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There's a particular kind of freedom that comes with waking up above Los Angeles — city lights still glittering below as the morning marine layer burns off, a supercar waiting in the driveway, and seven full days ahead with nowhere to be and nothing to prove. A week-long stay in the Hollywood Hills isn't just a vacation; it's a full immersion into one of the world's most iconic luxury lifestyles. But pulling it off seamlessly — the right home, the right car, the right experiences on the right days — takes more than a wishlist. It takes a plan.
Consider this your insider blueprint. We've mapped out seven days of Hollywood Hills living at its finest, pairing specific homes and cars with curated experiences across LA's most legendary neighborhoods. Whether you're celebrating a milestone, hosting a group of discerning guests, or simply giving yourself the week you've always promised, this itinerary is designed to make every hour feel intentional.
Choosing Your Base: The Right Hollywood Hills Home for an Extended Stay
The foundation of any great week-long retreat is the property itself. For extended stays, you're not looking for a showpiece — you're looking for a home that lives as beautifully as it photographs. Fortunately, the Hollywood Hills inventory delivers on both fronts.
For groups seeking maximum drama and scale, the Mount Olympus Modern Glass Mansion is a statement property in every sense. Floor-to-ceiling glass walls, sweeping canyon and city views, and the kind of architectural confidence that makes you feel like you're living inside a design magazine. It's the ideal anchor for a group retreat or a special occasion week where aesthetics matter as much as comfort.
If the goal is something more secluded — intimate dinners, morning meditation with canyon views, and fewer neighbors — the Hercules Heights property delivers that rare combination of privacy and proximity. You're minutes from the Sunset Strip, yet the property feels worlds away. For longer stays, that insulation from the city's energy becomes genuinely valuable.
Those who want to split the difference between Hollywood Hills character and Beverly Hills adjacency should consider the Viewmont Iconic Hollywood Hills Mansion — a property that earns its name with views that are, frankly, cinematic. And for travelers who want the full palatial experience, the Alta Royale Palace brings grand-scale entertaining space, resort-style amenities, and a presence that commands the hillside.
Whichever property you choose, book for the full seven nights. The Hills reveal themselves slowly — and the best moments of any extended stay tend to arrive midweek, once you've settled in and the city starts to feel like yours.
Your Weekly Car Strategy: Matching the Vehicle to the Day
A week in the Hills calls for more than one car — or at minimum, a car that can shift roles depending on what the day demands. The smartest approach is to treat your exotic rental as part of the itinerary itself, not just a means of transportation.
For days built around driving — canyon runs on Mulholland, a coastal push down PCH, or a spontaneous trip to Malibu — the Porsche 911 GT3 Touring in Black with Blue Interior is the definitive choice. This is a car engineered for roads exactly like the ones threading through the Santa Monica Mountains, and it rewards a driver who actually wants to feel connected to the asphalt. According to Top Gear, the GT3 Touring remains one of the purest driving machines on the planet — and LA's canyon roads make a compelling case for that reputation.
For evenings on the town — dinner in West Hollywood, a Sunset Strip appearance, or a rooftop lounge arrival — nothing commands attention quite like the Rolls-Royce Dawn White Convertible with Black and Orange Interior. Drop the roof on a warm LA evening and let the city announce your arrival before you've even stepped out of the car.
And for days when you're moving the group — airport runs, day trips, or hauling gear to the marina — the Lamborghini Urus Matte Black with Red Lining handles it all without compromising a single moment of the experience. It's the rare car that can carry four people in genuine comfort and still make a child stop and stare in a Whole Foods parking lot.
Browse the full exotic car fleet if you'd like to mix and match throughout the week — a different car on different days is a perfectly reasonable (and deeply satisfying) strategy.
