FlipKey was an online vacation rental marketplace and a subsidiary of TripAdvisor."TripAdvisor Taking on Airbnb?" . Travel Trends, 20 July, 2015 Martin Kelly The platform was shut down in November 2024, resulting in the cancellation of all existing reservations."TripAdvisor/FlipKey Sudden Exit Leaves Hawaii Travelers in Limbo" . Beat of Hawaii, 11 September, 2024 In 2016 the company listed more than 300,000 properties in 179 countries. Its headquarters is in Boston, Massachusetts, United States."TripAdvisor inks lease in North Station". Boston Business Journal, Sep 18, 2013
Although rental owners were verified by the company's staff before being added to the FlipKey website,"Consumer Watch: How to protect yourself from building contractor scams". Times Free Press, August 9, 2015. by Ellen Phillips the site relied heavily on traveler reviews of rental properties. FlipKey also published ratings for travel-related items such as food blogs"Business buzz: Goodwill's Telly; Designers' outstanding event; Foodies' blog; Big Cat Habitat" . Herald Tribune. and in the United States it provided ratings of national historic sites."Fort Smith National Historic Site Named Top Place To Visit In Arkansas". 5 News, January 22, 2016, by Chandler Rogers
Citing complaints that FlipKey would not guarantee functional amenities in its rental sites, in 2016 Better Business Bureau gave the company an F rating.
History FlipKey was founded in 2007 as a house-swapping and vacation rental listing website."Giving Airbnb a Run for Its Money". New York Times, Feb 11, 2015. Stephanie Rosenbloom The company was acquired by travel website, TripAdvisor, in 2008. That year FlipKey was included in Travel and Leisure's list of top travel websites.
At first Flipkey sold subscriptions to homeowners, operating from offices on Lincoln Street in Boston."First look: TripAdvisor's new Boston office near North Station". Boston Globe: BetaBoston, by Scott Kirsner January 9, 2014 After 2013, FlipKey changed its sales model, giving property owners the option of paying a percentage commission for each property rented."Apartment Rentals Are FlipKey’s Fastest Growing Category". Skift, Dennis Schaal, Jun 16, 2014"TripAdvisor’s Flipkey Raises the Fees It Charges Vacation Rental Property Managers". Skift, Dennis Schaal Nov 03, 2014
In 2014, FlipKey moved its offices to Causeway Street in Boston, which was also expected to house another Tripadvisor subsidiary, Smarter Travel. That year Flipkey created a virtual tour of Boston for its website, to promote its property listings there."FlipKey creates awesome virtual tour of Boston as the first in a series of traveler guides". Beta Boston - The Boston Globe, 2014/05/06.
In 2015, FlipKey updated its technology platform, resulting in complaints from some large property managers that they were being overcharged."TripAdvisor In Tiff With Vacation Rental Managers Over FlipKey Changes". Dennis Schaal, Skift - Aug 28, 2015 In 2017, the city of Coral Gables, Florida, sued FlipKey, claiming that the company had ignored city statutes prohibiting commercial activity in residential areas."Coral Gables sues FlipKey over illegal short-term rentals". The Real Deal, By Francisco Alvarado | May 17, 2017
In September 2024, TripAdvisor announced that FlipKey would be shutting down on November 1, 2024, noting that any reservation after that date would be cancelled and refunded. The company said the decision was part of a broader restructuring strategy.
See also Holiday cottage Vacation rental
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