How to Find the Perfect Vacation Rental: Tips for Your First Time, or any Time

I’m a villa rental convert.

I wanted to do something special for my most recent birthday. But with a three-year-old at home, a weekend jaunt to Paris was not in the cards: Long flights are exhausting, and hotel stays can be tough, forcing us all onto a toddler’s sleep schedule. Plus, I wanted some time with my girlfriends. How to make it work? I hatched a plan to rent a house so that we could all spend a few days together, somewhere a bit exotic but with all the comforts and conveniences of home. We ended up with wonderful memories from our trip to Cabo San Lucas, Mexico (which took place before Hurricane Odile hit the region in September; though the damage was significant, most hotels and villas have already reopened, including the place we stayed). Moreover, I came away with several valuable tips for first-time villa renters like myself:

My birthday dinner sunset at Villa Miguel

Know your destination’s neighborhoods—or find someone who does.
Cabo was a natural fit for our California-based group—a sunny respite for my friends mired in San Francisco’s summer fog—but I knew nothing about the area. So when I logged onto VRBO.com—a popular vacation-rental website—to start searching for a rental property, I was flummoxed by the options: VRBO’s 1,200 Cabo-area rentals are divided among Cabo San Lucas and the Los Cabos Corridor, then grouped by headings such as Costa Brava and Sirena Del Mar—all of which meant nothing to me. (I’d later discover that most of these are the names of neighborhoods or gated communities.) If I hadn’t finally thrown up my hands in defeat and called Julie Byrd, one of Wendy’s WOW List experts for villa vacations—Julie is the Cabo vacation-rental expert whom Wendy has been recommending to travelers for years—I might have booked a house in noisy, party-central Pedregal instead of in the family-friendly Cabo del Sol gated community.

Interestingly, many travelers who contact Julie Byrd with a particular villa in mind end up booking a different one based on her advice, most often because the location of the original house doesn’t fit their needs. If you plan to book a place without help from an expert like Julie—popular websites for this include VRBO, HomeAway, Craigslist, FlipKey, and TripAdvisor—make sure to familiarize yourself with the destination’s neighborhoods first. Sure, this is good advice for any trip, but it’s particularly important when renting a villa that may have been built originally as a private home without considering convenience for travelers.

Glean intel from online reviews.
These are full of essential information, especially if you read between the lines. You can figure out not just whether a villa is shabby or well-kept, but what kinds of travelers stay there and whether that beach you see in the photos is an easy stroll from the house or requires scrambling over a rocky path. (See these tips from an expert TripAdvisor reviewer on how to extract useful information from all those user reviews.)

The pool at Villa Cielito

Consider which hotel amenities are essential to your happiness.
Daily maid service? Wi-Fi? A full hot breakfast? Don’t skimp on what makes you happiest at a hotel. If making your bed and cooking your own breakfast each day doesn’t sound like vacation, know that there are staffed villas with every level of service—and corresponding price points. A different house we visited, Villa Cielito, had an indoor-outdoor living area with blockbuster ocean views that sparked destination-wedding fantasies among my girlfriends, but the bedrooms were generic and motel-like, without the knickknacks and local art that gave our own Villa Miguel a charming, homey atmosphere.

The dining and living room areas at Villa Miguel

Do some menu planning in advance.
I was initially attracted to the thought of cooking my own meals—until I realized the waste of time and ingredients involved for a trip as short as ours. Instead, I carried some granola and coffee from home, bought milk at a nearby grocery store, and spent the money we saved with our quick-and-easy breakfasts on a few splurge meals. Best of all was a catered dinner at our villa on the night of my birthday; my son never would have sat through a five-course meal at a restaurant, but here he was free to wander around with his toys while we dined at a relaxed pace.

Villa Miguel entryway

Stay a week.
I’d hesitate before renting a villa again for less than a week. Villas have a higher start-up cost than a hotel room but greater efficiency in the long run. It would have been more cost-effective to cook for ourselves if we could have bought and used a week’s worth of groceries. And the quirks that can make a private home so appealing—perusing the owner’s book collection, say—can take a while to discover. Similarly, don’t overextend yourself with activities. Julie Byrd advises clients to pre-book activities only in the extreme high season; travelers often discover that they want to spend most of their time relaxing at their villa, not snorkeling or mountain biking. And if you have a large group, it can take longer than you expect to get out the door, so don’t count on fitting in more than one event per day.

Choose your companions wisely…
Traveling with extended family or friends can make renting a villa cheaper than an equivalent hotel—especially if people are willing to share bedrooms, as we did—but make sure you’ll all travel well together, as there’s little privacy in a shared house. (If you’re doing the math, it’s only fair to compare a villa rental to a hotel suite because a standard room doesn’t offer space that you can share only with your fellow travelers, away from the hotel’s other guests.)

The beach-entry pool at Villa Miguel

…And cater to kids.
If our son’s not happy, we’re not happy; there’s nothing relaxing about a grumpy kid. An expert villa-rental agent (Wendy knows the best, so if you need a recommendation, ask her) will know which properties are best for little ones. If you’re going it alone, ask the villa owner not just whether the house is kid-friendly but what ages of kids have successfully stayed there; a two-year-old has much different needs than an eight-year-old. A property like ours, Villa Miguel, which was perfect for a toddler, would have been a death trap just a year ago (think wrought-iron railings and slippery stone staircases). Julie Byrd chose it for our group in part because of the beach-entry pool—which my son loved—and the easy access to restaurants at the two hotels in the same development.

Rent a car.
Except for city apartment rentals, in most cases you’ll need a car to explore the region around your villa. It’s a lot harder to call a taxi from your villa than it is to walk down to a hotel’s concierge and hire one. Make sure you’re comfortable driving in a foreign country.

Balcony at Villa Miguel

Get a thorough walk-through of the property upon arrival.
I later regretted rushing our house manager through his 45-minute introductory tour. At the time, it felt like a waste on a 72-hour trip. Instead, we shivered through our late-night hangout sessions, not knowing how to adjust the living room air conditioner, and one of my friends was heartbroken to discover on our last morning that the glass doors to her balcony slid all the way back into the walls, opening up an entire corner of the room; had she known earlier, she would have slept with them open every night. Hotel rooms are built so that a new guest every night can intuitively find the light switch; private homes are not.

START PLANNING YOUR OWN VILLA VACATION

Disclosure: CaboVillas.com was kind enough to provide the writer’s three-night villa stay free of charge. In keeping with WendyPerrin.com standard practice, there was no request for or expectation of coverage on CaboVillas’ part, nor was anything promised on ours. You can read the signed agreement between WendyPerrin.com and CaboVillas here.