Westgate Resorts

Westgate Resorts is an American resort and vacation-ownership company headquartered in Orlando, Florida. The business was founded in 1982 by David A. Siegel, beginning with a 16-unit property at Westgate Vacation Villas in Kissimmee, Florida. It subsequently developed and acquired resorts in several major leisure destinations, including Central Florida, Las Vegas, Park City, Myrtle Beach, Branson, the Smoky Mountains, and New York City. The company’s principal business is timeshare and vacation ownership: customers purchase an interest in a resort accommodation and receive usage rights, subject to the terms of the relevant ownership program. Westgate also operates hotel and resort accommodation for owners, exchange guests, vacation renters, and other travelers. Its portfolio has included large destination resorts with condominium-style units, family-oriented facilities, spas, pools, recreational amenities, and access to nearby attractions. Westgate expanded particularly actively during the 1990s and early 2000s. Properties opened or entered the portfolio during that period included Westgate Lakes Resort & Spa, Westgate Towers, Westgate Town Center, Westgate Smoky Mountain Resort & Spa, Westgate Flamingo Bay, Westgate Blue Tree Resort, Westgate Park City Resort & Spa, Westgate River Ranch, Westgate Palace, and Westgate Historic Williamsburg. The company later broadened its presence beyond traditional timeshare destinations. In 2018 it acquired the former Hilton New York Grand Central, a 23-story, 300-room hotel in Manhattan, and rebranded it Westgate New York City. Westgate has also operated the Westgate Las Vegas Resort & Casino and used its International Theater for entertainment programming, including Barry Manilow’s Las Vegas engagement announced in 2018. Westgate operates as a subsidiary of Central Florida Investments, Inc., a privately held Central Florida business founded by Siegel as a real-estate development company. CFI has interests and activities associated with real estate, hospitality, vacation ownership, and related operations. As reported in the company’s reference material, the wider organization employs more than 10,000 people, although Westgate’s standalone employee count is not specified here. Leadership changed in March 2024, when longtime executive Jim Gissy became chief executive officer. Founder David A. Siegel moved into the roles of executive chairman and president and continued to provide strategic direction. Siegel died in April 2025. In February 2025, Westgate announced the acquisition of VI Resorts through its Vacation Ownership Sales affiliate. The transaction added more than 40 properties, largely on the U.S. West Coast, and represented one of the company’s largest portfolio expansions. The brand’s positioning combines resort accommodation with vacation ownership, emphasizing destination-based stays and access to resort amenities. Its business has also attracted legal and regulatory scrutiny. Matters described in reference material include a federal telemarketing settlement, disputes involving former sales employees, construction litigation connected with the pH Towers, and a defamation action concerning the documentary The Queen of Versailles. These cases form part of the company’s public record but do not by themselves establish a general characterization of its current operations.

