Puerto Vallarta, Mexico
Round up the troops because you’re going to a Mexican mansion. Villa Mia has 15 bedrooms, 19 bathrooms (!!), a barbecue and bonfire area, two palapa bars, a squash court (for all of that exercising you’ll be doing), a 16-person hot tub, and a cliffside infinity pool. You won’t have to lift a finger the entire time you’re there thanks to the housekeepers, chefs, and waiters whose services are included in the price. Admittedly, it's a little steep over the holidays ($4,200/night) but much more reasonable from January-May ($3,700/night). But hey, you only have to stay four nights minimum and with 30 people, that’s a mere $500 a head!