Thanks all. Op here. I'm not comfortable having someone waiting on us if we're not at an actual restaurant but the idea of giving input on a menu and having someone prepare everything sounds great. These experiences are helpful to hear and give me a sense of what to look for or what questions to ask.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:FWIW, we were excited about staying in a villa/house in Jamaica a friend owned as a rental income, and which provided a cook.

Until we got there. Despite the allure of it we found we really did not like someone being at our "beck and call" like this. Especially when we found out the woman did not stay on property but took several buses and spent hours each way just to get to the house.

We ultimately told her to just pick up some groceries for us, then take the week off and spend it with her kids, gave her a tip and cooked our own simple meals and made our own beds.

We told our friend/owner and he was OK with it.

And did she still get paid? Maybe she had to work two houses the next week. There’s ways to make peoples lives easier as they go about their jobs.

Yes, of course she still got paid or we wouldn't have done it. As mentioned, the owner is a friend and we know for a fact he still paid her.

Would it have been better if she had stayed on the property away from her family? How did you think this worked? Did you think she got picked up by a chauffeur every day from her matching villa across the street?

How about you hang-up your attitude? We had NEVER done this before so we had no preconceived idea. When we found out "how it worked" we decided it wasn't for us. If you want to shoot poison judgemental arrows at someone, how about you aim them at the people on this thread who are seeking out such an arrangement, purposely. Not that it's any of your business anyway. The point of my post was to say that having people wait on you like this may not be so comfortable or enjoyable.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:FWIW, we were excited about staying in a villa/house in Jamaica a friend owned as a rental income, and which provided a cook.

Until we got there. Despite the allure of it we found we really did not like someone being at our "beck and call" like this. Especially when we found out the woman did not stay on property but took several buses and spent hours each way just to get to the house.

We ultimately told her to just pick up some groceries for us, then take the week off and spend it with her kids, gave her a tip and cooked our own simple meals and made our own beds.

We told our friend/owner and he was OK with it.

And did she still get paid? Maybe she had to work two houses the next week. There’s ways to make peoples lives easier as they go about their jobs.

Yes, of course she still got paid or we wouldn't have done it. As mentioned, the owner is a friend and we know for a fact he still paid her.

Would it have been better if she had stayed on the property away from her family? How did you think this worked? Did you think she got picked up by a chauffeur every day from her matching villa across the street?

Anonymous wrote:

Anonymous wrote:FWIW, we were excited about staying in a villa/house in Jamaica a friend owned as a rental income, and which provided a cook.

Until we got there. Despite the allure of it we found we really did not like someone being at our "beck and call" like this. Especially when we found out the woman did not stay on property but took several buses and spent hours each way just to get to the house.

We ultimately told her to just pick up some groceries for us, then take the week off and spend it with her kids, gave her a tip and cooked our own simple meals and made our own beds.

We told our friend/owner and he was OK with it.

And did she still get paid? Maybe she had to work two houses the next week. There’s ways to make peoples lives easier as they go about their jobs.

Yes, of course she still got paid or we wouldn't have done it. As mentioned, the owner is a friend and we know for a fact he still paid her.

We did this in Italy, not the Caribbean, so it may vary. We had the chef for breakfast every day and she’d put out a whole beautiful spread of cornettos and pastries and little baked items, quiches, along with cut fruit platters, cheeses, yogurts with toppings, cereals etc. and then things like eggs and pancakes and cappuccinos she made to order when you got to the table. For dinner, we did it only a few nights for a few reasons. One was that we were doing day trips and didn’t want to race back, two was that it was designed as a 3 or 4 course meal and was too long for all the young kids, and three was our multigenerational group is a royal pain in the neck with dietary restrictions and preferences (lactose intolerance, nut allergies, gluten free, kosher, etc.) and you had to have the meal be the same for everyone (although they could sub gluten free pasta for some). So they gave us a long menu to choose from ahead of time, and our family of 4 would have eaten literally everything, the broader group was sort of stuck with grilled chicken/steak/fish and veggies as the only thing everyone could eat and it didn’t seem worth having a chef and better to each order our own dishes at a restaurant. The chef did buy and bring everything and cleaned up.

Anonymous wrote:FWIW, we were excited about staying in a villa/house in Jamaica a friend owned as a rental income, and which provided a cook.

Until we got there. Despite the allure of it we found we really did not like someone being at our "beck and call" like this. Especially when we found out the woman did not stay on property but took several buses and spent hours each way just to get to the house.

We ultimately told her to just pick up some groceries for us, then take the week off and spend it with her kids, gave her a tip and cooked our own simple meals and made our own beds.

We told our friend/owner and he was OK with it.

And did she still get paid? Maybe she had to work two houses the next week. There’s ways to make peoples lives easier as they go about their jobs.

Anonymous wrote:FWIW, we were excited about staying in a villa/house in Jamaica a friend owned as a rental income, and which provided a cook.

Until we got there. Despite the allure of it we found we really did not like someone being at our "beck and call" like this. Especially when we found out the woman did not stay on property but took several buses and spent hours each way just to get to the house.

We ultimately told her to just pick up some groceries for us, then take the week off and spend it with her kids, gave her a tip and cooked our own simple meals and made our own beds.

We told our friend/owner and he was OK with it.

Found the Americans.

FWIW, we were excited about staying in a villa/house in Jamaica a friend owned as a rental income, and which provided a cook.

Until we got there. Despite the allure of it we found we really did not like someone being at our "beck and call" like this. Especially when we found out the woman did not stay on property but took several buses and spent hours each way just to get to the house.

We ultimately told her to just pick up some groceries for us, then take the week off and spend it with her kids, gave her a tip and cooked our own simple meals and made our own beds.

We told our friend/owner and he was OK with it.

OMG, not PP, but grocery shopping in St. Martin is a dream. Huge French grocery store brands were lovely to shop in!

We did it with an independent Villa in St. Martin. I think we handled lunch and they did breakfast and dinner. It was tricky because there was some level of self-provisioning and it was really tough to get the quantities of groceries we needed that were of ok quality to feed a big group daily. I would find a situation that included all food purchasing depending on what country and area you choose.

Many of the resorts I have been to have villas. Off the top of my head -- The Caves in Jamaica has one, and both The Body Holiday and Jade Mountain in St Lucia have several. So if there are any particular resorts you are interested in, you can check on that.

I've had the chef come cook, and I've also had the meal delivered already cooked, depending on the villa and the meal. How this works depends on the resort. I don't have experience renting a villa that is not connected to a resort.

This sounds like a job for a TA.

You can give the menu either as positive orders (we want grilled chicken with coconut curry) or negative orders (no tomatoes or onions in any dish).

I have done this in a few countries over the years, most recently in Jamaica. In each case the villa owner or property manager will set this up for you, allowing you to choose for which meals you’d want the service. We never did breakfast but did a few lunch and dinners. They would charge by meal for food and labor, and share menus upfront (which you can modify for dietary restrictions and preferences). It was all within reason (compared to when we did this in Mykonos in which case it was highway robbery, but that’s the entire island IMO).

It's anything you want!

I love the idea of renting a big house in the Caribbean for a multi generation trip and hiring someone to do the cooking but how does this work? Does someone show up every night at a set time, cook, and then clean up? Do you give a menu in advance? I assume breakfast and lunches aren't typically included in the service?