Westgate Resorts began in 1982 when David A. Siegel opened a 16-unit resort called Westgate Vacation Villas in Kissimmee, Florida. The property established the company’s core model: combining destination lodging with vacation ownership. Westgate grew from the Central Florida tourism market as Siegel expanded his broader real-estate interests through Central Florida Investments, Inc., a privately held company he had started as a real-estate development business. During the 1990s and early 2000s, Westgate added properties in several major U.S. vacation markets. Westgate Lakes Resort & Spa opened in 1996, followed by Westgate Towers in 1997. Westgate Town Center and Westgate Smoky Mountain Resort & Spa were added in 1999. The portfolio continued to expand with Westgate Flamingo Bay in 2001; Westgate Blue Tree Resort, Westgate Park City Resort & Spa, and Westgate River Ranch in 2002; and Westgate Palace and Westgate Historic Williamsburg in 2003. This expansion gave the company a presence in Florida, Nevada, Utah, Tennessee, South Carolina, Missouri, Virginia, and other leisure-oriented markets. The company’s properties generally serve multiple customer groups. Timeshare owners receive contracted usage rights, while resorts may also accommodate exchange guests, vacation renters, and other hotel guests. The properties commonly use condominium-style units and provide amenities intended for longer family stays, such as kitchens, pools, recreational facilities, restaurants, spas, and proximity to major attractions. Westgate also developed or operated resort and entertainment assets in Las Vegas, including the Westgate Las Vegas Resort & Casino. Westgate’s public profile increased through both its resort growth and disputes connected with its business activities. In 2009, the company agreed to resolve federal allegations involving violations of telemarketing rules and Do Not Call Registry provisions. It later faced litigation involving sales commissions, construction work at the pH Towers, and claims arising from the documentary The Queen of Versailles. The latter dispute was ultimately decided in arbitration in favor of the filmmakers. In 2016, Westgate Smoky Mountain Resort suffered extensive fire damage. Reconstruction reportedly began soon afterward. In 2018, Westgate expanded into Manhattan by acquiring the former Hilton New York Grand Central and renaming it Westgate New York City. That same year, the Westgate International Theater in Las Vegas hosted Barry Manilow for an exclusive headlining engagement, reinforcing the company’s effort to connect resort operations with entertainment programming. Leadership changed in March 2024. Jim Gissy, a longtime Westgate executive, was appointed CEO, succeeding Siegel in the operational leadership role. Siegel became executive chairman and president and continued to direct the company’s strategic affairs. In February 2025, Westgate announced the acquisition of VI Resorts through its Vacation Ownership Sales affiliate. The transaction added more than 40 properties, largely on the U.S. West Coast, and materially broadened the group’s resort network. Siegel died in April 2025. Westgate remains associated with Central Florida Investments and operates as a privately held resort and timeshare group. Its later-stage strategy has combined organic development, property acquisitions, vacation-ownership sales, hotel operations, entertainment, and destination-focused hospitality. The available reference material does not establish a complete current property list, standalone financial profile, or detailed post-2025 leadership structure.

• 2025

  VI Resorts acquisition announced

  [1]Westgate Resortsen.wikipedia.org

  Westgate announces an acquisition adding more than 40 VI Resorts properties through its Vacation Ownership Sales affiliate.

• 2024

  Jim Gissy becomes CEO

  [1]Westgate Resortsen.wikipedia.org

  Longtime executive Jim Gissy succeeds Siegel as chief executive, while Siegel assumes executive chairman and president duties.

• 2018

  Westgate enters Manhattan

  [1]Westgate Resortsen.wikipedia.org

  The company acquires the former Hilton New York Grand Central and rebrands it Westgate New York City.

• 2016

  Smoky Mountain resort damaged by fire

  [1]Westgate Resortsen.wikipedia.org

  Westgate Smoky Mountain Resort sustains extensive fire damage, followed by reported reconstruction efforts.

• 2009

  Federal telemarketing matter settled

  [1]Westgate Resortsen.wikipedia.org

  Westgate agrees to resolve allegations involving the Telemarketing Sales Rule and Do Not Call Registry requirements.

• 2003

  Westgate Palace and Historic Williamsburg added

  [1]Westgate Resortsen.wikipedia.org

  The portfolio grows with properties serving Orlando and the Williamsburg, Virginia, tourism markets.

• 1999

  Westgate Town Center and Smoky Mountain properties added

  [1]Westgate Resortsen.wikipedia.org

  Westgate expands its destination resort network with properties in Florida and Tennessee.

• 1996

  Westgate Lakes Resort & Spa opens

  [1]Westgate Resortsen.wikipedia.org

  The company adds a major Central Florida resort to its expanding portfolio.

• 1982

  Westgate Vacation Villas opens

  [1]Westgate Resortsen.wikipedia.org

  David A. Siegel launches Westgate Resorts with a 16-unit vacation-ownership property in Kissimmee, Florida.

Destination-oriented, midscale to upscale resort accommodation and vacation-ownership services, with a portfolio spanning family vacation destinations, urban hotels, and leisure resorts.

