Originally Posted by
marinkitty
Look into renting a house/villa that comes with staff. It sounds extravagent - but it really isn't. Sure, there are some super expensive places, but there are more mid-range spots too. Best of both worlds. We've done this in Mexico (Tulum - three generation extended family trip), Jamaica (Negril - girls trip) and Costa Rica (Cabo Matapalo - immediate family trip) and have been very happy. And it usually prices out the same or less than a resort stay for the same number of people. Some locations seem to have more staffed houses than others where a self-catering rental is the norm - besides the ones I already named, check out Dominican Republic and the Bahamas (the smaller, less touristy islands).
At each place we've had a caretaker couple or a group of staff who will stock the house, mix drinks, make whatever meals are desired for reasonable costs, clean the house, help arrange outings and secure reservations. Usually the meals are cost of groceries, sometimes a small up charge to cover transportation to and from the market and then a cost per person for the meal - breakfasts about $6 pp, dinners maybe $12-15. Super reasonable and amazing service all in the comfort of your private house with plenty of space to hang out.