PS Joshpal,
this website helped me when I was planning for Culebra- www.islaculebra.com- click through some of the links to see photos of some of the beaches, although our favorite, Zoni, is not pictured. There is good general info about the island. There is a "sister" site that might be www.isla-vieques.com (can't remember) but there is a link to it on the Culebra site. Happy reading!

I used to live on the west coast and vacationed in Hawaii, which I loved.

Now that I live on the east cost I have been travelling to the Caribbean and finally found true paradise....St. John! Plenty of hiking, going to different beaches, off beach snorkeling...I love it even more than Hawaii...especially Caneel Bay.

Hi Joshpal. I stayed at Caneel Bay on St. John so I can't really help with specific villas or even rental companies. My suggestion is to do a search here by putting in St. John in the Search the Forums box and see what comes up. I would also Google St. John, or St. John villas, or something like that. A lot of people use vrbo.com and have been very happy and I wouldn't hesitate to use a recommendation by someone on these forums. I think you should easily be able to find nice accommodations in a villa or cottage for around $1,500 a week, particularly in May.

Here's an example of an older thread on this site that has some good information:

http://www.fodors.com/community/cari...vi-cottage.cfm

As to the driving on St. Lucia, that is one of the few islands where we did not rent a car. We stayed for a week at Le Sport, an all-inclusive where we certainly didn't need a car, and then moved to a resort on Rodney Bay for a few days. We did a few tours from our Rodney Bay hotel where transportation was provided and then we just used taxis if we needed to. There were restaurants and shops within walking distance of our hotel so we didn't feel the need to rent a car. The driving is a bit challenging there although if we go back we will undoubtedly rent a car. It's a large island with very hilly terrain and not so great roads in the hilly areas.

Other suggestions for islands for you to consider are the aforementioned Grenada and Bonaire. I think I mentioned Grand Cayman up-thread and I still recommend that. It's an expensive island for the most part but there are nice, reasonably-priced places to stay (condos) and they have a large, modern grocery store where you can stock up on breakfast and lunch items to save a little money.

If you are still considering St John, have a look at Grande Bay Resort. We have stayed at Gallow's Point several times and it was just getting out of our price range. Grande Bay is a group of condos and has been a work in progress for some time. We stayed there last time to save some $$, knowing what we were getting into. Basically, our unit was brand spanking new but there was still some construction going on but nothing loud and obnoxious. The pool and hot tub were being filled during our stay. Our unit had a stackable washer and dryer and I'm pretty certain that most if not all do. It is EASY walking distance to Cruz Bay restaurants and shops. Also has a parking garage. I'll post the link to the website, but check out vrbo (look for St John, Cruz Bay) because I have seen some varied rates. You should be able to get what you want for about $200-$250 per night.

http://www.grandebayresort.com/

Just had a closer look at that website. While it is beachfront, it is not "swimming" beachfront. Ferry comes in nearby and lots of other boats there.

Whoever above mentioned Grenada, I'll second it. It's lush and mountainous with interior activities like hiking to waterfalls and exploring historical sites. But it's also got really beautiful beaches, a wide array of restaurants and accommodations, and fun water sports. The West Indian flavor is really strong, too, so you'll definitely get that "I'm outside the US"feeling that one doesn't get (or at least I didn't get) in Hawai'i. The island is very safe for traveling around alone as a family, but part of the fun would be to find your own private tour guide (any taxi driver can give a tour, but there are some, like Mandoo, who specialize in tours) to get the real scoop on all of the things to do.

Take a look at www.grenadaexplorer.com for lots of general information about Grenada. Then take a look at www.spiceislevillas.com to find some great villa deals--your dollar will go a lot further on Grenada then many other Caribbean islands.

Thanks a lot for all the great answers. While looking for places on St Jonh, we found a place called Coconut Coast Villas. Their prices are very reasonable compared to other places, so I wonder if there is any "catch" there?

Did I miss why you discarded the idea of Virgin Gorda?
I think it's an ideal place given the age of your child, the beaches and your budget.
Take a look at the special rates at Mango Bay for May. The property is right on the beach so you don't have to drive to another beach unless you wish.
There are other hotels and villas with a similar feel...

What time of year are you planning to go?

He mentions the beginning of May as when he wants to travel...

we just returned from Costa Rica. It was very Hawaii like. Yes, I know it is not in the carribean, but the flight is just as close.