Caribbean from Boston with Kids
 

Looking for a sun and fun-filled vacation for a family of 5 including 3 active boys ages 7,5, and 3. Ideally would like a trip from Boston under 5 hours long and will look to rent a villa w/ kitchen somewhere around $500/night. We DO love nature, hiking, biking, swimming, connecting with a new culture. We DON'T like big crowds (i.e. swarms of people coming off cruise ships), overbuilt beaches, panhandlers, and tacky trinket shops. Is there a Caribbean island out there for us? Or should we suck it up and spend more time on a plane to go to Costa Rica??

When are you planning to make the trip? That will be a big factor when trying to find a rental villa in your price range. Quite honestly $500/night is on the low side if you are planning to travel in High Season (December 15 through Easter Week). If you are going in summer you'll have a better chance.

Aso, you might be able to save money if you rent a multi-bedroom condo rather than a stand alone villa so give that some consideration.

Depending on the time of year you are traveling you can find quite a few 2 & 3 BR villas on both Tortola and Virgin Gorda that are in the $550 to $600/night range (in Low Season) but you'll find getting there, especially Virgin Gorda, is somewhat difficult and will add to your travel costs.

Also, look at rental villas & condos on St. Kitts and Nevis - both are relatively quite islands and you should be able to find plenty of nice accommodations in your price range.

Personally I'd skip St. Martin as that island is quite crowded with cruise ship passengers which you said you want to avoid.

HINT: Simple internet searches using such topics as "Villa Rental, NAME OF ISLAND" or "NAME OF ISLAND condos" will give you lots of links. Also, go to the TripAdvisor Travel Forums and click your way through to the islands that interest you then click on the "Vacation Rentals" link at the top of the page. You'll be directed to a list of most of the rental properties on that island. You can sort by number of bedrooms and by price.

Good luck in your search.

I suggest Puerto Rico, St. Croix, St. John, St. Kitts and Nevis.

In addition to the locations already listed by other posters, I think St. Lucia would also work for you. Check out Marigot Bay and Windjammer Landing. Windjammer has the option to be all-inclusive if you prefer to go that route.

I'm not sure you can get there in 5 hours from Boston but as you know there are very few direct flights to the Caribbean from Boston. I'm from Boston so I know. But you should be able to get there with one connection, just like most places in the Caribbean.

We flew to St Croix from Boston last June, on JetBlue to Puerto Rico, to STX. It was easy.

Stayed at The Buccaneer Resort, which we liked a lot and I highly recommend for you with kids. There is a free kids' camp, even. Also golf, tennis, free snorkeling gear, free kayaks, full hot breakfast buffet included, sundries shop, spa, fridges in rooms, snack bar at the pool, oceanside casual restaurant, full-on dining room in the main house.

It's a fabulous property with great customer service.

They could meet your budget. We had three oceanfront deluxe rooms, with 2 Queen beds, for $300/night.

Search under my name to find more details about it, and others' comments on the Buccaneer.

$300/night each room, of course.

we stayed in this villa near tulum, mexico a few years ago and friends have been more recently.
/www.locogringo.com/mexico/accommodations/riviera-maya/villa-rentals/casa-cavu/
the beach it's on is quiet (no vendors) and has good snorkeling. you need to rent a car but driving is no problem
you don't say when you're traveling but check american & jet blue for non'stop.
there are tons of houses on this coast if casa cavu seems to remote. and more things to do than any island from kayaking to ziplines. there are 2 wonderful water parks the kids would love: xel-ha and xcaret
houses listed on locogringo.com or bill-in-tulsa.com