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Live the Good Life at Villa Rentals Around the World

June 24, 2015
8 min read
Cowboy Manor View of Spanish Peaks-3
Live the Good Life at Villa Rentals Around the World
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Chances are, if you're a regular reader of The Points Guy, you love hotels — or at least the rush of staying at amazing ones for little to no cash outlay. But no matter how fantastic the property or spacious the suite, it’s hard to compare to the glamour of renting your own villa. TPG Contributor Adam Erace gives you the intel on seven markets with unbelievable residences you can rent by the week.

As you read on, you'll see that renting a villa could quite possibly earn you your newest credit card's sign-up bonus in one fell swoop — and then some. Also remember that villa rentals like these may be categorized as bonus-earning travel purchases by the Chase Sapphire Preferred (2 points per $1), Barclaycard Arrival Plus World Elite Mastercard (2 miles per $1) and Citi Premier® Card (3 points per $1).

Pool at the Don Arcangelo all’Olmo in Sicily. Photo courtesy of Thinking Traveler.


Whether you’re a splurging honeymooning couple or you're hosting the family reunion of a lifetime, Italy makes a mega-appealing destination for renting villas like Don Arcangelo all’Olmo, a fully-staffed, twelve-bedroom sea castle half an hour from the glamorous resort town of Taormina on Sicily’s eastern coast. Inside, vaulted ceilings and sloping archways give the rooms in this villa the look of a whitewashed beehive. French doors and leaded glass windows look out on tropical gardens surrounding the pool. Ivy covers al fresco dining nooks. Olive trees shelter doors.

You won’t want to leave, but in case you do, the villa’s manager, the Thinking Traveler, pairs clients with on-the-ground concierges who can coordinate chefs, yachts, art classes and even Christmas trees. All this will run you $23,000 a week, which sounds like a lot until you break it down: At full occupancy, you’re looking at $958 per person, or just $136 per night.

Waterbuck Villa at Kings Camp in South Africa. Photo courtesy of Rental Escapes.


Even working the points game, between airfare, lodging and guides, an African safari can be a major expense. This makes an ideal opportunity to gather a group and rent a residence like Waterbuck Villa at Kings Camp, a four-bed, four-bath compound with a prime location in South Africa’s Timbavati Nature Reserve. Inside, crystal chandeliers, leather steamer-trunk end tables, clawfoot tubs and animal-skin rugs create a vintage safari vibe. Outside, a firepot flickers at the boma, a traditional stone enclosure ringed in torches, the perfect spot for recounting details of the day’s game drive with your dedicated ranger.

All this doesn’t come cheap: $41,090 (or a little over $5,000 per person for eight people) a week through Montreal-based Rental Escapes, but at least there’s a silver lining: Rental Escapes has a built-in loyalty program unique to the villa rental industry; guests earn two points for every dollar spent on reservations, which can be redeemed for future stays.

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Bidadari Cliffside Estate, anyone? Photo courtesy of Bali Luxury Villas.


A private elevator carries you up from the beach to the bluff-top villa, Bidadari Cliffside Estate. You can walk it, sure, but when’s the last time you got to ride your own private elevator? (Here in Bali, it's called an “inclinator," by the way.) The island’s villa game is strong, and Bidadari comes correct with gorgeous furnishings, architecture and amenities (infinity pool, gym, Batcave), plus a full-time staff that includes a private chef and chauffeur. The price? You’re looking at about $13,000 a week in peak season, but at max capacity (eight guests), it’s a mere $1,636 per person for the week — and bookable through Bali Luxury Villas.

Villa Croisette. Photo courtesy of Red Savannah.
Make yourself at home in Cannes at Villa Croisette. Photo courtesy of Red Savannah.


Villa La Croisette gets its name from the crescent-shaped promenade that follows the curve in Cannes’ coastline. Lined with palm trees and regal hotels, the street is the center of the see-and-be-seen action in the Riviera resort town; just ask TPG founder Brian Kelly, who was just there for the Cannes Film Festival. This villa sits in a residential enclave 885 feet above the crush, functioning as a sanctuary with its cool, soothing color scheme of creams and lilacs, lush garden and wraparound sea-view terrace. Four bedrooms mean that up to eight guests can share the cost: $5,396 for a week in the low season, or about $96 per person, per day. La Croisette is bookable through the villa arm of luxury tour company Red Savannah.

On St. Martin, you can relax poolside (and seaside) at the Lotus. Photo courtesy of Villas of Distinction.


There are exceptions to the rule, but by and large, if you don’t enjoy hurricanes then you'll need to spend a lot of money or points on a Caribbean hotel. That’s to say nothing of surprise resort fees, crazy expensive on-site food and sputtering Wi-Fi. Happily, villas can make a (reasonably) affordable alternative.

Take Lotus, a three-bedroom St. Martin residence available through Villas of Distinction. The villa boasts gauze-framed four-poster beds beneath white-beamed cathedral ceilings, a palapa-topped outdoor lounge and pool deck overlooking Long Bay. Lotus is going for $557 a night and sleeps six, so about $93 per person per night — for a mansion. Compare that to the very luxurious Belmond La Samanna, where ocean-view rooms in July are fetching $356, or $178 per person per night — a no-brainer. (Of course, if money is no object, you could also rent an entire island for about $210,000 a week. Just saying.)

Mariby Mansion in Havana, Cuba. Photo courtesy of Airbnb.


Louvered wooden doors swing open onto a tiled terrace furnished with a wrought-iron patio set and surrounded by encroaching jungle at the five-bedroom, gated Mariby Mansion in Havana. According to its listing on Airbnb, this terrace was once home to a famous cabaret show in the tropical capital. Now, it could be you sipping mojitos and daiquiris out there, thanks to enterprising owners who are capitalizing on the recent deregulation for American tourists. (“According to Airbnb Chief Executive Brian Chesky, in the 40 days since the company launched in Cuba with about 1,000 homes, Airbnb has already doubled its listings to 2,000,” TPG’s Eric Rosen wrote last month.)

Keep in mind, this still is Cuba, and expectations should be realistic. Mariby Mansion might drip with history and craftsmanship with its tufted fuchsia sofas and stained glass transoms, but you won’t find Wi-Fi or TV (or smoke detectors, for that matter). The property is currently listed at $480 a night.

Cowboy Manor, in Montana's Moonlight Basin. Photo courtesy of Big Sky Luxury Rentals.


Renting a villa isn’t only for far-flung vacations. You can do so right in here in the US of A, through democratizing sites such as Airbnb and HomeAway and specialized ones like Big Sky Luxury Rentals, an excellent resource if you want to relax in a posh lodge after hiking through Yellowstone. For instance, the six-bedroom Cowboy Manor features ski-in/ski-out access, outdoor hot tub, a home theater and unforgettable views for $34,933 per week. You could also consider a Mediterranean-style Malibu beach house with a stone fireplace, grand furniture and direct beach access for $3,500 a night. Or how about a private island off Deer Isle in Maine that starts at just $375 a night?

See these related posts:

Tips & Tricks for Booking Rental Homes
4 Great Sites for Booking Short and Long Term Accommodations
Hotel Alternatives: Booking Rental Homes For Travel

Ever rented a villa near home or abroad? Please share your tips and experiences with us in the comments below!