• Timeshare · 1982

  Vacation ownership interests

  Westgate’s core offering is vacation ownership, under which customers acquire contractual rights to use resort accommodation according to a specified ownership structure. The product is supported by resort amenities and destination access, and may involve owner services, exchange arrangements, usage reservations, and related hospitality operations.

• Hospitality · 1982

  Resort accommodation

  Westgate operates destination resorts with suites or condominium-style units, often designed for family and extended stays. Typical facilities can include kitchens, pools, recreation areas, restaurants, spas, and guest services. Accommodation may be available to owners, exchange guests, renters, and other travelers.

• Hotel · 2018

  Urban and destination hotels

  The company has extended beyond traditional timeshare destinations through hotel assets such as Westgate New York City, the rebranded former Hilton New York Grand Central. These properties provide conventional hotel accommodation alongside the broader Westgate resort and vacation-ownership network.

• Entertainment · 2018

  Entertainment experiences

  Westgate has used resort venues to host entertainment programming. The Westgate International Theater in Las Vegas has presented headline acts, including Barry Manilow, linking the company’s hospitality assets with destination entertainment.

• 2014

  Former sales employees’ commission dispute

  Former Westgate sales employees pursued claims concerning unpaid commissions. The matter continued through later proceedings, and Westgate subsequently brought claims against some former participants, which opposing counsel characterized as retaliatory.

  Source

• 2014

  Defamation arbitration concerning The Queen of Versailles

  David Siegel and Westgate sued the Sundance Institute and filmmakers associated with The Queen of Versailles. The dispute went to arbitration, where the filmmakers prevailed and an award was entered against Westgate.

  Source

• 2013

  pH Towers construction litigation

  A Nevada court dispute involving Westgate and Tutor-Saliba concerned unpaid construction bills and alleged building deficiencies at the pH Towers project. The court issued awards addressing claims on both sides.

  Source

• 2009

  Telemarketing and Do Not Call Registry violations

  Westgate was found to have violated federal telemarketing requirements, including provisions related to the National Do Not Call Registry, and agreed to a settlement with the U.S. government.

  Source

Read more

• 2018Barry Manilow Las Vegas engagement

  Las Vegas, United States

  Westgate promoted Barry Manilow’s return to Las Vegas as the exclusive headliner at the Westgate International Theater, using a high-profile entertainment residency to support the resort’s destination positioning.

  Outcome. The engagement strengthened the entertainment profile of the Westgate Las Vegas property.

  Source
• 2015Victoria’s Voice Foundation

  United States

  Following the death of Victoria Siegel from a drug overdose, David and Jackie Siegel established Victoria’s Voice Foundation. The initiative focuses on youth substance-abuse prevention, education, awareness, family resources, and overdose-prevention efforts, including work connected with naloxone access.

  Outcome. The foundation continued as a nonprofit initiative associated with drug-prevention education and community outreach.

  Source

• 2025

  Acquire VI ResortsM&A

  Background

  Westgate pursued a significant expansion of its vacation-ownership network, particularly in western U.S. markets.

  Action taken

  Through its Vacation Ownership Sales affiliate, Westgate announced the acquisition of VI Resorts and more than 40 associated properties.

  Aftermath

  The transaction became one of Westgate’s largest reported portfolio expansions and increased its presence on the U.S. West Coast.

  Source

• 2024

  Transfer of CEO role to Jim GissyStrategy

  Background

  After decades of founder-led management, Westgate changed its operating leadership while retaining Siegel in senior strategic roles.

  Action taken

  Jim Gissy became CEO; David A. Siegel became executive chairman and president.

  Aftermath

  The move created a formal succession structure while preserving the founder’s involvement in strategic direction.

  Source

• 2018

  Acquire and rebrand Hilton New York Grand CentralM&A

  Background

  Westgate sought to broaden its portfolio beyond resort destinations and establish a presence in Manhattan hospitality.

  Action taken

  The company acquired the former Hilton New York Grand Central and relaunched it as Westgate New York City.

  Aftermath

  The transaction added an urban hotel to Westgate’s primarily resort-oriented network.

  Source

1. 1Westgate Resortsen.wikipedia.org