The Nitty Gritty of Luxury Villa Rentals

Vacations, by definition, are supposed to be relaxing and enjoyable. And I think I speak for everyone when I say, all of us need some of that, now more than ever. With the growing number of options and a wide array of services being offered, people are opting for luxurious villa stays. A recent travel sentiment survey by Indagare found that travelers “feel more comfortable renting a home or private villa for added privacy” and that “more than half of those surveyed said that they are 54 percent more likely to rent a home than they were prior to coronavirus, preferring to ‘stay at homes not hotels,’ for added security and peace of mind.” Other reports tout the key advantages of private luxury villa accommodations, with privacy and exclusive use entrenched among them. Additionally, proximity is one overarching booking factor noting that “for some travelers, a house close to town or affiliated with a nearby resort or hotel provides the perfect combination of exclusivity and access (to restaurants, coffee shops, fitness classes, etc.). Others prefer staying someplace further removed, opting for a home with fewer amenities or a lavish villa with every convenience under the sun.”

Choosing a luxury villa, more often than not, involves choosing a stay that specifically caters to your precise needs. However, finding a villa with the right amenities, in the right part of the world can be a daunting task. When it’s time to reserve, it’s important to understand the difference between available booking options. In general, booking through a trusted travel advisor is much less risky than renting through an online booking platform and provides many potential benefits. The primary benefit is the advisor’s knowledge of many available quality villas, as well as surrounding areas and popular attractions. An advisor will not only book your villa, but they can also help plan your entire trip and offer you tips and advice to make the most of your stay. Whereas online booking platforms like VRBO and Airbnb operate more like bulletin boards: They post available rentals and facilitate arrangements, but they are not principals in the rental transactions. Though they’re often grouped together, established villa management companies (booked through a travel advisor) and online booking platforms work differently and provide different levels of assistance and coverage if something goes wrong. The established villa management companies are familiar with all of the properties in their portfolio, and in most cases, staff has personally inspected each property. 

Here’s a roundup of some of our favorite villa destinations…


The Resort at Paws Up ~ Montana

Spread out over 27,000 acres, the wilderness destination, Resort at Paws Up, offers 27 villa accommodation options from 1-4 bedrooms sleeping up to eight persons. Your stay is an all-inclusive of meals so guests can eat in the common dining areas or hire a private chef to prepare a meal inside or an outdoor BBQ. We love the rustic luxury feel of the Big Timber Homes that feel like a modern-day homestead with all the amenities you would want in a vacation rental. The homes feature a wide porch perfect for taking in the rugged Montana landscape, and a private hot tub for soaking after a busy day horseback riding or cattle wrangling. Each home comes with its own Lexus vehicle for driving around the resort and during the summer months, some of the homes come with its own private tent for playtime or outdoor sleeping.

Blackberry Farm & Blackberry Mountain ~ Tennessee

The luxurious Blackberry Farm nestled in the foothills of the Smoky Mountains is a luxurious resort that combines elegance, comfort and quality into special experience catering to young and old alike. Three-to-five bedroom fully equipped homes provide space for families or friends to comfortably socialize and lay their heads in between partaking in of the resorts many activities and services. Blackberry Farm’s wilderness and wellness sister property, Blackberry Mountain, includes seven home options for 2-4 bedrooms complete with wood-burning fireplaces and outdoor dining spaces. We love the diverse offering that Blackberry Farm and Blackberry Mountain provides for our clients and the consistent high-quality dining, activity and accommodation offerings.


Stay HVN

The beach resort regions of Mexico are perennial favorite destinations for families and friends alike. From oceanfront villas to villas within a resort, guests can enjoy private stays in fully serviced villas with amenities ranging from private pools, outdoor kitchens, complimentary villa kayaks and paddle boards to private cinemas and beaches. We love the wide range of aesthetics, service and amenity options and the abundance of options.


Casa de Campo ~ Dominican Republic

We love the over 50 luxury villas at this exclusive resort that caters to both families and adults with access to three golf courses, 8 restaurants, 7 bars, multiple beaches and, depending on the day, you might even be able to take in a performance by one of the many international singers and performers who entertain here. This self-contained resort means that you do not have to venture beyond this 7000-acre property for all of your dining, activity and entertainment needs.

Hawksbill ~ Turks and Caicos

When a momentous occasion requires an equally momentous location, this villa/beach house combo delivers. Whether it’s for a wedding, a special reunion, even a corporate retreat, Hawksbill is a great choice. Featuring a total of 10 bedrooms that are spread out over the main villa and a 2-bedroom beach house, you’re right on the beach in the coveted Grace Bay area. There’s a large pool, a private tennis court, a gym, and a large stone terrace and elegant formal dining room that are perfect for entertaining. Stretch out under the sun or on one of the many comfortable couches inside.


Rosewood Castiglion del Bosco ~ Italy

11 unique villas and 6 residence options sit on over 6000 acres at the beautifully appointed Rosewood Catiglion del Bosco in Italy’s culinary and culturally rich Tuscany. Villas and pools each come with a private heated pool and some come with its own tennis court and outdoor kitchens. A stay here offers a private stay experience with the benefits of accessing the main hotel’s amenities: kids’ club, spa, fitness center, on-site cooking school, walking tours and multiple dining venues.

Abercrombie & Kent ~ Greece

Escape to your own private retreat on one of Greece’s magical islands. Villas here range in size up to 14-bedroom villas for 32 guests in a wide variety of options. Private pools, oceanfront or village locations and full services from transportation to dining to guided tours and activities, we love villas here for the immersion into the local environment and the elevated quality of accommodations and service to suit every guest.



  • Luxury Villas