Lot's of rental villas on Grand Cayman, that meet your descriptions. Go here for starters: www.caymanvillas.com or do a google sear for "Grand Cayman Rental Villas).

FYI - very few rental villas come with chefs but all will have a housekeeper (either full or part-time, reed descriptions for more details). The management company will be pleased to hire a chef for your stay but understand doing so could add significantly to your cost. Professional chefs can be expensive - perhaps you meant someone who does the housekeeping and do a little "cooking" but not a chef who does gourmet meals.

barbados will offer everything you want except the short flight - around 8 hrs stopping in miami

Only high end villas ($1000s nightly) will come with a chef, and you still pay for food.

Chef in Caribbean usually is more than eating out there, definitely won't find it at your budget.

Most villas come with 1 light midweek cleaning at your budget too, you can pay additionally if you need it daily. (guess, $100-$200 per cleaning)

So if you give up the chef part, and settle for a mid week light cleaning, you can find beautiful villas in your price range.

Now if you don't mind Central America (which doesn't meet your flying criteria) you can get more of what you want.

Or stick to Mexico. The rest of the Caribbean won't meet your criteria at your price.

http://www.islandhideaways.com/barbados/villas/west-shore/

Thank you all for your responses. I guess we have been very spoiled with our rentals in Mexico, daily maid service, chef, full-time bartender Only problem is that we won't be heading back to Acapulco anytime soon

I love Costa Rica, but it is just too much for us to undertake with our little one who is a horrible, horrible flier.

Giving up the chef, etc., are there any particular villas that you recommend?

There are literally thousands of rental villas throughout the Caribbean. Your best bet is to first choose an island then begin your search from a villa that fits your needs. That will help narrow down your choices.

Islands (which could meet your definition of being "one reasonable flight away) with lots of rental villas include:

Grand Cayman
St. Thomas
Providenciales (Turks & Caicos)
St. Martin

Good luck!

I think your best two options for locations are Grand Cayman or Turks and Caicos. I don't have specific villa recommendations, but I do know both islands offer plenty of choices, including beachfront. As for the staff, I think you'd have to raise your budget.

Best of luck

I am trying to find almost the same, but kids are 19 and 14.. would you mind sharing villa info for Acapulco.. I especially like the chef/bartender! You should look at St.John. Turks is very expensive.

Conlon10 - our villa was in Acapulco right in the heart of all of the violence right now so I can't recommend doing anything along those lines. Sorry

this house is on the south side of provo in t&c. approx 15 min drive to the main beach, restaurants, grocery so you would need a car. taylor bay beach is perfect for your kids to play as it's only knee deep for a long way out. http://www.vrbo.com/328823#rates

you won't find any villas on st. john on the beaches & will need car there too.

you could look at the area south of cancun. loads of villas (some with staff) locogringo.com lists villas & condos. good prices. very safe -no violence like acapulco.

i've never been on jamaica but know that many of their villas come with staff

we liked this house on grand cayman enough that we're thinking of returning this fall. the beach was a bit rough for walking a couple yrs ago, but may have filled back in from new storms. it is 45 mins from seven mile beach & georgetown. 1 small grocery about 6 min drive another about 20.
http://www.grandcaymanvillarentals.com/villa-listing/thatch-hill

this house is on the south side of provo in t&c. approx 15 min drive to the main beach, restaurants, grocery so you would need a car. taylor bay beach is perfect for your kids to play as it's only knee deep for a long way out. http://www.vrbo.com/328823#rates

you won't find any villas on st. john on the beaches & will need car there too.

you could look at the area south of cancun. loads of villas (some with staff) locogringo.com lists villas & condos. good prices. very safe -no violence like acapulco.

i've never been on jamaica but know that many of their villas come with staff

we liked this house on grand cayman enough that we're thinking of returning this fall. the beach was a bit rough for walking a couple yrs ago, but may have filled back in from new storms. it is 45 mins from seven mile beach & georgetown. 1 small grocery about 6 min drive another about 20.
http://www.grandcaymanvillarentals.com/villa-listing/thatch-hill

In Jamaica, there are wonderful Villas in the areas of Portland...St. Mary and Trelawny.. These villas do come with staff members and would definitely suit your liking base on the requests i see in previous post.

There are great villas in Antigua which should meet your price requirement. Very friendly and safe island. Great beaches for young children. We went last year with our 2 year old and she loved it.

In 2005, we (including two toddlers) stayed in a villa at Silver Sands, Jamaica (see www.mysilversands.com). All of the villas there are privately owned and are of various architectural styles. Many have private pools, and the prices are reasonable. So far as I know, all of them come with housekeeper/cook. In our experience, the staff were especially helpful and fond of the children. A rental car was not necessary because Silver Sands provided round-trip transportation between the airport and the villa. Also, they provided a variety of reasonable-priced daytrips. To us, it was the perfect place to relax!
The villa we stayed in is no longer in their rental pool, but the one next door, which we visited, is. Both of these are up on the hill (providing lovely breezes as well as a good view of the water), about a 3-minute easy walk to the beach, but the one next door comes with a free golf cart. We all loved the beach and felt very relaxed with the children playing in the water near the shore. lAl of the villas looked lovely from the outside.