Private Villa & Multigenerational Travel Agent

Our Grand Cayman Villa Vacation

Everybody under one roof. That's the whole appeal, and it's also the whole challenge. My personal villa stays brought me to Grand Cayman. Our own house, own beach & we had a private chef come cook for us one night. The best way to see that island.

I 100% recommend the lobster poutine at Tukka's on the East side!

I'm Tamara Lidbom, owner of Anytime Travel Agency and a Certified Travel Associate, and I plan private villa vacations for families, multi-generational groups, and groups of friends traveling together. I've rented villas myself in Grand Cayman, so I know what the listing photos leave out.

Why a villa instead of a block of hotel rooms

When a family books six hotel rooms, they spend the week texting each other about where to meet. When a family books a villa, they spend the week together. Breakfast happens in the same kitchen. The grandparents are down the hall instead of on another floor. Somebody's cooking, somebody's in the pool, and nobody's coordinating.

For milestone birthdays, reunions, anniversaries, and any trip where the point is the people rather than the place, it's usually the better structure and often the better value.

The questions I'll ask you

Do you need four bedrooms or eighteen? Ocean, jungle, or mountains? Is a pool mandatory, and does it need to be heated? Game room, movie room, gym? Do you want it staffed, and if so, how much: a housekeeper, a chef, a driver, or all three? Are there ages in the group that change what's safe, an unfenced pool or a staircase with no railing? Who's paying, and are you splitting it?

Those answers narrow a field of thousands down to a handful, and that's before I've looked at a single photograph.

What I handle that a rental site doesn't

Villa bookings carry moving parts a hotel reservation doesn't have. Contracts and cancellation terms that vary property to property. Damage deposits. Staffing arrangements and what they cost. Provisioning, so there's food in the house when you arrive instead of a grocery run at nine at night. Transfers for a group landing on five different flights at four different times. Who has the key, who meets you, and who you call if the air conditioning quits on a Sunday.

I book through vetted, contracted suppliers with verified permits, licenses, and insurance. That matters more with villas than with almost anything else, because the listing economy is full of properties nobody has ever inspected and owners nobody can reach. I don't put a family in a house I can't stand behind.

Lead time

Larger villas in good locations book out further than hotels, and the best ones go a year ahead for peak weeks. If you're planning a reunion or a holiday week, start early. Groups also need longer simply because decisions take longer when nine adults have opinions.

Twelve months or more for group travel. Sooner is better.

Certified Travel Associate (CTA). Anytime Travel Agency is a member of ASTA, CLIA, and Travel Leaders Network, and is IATAN accredited.If you're pulling a group together and a villa sounds right, give me a call and we'll figure out what you actually need.