You can do quite well on $5000 in Bermuda. You will spend about $300/pp on airfare from the east coast of the US, and probably $200/day on food and drink for four, if you eat modestly and aren't big spenders. That leaves you a budget of around $2500-$2700 for accommodation and local transportation. You're looking for a place appropriate for four adults, two of whom might enjoy sharing a king sized bed and a little privacy. That shouldn't be a problem in Bermuda. Bus passes good for both ferries and buses are inexpensive, and make for good access to Hamilton, the beaches, and both ends of the island - St. Georges and Dockyard. I think they are $40/pp for a seven day pass.For accommodation, I am a fan of Kingston House. It's a little B&B that's run by a couple. It should be around 300/nt for two rooms - book early - they have only four rooms. Harry and Marley also belong to a network of like properties here, so may be able to place you somewhere if they don't have space available. See http://www.bbbermuda.com If a guest house doesn't appeal, you might try the Wharf Executive Suites. The suites have a bedroom, kitchen and living room with a pull out hideaway bed. I think they'd be in that budget range. They are on a ferry route, and are a 10 minute walk to a bus stop, plus have a great harbour view. http://www.wharfexecutivesuites.com/Alternatively - you could hit the vacation rentals site and rent an apartment or cottage somewhere. You could expect to pay around $1500-$2000 maybe a little more, maybe a little less for a suitable place for a week. See http://www.vrbo.com/vacation-rentals/caribbean/bermuda/You can accomplish a great family vacation on that budget, complete with adventures and beaches. Good luck!