Dive Brief:

• Trinity Investments has entered into an agreement to sell the Grand Lakes Orlando Resort, a 409-acre resort in Orlando, Florida, anchored by two luxury hotels, to Ryman Hospitality Partners for $1.38 billion, according to a Monday news release.  
• The deal, comprising a 582-key Ritz-Carlton and 1,010-key JW Marriott, is expected to close in the third quarter of this year, per the release, and marks what Trinity claims is the “largest non-gaming U.S. resort transaction on record.” 
• Upon closing, the transaction will represent the Miami-based firm’s third disposition in the last 15 months, per the release. The sale arrives as hotel investors are zeroing in on high-end assets, with the luxury segment poised to enter a “compelling” investment cycle, according to a June report from JLL. 

Dive Insight:

Since Trinity first acquired the property in December 2018 for $870 million, the resort has undergone a makeover that “significantly” enhanced the guest experience, per the release. 

Overall, Grande Lakes Orlando Resort features 320,000 square feet of indoor and outdoor meeting space, 14 food and beverage outlets, a 40,000-square-foot spa and an 18-hole championship golf course, per the release.

Sean Hehir, managing partner, president and CEO of Trinity, said in a statement that the deal aligns with the company’s ability to “identify complex, large-scale opportunities and execute on a value-add plan that meaningfully repositions the asset.”

“Grande Lakes Orlando joins a growing list of resorts where our team has driven significant operational improvement and created lasting value for our investors and partners,” Hehir added. 

Trinity's pending deal of the Orlando resort comes after Trinity and Certares Real Estate Management exited from the 352-key East Miami hotel in September 2025, selling it to funds affiliated with Blackstone Real Estate. Additionally, last June, Trinity sold the 950-key JW Marriott Phoenix Desert Ridge Resort & Spa in Arizona, also to Ryman Hospitality, for $865 million. 

The sale comes just a few months after Trinity, in a joint venture with Sculptor Diversified Real Estate Income Trust, acquired the 809-key JW Marriott Marco Island Beach Resort in Florida. The pair bought the property in a deal valued at $835 million in May 2026. 

Amid a growing wealth bifurcation industrywide, luxury remains a winning asset class for investors, due in part to capital markets aligning and a stronger debt market, per JLL. Ultra-luxury, in particular, has shown “exceptional resilience,” driven by rapid growth in the sector. 

So far in 2026, luxury hotel deals have gained some traction. Earlier this year, Host Hotels & Resorts sold the Four Seasons Resort Orlando at Walt Disney World Resort in Florida and the Four Seasons Resort and Residences Jackson Hole in Wyoming for a combined $1.1 billion. 

Also in the luxury segment, Miami-based Gencom acquired the 253-key Ritz-Carlton New York, Central Park for an undisclosed sum earlier this year; and Dallas-based Braemar Hotels & Resorts sold the 193-key Park Hyatt Beaver Creek Resort & Spa, a ski-in/ski-out destination in Colorado, for $176 million in May.