Private Villa at the Haystack Tryall Club in Jamaica | Value: $37,000
Week-long stay in an exclusive, gated resort. Villa has eight bedrooms and accommodates 16 guests to be pampered by a personal staff of seven.
Luxury features include a pool, outdoor bar, game room, gym, fire pit, three dining areas, and three golf carts to travel around the property.
Views of the Caribbean Sea and a short swim to a beautiful coral reef.
Fine print: Bookings are Saturday-Saturday. Tennis, golf, water sport excursions, and airport shuttles are available for a fee. Suggested tip to the villa staff is $1,750-$2,500. Guests are required to a pay resort fee of $135 per adult per week.
Donated by Emily and Teddy Greenspan