previous owner of the domain, consented to a contract that included an initial payment of $12 million. According to the financial papers, LasVegas.com was sold for a whopping $90 million in total payments. The payment plan will be completed over 35 years, from 2005 to 2040.

VEGAS.com, LLC signed a purchase agreement for LasVegas.com in June 2005. The deal stipulated a $12,000,000 one-time payment upon agreement completion, followed by monthly payments of about $83,000 for 36 months, $125,000 for the next 60 months, and then $208,000 for the next 36 months.

According to the provisions of the agreement, VEGAS.com, LLC may terminate the agreement and forfeit the domain name after June 30, 2016, following the 132 first monthly payments. If VEGAS.com, LLC does not terminate the agreement, they will continue to make monthly payments of about $208,000 until June 30, 2040, at which point the seller will transfer the domain name to VEGAS.com, LLC at no additional expense or payment.

Using a discount rate of 6.25 percent in June 2005, the present value of the future payment commitments was calculated to be roughly $12,264,000. The initial $12,000,000 payment has been capitalized and will be amortized over the 35-year life of the agreement.

The present value of the future purchase obligation of about $12,264,000 was capitalized and is being amortized beginning in July 2005 and ending in June 2016, the period during which VEGAS.com, LLC is legally required to continue paying payments under the agreement. Following June 2016, the agreement will be renewed on a month-to-month basis through June 30, 2040, with all payments reported as an expense.

Price: $90 million

QuinStreet, a California-based vertical marketing and online media company made news at the close of the past decade with some of the most costly domain name purchases ever. In just 13 months, the business has bought three massive domain names in the insurance industry, culminating in the purchase of CarInsurance.com on November 8, 2010.

QuinStreet's crown jewel was already a highly lucrative consumer site for evaluating and purchasing auto insurance plans. With that single purchase, the firm cemented its position as the industry leader in online insurance at a time when internet purchasing was exploding.

CarInsurance.com, like other domains owned by QuinStreet Inc, is intended to assist users to find services – in this case, vehicle insurance. "We help you make wise insurance decisions," the business says.

According to a prominent web host, the typical price of a secondary market domain is in the thousands. QuinStreet paid $49.7 million for carinsurance.com in 2010. QuinStreet, situated in Foster City, California, is a publicly-traded marketing business. QuinStreet has previously purchased other insurance-related domain names before acquiring CarInsurance.com. QuinStreet paid $16 million for the domain name and website of Insure.com in 2009, and $35.6 million for insurance.com (along with other associated assets) in 2010.

Price: $49.7 million

Insurance.com is ranked second, with a market capitalization of $35.6 million. QuinStreet purchased the second of three insurance domain names for $35.6 million in August 2010, together with all of Insurance.com's existing media and technological assets. This online platform, like CarInsurance.com, was viewed as helpful since it was a popular site for comparing insurance quotes on vehicles, health, life, house, and renters insurance.

According to media sources, QuinStreet Inc.'s purchase of Insurance.com was about more than just the domain name. According to one writer, the value wasn't simply in the domain name. And it's easy to see why. While Insurance.com is now used to compare insurance policies, it was originally run as an insurance agency. As a result, the domain had an established online presence before QuinStreet Inc. purchased it, so the corporation was essentially purchasing a full business rather than a mere name.

Insurance.com compares prices for auto, house, health, and life insurance.

Price: $35.6 million

Tourism has never been more popular than it is today, with various options to market, explore, and locate the best available deals to meet your travel demands. Not surprisingly, one of the top five most costly domain names for sale was related to holiday rentals.

Unlike some of the other top domain names on this list, VacationRentals.com was purchased simply to prevent another competitor from acquiring it first. It was 2009, when Brian Sharpies, CEO of HomeAway, managed to sneak in and buy the domain after learning that his competitor, Expedia, was about to do so.

VacationRentals.com was already an active site before the acquisition and now serves as a global marketplace for vacation deals.

VRBO is a popular vacation rental business that allows users to schedule short stays in the homes of other customers. Surprisingly, the company was not always known as VRBO. Before its name change in 2019, the company was known as HomeAway, however, the parent corporation updated the name and branding. According to Forbes, the update was motivated by a desire to get consumers "excited about a vacation rather than annoyed by organizing it."

Users can now easily search for vrbo.com or go to VactionRentals.com. That domain instantly redirects to VRBO's website, so users are directed to the newly rebranded company.

VacationRentals.com is worth $35 million, making it the world's fifth most expensive domain name.

