Trying this again, because I have a better idea of what we are looking for:
-small resort/hotel inn ON THE BEACH
-Tennis courts
-Restaurant on-site
-Breakfast included
-Warm, attentive staff
-Good snorkeling
-Ability to walk into a town with restaurants, shops, etc. Doesn't have to be the biggest town on the island, but not in the middle of no-where.
-Lush feel w/ beautiful beaches

Things to keep in mind. I LOVED St John but
1) we can't get a place right on the beach in St John
2) with the exception of Caneel Bay, which runs around $600, night, I can't find a place w/tennis courts
3) We'll spend up to $350/night
4)We're only going for 5 nights so ideally our travel time will be short.

Help!
I was thinking of Anguilla but it looks like there's only one flight leaving from PR at night, so we lose the whole day of travel.

How about St Lucia? I've found a bunch of good places, I just wish I could find one w/tennis courts!

Could look into Virgin Gorda too. Any other advice? I'm open to just about anything and would love to hear abt other's experiences.

Thanks.

You might look into St. Kitts. We'll be staying at Timothy Beach in a couple weeks, it's web site mentions tennis 'a ten minute walk away'. I don't know about breakfast. Town is three miles away, but there are serveral bars/restaurants within easy walking distance. Also, the Marriott is close by, with a huge casino, if you're interested. They may have tennis as well, but it certainly isn't a small hotel. The Marriott is on the Atlantic side, the water is rougher, I've read that there is decent snorkeling (not great) off the beach at Timothy Beach.

You can get to Anguilla mid-day from anywhere on the east coast by flying thru St. Martin (SXM) which is a 20 minute ferry ride away. However, The Valley, which is the capital of the country, doesn't really have much in the way of shops or restaurants and is nowhere near a beach; moreover, the island is not lush but is rather arid and scrubby and flat. Gorgeous beaches (33) and great retaurants (around 80). I can't remember if CuisinArt has tennis courts but there's isn't good snorkeling on that beach anyway. Shoal Bay East has decent snorkeling but I can't think of any tennis courts there. Probably not the right island for you.

Well, I can think of only one place I've stayed that fits most of the criteria on your list. It's the Long Bay Hotel on Antigua. It's a small, family owned and run hotel on the north east coast. Situated on a peninsula, the beach is on one side of the hotel and a large bay good for windsurfing and kayaking is on the other side. Both breakfast and dinner are included in the rates, and the staff there is hands down the warmest I've ever encountered in my travels. There is one tennis court on site and it is not lit for playing at night, but it's shared only by about 20 rooms.

There is snorkeling off shore that's among the best in Antigua, but the best Antigua has to offer will certainly pale in comparison to the snorkeling on St. John.

AS for being within walking distance of things, that's the drawback. In addition to the hotel's beach bar & restaurant, there are two others right on the beach to choose from, and you can walk to the restaurant at Dian Bay, just up the hill from Long Bay. There's one other hotel on the beach there, but it's an AI so I don't know if a non-guest could stay there or not.

There's the small village of Willikies about 1.5 miles away, but it offers a rum shop and a place for ice cream as far as comestibles are concered. Devil's Bridge is also within walking distance, about 1.5 miles, from Long Bay. But for shopping or other restaurants you'd have to rent a car or hire a taxi.

From Long Bay you can also take a water taxi to Harmony Hall for the day, which offers wonderful food, an art gallery, small gift shop, and time spent at the offshore Green Island for sunning and snorkeling.

You might check out Tortola.