Day-by-Day Highlights: Building a Week Worth Remembering
Structure gives a long stay its rhythm. Here's how to think about pacing your seven days across LA's most compelling experiences:
Days 1–2: Arrival, Orientation & The Sunset Strip
Arrive in style — if you're flying in, consider booking through our private jet fleet to land directly into Van Nuys or Burbank and avoid the LAX chaos entirely. Settle into your home, take a proper tour of the property, and let the first evening be unhurried. Day two is for the Sunset Strip: dinner at a West Hollywood institution, a walk through the boutiques on Melrose, and a late evening back on your terrace with the city below you. Drive the Dawn. This is the appropriate occasion.
Days 3–4: Canyon Drives & Malibu Days
Pull the GT3 out of the driveway early — before traffic, before the heat — and head west on Mulholland Drive. The road north toward Malibu via Kanan Dume is one of the most satisfying driving routes in Southern California: sweeping elevation changes, ocean views that materialize without warning, and almost no traffic on weekday mornings. As Robb Report has noted, the stretch of Pacific Coast Highway from Malibu to Point Dume remains one of America's great scenic drives — pair it with lunch at Nobu Malibu and you've just had a perfect day. Day four can be a slower Malibu beach day: arrive mid-morning, linger over lunch, and return to the Hills as the sun drops behind the Pacific.
Days 5–6: Beverly Hills, Arts District & A Night on a Yacht
Mid-week is the time to shift into Beverly Hills mode. Rodeo Drive, the Paley Center, a gallery visit in the Arts District — then a transfer down to the marina for an evening charter aboard the Sunseeker 90 ft. Watching the sun set over Santa Monica Bay from a yacht deck, with the city lights coming on in the hills behind you, is one of those experiences that genuinely recalibrates your understanding of what an evening can be. Day six can breathe a little — a late morning, a swim, a chef's dinner at the estate. The Hills are best appreciated from within them, sometimes.
Day 7: A Grand Finale
Your last full day deserves a full-circle moment. Take the Urus up to Griffith Observatory in the late afternoon — the view of the city from that vantage point never gets old, and arriving in a Lamborghini SUV is exactly the kind of absurd, joyful punctuation a great week deserves. From there, head down into Los Feliz for a final dinner at one of the neighborhood's beloved bistros, then back up to the Hills for a last evening on your terrace with a glass of something extraordinary. Tomorrow can wait.
Practical Planning: What to Know Before You Book
A seamless week-long Hollywood Hills stay requires a bit of logistical forethought. A few things worth knowing:
- Minimum stays and pricing: Most of the luxury homes in the Hills have minimum stay requirements that make week-long bookings ideal — you'll often get better nightly rates on extended stays, and you won't spend half your trip in check-in/check-out limbo.
- Vehicle delivery: ASR Luxury delivers vehicles directly to your rental home. There's no rental counter, no shuttle, no waiting. The car is in the driveway when you arrive.
- Staffing and provisioning: Many of the estate-level properties accommodate private chefs and house managers. Plan ahead, communicate with our team, and we can coordinate what you need.
- Parking and street access: Hollywood Hills driveways are not uniform. Some are gated and expansive; others are tight and switchbacked. When booking a supercar, we'll advise you on what's practical for your specific property.
- Yacht and jet add-ons: Day charter and jet bookings can be layered into your week seamlessly. Reach out to our team early and we'll help you build a full itinerary across all categories.
According to Architectural Digest, the Hollywood Hills has become one of the most sought-after short-term luxury rental markets in the country — and the properties available today reflect that demand with increasingly sophisticated amenities and design. Book early, especially for peak season stays between May and October.
Make Every Day of Your Hollywood Hills Week Count
The best weeks in the Hollywood Hills are the ones that feel curated without feeling scheduled — where the right car is always in the driveway, the home never loses its ability to impress, and every experience flows naturally into the next. That's exactly what ASR Luxury is built to deliver.
From the estate you call home base to the car you take on your morning canyon run, every element of your stay is available through a single point of contact. Explore our full collection of luxury short-term rental homes in Hollywood Hills, Beverly Hills, and beyond — then pair your property with the perfect vehicle from our exotic car fleet. Add a yacht charter, a private jet arrival, or simply let us know what kind of week you have in mind.
The Hollywood Hills are waiting. Let's make sure you're ready for them.
