The Hollywood Roosevelt: Old Hollywood Vibes

Exiting the Hollywood Freeway (US 101) at Hollywood Boulevard, you're immediately dropped into the heart of the action—tourists crowding the sidewalks, open-top buses inching along, street performers drawing crowds. It’s loud, hectic, and unmistakably Hollywood. But just a few blocks later, you pull into the Roosevelt’s valet and everything shifts. The chaos fades. Palm trees frame the entrance, the courtyard feels like a hidden garden, and the vintage glamour of the lobby welcomes you into a world apart. You’ve arrived at a true LA sanctuary.

My favorite time to visit The Hollywood Roosevelt is during the summer. Booking an upper-floor cabana room overlooking the Tropicana Pool gives you a front-row seat to all the action—prime views of the scene below and a perfect earshot of the DJ spinning poolside.

View from a Pool Cabana Room

Check the event calendar before your stay—you won’t want to miss one of the Roosevelt’s signature outdoor movie nights by the pool. Catching a classic film under the stars, cocktail in hand, is pure LA magic. If you're lucky, you might also time it right for a late-night swim during one of their night pool parties.

Inside, you can find a concert at Teddy’s, surprise speakeasy pop-ups, or even a bit of close-up magic in the cozy Library Bar. The Spare Room—the hotel’s hidden upstairs lounge and vintage two-lane bowling alley—is a gem I didn’t discover until a few stays in. Tucked just above the lobby, it’s one of LA’s coolest spots for a craft cocktail and a little friendly competition.

If I had to choose a last meal, it would be a burger and fries—and 25 Degrees delivers the absolute best. Perfectly seared patties, buttery buns, hand-cut fries, and just the right amount of indulgence. It’s comfort food elevated and somehow always hits the spot, whether it's noon or 2 am. This place has become a ritual every time I stay at the Roosevelt.

Shirley Brasserie is the kind of place that feels both grand and grounded—a perfect spot for a relaxed yet elegant dinner. It channels Old Hollywood charm with glowing chandeliers, polished wood, and a soft, cinematic glow. The menu leans French-Californian, with thoughtfully crafted dishes meant for sharing.

Step outside The Hollywood Roosevelt and you’re immediately on the legendary Hollywood Walk of Fame. Just across the street is the iconic TCL Chinese Theatre, where handprints of stars past and present line the forecourt. A short stroll down Hollywood Boulevard takes you to Musso & Frank Grill, the oldest restaurant in Hollywood and a beloved institution since 1919—perfect for a martini and a taste of Hollywood history. And if you're up for a scenic view, head up the hill to Yamashiro, a hilltop Japanese restaurant with sweeping views of the city and a garden setting that feels worlds away from the boulevard below.

Hollywood Walk of Fame: Nancy Sinatra’s star steps from the hotel's entrance

Tommy Dangcil, a Hollywood-born film historian, has this to say about The Hollywood Roosevelt in his book Hollywood 1900–1950 in Vintage Postcards (2002): “The Roosevelt is a reminder of Hollywood’s visual splendor from the magical 1920s and is one of the most visited hotels in Los Angeles.”

Timing is everything when it comes to Hollywood traffic. To avoid the gridlock, aim to arrive mid-morning (10–11:30 am) or mid-afternoon (2–3:30 pm)—you’ll breeze in between rush hours and beat the late check-in crowds. If you're arriving later, shoot for after 8:30 pm, when the boulevard begins to quiet down. Once you arrive, skip the street chaos and head straight to the valet entrance on Orange Drive (just south of Hollywood Blvd). It’s fast, easy, and drops you right into the heart of the Roosevelt’s entrance.

For more inspiration and insider recommendations, visit our Los Angeles page.