Price: $35 million

PrivateJet.com is the only domain on the list that caters nearly entirely to the richest of the rich, providing luxury jet charter rentals for international business flights. It just seems natural given its purchase in 2012 was the purest sale of a domain name in history!

Nations Luxury Transportation, LLD, an Atlanta-based travel services company, paid $30.1 million for the name PrivateJet.com. It was purchased from Don't Look Media.com, an intellectual property holding company, in the belief that the new website will help attract high-net-worth clients. According to the corporation, PrivateJet.com would be utilized to establish a "destination website" for private jet enthusiasts, pilots, and passengers.

The company has stated that it expects to have over 250,000 monthly website visits by the end of 2012 — but that's where things get strange. PrivateJet.com redirected viewers to oceanfrontdomains.com, a website that claims to deal with digital real estate investments and acquisitions. We don't know what happened to PrivateJet.com; all we know is that the domain name was quite pricey in 2012.

Nations Luxury Transportation's CEO indicated at the time of the domain's sale that it would assist in revolutionizing the super-luxury market of Private Jet transportation.

Price: $30.1 million

voice.com is the most recent domain name sale on the list, after what seemed like an eternity of no significant acquisitions. It was purchased by Block.one and quickly topped the list of the most expensive domain names in 2019.

According to the company, Voice.com works with "innovative" enterprises. When the business bought voice.com, executives stated that the domain would be turned into a social media platform. According to a company spokesman, the word "voice" was chosen since it is "universally recognized." According to the website, voice.com makes "NFTs easy for creators like you" – implying that the company is involved with digital assets and blockchain.

This is most likely the most expensive publicly announced pure domain name acquisition of all time. While the previously stated heavyweight domain sellers on our list were all worth more money, the truth is that all of these names were already web companies before they were sold. However, voice.com was not an operating website prior to being purchased, and the ultra-premium domain name will undoubtedly aid Block.one's desire to become Facebook's largest opponent yet.

voice.com became entangled in the technology business, thus it's no wonder that the domain is pricey. According to 2019 reports, the site is worth $30 million.

Price: $30 million

We already reported how QuinStreet went on crazy buying in 2009, acquiring the largest insurance-related domains that are now firmly in the top five of all time. In addition, the corporation paid $18 million in cash for one of the most expensive domain names, Internet.com.

WebMediaBrands, a global source of news and unique content, was the seller. The company intended to sell domain names in order to increase its net balance and focus on its core business ideas. According to reports, buying Internet.com grants QuinStreet Inc. access to a market of 15 million internet users.

According to recent sources, Internet.com has a rather big name, but the site doesn't offer anything. Despite being sold to QuinStreet Inc. in 2009 for approximately $20 million, the website has stayed mostly unchanged. According to a recent report, the site will one day provide a private and secure email service for the entire world.

Price: $18 million

360.com is the only number-based URL on our domain name value list, and it is one of the few domains of its kind that has made a fortune. The transaction occurred in 2015 when Qihoo CEO Zhou Hongyi intended to build a new brand that would unify and embrace all of his products and services. The audacious move cost $17 million.

360.com was sold by Vodafone, the telecommunications corporation that once produced a phone of the same name. While number-based domains are becoming less popular in the West, the acquisition was a smart move for a corporation primarily focused on the Chinese market. In China, where numbers have cultural significance, short names and digits are significantly more prevalent. As a result, the high domain name fee is completely justified.

Surprisingly, when compared to the other sites on this list, 360.com is far more popular outside of the United States. Qihoo, a leading security brand in China that sells a wide range of internet security products, owns the site. 360.com claims to be China's largest provider of Internet and mobile security products. The company claims to be a pioneer of free online security products, having been founded in 2005.

Price: $17 million

QuinStreet Inc. owns the website. According to 2009 sources, the corporation paid $16 million for Insure.com. Following the devastating first year of the Great Recession, the sale increased future domain values.

QuinStreet Inc. appears to work in a variety of industries, but the company describes itself as a pioneer in powering decentralized internet markets that allow customers to compare companies.

This $16 million deal was worth 10 times more than the prior purchase of Insure.com in 2001. Insure.com differentiated itself from other large domains such as insurance.com by providing more than just a platform for following new insurance deals. It also supplied articles, quotes, and news about this industry sector. Such valuable information contributed to its status as one of the most expensive domain names.

People acquainted with domain transactions mentioned additional pricey names in the same publications addressing the sale of Insure.com. Toys.com, which ToysRUs purchased for more than $5 million, is one of these costly websites. Meanwhile, Ad.com was sold for over a million dollars.

Price: $16 million