Destination like USVI or BVI (topography) where I can rent a private villa
 

My husband and I are looking to rent a villa the last week for October with our one-year old. We love the topography of the USVI and BVI and we enjoy having our own place to stay. With the baby, we def do not want to stay in a hotel or condo. For some reason, the return leg of the flight from Boston to STT is shooting the price per ticket to $800+pp so we are looking for somewhere new to visit. Any thoughts on another island where we can rent a villa with a view? We like to snorkel and explore with our own car.

St. Martin is hilly but I have already been there, unless anyone can recommend a great villa there with a view in the $2K range. Any recommendations on villas in Puerto Rico? I have stayed in San Juan and was not wowed. St. Barths is out of our price range.

I have heard T&C, Anguilla and Grand Cayman are flat with good snorkeling but are there villas? Seems to be just condos. St. Lucia is too far with the baby, we have already been to Barbados, Negril, Curacao. We would consider Aruba if we had a private place to stay - away from the crowds. Any thoughts or advice are appreciated, especially if you have a favorite villa somewhere! Thanks!

Villa Oceana on Anguilla. Anguilla is unlike the virgin islands but the beaches are stunning. Would you consider the bahama out islands (Eleuthera or Exuma)? Many villas directly on the beach in your price range. Less developed and you will have multiple completely uncrowded beaches to explore.

We are actually VERY interested in the Bahamas and would love to explore the out islands. What does it entail to get there though? Flying into Nassau and then a boat ride? And the best way to get to Anguilla is to take a boat from St. Martin, correct? I am trying to make the travel with the baby as painless as possible but there are limited nonstop flights to islands in the fall.

Yes, there are rental villas in the T&C's (mostly on the island of Providenciales) and on Anguilla and Grand cayman (more condos, though). Google "Villa Rentals NAME OF ISLAND" for lots of links.

Easiest way to reach the Bahamas Out-islands is usually to fly to Nassau then get island hopper flights to the Out-island of your choice. Sa couple of the Out-Island can be reached by flights from Miami or Ft. Lauderdale. Going by boat between islands is often time consuming because of ferry schedules and/or distance involved - flying is the smart option if you only have a week.

Yes, to reach Anguilla it's easy to fly into SXM then take ferry or water taxi to Anguilla.

It depends on the island. Eleuthera (Gov harbor airport which is central) can be accessed via fligts from fort lauderdale. Here is a link that has details about flights to exuma.
http://www.exumabahamas.org/flights.html

Certain other islands in the bahamas such as long island require a flight to Nassau and then an onward short flight to the island.

Yes I think the best way to Angulla is direct to St martin and then a short boat ride.
Grand Cayman (if you are open to doing a condo on 7 mile beach) is probably the most painless bet for you.

You can fly into Anguilla on LIAT from San Juan or St Thomas.

http://www.thebuccaneer.com/buccaneer-beach-house.htm

I'm dying to stay here! We stayed in lovely oceanfront rooms at the Buccaneer resort. It's a great place, with awesome service.

Not hard to fly to STX. JetBlue might be having a sale through November.