The Coachella Valley has long been the playground of movie stars, mob bosses and millionaires, many of whom built sprawling estates to call (a second) home. Some of these abodes are now available as venues, base camps or honeymoon head starts. Here are five of our favorites.
Also known as The Frank Sinatra House, this mid-century manse was designed by famed architect E. Stewart Williams and commissioned by Frank Sinatra. The name, Twin Palms, is a nod to the two perfectly placed trees by the pool. Perfect for a swinging soiree for 150 cool cats, the home is filled with period furniture and reminders of the Rat Pack days, such as Sinatra’s vintage recording equipment. Ceremonies are usually held on the lawn, followed by cocktails in the living room (where giant sliding doors open to seamlessly blend the inside with the out), and dinner on the circular driveway. Cost for one-day site rental (ending at 10 p.m.) begins at $5,000; day stay and rental, $2,600 per night, plus tax and $2,000–$3,000 event fee. A $350 cleaning fee is applied to all rentals. 
An elegant 1933 Spanish villa rumored to have been a frequent hideaway for Marilyn Monroe and Joe DiMaggio, the estate is tucked behind giant hedges and 15-foot wooden gates in the Movie Colony neighborhood. The property’s lush lawns, beamed ceilings, plank-and-iron doors, tiled staircases, outdoor fireplace, water fountains, cobblestone courtyards, pool table, grand piano, tennis courts and mountain views make it a luxe place for making it legal. Posing on the octagonal tower suite’s picture-perfect balcony is almost reason enough to invite as many as 250 guests. Cost for one-day site rental (ending at 10 p.m.) $5,000. A three-day stay and rental is $1,800 per night, plus tax and a $2,000–$3,000 event fee. A $350 clean fee is applied to all rentals. 
Throw an affair to remember at Cary Grant’s blue-and-white, Spanish-meets-Southwestern cottage residence, which still has initials on its front gates. You could be one of the first to shoot your pictures on the 1927 cottage’s picturesque balconies and staircases, in front of the rustic fireplace or out in the twinkle-light-lit, bougainvillea- and cactus-covered yard, as the space only became available for events last May. The current owner has a 1965 Rolls-Royce Silver Cloud to round out your old Hollywood experience. Prices start at $10,000 and depend on size and date of the event. 
Step back in high desert history to the opulent O’Donnell House, a Mediterranean Revival–Monterey residence built in 1925 for an oilman and his osteopath wife. As it was the highest mountainside home in Palm Springs until the ’60s, part of the fun for guests (as many as 125) is the golf cart shuttle up a treacherous trail that leads to sweeping views of the city, spectacular sunsets, verdant gardens, stone patios and a 4,100-square-foot home bathed in natural light. The wraparound porch, scrollwork gates, original elements—including a first-generation doorbell—and rock hardscape are fetching settings for pictures. The curved staircase makes for a dramatic bridal entrance to the side lawn, which has a raised tier for musicians. There is no minimum overnight requirement in order to host an event; you may rent the venue for the day only. However, if you would like to secure lodging at the O’Donnell, the nightly rate of $2,500 will be discounted to $2,000 per night with the purchase of any event package; the “Basic” package for the O’Donnell is $7,500–$9,000. Cost will reflect estimated guest count and the day of the week being secured. 
The O’Donnell is run by the same folks who operate the adjacent Willows Inn, an eight-room B&B that hosted plenty of famous folks, including Clark Gable and Albert Einstein. The gourmet breakfast served at the base of the patio waterfall is reason enough to book your VIPs here, and the meticulously restored mansion is gorgeous for pre and post events.
A collection of six distinct villas reminiscent of a hillside European town and built as an artists’ colony in the 1920s, Colony 29 has been restored and modernized to accommodate everything from a small dinner in the spectacular main house, butted up against the mountains, to “splendor in the grass” nuptials with 400-guests, under pergolas or on a backlit concrete stage. The entire complex must be booked for three nights, but the requirement does provide ample time for discovering the many delights situated on these 7 acres, including outdoor bathtubs, meditation gardens, hiking trails, bridges over seasonal streams, an adult-sized tree house and butterfly-bespeckled day-after brunch spots. Prime season rental rates are approximately $4,000 a night (not including additional event fees). 
